Cold Deck: Days and Nights with a Mafia Wiseuy

 

September 2013: In the Dark, Close to Dawn

I couldn’t sleep.

Chasing Easy Street playing poker in St. Louis, I was wired after another late-night session at the tables. Time for a high-tech tranquilizer, I thought. Hopeful the hum and electric-blue haze would ease the torture, I fired up the laptop. But instead of dosing naked girls or Sticky Fingers, I took off on a Google-strength trip back in time. Beginning with my 1st-grade teacher, I looked for some of life’s long-since considered passersby. And then I typed “Jackie Messina” into the search box.

Jackie flashed into my life in the fall of 1996. He owned a small vending company and a dubious past, and, not long after we met, I took a job as his assistant and all-purpose errand boy. A want ad declaring “Drive around with Jackie all day” would have been as accurate as it was brief. Fighting traffic and on the ropes, we traded jabs—baseball, gambling, politics and everything else—in countless bouts of brawling conversation. Soon enough, root beer and Twix begat real beer and nightclubs, and a most unlikely pair had become good friends.

But not even Google’s fancy machine could find my onetime boss and former friend. Why? More on that in a minute …

By 2013, my gambling-as-profession venture was teetering towards disaster. Despite having kept the high-wire act alive for 10 years, doom felt no less imminent. Countless poor decisions had pushed me to the wall, yes. But the real culprit—the one that put the lethal-type screws to the operation—was a criminally sanctimonious federal government. You haven't truly gambled until Uncle Sam's Grifters turn up seated across the table. While I may have never played serious poker until the early 2000s, I’ve been a gambler since before I was born. I was destined to take a shot.

On second thought, fuck that—destiny’s nothing but a fairy tale. There's DNA and environment, and, like everyone else, I’m a product of both. My first visit to a racetrack came in utero, to now long-gone Cahokia Downs. When my 21-year-old mother finally went into labor with my late-arriving self, the hospital found my 33-year-old father in a days-long poker game. Like I said, since before I was born. And if memories flicker like old movies, then gambling stars in a slew of boyhood favorites.

Big race days were the best. My dad would wake my younger brother, Andy, and I early, and we’d take off for sketchy South Broadway, in South St. Louis. We’d hit the newsstand to grab a Daily Racing Form, then swing into a diner for bacon and eggs. After talking horses over breakfast, we’d stroll a couple blocks to an old-school tavern. While my dad studied last-outs and morning lines, Andy and I kept busy at the bowling machine. A few-too-many Cokes later, we’d hop in the car, cross the bridge, and, finally, arrive at our ultimate destination: Fairmount Park. Then and now, the racetrack—any racetrack—is my one true love.

Nothing beats the track. Call it “atmosphere,” or “culture” or whatever you wish—it captured me whole and turned the trick long before will-pays and exacta sweats ever had the chance. Beyond racehorses and risk, the track’s got enough actors—from super-rich to dead broke and slightly regressed to highly depraved—to start its own company. It’s human drama at its rawest and realest. Forget Shakespeare. Obviously, Macbeth rates a pretty poor player when the track’s got tragicomic genius like “Two-Dollar Desperados Sweat a Photo.” As much as picking a winner, a kid got hooked by the people and stories of a most peculiar place. 

And it wasn’t just horse racing. Like so many dusty dice, Sunday poker games tumble in my memory, too.

I can still hear Val, a bookie sentenced to life in a wheelchair, droning to my mom: “Hon, will you bring me a Dr. Pepper?” Or how about Buster? A pistol-toting hotshot in the Mafia’s St. Louis office, he shaded the table with his pleasantly felonious hue. And Buster’s illicit vibrancy somehow paled aside one Grady “Red” Beason, the game’s esteemed, star outlaw. Born in 1900 and by then operating a part-tavern, part-gambling joint, Red enjoyed youthful jags in both bootlegging and bank robbery. Other Lord’s Day regulars included Scottie the Stockbroker, some guy called Nappy, and a living, breathing ATM named Sunoco Mike. Sunoco inherited a string of gas stations from his grandmother, and, every Sunday, he dispensed the fortune one call at a time.

That’s quite a crew to find gathered in your kitchen. Standing beside my dad, I’d gaze upon the colorful cast and the thousands at stake. I could barely see over the table.

The action life got me in its sway. When I was 5 years old, I dressed as Triple Crown-winning jockey Steve Cauthen for Halloween. Later, I was the only kid in St. Simon’s 7th grade able to understand the baseball money lines printed in the sports page. By the time I’d turned 15, and despite looking 12, I was betting for myself at the Fairmount Park windows.

At the same time, my brother and I were raised like most suburban, middle-class kids. We played sports, ran with our friends, and, thanks to two attentive, hard-working parents, we had everything we ever needed. There were only two rules: "Do the best you can" and, from my mother, "Don't be a fucking sheep, because sheep get slaughtered."

I guess you could’ve called us a risky-side-of-normal family. While Andy and I indeed grew up along shadier outskirts, we were sheltered from any real danger. Sure, my dad played cards with some characters, but, as far as we knew, proper gangsters were only in the movies.

Things change.

The human animal has long assumed a controlling interest in his own life. To this day, billions of people somehow remain oblivious of life’s majority shareholder. Gamblers know it as variance, but no matter what you call it, you can rest uneasy knowing this: you’re nothing but a plebe. A company man punching the clock. Because out there, somewhere, floating in the ether always, now and forever, the real boss—randomness—awaits. And its signature is stamped on every check that’s ever been cashed.

So, you’re squeezing your hole cards and pondering the flop. But don’t forget to think ahead, too. Still two cards to come. A scare card could fall on the turn and flip everything. In other words, you never know who might walk into your life.

Only later did I realize what a total mismatch I’d run into. Years of overpriced, private-school education hadn’t offered any such instruction. In fact, nothing in my 20-plus years had prepared me for such an encounter. And Jackie knew it.

But here in my dark, blue-tinted bedroom, Google didn’t seem to know Jackie. Choosing a different path, I punched in “John Castagna Mafia.” That’s the name and employer of Jackie’s father. The first hit was a link to a recent article posted by the Hartford Courant on August 31. The headline read: “Mobster’s Death Disrupts Renewed Probe into Boxer’s Murder.”

What the fuck? What are the odds this is Jackie’s father? If it is, he’s dead? And what boxer?

According to the Courant:

Detectives working a stubborn Hartford mob murder lost one of their best leads two weeks ago when John F. "Sonny" Castagna, one of the city's most notorious gangsters, died in Florida, where he was living under a phony name … a mile from Sarasota Bay.

An FBI informant once called Castagna "one of the most treacherous persons in the city of Hartford." He was a swindler and a killer. When the Mafia was a force in Hartford, Castagna and his son, John "Jackie" Johns, were two of its most visible faces, fixtures in the backroom gambling clubs that the mob ran along Franklin Avenue.

The two disappeared into the federal witness protection program in the 1990s, saving themselves by becoming government witnesses in a racketeering case that annihilated their associates in the Patriarca crime family, then New England's dominant criminal outfit. But even after having joined the government team, their names resurfaced as investigators took a fresh look at the extraordinary murder of a scrappy Hartford boxer named Eric Miller.

Last I’d heard, Jackie's father was indeed living a quiet life in the Sarasota-Bradenton area of Florida. He would’ve been about that age, too. The clincher, however, was Jackie’s last name. “Johns” is an odd surname for an Italian. Odder still, given I knew Jackie’s to be Messina. Johns was a name I knew, though, and it airdropped me smack into March of 1998. Oh yeah, this was my Jackie.

Still, the witness protection program? And who is Eric Miller? I knew Jackie sometimes strayed off the righteous path, but far enough for murder? And what’s this about Hartford? The deeper I dug, the clearer it became I hadn’t known Jackie like I thought I did. I’d come to pride myself on reads at the poker table, but I missed—I missed big time—on Jackie.

Fall 1996: Steve’s Got a Guy

"Hey dude, what's up?"

It was Julie calling from Sam's Steakhouse. A 24-year-old, tomboyish blonde, she was almost four years my senior. We’d become fast friends after meeting at the mid-scale, suburban restaurant where we both worked. Tackling my junior year at Saint Louis University, I was off that night and buried in homework. I was majoring in International Business, minoring in Spanish and quickly losing interest in both.

Julie, two others and I had just returned from Phoenix. An old friend of Julie’s was living there and invited her out for the Rams-Cardinals game and a long weekend. Julie agreed and, true to her tomboy rep, invited three guys to tag along. At least in this guy’s view, M.I.S. and accounting were no match for football and a desert adventure.

Now, the potency of a football-alcohol-testosterone blend is no secret. Mix in 1500 miles from home and you’ve got one powerful concoction. Its principal side effects include dialing, sweating, and, in cases involving unfortunate final scores, prolonged remorse.

Let the dialing begin. We bet anywhere from $50 to $200 on who-could-remember how many games. We placed our bets with Steve, then the manager at Sam’s. Why Steve? Because he “had a guy,” why else? For three days, we blasted Steve with a redial blitz from hell.

And all we did was win. We ran hotter than a Caddyshack priest in the pouring rain. But instead of draining putts at a storm-ridden Bushwood, we picked winners under the blazing sun. We simply couldn’t lose.

"So,” Julie said. “Steve’s guy’s up here. You know, that’s been taking our bets. He says he only owes us like $1100.”

"Oh, come on,” I said. “You’re joking, right?”

“No, that’s what he said. He’s got us down at $11—"

“Goddammit. I knew we’d get fucked on this somehow. I fucking knew we’d get fucked. $1100? Seriously?”

“Yeah. $1100. Ste—"

“I mean, I don’t even get it. It’s not even fucking close. Like, how’s he come up with $1100? You see what I'm say—fuck it. Never mind. I’m coming up there.”

"No, no, no,” Julie said. “Steve just messed up the bets or something. This Jackie’s a really cool guy. I’ve been talk—"

"A cool g—Jesus Christ, Julie. What the f—I’m on my way.”

Oh, I'll bet he’s a cool guy. Really cool. And my whole stack says we’re getting fucked.

So, I hopped in the car and headed for Sam’s. I’d compiled a tidy list a few days prior and aimed to set things straight. After reviewing the scraps of paper noting our plays, I figured we were collectively owed $1600.

Out-of-town, sports-loving kids who’ve been over-served and like to gamble? Talk about dead money. Sometimes, even dead money gets lucky.

By the way, I hadn’t actually known we’d get screwed. However, I’d been making bets since before my voice changed and knew that picking a point-spread winner is only half the battle. You must collect, too. Let’s just say I’m a pessimist.

“Hey, what’s up?” Steve said.

Steve was waiting just inside Sam’s main entrance. A giant man with thinning hair, Steve was 27 but could’ve passed for 40. As usual, he was draped in a flashy, ill-fitting suit: electric-blue jacket, black shirt and a multi-colored tie that reminded me of vomit.

“Chris,” Steve said. “This is Jackie.”

Will you look at this fucking guy, I thought?

Steve’s “guy” looked like he’d been pulled, still in wardrobe, from the set of a gangster movie: slicked back, short, dark hair, with a tinge of gray; button-up short sleeved shirt, perfectly pressed black pants; and, of course, gold aplenty hanging around his neck. At about 5’9” and maybe 210 pounds, he looked like a pit bull slung in collars from Mr. T’s canine collection. Simply, he could’ve been the poster boy for a “Don’t fuck with me” ad campaign.

So, we had in one corner: a self-assured tough guy fresh from the Goodfellas set. In the opposite corner: a 160-pound, 20-year-old college kid clutching a worthless piece of paper. Once pleasantries were exchanged, the sparring over money went down as you might’ve expected—not well for me. Steve and Jackie both laid the blame on Steve. Jackie even broke into semi-hysterics, hard-selling his annoyance at Steve’s blunder—all delivered in a thick, Brooklyn-sounding accent.

After choosing several games from my list and noting amounts owed, they advised said games as “the ones Steve forgot to call in.” They made it clear, albeit nicely, that $1100 was the amount due; or, at least, the amount I needed to accept.

The fight was over. No climax, no contest. It simply ended. The skinny kid armed with the list never stood a chance. Never mind that the list told the truth.

It struck me as plausible enough, I guess. Steve was hardly a mental gymnast, plus I had no reason to think he’d lie to me. Jackie's persona aroused my suspicion, sure. But how do you know? And what the fuck could I do about it, anyway? So, scammed or not, I had my share of $1100. Life goes on.

I soldiered through the fall semester and resented it more by the hour. I loved college—the challenges it offered, the new information and theories it presented—until classes towards a business degree began in earnest. That’s when I started to shut down.

Sure, I could've changed course. But in which direction? I hadn't the faintest clue what I wanted to do. I never did. I must've been the only 10-year-old boy that couldn't answer, "What do you want to be when you grow up?" Not even usual suspects like firefighter or center fielder appealed to me. Anyway, I was already leaning toward a temporary leave when Steve approached me one night at the restaurant.

“What’s your schedule look like when school starts back up?”

Jackie needed someone to help with his vending route. It was the only nudge I needed.

We’d become a bit more familiar over that fall. The Yankees rallied to another World Series title and Jackie, a proud New Yorker, sweated every pitch. He’d been coming into Sam’s to sip cocktails and curse at the games on the bar television.

During those cool autumn nights, we stumbled onto some common ground: a shared love of baseball, horse racing, and, of course, point spreads and money lines. We hadn’t become friends exactly, but we weren’t strangers, either. Given my apathy towards school, it seemed like a good fit. Toss in Jackie’s mysterious, and perhaps dangerous, past, and I couldn’t say no.

I was to be paid the tidy sum of seven dollars per hour, in cash. Between days with Jackie and five or six nights a week at Sam’s, I figured I could at least put some change in my pocket. School could wait. Maybe humping Doritos’ boxes will help me divine a career, I thought.


DAYS

January 1997: Soda, Snacks and How Jesus Got Whacked

In route to the vending office that first day, my mind swirled with ... I don't know what. It wasn't nerves, exactly. Excited couldn't describe it, either. Uneasy? Close enough.

Courtesy of Steve, slivers of Jackie's history had come to light: "Jackie did a short stretch in prison back East ... He beat a man to death with a baseball bat ... Jackie was told to leave New York.”

Or had they? Steve told a vague and splintered backstory. The more he spewed, the less credible he sounded. Sealing each vignette with a knowing smirk, Steve seemed tickled to be privy to information I wasn’t. Almost too tickled.

One bit I got straight from Jackie revealed how he and Steve met. Holed up in Sam's dark lounge late one evening, only a few customers remained. With the boozy piano player keying out the soundtrack, Jackie recalled their chance meeting outside of a nightclub. Steve had been jumped and Jackie sprang into action to save the day:

"I'm on the one guy's back, chokin’ him out, right? And his buddy’s trying to yank me off. So, you know what I did? I bit the motherfucker’s ear off. Well, half off. You know, it’s hanging there, bleeding like a cocksu—fuckin’ blood just shooting out. That was the end of him. So, I turn around to get the other guy, right? I spin this motherfucker 'round fast—I mean, fast—and get him in a fucking headlock. Would you like to guess what I did then, sir? [no, I did not] Wanna know what I did? I'll tell you exactly what the fuck I did—I took his fuckin' wallet. No shit. Swear to God. Anyway, the cops finally show up and break it all up. Whole time, this big fuckin' mamaluke [nodding his head in Steve's direction] is standing there in shock. He's just in shock, Chris. With his fuckin' fruity pink Polo sweater tied around his neck. This fuckin' guy.”

So, violence rattled in my skull as I neared Messina Vending. Situated in a sprawling office park, I managed to locate the address 15 minutes early.

Knowing Jackie drove a white minivan (for vending purposes only; otherwise, he tooled around in one of a rotating cast of DEALER plated Cadillacs), I soon realized I’d beaten him there. Despite being clear and sunny, it was far too cold to be standing outside. I waited in my car, listening to music.

The van rumbled up the drive at about 9:40 and parked. Jackie hopped out. Dressed in black track pants, sweatshirt and a black jacket, it was odd to see him in anything but cabaret clothes. I met him at the door.

"What's up, man? Sorry I'm late. Got tied up with this cocksucker. Fuckin’ guy just …”

He stopped talking and I didn't ask.

We stepped inside the cramped office. There was a medium-sized metal desk, loose papers and documents strewn about; a few trinkets marked "Italy" and "Little Italy.” Behind the desk sat a bulky, metal change counter and a generic New York Yankees poster stuck to the wall.

Jackie removed his jacket and got comfortable behind the desk. I took note of his “Property of Syracuse Lacrosse” sweatshirt.

"You a big Jim Brown fan?" I asked.

"What? Oh. What the fuck you know about Jim Brown?"

"A little bit,” I said. “I know he played lacrosse at Syracuse.”

"How the fuck you know that?”

I shrugged.

“Not many kids your age would know that, you know?"

I did know. Showing I know something I’d seem unlikely to know, given my age, is a favorite trick of mine. It works best on people at least 15 years older. It disarms them and prompts a measure of respect. “Well now, this guy knows something.” All the better for having your future arguments heard.

Jackie handed me a shabby piece of notebook paper listing locations of his vending machines in hotels, medical buildings, apartment complexes and Wal-Mart break rooms. Under each location was a list of the snack and soda varieties required. He told me to take the list to the back room and start filling cardboard boxes. I bounded to the backroom, my vending adventure underway.

Once I had the van loaded up, we rolled out of the office park—Jackie behind the wheel, me riding shotgun, and the back overflowing with 12-packs of soda and boxes of snacks.

“So,” Jackie said. “What’s up with your girl?”

“Huh?”

“The Italian broad from Sam’s. C ‘mon, you know. The one with the big tits.”

“Oh, Angie?”

“That’s it. She’s cute. Steve says you follow her all over the restaurant.”

I laughed.

“She reminds me of a chick from back home. Italian, too. The ass on that broad. Marone.”

We’d grown more acquainted during the baseball playoffs, but this was different. Tooling around the city, it was just the two of us—no Steve, no drinkers at the bar, nobody to engage beyond each other. So, despite Steve having outed me as a puppy dog, such exchanges set me at ease.

We hit about four locations, a drive-thru for lunch, and five or so spots in the afternoon. We crisscrossed all over town, talking all the way. Only the first day and already I’d seen parts of the city I hadn’t known existed. We arrived back at the office around 4:30. Jackie ducked inside to run the coins through the counter while I unloaded the van.

“Gotta run, Jackie,” I said. “Gotta get to Sam’s.”

“Oh, right, okay. See you tomorrow. 9:30.”

Vending-wise, the first day proved typical. Jackie had mapped out the schedule based on a spot’s performance. For instance, the Wal-Mart stops rang like slot machines and needed filling two or three times a week. Others, such as the ancient Pepsi machine in an East St. Louis, Illinois, junkyard, called for service every couple of months.

Of course, filling the machines required inventory. Snack supplies were replenished with visits to Sam's Wholesale Club, while QuikTrip served as the primary soda source. With just a few days under my belt, I received a lesson in the dark art of soda procurement.

QuikTrip stored large quantities of soda outside, in the front of the building. We rolled onto QT’s lot, then Jackie backed into a spot near the end of the front row. He popped the back hatch.

"I'm gonna go in and pay. Start grabbin’ regular and Diet Coke, regular and Diet Pepsi, Dr. Pepper and Sprite. We'll worry about the others later."

"Okay,” I said. “How many of each?”

"Just load up. We’ll figure it out.”

What the hell does that mean?

I hopped out and followed orders. We hadn't yet stocked the van for the morning run, so there was room for plenty of 12-packs. I grabbed two at a time until I covered the bed, then stacked on several more to form a partial second layer. Jackie strutted out, took a glance and slammed the hatch.

Jackie gripped the receipt as we drove the mile or so back to vending HQ.

"Let's see what we got 'em for," Jackie said, shifting into park.

He popped the hatch then hustled to the back. After getting a count, Jackie checked the receipt.

"Nice,” he said. “Looks like we robbed 'em for about nine."

A neat little trick. Clearly, Jackie had advised the cashier of wishing to purchase X amount of each variety and knew full well they wouldn’t check the van.

Life moves like a bullet. In less than 60 days, I’d shot from philosophy and calculus to low-level larceny and Funyuns. My mother would’ve described the transition—upstanding college student to carbonated-beverage thief—with any number of colorful adjectives. You won’t find those words in a thesaurus. And not a single one is a synonym for “nice.”

But I was less concerned with defining the move. I was having too much fun. Daring, twice-a-week soda heists were just the beginning. Each day seemed to bring a new and unusual character onto the scene. And sometimes, they came in pairs.

Not two weeks on the job, we called on Harry and Darwin, the duo known as “The Jews.”

"We gotta stop and see The Jews,” Jackie said.

A mile or so from the vending office, we pulled into a strip mall and parked. Jackie hopped out, but I sat still in the front-passenger seat.

"Come on in. Never know with these two.”

Without knocking, Jackie turned the knob and we stepped inside. Smelling of stale cigarette smoke, the large office hadn’t enjoyed a makeover since Spinks jinxed Ali for the heavyweight crown. I was introduced first to Harry, who was seated behind his desk fussing with papers.

"Good to meet you,” Harry said. “Now, Chris, you look like a fine young man. Why on earth are you running around with this maniac?”

Everyone laughed.

With his nearly full head of tousled gray hair and pullover sweater, Harry could’ve been a college professor. Darwin, however, was cut from a greasier cloth. His little remaining hair was unwashed, and he fashioned a gold chain, pinky ring and tinted glasses. Darwin lit a cigarette and offered a hello. I’d have guessed both men to be in their late-60s.

I flopped onto the couch and noticed several candy machines scattered about. All sat empty and in varying stages of disrepair. The three men carried on for a spell, discussing mutual business, but before long shop talk turned to bloodlines. Darwin shot first.

“Hey, Chris, now do me a favor. Keep an eye on this fucking guinea loon, huh?”

The laughter faded, then Jackie fired back.

“O-hhh, fuck yeah. You know all about loons, you killing-Jesus Christ motherfucker. You know, not for nothing, but it takes some pretty fucking loony cocksuckers to whack Jesus.”

The laughter slowed and Jackie turned to me.

“Believe that, man? These are some sick fuckin’ guys, you know?"

Clearly, the PC army hadn’t conquered the St. Louis vending rackets. With the verbal warfare completed, Harry handed an envelope to Jackie.

“You ready?” Jackie asked me.

I popped up, and two minutes later we were back in traffic.

“Those two guys, man,” Jackie said. “Only two Jews I ever met with no money.”

I laughed.

“I ain’t kiddin’. That’s two broke motherfuckers right there. Worst part is, they’re not dumb guys. Well, Harry ain’t, at least. Fuckin’ Harry—get this shit. Harry had a stake in Bit-O-Honey candy bars. Now he’s broke?”

“No shit?” I said. “What about Darwin?”

“U-hhh-huh, now he’s a different story, sir. He must’ve been the one kid in the family that got no br—he’s got a brother. Herschel. Fucking guy owns all kinda shit. I don’t know what happened to Darwin.”

And the envelope? As usual, I didn't ask questions. Given our dynamics, I wasn’t comfortable asking any. I was 21, Jackie was pushing 40; I’m a product of the suburbs, he sprang from the Northeast mean streets. Mostly, though, I liked the gig and didn’t want to screw it up. And anyway, the envelope seemed to explain itself quite nicely. The fine print didn’t matter.

As the weeks rolled by, a somewhat clearer picture of Jackie came into focus. Throughout the natural course of conversation, Jackie offered glimpses into his past. He had an ex-wife and two young children, a boy and a girl, back home. He had indeed served a short stretch in prison for “trumped up government RICO bullshit, invented only to persecute Italian-Americans.”

Upon release in 1991, he’d relocated to St. Louis. Soon after arriving, he spent a rare stretch working in another’s employ, tending bar at Federko’s. The popular hangout was named for former St. Louis Blues’ star, Bernie Federko, and business was good. Renting a modest home, Jackie socked away his tips and charted his vending course.

Jackie’s launch into the world of soda and snacks was aided by a man he called the “Other Jew.” I never saw anyone who so commanded Jackie’s respect.

Returning from the day’s final run late one afternoon, we rounded the corner to the office—the Other Jew leaned against his white Porsche, waiting. He stood perhaps 5’9” and 20 pounds too much, with almost white hair and a goatee. I pegged him in his early-60s.

Upon spotting the overweight, Colonel Sanders lookalike, Jackie’s tone completely changed. Normally loud and boisterous, Jackie acted like a nervous teenager arriving home late to a clock-watching father. He told me to unload the van, and that he'd be in shortly to pay me. I hadn’t even been introduced. Usually, Jackie introduced me to everyone.

I'd seen enough to know the Other Jew was due a payment. After that, we regularly delivered an envelope to his ranch-style spread in an old-money section of town. I often wondered how the Italian ex-con from New York had made the acquaintance of the moneyed, St. Louis Jew.

Who was this guy? A conventional loan shark? Did the Other Jew have ties on the East Coast? Jackie didn’t stand up straight for anyone; nobody that I met, anyway. Jackie wrote the rules, and everyone fell in line. Not the mystery man, though. The only thing I’d bet is that if Jackie didn’t pay, someone above and beyond the Other Jew would have to be reckoned with. Whoever that was, Jackie took the necessary measures to avoid him.

But for all the personalities on display, Jewish and otherwise, Jackie’s was easily the most interesting. Not his history or his police record, but him. He somehow managed near-constant motion while keeping a cool exterior. He was brash and tough talking, but a nice guy. All walks of life responded well to him, from the Hostess delivery man to the lady working the hotel front desk. They were drawn to his accent, his style, his manner of being. These days, the cool kids would call it his "vibe."

And Jackie vibed with everyone. He made people laugh as easily as I start my car. He even triggered hilarity when doing so was the furthest thing from his mind. For instance, Jackie had a litany of what I’d call “linguistic quirks” he’d reveal when you least expected it. The groggy Monday morning after the 1997 Masters Tournament is a good example. The day before, a 21-year-old had demolished the field in record fashion.

We’d stocked up with supplies and were already on the road.

“You watch the golf?” Jackie asked.

I had.

“Yeah, I ain’t really into golf, but it was all over the TV. I guess this Spider Woods is a real motherfucker, huh?”

On another occasion, Jackie and I were talking movies with a man at a vending stop. After searching the hidden corners of his mind, Jackie, at last, identified his third favorite actor: “Harvey Karteal.”

As with “Spider Woods,” I burst into a fit of laughter. When advised of his error, Jackie replied, “Whatever. You know what I mean, you cocksucker.”

I had no qualms telling Jackie he was mistaken. He'd spit a political rant and I’d tell him he was full of shit. He might yap about a Yankee, and I'd mention two or five players that were better. Sure, Jackie likely shot back, “Get the fuck outta here, you skinny cocksucker.” Still, he often followed that up with a sincere inquiry into my thoughts.

Maybe this helped explain how two guys so mismatched got along so well. While I didn't nose into Jackie's personal affairs, I was quick to give opinions I stood behind. He was used to dominating conversations by the sheer force of his personality. If bold enough to counter, perhaps I had something worthwhile to say. That’s not to say I was always right, of course. But it was rare for Jackie to be told he was wrong. My temerity afforded me some measure of immediate respect.

July 1997: Way Back Wednesday

It started like any Wednesday. We’d prepped for the morning stops and hit the streets. Wednesdays were cause for minor celebration because a local radio station ran a program they called “Way Back Wednesday.” The all-day playlist featured Jackie’s beloved soul music from days gone by: Marvin Gaye, The Spinners, Teddy Pendergrass, among many more.

Jackie’s enthusiasm for the show never slumped. Whatever time he happened to tune in, he’d announce that it was, in fact, Wednesday. That Wednesday was no different.

“O-hhh, it’s ‘Way Back Wednesday.’ Why didn’t you tell me?”

He tapped the radio button, then slugged me on the shoulder and smiled.

“This is from back in the day, you prick.”

Just across the Missouri River, in St. Charles, we arrived at the Fairfield Inn.

In relatively low-tech 1997, Jackie was my only acquaintance with a cell phone. As we stocked the machines in the first-floor hallway, the phone rang, and Jackie answered. He walked away, leaving me to finish up.

When I reached the parking lot, I found Jackie pacing with the phone stuck to his ear. He tossed me the keys.

"You drive.”

His tone was oddly serious.

As we approached the highway, Jackie turned down the radio and changed the plan.

"Go east, Chris. Head back to the office."

Jackie jabbered into the phone.

"What the fuck, man? A-hhh, c ‘mon. You guys’re killing me.”

Probably Harry and Darwin, I thought.

Speeding down Highway 70, Jackie shut off the phone. He rubbed his eyes and groaned but didn’t elaborate.

Jackie wasn’t just agitated—he was angry. As we flew down the highway, I waited for him to say something. The silence in the van made his anger all the more unsettling. My mind raced.

Okay, we’re going back to the office. There can’t be too much trouble there, right? Or maybe he plans to drop me at the office, so he can take care of this?

I veered off the highway and another shift in plans broke the quiet.

“Go left at the light. Pull into Harry and Darwin’s.”

Really? Okay, maybe it’s not Harry and Darwin. If a heated confrontation with The Jews is coming, Jackie wouldn’t have me tag along. I guess we’ll hit the office after a quick visit with these guys.

I pulled onto the lot and hadn’t yet parked when Jackie popped the passenger door.

"Wait here. Gotta talk to these fuckin' guys."

Oh, fuck.

I’d never waited in the car at Harry and Darwin’s office. Not once.

In the brutal St. Louis heat, I opened the windows to get some air moving. I turned the ignition off, then back on to listen to music. “Cowboys to Girls,” one of Jackie’s favorites, played on the radio. All I could think about were bloody ears and baseball bats.

Maybe this is normal, I thought. Maybe when Jackie's tough talk doesn't work, a surprise visit nudges them to cut loose with the cash? No way Jackie starts swinging on the old guys, right?

Who are these fucking people? Where am I and how the fuck did I get here?

I’d shrugged off the shelter of campus life and wandered into a shitty Tarantino knock-off. I was anxious and confused—and exhilarated.

A few minutes after Jackie hustled inside, I heard a loud thud. It sounded like something—or someone—smashed into the front door. Two seconds later, I spotted the curtains swishing about.

I shut off the radio and heard shouting. It was Jackie’s voice, but I couldn’t make out the words.

Fuck me, this might be getting ugly. But what am I supposed to do about it? Jesus fucking Christ, I hope Harry and Darwin aren’t getting savaged, but there’s no shot I’m going in there.

And then it stopped. No more yelling. Nothing.

A couple minutes later, the front door swung open, and Jackie rushed out. He slammed the office door and crashed into the van.

"Fuckin' guys. How many times?”

I shifted into reverse and, finally, asked a question.

"What the fuck was that about?"

"A-hhh, these fuckin' guys. Sometimes you gotta play tough guy to get the fuckin' money. Go left at the light up here, gotta stop by the office.”

"Nobody got hurt, right?"

"Nah, no, no. Sometimes you just gotta throw some shit around, you know? Throw a couple chairs, flip the fuckin’ couch. Fughetaboutit. They hand it over."

Then Jackie laughed.

"Lemme tell you something, Chris. Listen to me now. You get older, get into business, whatever, you gotta remember: Jews will always get the best of you. It's just gonna happen. Trick is to make sure it ain’t too much, and—and—you gotta make 'em think they're getting it even better than they actually are. Understand?”

“Okay,” I said.

“I'm serious, Chris. I been around. I've had to deal with all kinda people. And Jews are the sharpest motherfuckers around. Even Darwin."

I was used to business lectures in a classroom. Jackie gave them in a minivan.

I believed him when he said nobody got hurt, but I did revisit Steve’s tales of Jackie’s baseball-bat past. Honestly, though, I didn’t know what to think. Only one thing was certain—I sure as hell didn’t miss Saint Louis University.

Jammed Up

If history, philosophy and political lectures had been the extent of it, I would’ve never left college. Christ, I might still be there. But all too soon, it became accounting, group projects and emails.

“I’ll email you the time we’re gonna start the project. Should we meet for coffee first?”

Jesus Christ, I hated it. I hated the emails, the projects, the coffee and the kids that loved them.

But still, what was I doing now? What sort of operation had I signed up for? I didn’t like stealing soda or driving Jackie to couch-tossing appointments. At least I don’t think I did. Hell, I don’t know.

All I know is we were two guys out bouncing around and we didn’t answer to anyone. Sure, Jackie was the boss, but he never played that card. It didn’t even feel like work. I saw the job as a paid adventure; or, perhaps more to the point, being paid to watch Jackie’s adventures. Almost like watching a documentary on this crazy Jackie fellow. But instead of TV, I viewed everything in person, via ride-along.

It's my nature to observe and analyze, and Jackie presented a fascinating case. I marveled at how he navigated through a workday. It was especially fun when a “jam” would arise. For Jackie, all forms of the word were in play.

“This guy’s gonna get us all jammed up … This thing’s gonna be jammin’ us all day now … Look at this fuckin’ jam, sir.”

Early one evening, I thought we’d filled our last machine when Jackie suggested one final stop.

"Oh, you know what? We gotta do one more.”

"What?” I asked. “Where?”

He looked at me and smiled.

"Junkyard. East St. Louis."

"Fuck me,” I said. “Now?”

"Yeah, yeah, we'll knock it out quick. We got enough soda back there. We'll just knock it out. Boom-boom. We’ll knock it right the fuck out.”

We crossed the Mississippi River and arrived at what could’ve been the set of a horror movie: a few acres of partially intact cars and car parts, a rickety shack for an office and a Pepsi machine dating back to the Carter administration. We stocked the machine and were back on the road in minutes.

Sailing down Martin Luther King Drive, the sun was setting on the annual contender for per capita murder champ. Then, almost as if on cue—boom. Flat tire.

A blown tire smack dab in the middle of that hellscape? I considered calling my mom to discuss color options for the casket. Jackie, however, had a different reaction. His blood boiled over the indignity of it all.

“Motherfuckin’ cunt. What the fuck, man? How fuckin’ miserable are we? Miserable fuckin’ cunt cocksucker. Just fucked us right in the ass.”

But the next-level tirade exorcised the trouble. His mouth played the role of conductor, releasing the electric anger within.

And then? Jackie simply commenced de-jamming: Ain’t nobody gonna fuck with us. Let’s change this fucker and go eat.

It was the attitude, not the tire change, that impressed me.

And speaking of jams, Hostess snack cake deliveries served up about one a week. A jovial, middle-aged black guy named Mitch was our delivery man. Whether problems arose from Jackie’s last-minute order changes or miscommunication between the warehouse and Mitch, I have no idea. But, inevitably, there was a jam.

“Where’s my man, Mitch? Fuckin’ good old Mitch. He should’ve been here by now, no?

I’d shrug.

“You know, we’re gonna need more Twinkies for the Wal-Marts. Where the fuck is this guy? Guess I better call him, huh?”

Like I was supposed to know?

I swear I never knew if we were on Mitch’s route that day, or if Jackie just thought we were. When Jackie reached Mitch by phone, he’d swing by in short order.

“There he is—Mitch. How’s the family, buddy?”

Mitch adored Jackie.

“I got you, Jackie, I got you. What kinda cake you need, brother?”

Other times, though, Jackie’s last-minute calls to Mitch went unanswered.

“What the fuck? This guy don’t answer his phone now? Why's—You know what? Fuck it. Finish loading up the truck, Chris. We gotta go find this fuckin’ guy.”

And off we’d go, trawling the neighborhood. We found him damn near every time, too.

“Is that a Hostess truck over there? Yep, that’s him.”

Did Jackie know Mitch’s route? Were we simply hitting likely spots? I have no idea.

We’d pull up alongside Mitch’s truck.

“M-iiitch.”

“Hey, Jackie. What you need, my man?”

Mitch was always happy to help. Vending newbie or not, I assumed it wasn’t industry standard to search for delivery trucks. Not for anyone but Jackie, of course.

And not even a traffic jam slowed Jackie down—if we found ourselves in the left lane. Darting his eyes in every direction, Jackie looked for cops. All clear? Okay.

“Watch this,” Jackie said.

After a rattling, hard left over the median, we moved freely in the other direction and Jackie laughed.

“How’d you like that move, sir?” Jackie said, slapping me on the arm. “Nice, right?”

Jackie’s can-do nature more than offset whatever he might’ve lacked in efficiency. He met everything head-on, certain he'd find a way. Whatever was broke, Jackie had a fix. If not, he'd invent one on the spot. It's an admirable quality and I never tired of seeing it in action.

The knock-it-out approach served Jackie well. While that usually meant conquering jams, it went for tackling new ventures, too. He inched further into the used car business throughout 1997. He’d been buying cars, perhaps a few per month, at area auto auctions.

We’d move the cars to Jackie’s mechanic near downtown. That’s if the cars ran. Some of the newly acquired heaps needed a tow. Once Rob, the mechanic, coaxed a car into anything near operational, it was put up for sale in front of Rob’s shop.

As 1997 ended, Jackie had been buying more cars in attempts to leave the vending business behind. He slowly sold off vending machines, as well as the rights to locations. Jackie secured a spot in the less-than-affluent township of Vinita Park as headquarters for his flourishing car business. It conveniently sat about five miles from the vending office.

The transition resulted in less work for me. So, as the calendar turned to 1998, I wasn’t working for Jackie on anything near a full-time basis. He largely handled what vending remained as he built up auto inventory. Still floating through my early 20s with no life plan whatsoever, I picked up more hours at the restaurant.

When Jackie hit a busy stretch, he’d call on me. I might work three days one week, then not at all for a couple weeks. When I handled vending, it was solo and sort of boring. The first day I handled vending alone, though, is one that still sticks with me.

I started the day by meeting Jackie at the car lot to grab the keys to the van. He told me what machines needed servicing and gave me his cell, should any jams arise. Sometime early afternoon, Jackie called to remind me to leave the soda at the office. It’d freeze in the van.

I dropped the van and the soda at the office around 3:30, then drove the day’s collections to the car lot. I brought the zippered bank bags into the office and dropped them on Jackie’s desk.

“You have any problems?” Jackie asked.

“Nah, everything’s good. That’s the hotel, The Pavilion, the laundromat and the Wal-Marts,” I said, pointing to the bags.

“Okay, good. How much you rob?”

“Huh?”

“It’s okay you know. Just so you don’t rob so much that I notice. Know what I mean?”

“Yeah, I hear you, but I didn’t steal any money. What the fuck?”

“Okay, okay. Take it easy. Was just kiddin’ you.”

I hadn’t stolen any money and didn’t appreciate the insinuation—the assumption—that I had.

He said it jokingly because he feared looking foolish. Once met with honest surprise, he tried to dismiss it with the kidding excuse.

I didn't need a psych degree for this one. It offered a clear window into Jackie's mind. Always hunting angles, he tried to get the best of every person and situation. Naturally, he figured everyone else was doing the same. Well, I wasn't.

He was right, by the way. I could've easily skimmed four bucks from a machine that had $51, or seven from one with $76. Each spot yielded pretty steady figures, but not so steady he'd notice. On future solo runs, perhaps I took Jackie’s advice. I simply can’t remember.

Thursday, March 12, 1998: Jammed Up [For Real This Time]

A call from my dad woke me around 9 AM.

“You might wanna look at a paper," he said. "Your buddy’s on the front page.”

“Who?”

“Jackie. Him and his dad and Steve got arrested at the casino the other night.”

“What?”

“Yeah. Says they got nailed capping blackjack bets.”

Bet capping is when a player increases his bet after he’s made a winning hand.

“You gotta be fucking kidding me?” I said.

I couldn’t believe Jackie could be so stupid. Cheating? No, that didn’t surprise me. But in a casino? They’re wired wall-to-wall with cameras, every move watched and recorded.

“Nope,” my dad said. “That’s what the paper said, anyway. Pretty fucking dumb. You heard from Jackie lately?”

I hadn’t. It’d been a couple weeks since my services had been needed.

“Maybe give him a call, I don’t know. What a fucking deal. And poor Steve. My God. At least his picture’s below the fold.”

My mom and dad occasionally dined at Sam’s, and Steve had always been good to them.

“Jesus Christ,” I said. “Fucking Steve on the front page?”

“I know. I about shit when I saw it. Oh, and it talks about Jackie and his dad having mob ties.”

“Mob ties?”

I got dressed and stepped into the cold, late-winter day to grab the St. Louis Post-Dispatch. Sure enough, Jackie topped the front page.

Two of the three men arrested Monday night for trying to cheat the Players Island Casino out of more than $11,000 once had ties to organized crime, authorities said Wednesday.

All three men’s mugshots ran along the left margin, top-to-bottom: Jackie and his dad above the fold. Under Jackie’s father’s picture was the name “Castagna.” The name under Jackie’s picture read “Johns.”

What the fuck?

I left that thought for the moment and sped through the article. It mentioned Castagna’s ties to crime syndicates on the east coast. He’d been convicted of, among other things, first-degree manslaughter.

Wow.

Jackie’s only conviction was on RICO—Racketeering Influence and Corrupt Organizations—charges, in 1990. Jackie’s connections to the crime families were through his father, authorities said.

The article indicated they’d been under surveillance over several visits to the casino to allow authorities time to gather more information. According to the paper, Jackie’s father was a straight-up gangster. I knew Jackie took the odd weekend trip to visit his dad, but otherwise hadn’t mentioned him much. I’d never met him.

As for Jackie, he told me about the RICO conviction. That checked out. Two items didn’t.

Authorities believe that the men now work as independent ‘wiseguys,’ con men who travel the country and make their living through illegal gambling, cheating and theft.

I couldn’t speak for Jackie’s dad, but I didn’t think it suitably described Jackie.

Illegal gambling? Sure, but on the smallest level. He took only a few calls related to sports betting. Cheating? This instance, of course, but anything beyond that would’ve been news to me. What about theft? Other than our low-level soda lifts, I couldn’t imagine what else he might’ve been stealing. And Jackie didn’t travel the country to do any of it.

It smacked of typical police bullshit, hyping their bust. Hadn’t the truth been juicy enough?

Second, and more importantly, the name Johns mystified me. I worked for Jackie Messina, and that was plainly his picture on the front page.

What’s going on here? Johns? It’s not even an Italian name. And why does he have a different name than his father? Who the fuck is Messina?

The only thing I could figure was that Johns was an alias. They’d gotten busted and Jackie handed over a phony ID. It sure seemed like something he’d do.

I called a few friends to break the news, then jumped in the shower around 3. I had to get to work.

I’d had Sam’s as a fall back when work with Jackie turned sporadic. Only thanks to Steve did I still have that. The owner overheard me calling in bets to Jackie on the house phone and fired me. They weren’t my bets, but those of friends and coworkers. Jackie had been tossing me a small piece of whatever action I sent his way. Thankfully, Steve pleaded my case and got the dismissal overturned.

Sam’s didn’t open for dinner until 5, so except for a few employees prepping for the dinner rush, the place was empty. Greg, the head waiter, greeted me right away.

“You see the paper?” Greg asked.

“Yeah. What the fuck, man? Anybody heard outta Steve?”

“Yeah,” Greg said. “I didn’t talk to him, but he called up here. I think they’re all still in jail.”

“Unreal,” I said. “Just unreal. What were they thinking?”

A few minutes before opening, I was looking over the reservation book and the phone rang. Greg hollered from across the dining room.

“Dude, you got a phone call.”

“Me?”

“Yep. It’s your boy—from jail.”

“Jackie?”

Greg nodded his head yes and howled with laughter.

Really? He’s calling me? I can’t believe this guy’s calling me from jail. And at work?

“Hello?”

“Chr-iiis.”

“Hey, Jackie, you alright?”

“I’m not alright, sir. I’m in fuckin’ jail.”

“Yeah,” I said. “I heard ab—”

“I am really fuckin’ jammed, man.”

His voice was different. He sounded tired.

“You gotta help me, Chris. I been in here since Monday night. Can you please get out to the vending office tomorrow? Maybe catch me up a little? Whatever you can do, man.”

“Okay. No problem. So, when the fuck you getting out?”

“Dunno. Got my lawyer working on it right now.”

And that’s the last thing I remember from the conversation—but the call shook me.

If I went to the vending office, would I be watched? Was I being watched at Sam’s? After all, I had a direct link to two of the three culprits. My non-criminal brain did backflips in my head.

At the same time, I liked that Jackie trusted me enough to call. Not that we were involved in any deep criminal conspiracies together, but he obviously depended on me. And I’d be lying if I said I didn’t get a kick out of the would-be gangster calling me in a tight spot.

But I didn’t go to the office the following day. Did I call Jackie back, or anyone who might be in contact with him, to say I wasn’t going? I can’t remember.

I suppose the criminal histories weren’t a total shock. As far as Jackie, the paper didn't reveal anything I hadn't already heard straight from his mouth.

Authorities created RICO as a catch-all to help fight organized crime, so it’d clearly suggested ties to the Italian Mafia. All kinds of people, though, have all manner of ties; many of them law-abiding citizens. Jackie couldn’t be called law abiding, but connections alone shouldn't stamp someone as a menace to society.

Then again, Jackie's link to East Coast crime syndicates hit close to home. A father convicted of a slew of crimes, including manslaughter? Along with Jackie’s RICO conviction, the news presented a pretty compelling tie.

A couple weeks went by. There had been no sign of Steve nor any word from Jackie when I got another phone call at the restaurant.

“Chr-iiis.”

Every phone greeting was the same. That long, drawn-out rendition of my name.

“What’s new, man?” Jackie asked. “Where you been?”

“Not much. Same old shit. Been up here most nights.”

“Yeah, I hear you. Hey, you wanna go out bouncin’ Saturday?”

“Uh, well, shit. I’ll be up here ‘til 10:30, at least.”

“Oh, yeah. Right, right. Well, any shot you could get off? See if you can and we’ll go eat. You wanna?”

With two weeks gone by, my wariness about Jackie had somehow vanished and I agreed. Aside from him being out of jail, nothing had changed. I’d been out with him a few times and always had fun. Not to mention, I’d have no better shot to get the straight story. So why the hell not, right?

Jackie asked me to pick him up at home, about 7:30. He lived at the high-rise Pierre Chouteau building in the high-rent Central West End section of town.

The West End is a colorful part of St. Louis. It boasts a mixed bag of ages and races and blends old money with new. Home to many a hip restaurant and bar, it borders some of the tougher parts of town. Out for a little fresh air, you might pass a wealthy widow walking the dog, then brush against a beggar 20 steps later.

I’d never been inside Jackie’s home, so the assist from a uniformed doorman came as a surprise.

As I strolled through the immaculate lobby, a woman's voice startled me.

“Can I help you, sir?”

“Oh,” I said, spotting the stylish older woman seated behind a desk. “Yes. I’m here to see Jackie Messina?”

“Yes, of course. Your name?”

“Chris.”

“Sure, Chris. Jackie’s expecting you. You can go right up.”

I’d never known anyone with lobby personnel at their home. Pretty swanky. I hopped on the elevator, bound for the 14th floor.

How the fuck does he afford this place? Maybe he’s moving more cars than I thought. No shot vending paid for all this.

The door to the apartment was cracked open. I walked in and found Jackie slipping into his suit jacket.

“There he is,” Jackie said. “Just about ready.”

I scanned the spacious apartment. I wouldn’t call it opulent, but it was clean, well-decorated and obviously costly. I’d only been inside for a minute when Jackie suggested we go.

Driving to the restaurant, you’d never have guessed we hadn’t seen each other in a month. Among other things, we talked about the new baseball season.

Jackie picked a trendy Italian joint for dinner. We would’ve been quite a study in contrast to anyone paying attention: he in customary suit and tie, and me sporting jeans and a 1970s shirt from my favorite vintage clothing store, Rag-O-Rama.

Once we were seated, Jackie ordered a glass of red wine and I grabbed a beer.

“So what the hell happened to you that day?” Jackie asked.

“What day?”

“Whaddya mean, ‘what day?’ When I called you from jail to do the vending.”

“Oh. Well, fuck, man, I don’t know. It was all pretty crazy, you know? Steve not at Sam’s and then you calling me from jail? I don’t know.”

“Yeah," Jackie laughed. “Nuts, huh? I’m just fuckin’ with you, anyway. Don’t worry about it.”

Good.

“I mean,” I said. “I was kinda freaked out by the whole thing anyway, but then you calling me at Sam’s? I don’t know, man. I guess I just kept thinking, ‘These fucking cops might see this guy that’s with you during the day, and then Steve at night.' Maybe start asking questions, you know?”

Jackie laughed harder.

“I know, I know. I got you. I ain’t sweatin’ it. So vending got a couple days behind. Who gives a fuck? Listen to me, Chris. I ain’t never gonna drag you into some kinda shit where you get pinched, or questioned, or whatever.”

I nodded my head.

“Okay,” Jackie said. “So we rob some fuckin’ soda. Nobody’s getting busted on that.”

We both laughed and left it at that.

Jackie picked up our baseball talk from the car ride, and we enjoyed a delicious meal. Like every other time I’d eaten with Jackie, drive-thru or expensive dinner, he paid the tab.

From the restaurant, we drove a few miles to a jazz club. We’d been there before and, as usual, I was the youngest person by 10 years. It didn’t faze me. I liked the age and other differences that came with running in Jackie’s circles.

Anyway, I knew Jackie got loose when the vodka started to flow, so I sat tight. After the cocktail waitress delivered the third round, I let it fly.

“So, what the fuck with the casino, man? Nobody’s getting outta there without getting nailed.”

Jackie smiled a big smile. Almost as if to say, “I was wondering when this cocksucker would bring it up.”

“Yeah,” he said. “But, we thought we had a couple dealers.”

Huh? What difference does that make? Then your crew and the dealers all get busted.

“A dealer actually approached me, Chris, a couple weeks before. Turns out, I think the F.B.I. put ‘em up to it.”

“Are you fucking kidding me? Why?”

“Shit from back home. Those cocksuckers’ll never leave me alone. Miserable, miserable.”

“Isn’t that entrapment?” I asked.

“That’s what I said. What the fuck, no?”

Jackie turned to a lady he knew from the club. Once I had his attention, I chose to not press further. However, I was curious what punishment they were facing.

“So, what’s gonna happen? You gonna have to go to prison?”

“Nah. My lawyer’s good, sir. That Rosenblum’s a real motherfucker. Looks like me and my father’ll get like five years’ probation.”

I nodded my head.

I knew next to nothing about lawyers, but even I’d heard of Scott Rosenblum. He was recognized as the finest criminal defense attorney in St. Louis.

“What about Steve?” I asked.

“He’s gonna be fine. He ain’t got no record.”

“Well,” I said. “That’s good, at least.”

“Yeah,” Jackie said. “But I still feel bad. Never should’ve got him involved, you know?”

“He’s a big boy.”

“He’s a big boy alright,” Jackie laughed. “Seriously though, he’s fucked at Sam’s now. Those cocksuckers’ll never take him back.”

“He’s done for sure?”

“Yeah, looks like it.”

“Yeah,” I said. “That is brutal, man.”

“And Steve’s wife already hated me. Oh, wow, does she hate me. I’ll be off limits now for sure. She’s a miserable bitch. Miserable.”

I’d never met Steve’s wife, but knew she thought Jackie was bad news. Certainly, the casino fiasco confirmed her worst fears. I’d imagine Steve’s bedroom was cold as a playoff game at Lambeau Field for weeks after.

We cut the casino talk and enjoyed the music. Any further discussions were much less serious.

Eventually, we closed the club and called it a night. When I pulled up to Jackie’s building, he questioned me.

“So, whaddya think? You wanna still help out around the lot or whatever? When I need some help? You know, when you can.”

“Yeah, man, whenever. Just gimme a call. And thanks again for dinner.”

“You got it, sir. I’ll talk to you.”

As Jackie opened the front door, I hit the music—the Rolling Stones—and headed for home. I’d turned the volume low while we talked on the drive. Jackie didn’t like the Stones, anyway; except for “Wild Horses,” because, he’d told me, “It makes me think of Belmont Park.”

Keith ripped the opening riff of “Can’t You Hear Me Knocking” and I began to ponder.

Why wasn’t I included in the casino scheme? But what if I had been? Would I have gone along? No shot in hell I’m doing that shit. Casino security is the stone-cold nuts. Fucking Steve. You just know he’s going. It’s his own fault, but, still, this really sucks for Steve. He’s no criminal.

Maybe “Sympathy for the Devil” should’ve been the soundtrack that night.

Why Steve and not me? And why had Steve not been afforded the same “protection” from serious trouble? The funny thing is that Steve needed the protection much more than I did.

It’s amazing what one newspaper article did to my perspective. Before, I’d have laughed at Jackie’s suspicions about the F.B.I. setting him up or watching him at all. Even still, why might they be watching Jackie? He’d been convicted on RICO charges and done his time. What else was there?

But that was that. Low-rent Ocean's Eleven quickly faded to a memory. As Jackie figured, he avoided prison and was sentenced to five years of probation. No trial ever took place. Apparently, Rosenblum had been a motherfucker of the first order. Jackie's father skedaddled back to Florida, San Diego or whatever sunny locale he lived that year. It was tough to keep track.

As for me, I was badly adrift with no port in sight. I thought about going back to school less each day. In my mind, it'd become a business degree or nothing. Why? What else was there?

I have immense respect for researchers and scientists, but that wasn't for me. I never had any desire to be a teacher. What about journalism? Jesus Christ, that would've meant writing for the school paper. I figured nobody liked emails like the J-school crowd. So, it was business or bust. But every time I imagined a career in business, all I saw were traffic jams, neckties and eternal tedium.

I’d always enjoyed learning and blew a small fortune on books. For what? A career on Jeopardy!? If you don’t know the feeling of thirsting for knowledge and willing to work, but not a clue where to apply yourself, I hope you never do.

Jackie knew it was a sore subject, but even he asked about school.

"Thought you were going back to school? Not for nothin’ but seems like you’re takin’ a lot of fucking semesters off, you know?"

I didn’t know how to respond when people questioned my plans.

I kept my word to Jackie about helping, but the vending and car hustles offered less work all the time. It became far likelier I’d see him on a Saturday night than a Wednesday morning. Still, while days with Jackie might’ve been lacking in quantity, the quality was as high as ever. By quality, I mean a “what the fuck?” moment waited around every corner.

It was mid-afternoon on a Friday, and I’d been out all day tending to machines. I’d hoped to finish up by 4 to get a jump on rush hour traffic. Jackie was posted up at the lot and called the cell about 3.

“Yeah, you in a hurry to get done?"

“Oh, I don’t know,” I said. “Not going to Sam’s tonight, but I kinda wanted to beat some traffic. Why?”

“Whaddya think about hittin’ Slice of Manhattan and grabbin’ us a couple pies? I got a fuckin’ repair guy here and can’t leave.”

“Yeah, whatever. That’s cool.”

“Okay,” Jackie said. “Just pay for the pizza outta the money you picked up. You can stay on the clock ‘til we’re done eating. How’s that for a deal?”

I shot down 170 to the Clayton business district. Jackie had introduced me to the New York-style pizzeria in the early days and it’d become a favorite. Traffic or not, I couldn’t refuse that offer. I grabbed the pizzas and tore off for Vinita Park. I didn’t need to hear Jackie moaning about his precious pies showing up lukewarm.

I arrived at the lot and saw a commotion at the front of the building. A repairman was replacing the glass in the ancient, wood framed front door.

I squeezed through the small gathering and set the pizzas on Jackie’s desk.

“What the hell happened here?” I asked.

“Just a lil’ Vinita Park excitement, sir. You get soda?”

I'd left our drinks in the van. I turned around to fetch the soda and Jackie cut loose.

“Hey, cocksucker. What the fuck is this?”

I looked to find two pizzas whose toppings had slid completely off the dough. It was a horrifying sight, all the cheese clumped to one side of each box.

“You didn’t lay ‘em flat, did you?” Jackie asked.

“Fuck me. I’d say that’s fucking obvious.”

After fighting traffic and lugging boxes all day, I was in no mood for his shit.

“Fuck it,” Jackie said. “We can fix it. Just grab the soda.”

The repairman had finished and prepared to leave. I stepped outside and found Jeff surveying the scene.

Jeff worked as the lot handyman and lived on the property, in the garage. He didn’t live in an apartment above the garage, but inside the actual garage. The guy was a first ballot, Hall of Fame derelict. His jobs included auto mechanic, porter, landscaper, and who knows what else. Jackie compensated Jeff with a free garage and heroin.

Jackie didn’t sling drugs on any serious level. I don’t think he did, anyway. He found a junkie willing to do the lot’s dirty work, so Jackie gave him the keys to the garage and a daily fix. I didn’t ask or care where he got the dope.

“So, what the fuck happened with the front door?” I asked Jeff.

“Oh, you missed it, man. Dude that owns the property came lookin’ for rent two days early and Jackie got fuckin’ pissed.”

“Oh, yeah? How’d the glass get busted?”

“Well, first, Jackie told him he could fuck off. Told him he’d get his money in two days. But dude just wouldn’t stop, so Jackie put his ass through the door.”

“Jesus Christ,” I said. “That sounds about right.”

“What a mess. Dude had to have glass up his ass leaving here. Fuckin’ crazy, man.”

It might’ve struck Jeff as crazy, but not me. How could it? I’d been an ear witness when Jackie flipped the kosher couch. Then toss in revelations of mob ties and a father once locked up for manslaughter, and this was supposed to be a big shocker? Okay, so the violence ticked up a notch or two. Out of character, though? Hardly.

I was near certain by then I wasn’t in any physical danger, so fuck it. What did I care? Maybe it should’ve weighed on my conscience, or at least bothered me more, but it didn’t.

When I got back inside with the soda, Jackie's face was full of pizza.

“Look here, cocksucker. I fixed your fuck up. Looks like shit but tastes okay.”

Jackie laughed.

He’d wrapped his hands in napkins and smoothed out the toppings as best he could. I sat down and grabbed an ugly slice.

“See?” Jackie said. “Tastes fine, no?”

Like I said, Jackie had all kinds of fixes for all kinds of jams.

But “Vinita Park excitement” and its cousins visited less all the time. I missed the everyday aspect of working for Jackie. Not hauling boxes or moving machines but driving around and shooting the shit. I missed the feeling of “What on earth is gonna happen today?” I missed the characters, like Harry and Darwin.

Like the wise old Jew in the movies, Harry beamed an air of reserve. Like he’d seen it all. I got the impression he never made a key decision in haste. Darwin played the part of Harry’s impulsive partner that’d crossed to the wrong side of the tracks decades ago. Harry loved him anyway. Those two guys told enough stories to fill four lifetimes.

Of course, I wanted to know more about the Other Jew. Speeding in and out of scenes behind the wheel of his Porsche, the O.J. would have to remain a mystery.

And for his supporting role, let’s not forget Mitch. He was a helluva nice guy and worked his ass off. Mitch saved us from countless snack cake shortages.

But that was history. With a chunk of ’99 already gone, I’d finally hatched a plan—sort of. I’d somehow persuaded my miserly maternal grandfather into floating me a couple grand. Destination: Las Vegas.

Not to gamble, but to learn to deal blackjack. A friend of my brother had an 80-year-old grandmother in Vegas who’d somehow agreed to let an unknown young man live with her for two months, rent free. I hadn’t yet decided if I was going to look for work out there or deal at one of the gambling boats in the St. Louis area. The plan only looks half-baked because it was.

I still had some time before embarking on my journey when Jackie called. He needed a hand moving some recently acquired cars to his new lot. It sat in western St. Louis County, not far from the old vending office. Jackie had clawed up the used car hierarchy with a bigger lot in a better neighborhood.

I arrived at the lot to find the team of assembled drivers. Jackie was one, of course. Another was a cute, mid-20s gal named Kristy who’d helped us before. Jackie knew her from a cocktail lounge he sometimes hit up. The anchor, or so I thought, was a man in his mid-60s who it turned out had never had a driver’s license.

It was the first and only time I met Jackie’s father, John “Sonny” Castagna. Jackie had spoken little of him, so all I knew was what I’d read in the paper: a life of organized crime and a lengthy record that included first-degree manslaughter. He was in town visiting and along for the ride that day.

But something stopped us from moving the cars. Maybe the all-day downpour, I don’t know. Kristy finally left, leaving me alone with the delinquent, father-son duo.

Jackie’s dad loved baseball, too, so naturally it was the main topic of conversation. I relayed the tale of John Kruk and how his career had ended. Kruk singled early in a game, touched first base and walked off the field. The single bumped his career batting mark to a handsome .300 even. He never played again.

“But Chris,” Jackie said. “Is .300 really all that great? I mean, I get it’s a nice average. But lots of guys hit way higher, no?”

“Yeah, no doubt. But in the big scheme, just not many guys that have real careers do it, you know?”

“Right, right."

“And shit,” I said. “There’s some all-time great hitters that didn’t hit .300 lifetime.”

“Like who?” Jackie asked.

Instantly, I knew just the player to use. A Yankees legend.

“How ‘bout Mickey Mantle? He’s short-list, all-time great and didn’t do it.”

“Get the fuck—"

But Jackie got cut off by his dad.

“Get the fuck outta here—you motherfucker. Mickey Mantle didn’t hit .300. Who is this fuckin’ kid?”

I was plenty used to name calling and verbal sparring with Jackie. It’s how we talked to each other. But Jackie’s father? Steam shot from the top of his mostly silver head.

“Well,” I replied. “He hit .300 or better a bunch of times. Just not for his career.”

“You sure about that, Chris?” Jackie asked.

“You wanna get some money down that I’m wrong?”

I’d have never offered the bet to Jackie’s dad. I’ve long stuck to a strict policy of not pissing off manslaughter guys. I hoped I hadn’t already done it.

“I ain’t gonna bet you,” Jackie said. “But I say bullshit.”

Jackie moved for the beat-up Baseball Encyclopedia behind his desk.

“Okay,” I said. “I say .298.”

Jackie grabbed the book and thumbed to Mantle’s page.

“Cocksucker,” he said. “He’s right. It’s .298.”

“Well,” Jackie’s dad mumbled. “What the fuck? That's that."

You need a tire change on the East Side at sunset? Need a car, or some money collected? Perhaps you need your landlord pitched through a plate-glass window? Then call Jackie. But if it's a career batting average you're after, I’m your man.

Besides Kruk and the rain, I have one lasting memory of the day I met John Castagna. That he was not intelligent—at all. I learned long ago to distinguish between educated and intelligent. They often go together, sure. But not always.

I never did learn the extent of Jackie’s education. If he finished high school, it wasn’t by much. But Jackie proved the myriad manners of intelligence. Sure his grammar sucked, but he could talk on a ton of topics. We’d go for hours, discussing movies, history, music, gambling, politics and whatever else. And to anyone paying attention, Jackie had an obvious social intelligence, or street smarts.

Castagna piqued my interest only insofar as how uninteresting he was. Given his natural curiosity and broad spectrum of interests, Jackie was a conversational delight. His old man, however, radiated the polar opposite. Was it simply a matter of old-school rules—shut the fuck up, motherfucker—cloaked in a costume of stupidity? It's important to note Castagna thrived for decades in the dangerous, high-stakes world of professional cutthroat. And I don't mean the card game.


NIGHTS

I prepared to wheel my weathered Mazda out west. A bunch of friends and acquaintances, my brother and Jackie included, joined together to give me a proper send-off. With my future uncertain, we soaked up the fun well into the night. My cautious grandfather had insisted I convert the two dimes into small denomination traveler’s checks. As I packed up the car, I had enough goddamn checks to fill the trunk. My long-time friend and roommate, Brian, joined me for the drive. He stayed the weekend for some mild desert debauchery and flew home.

Meanwhile, I checked into my temporary home with Ms. Betty. She may’ve been north of 80, but she was kind and quick. Unfortunately, Betty’s spare room didn’t have cable television, and I didn’t have a laptop computer. Dealer’s school took up four hours a day, every weekday, leaving the rest of my time free.

Let’s pause to examine the situation: a risk-seeking 20-something with free time aplenty, living in Las Vegas for two months, without a computer or cable TV; no friends nearby; and $2,000 in traveler’s checks tearing a hole in the trunk.

Yet facing that recipe for ruin, I stayed disciplined. I visited The Strip every day, but mostly to grab a cheap dinner and watch games in the MGM Sportsbook. I did, however, sample casino poker for the first time.

I first played poker with my younger brother, nicknamed Rudy as far back as I can remember, at the kitchen table for pennies. Our father taught us to play five-card draw not long after Rudy learned to walk. Beyond that, though, I’d hardly played any poker. For all my interest in gambling from an early age, poker hadn’t grabbed me like horses and sports.

I took a seat at a kiddie table for some limit hold ‘em. I’d never played Texas hold ‘em and quickly realized I was clueless. I lost $43 in that first session and decided a few instructional books were mandatory before I sat the game again.

In the meantime, dealer’s school hummed along nicely. With pretty good hand-eye coordination and a decent head for numbers, I was a quick study. Around six weeks in, I got a call from my dad. It looked like I was headed back to the Midwest.

From the time legal gambling appeared in the St. Louis area, my father had immersed himself in blackjack. He binged on basic strategy and card counting manuals in hopes of dampening, or perhaps overcoming, the house edge. So, once or twice a week, mostly at the Casino Queen riverboat in East St. Louis, blackjack was my dad’s leisure activity. As such, he’d made a fast friend in the casino’s manager, Dan. My dad and Dan got a kick out of quizzing each other on the finer points of proper blackjack play.

Anyway, my dad had mentioned my plans to deal blackjack and Dan told him that, if I came back home, I should come in for an audition. Assuming Dan gave me a leg up and a strong desire to be near family, especially my sick mother, I returned to St. Louis. I killed the audition and got hired on the spot.

The Queen set my schedule: 9 PM until 5 AM, Monday through Friday. It left weekends free to pursue my growing interest in poker and paint the town with Jackie.

And why was I still hanging out with Jackie? From waging the unwinnable war over football bets to carousing through the clubs, it just kind of happened. I can’t explain it better than that.

His dad’s police record, his RICO conviction, workday violence and the casino farce clearly painted a troubling picture. Yet somehow, a bit from the Post-Dispatch recap was the only thing that resonated with me. The paper said of Jackie that “his connections to the crime families were through his father.”

Jackie’s dad had logged a legit rap sheet, but what sort of dangerous east coast gangster hawks Honey Buns and Hondas in the Midwest?

I’d moved beyond Jackie’s past being an issue. The violence I’d seen and heard was gone. Out of sight, out of mind, I guess.

And I’ll admit the whiff of danger attracted me. It was more than that, though. Jackie was older, streetwise and brimming with qualities to be admired. Not long before I met him, he tended bar and rented a tiny house. Now, amidst a second successful venture, he had himself a spot in a sweet high rise. Better yet, Jackie set his schedule and called the shots.

Mostly though, I liked the guy and he liked me. We bitched, yelled and argued, and always had fun. And just like days, nights with Jackie brought a crazy mix of characters and situations I’d have otherwise missed.

Along with Rudy, my buddy Brian was a Saturday-night regular. They’d each been standout pitchers their entire lives, and spent summers playing semi-professional baseball in a tiny, southern Illinois town. Like me, they’d been floating aimlessly through their early 20s, and, like me, they got a big kick out of hitting the clubs with Jackie.

We hung out at places like Churchill’s in the Central West End. Black people, white people, rich, not-so-rich, athletes, musicians, old and young made for a great little spot. Jackie threw ice at star wide receiver Keyshawn Johnson in there one night. Why? He hated the Jets. Eric Davis, a childhood baseball hero of mine, dropped in a few times. Tongue tied and not wanting to intrude, I never did talk to him. Impossibly, he looked even cooler in street clothes than a baseball uniform.

From Churchill’s, we’d jump to Gene Lynn’s, a jazz club about two blocks from Jackie’s apartment. Gene was a local legend, known around town as “The Black Sinatra.” The club featured live music and Gene, in his Saturday night tux, always belted out a ballad or two.

Whether it’d been a week or a year since your last visit, Gene waited with a soulful handshake and a silky “Hey, baby, good to see you. Thanks for comin’ in.” Then in his mid-60s, Gene oozed cool.

The club drew mostly black couples, age 40 and over. Walking into Gene’s served them a double dose of surprise: Who’s the John Gotti motherfucker? And what’s he doing with those raggedy kids? We’d get shot a few strange looks, but then say hi to Gene and the bartenders and that would be that.

An old black man named Joe easily ranked as my favorite Gene’s regular. Standing about 5’7”, he always sported the same dress jacket and a pork pie hat that had to be older than me. We got to talking one night and Joe gave me the lowdown. While he’d boxed in his younger days, his lifelong profession had been music. A drummer, Joe didn’t play much anymore because age and arthritis had stolen his skills.

The first night we met, Joe talked, and I listened. And what a story he had. Once a sparring partner for the great Sugar Ray Robinson, Joe would ultimately play with a litany of music legends. Topping the list was none other than jazz giant and East St. Louis native, Miles Davis.

'Round about midnight, Joe had to take off. He said his daughter was waiting outside. Every Saturday, she drove Joe to and from the club so he could get his weekly jazz fix.

I’ll never forget that. Most people his age would’ve long since packed it in. Not Joe. He was nearing 80 and unable to drive, but still dying to take it out and chop it up on a Saturday night.

I weaved my way through the small, crowded club to find Gene. Was it all true?

“Yeah, man,” Gene said. “Ol’ Joe seen it all and done it all. All of it."

Joe and I became Saturday night pals. He called me “Youngblood” because he could never recall my name. Like the man said, “So What?” Youngblood sounded cooler than Chris, anyway.

The original Sugar Ray? And Miles? That’s what Joe called him. Miles said this and Miles did that. "That Miles was a stone motherfucker."

Jesus Christ. Joe had led some kind of life. Or, perhaps more to the point, Joe had fucking lived. Unless running with Jackie, how could I have possibly come across a gem like that?

Thanks to Jackie, the diamond-supply chain never quit.

Guys like sometimes Chicago bond trader, Lenny. Tough-looking for a white-collar man, Lenny was big and loud and loved to mix it up. According to Jackie, Lenny’s risk-it-all style in the markets left his bankroll in constant flux. Flush and buying drinks in April, but then “broke as a motherfucker” in May.

Freddie, an insurance broker in his mid-60s, rode the Saturday night waves, too. Freddie had long since given up alcohol but liked the music and conversation. Freddie always dressed in slacks and a suit jacket, but never a tie. Toss in a full head of neat, silver hair and goatee, and he just looked like success.

Whereas my crew wouldn’t connect with Jackie until 10 or so, Freddie often joined Jackie and a character known as Black Bill for dinner. Yes, Bill was African American. And Bill liked to drink. It wasn’t uncommon for Bill to go missing, but Jackie always had the scoop on his whereabouts.

“Fuck, you know that guy. He’s out in the car takin’ a nap. Long night ahead. Black Bill needs his rest.”

Sure enough, Bill would later materialize. In case anyone had missed Bill’s emergence from another alcohol-induced haze, Jackie announced it.

“There he is, there he is. Black Bill—black as a motherfucker. How was your fuckin’ nap there, sir?”

What a Saturday-night scene that was. However, as smooth as Saturday nights sailed by, dealing blackjack re-exposed a blemish of mine. Yes, I aced the audition—in front of one person. But once I hit the floor, pit bosses peered over my shoulder and gamblers awaited my every move. That posed a big problem for someone with a near paralyzing fear of public speaking. I wasn’t giving State of the Union speeches, but I was indeed on stage.

The fear first showed itself in a college speech class. A whopping total of 16 kids and one teacher, yet my hands shook so bad I could barely turn the pages. I hadn’t even considered the phobia before going the dealer route.

Early on, I visited a doctor to discuss the problem. He wrote a script for Xanax and said it’d help me keep calm as I acclimated to the job. In a frenzy before a shift, I was eating enough Xanax to knock a racehorse silly. But every time I’d scale back, the fear resurfaced with a vengeance.

The Queen was thrilled with my progress. They didn’t know I was a cinch to fail their stringent, random drug tests. I figured the prescription would save me but sweated the issue nonetheless.

Hours spent at the poker table, however, offered a less stressful casino experience. After that first Vegas sit, I’d plowed through a few books on the finer points of limit hold ‘em and poker theory. The play was so poor at the low limits that books alone made me a favorite in the games. As I gained more experience, my expectation only increased.

In the post-Rounders, pre-television boom period, players were slowly trickling into casinos around the country to try some poker. St. Louis was no exception.

Poker was perfect for me and I knew it right away. A solitary pursuit loaded with gambling action and strategy? Handicapping and betting horses was fun, but poker beat that all to hell.

Like the ponies, poker demands dissection. Not in having been dealt winning or losing cards, but in how the cards were played. Driving home after a session, my mind raced with possibility.

“Could I have won that hand? No way. But could I have lost less money? … I clammed up on that river and checked. Gotta bet that … Sure, I won the pot thanks to a lucky flop, but I should’ve never played the off-suit ace-Queen behind the old man’s raise.”

Endless possibility haunted my dreams. It was frustrating and maddening and mind-numbing. I loved it.

May 6, 2000: Dancing Between the Raindrops

The day broke sunny and warm. I couldn’t have cared less. It could’ve been cloudy and four-below as far as I was concerned. That’s because nothing can dampen my spirit on the first Saturday in May, known to racing fans and gamblers alike as Derby Day. The Kentucky Derby is America's most famous horse race and there’s not a proper action hound alive that doesn’t get down. That includes hounds who’ve been collared by probation.

I took off for Jackie’s car lot about 11 AM. He’d called the day before to ask if I’d drop by before heading to the track to play the races. Barred from casinos and racetracks for five years, he needed me to bet the Derby.

I pulled onto the lot and spotted a guy looking at cars. I climbed the steps to Jackie's second-floor office and found him at his desk, studying the Daily Racing Form. He'd doped out the winner the night before.

"There he is,” Jackie said. “I studied this shit all night, Chris. Lemme tell you. Let me just fucking tell you, sir. They ain't gonna beat this Fusa. Fusachachi…Fusachi, Fusa-whatever-the-fuck Pegasus. No shot.” 

The horse in question was the morning-line favorite, Fusaichi Pegasus. While I agreed he was indeed the likeliest winner of the race, I told Jackie I was focused on a higher-priced animal named Aptitude.

"Aptitude, huh? Okay. What about your father? Who’s he like?”

Ever since my dad had scored with Silver Charm in 1997’s “Run for the Roses,” Jackie wanted to know his opinion anytime the topic was a horse race. Having left the gate at odds of 4:1, Silver Charm was anything but a dark horse. Jackie didn’t care. Charm hit the wire first and my dad cashed. Nothing else mattered.

Anyway, I told Jackie that my dad and I agreed on Aptitude, but that he planned to include Impeachment on his tickets, as well. That sealed it. Jackie reached into his right-front pocket and yanked out a lump of cash. He flipped me two Franklins and a twenty, then fired instructions.

“Write this down. Gimme $100 to win on the Pegasus motherfucker. Okay. Then, then, gimme a $50 exacta with Pegasus over Aptitude and a $50 exacta with Pegasus over Impeachment. And then gimme two $10 trifectas. Pegasus over both the other two, both ways.”

To win an exacta, you must correctly pick the first two finishers in exact order. To cash a trifecta ticket, you must predict the top three finishers in exact order.

“Got it,” I said. “I’m outta here.”

“Okay,” Jackie said. “Thanks. And, well, shit. Now? What the fuck? Guess I’ll go see which one of my fine automobiles this jerkoff wants.”

“Okay,” I laughed. “I’ll call you later.”

Some 30 minutes later, I reached Collinsville, Illinois and Fairmount Park racetrack. It’s only 10 minutes from downtown St. Louis. As expected, gamblers of every stripe had packed the ancient, bush-league operation. That was somewhat of a problem.

The crowd would not only make it impossible to hear the Derby call, but, when it comes to racehorses, I’m as much fan as I am gambler. I love the TV coverage of the lead-up to the race, the sounds of "My Old Kentucky Home" and everything else. So, after whiffing on a few of the undercard races, I got our bets down on the big one and headed home.

Post time arrived at 4:29 PM. I stood up, walked to within two feet of the TV, and, finally, watched 19 colts bolt from the starting gate. Money in play or not, the race has cranked my pulse for as long as I can remember.

With $60 to win on the nearly 12:1 Aptitude, I had foregone the exotic wagers. Aptitude on top was my only personal financial concern.

After scorching the first half-mile in just under 46 seconds, Fusaichi Pegasus, Aptitude and Impeachment were 13th, 14th and 19th, respectively. But hope was not lost. Given the quick early fractions, the front runners could well be on empty by the time they turned for home.

And that’s exactly what happened. Aptitude briefly contested for the lead, but, just inside the 16th pole, the Pegasus motherfucker seized command. Several strides from the wire, Fusaichi Pegasus and Aptitude were clearly bound for a one-two finish. Knowing Aptitude was beat, I scanned back to see who’d get up for third.

Where’s Impeachment? Where’s—Who’s that flying up the rail? Is that?

Jesus fucking Christ. He’s gonna hit everything.

A few minutes later, the result was made official, and the phone rang. Before I even said hello, I heard Jackie shouting.

“Motherfucker! You see it? I hit the whole fuckin’ thing. All of it. Exacta, trifecta, everything.”

“Unreal,” I said. “Un-fucking-real. I looked back and was like ‘Where’s Impeachment? Wait, is this him on the rail?’ And it’s fucking him. I about shit.”

“I know,” Jackie said. “Crazy. And I wasn’t even thinkin’ about the tri. Well, I mean, I was— You know what I’m saying. You never think you’re gonna hit shit like that. But then here comes that fuckin’ Impeachment. My whole life I never cashed on that fuckin’ race. Goddamn. Finally.”

“Nice hit, man. Goddamn. Well done.”

“You get anything?” Jackie asked.

I told him I’d needed Aptitude to win.

“Ah, right, right. You were leavin’ Pegasus out. Right. So, you gonna go get my money?”

 I knew that question was coming.

“Now?” I said. “I’ve been driving all goddamn day, man. Tell you what. Gimme $200 and I’ll go pick it up tonight.”

 I might’ve cut my formal schooling short, but that didn’t mean I hadn’t gotten an education.

 “O-hhh,” Jackie said. “You’re a motherfucker now, huh? Nice fuckin’ shakedown there, sir.”

“Yeah,” I laughed. “I’m a real fuckin’ shakedown artist.”

“You know we’re going out tonight. Call Rudy, call Brian, call who-the-fuck ever. We’ll do dinner, too. All on me. And when you cash it, keep a $100. How’s that, you skinny cocksucker?”  

I told Jackie that worked for me and called the crew. After a quick shower, I got dressed and hit the road. With Brian in tow, I crossed the bridge and headed back to Collinsville. I had a collection to make.

A $2-win ticket on Fusaichi Pegasus paid $6.60 and Jackie had it 50 times. The $2 exacta returned $66, and he had that 25 times. Finally, Jackie hit the $435 trifecta payout five times. By the time the clerk paid out the winnings, I gripped just over $4,000.

My money or not, my blood was pumping pretty good. A nongambler would never understand, but, among us regulars, a buddy making a nice score feels good, too. It didn’t surprise me that Jackie planned to share the spoils with his Saturday-night crew.

I plucked a C-note from the fistful of dollars and slid it into my pocket for services rendered.

Then, Brian and I hopped in the car and I crossed the Mississippi River for the fourth time in six hours. After grabbing Rudy, we pointed for the West End to meet up with the big winner.

With the door cracked open, we walked into Jackie’s apartment without knocking. We found him standing at the living room mirror, slicking his hair back. Barefoot, he was clad in suit pants and a wife beater—gold chains and heavily-inked biceps on full display.

“There they are,” Jackie said. “Wanna go to Gian-Tony’s?”

That was fine by us. Gian-Tony’s is a traditional southern Italian restaurant on The Hill. We’d all eaten their delicious food a few times. “Old school” doesn’t begin to describe how old school the place is.

“I called Freddie to go with us, but he’s jammed up with that new broad. He might meet us later. Churchill’s or whatever. You got the money?”

“Right here,” I said, pulling the cash out of my pocket.

“Bring it back here,” Jackie said.

I followed him to his bedroom and handed off the sexy green chunk.

“All my life bettin’ that fuckin’ race and I finally got it,” Jackie said. “Thanks for Aptitude and tell your father thanks for Impeachment. He get anything?”

“Nah. He took a stand against Pegasus just like me. Fuck it. That’s the way it goes, you know?”

“Oh, I know,” Jackie laughed. “Believe me, I know. Especially that fuckin’ race.”

Jackie thumbed through the bills and jammed about half the haul into his pants pocket.

“You get your $100?” Jackie asked.

“Yep.”

Jackie then opened a large closet revealing at least two dozen jackets. The sheer number and collage of color about blinded me. He picked up a fine leather shoe from the closet floor and slid the remaining cash into the toe.

“Okay,” Jackie said. “Be ready in a few.”

By the time we reached the restaurant, the sun had disappeared. As dark clouds took the sky, high winds ripped down The Hill’s ancient, skinny avenues. A storm was due to arrive any second, but we’d be warm and cozy inside Gian-Tony’s dynamite little atmosphere.

Jackie started the party by calling for a $150 bottle of red wine. But he quickly reconsidered his order.

“You guys don’t drink wine, do you?” Jackie asked.

But before anyone could answer, he said, “Well I don’t give a fuck, cuz you’re drinkin’ it tonight.”

No, we weren’t wine drinkers. But if ever the practice of “when in Rome” were mandatory, this was it. Jackie wanted to celebrate by sharing his good fortune with us. It would’ve been the poorest form to refuse the wine.

The parade of savory Italian specialties soon began. Jackie shed his jacket and tucked a linen napkin inside his collar. Should any ill-mannered sauces get frisky, his pricey threads would need the protection.

Calamari, spicy pasta and breaded veal cutlets, sliced paper thin, arrived in three, well-timed waves. And that was all before the main course. As dictated by tradition, the salads came last. We washed it all down with another bottle of wine.

As we caught our collective breath, Jackie drained an espresso. Not even Brian’s 6’5”, near 300-pound frame could bear the thought of dessert.

Leaving the restaurant, it was obvious a thunderstorm had rolled through. The lightning may’ve been gone, but the rain had stuck around. Through the downpour, we trekked back to the West End. Freddie and a couple other friends planned to meet us at Churchill’s.

We arrived and found a reserved table with two bottles of champagne chilling. Uncultured brutes that we were, we’d never had more than a sip or two at weddings. On high alert, Jackie kept glasses full and drinks flowing. He’d hit a nice payday, and everyone would be taken care of, goddammit.

Rudy especially wasn’t fan of the bubbly, but that didn’t stop Jackie.

“Rudy, Rudy. You gettin’ enough champagne over there?”

Rudy held his glass aloft to signal it half full. No matter. Jackie popped up, grabbed a bottle and topped it off. Rudy nodded, smiled and reached for his Budweiser chaser.

We must’ve recounted the race 10 times. Jackie couldn’t get enough of Impeachment’s furious rally up the rail to snatch third prize.

“You know, gettin’ down to the wire, you knew I had the exacta? Right? Yeah. But that fuckin’ Impeachment, man. That fucker just kept comin’.”

In St. Louis, bars stay open until 1:30 or 3. Churchill’s was a 1:30 joint, so by 12:30 it was time to talk about the next stop. We decided on a new club downtown.

Washington Avenue, with spots like Monkey Bar and Velvet Room, was a regular stop on our raucous Saturday nights. And it was the downtown clubs where Jackie showed his mystifying best.

Long lines and cover charges awaited at most of Washington Avenue’s watering holes. For everyone but Jackie and company, that is. Bypassing the line, he’d whisper to the bouncer and in we’d go. Sure, they knew him at Monkey Bar and Velvet, but the new club on Derby night? We’d never been there. Not once. So? Jackie and his posse still got the VIP service. 

It was as if the bouncer momentarily lost his mind. Perhaps Jackie’s accent and flashy clothes placed him under a spell. He didn’t know Jackie, but it sure seemed like he should. Yes sir, you and your friends, right this way. I never—not once—waited in line or paid a cover when out with Jackie.

Once inside, we christened the club with a round of shots then splintered off. Jackie and Rudy hung around the bar, while the other guys and I soaked in the scene: maddening strobe lights, bone-blasting house music, and pack after pack of sweaty, bouncing females.

Around 2:15, I checked in at our meeting point. Brian had joined Jackie and Rudy at the bar. When I ordered a beer, the bartender gestured to Jackie and Jackie nodded. He had an announcement.

"Okay, you motherfuckers are on your own. Every dime I brought is gone."

We certainly understood. Enough was enough.

"Bunch of fuckin’ animals,” Jackie hollered. “2,200 hundred bucks, you fuckin' jackals.”

Everyone cracked up laughing, Jackie the loudest among us.

Was the wind blowing east? Across the river, clubs of every kind jumped until 6: coke-fueled dance clubs, strip clubs, as well as riskier, more adventurous establishments. But we figured the sharp play was to call it a night. Nursing our drinks, we heard last call before the ugly lights jolted us back to reality.

The rain continued to rage in the downtown streets and made for a slow drive home. We dropped Jackie at his apartment, thanking him for a great time.

I woke up Sunday morning around 11 and learned the city had been soaked by eight inches of rain. Outlying areas got as much as 13. But thanks to a talented trio of tough, hard-trying racehorses, not to mention enough luck for 20 Derbies, we never felt a drop.

Goddamn we had fun. I don’t care if you’re Phil Ivey, a grind-out-the-rent pro or a total sucker. Drilling an unexpected score soothes the gambling soul. Like Paul Newman said in The Color of Money: “Money won is twice as sweet as money earned.”

I was thrilled for my friend. That I’d tipped him onto two-thirds of the winning trifecta made it all the sweeter.    

Between betting the horses, the odd sports bet and perfecting my poker game, gambling had crept ever further into my life. Mix in dealing blackjack 40 hours a week and it’s all I thought about.

Unfortunately, dealing continued to be a problem. Xanax allowed me to perform well; well enough that I’d begun dealing other games. But what kind of life was that leading to? That of a pill-popping croupier?

My phobia was especially irksome because I liked the job. I worked with sharp, friendly people, and was making decent money with good benefits. Further, being the interested observer that I am, the Casino Queen served up a steady supply of subjects. Rich and poor, drunk and sober, once-a-year gamblers and everyday dupes, casino life has it all. Perhaps the most memorable experience, though, involved my father.

Upon being hired, all dealers were advised that no immediate or extended family were permitted to play at your table. The casino manager, Dan, had reiterated the rule to my dad. That wouldn’t be a problem. I worked the first floor and my dad regularly played on the third.

But one Friday night, casino paranoia came calling. A father drifted down to the first floor to check on a son. Not to play. Not even to sit at the table. He stood several tables away, in fact. A dad simply wanted to see how his son was handling the game. I never knew he was there.

The cameras and Dan were watching, though, and neither was pleased. I later learned that Dan approached my father on the first floor and asked what, exactly, he was up to. My dad answered truthfully, but it made no difference to Dan.

“If I ever see you on the same floor as Chris again, you’ll be permanently barred and Chris will be terminated. No exceptions. I don’t know what you’re up to, but I can’t have it. Understood?”

The first-floor manager similarly admonished me before my next shift. Why the house rules included entire floors for the Allsups was never made clear.

Dan ran a little hot even by industry standards, but the ordeal crystallized the casino mentality. And it calls to mind Jackie’s harebrained plan. What the fuck was he thinking?

That’s an easy one, really. Jackie was always thinking; or, better yet, always scheming. But personality traits are both strengths and weaknesses. A mind working tirelessly to find every edge is wonderful (leaving aside moral concerns, of course), but only if that mind is disciplined. Left unchecked, it’ll see opportunity where none exists. Like Jay-Z said: the gift and the curse.

No longer working for Jackie, I didn’t see his thieving, scheming side. Weekends brought the rollicking, generous Jackie out to play. We went to dinner, watched big fights and took in live music, but mostly got together just because it was Saturday night.

As far as Saturday nights, I was the common thread between Jackie, and Rudy and Brian. But that didn’t mean that Jackie didn’t also associate with Rudy and Brian independent of me.

For instance, Rudy and Brian delved into betting college football. The bets were called into Jackie, but booked by Martin, Jackie’s “old buddy from back in Boston.” There were never any problems with getting down or payouts and debts. Rudy and Brian’s success piqued Jackie’s interest enough that he probed them for information; calling them regularly to discuss upcoming games.

I’ve long been a casual boxing fan, but Rudy and Brian followed the fight game closely. As much as Jackie loved baseball and horse racing, boxing blew them both away. Jackie delighted in discussing the fights with those guys.

He boxed in his youth and sports the smashed nose to prove it. One of Jackie’s proudest achievements was winning a Golden Gloves title as a teen. First prize earned him a sparring session with middleweight great Marvelous Marvin Hagler.

Jackie described the encounter:

“I’m just a kid, man, you know? And Hagler’s a bad motherfucker. You know, I don’t really think he’s comin’ to fuck me up, but still, it’s still in the back of your head, right? And then soon as the first round—Right away, he pops me good. Right on the fuckin’ nose. You know, I’m wearin’ headgear, but ain’t no headgear on your fuckin’ nose there, sir. Anyway, that was really it. Think he just did it to say, ‘Look here, you little fuck, I’m the boss.’ After that, we just danced and threw a little bit. Just fun, you know?”

Jackie loved telling the Hagler tale and would happily talk boxing all night.

And a blockbuster boxing match had sealed Rudy’s standing with Jackie. About a year before Jackie drilled the Derby, Oscar De La Hoya fought the fierce Ghanaian, Ike Quartey.

Leading up to the bout, Jackie and Rudy debated possible outcomes. Jackie held intense dislike for De La Hoya, viewing him as a pretty boy looking to win on points. Jackie didn’t believe De La Hoya would tangle with a talented bruiser like Quartey. Rudy argued that it was De La Hoya’s good looks that fueled this misperception. When confronted with Quartey’s power, De La Hoya would gladly mix it up and a street fight would ensue.

Jackie invited us to his apartment to watch what would go down as perhaps the fight of the year. Oscar might’ve looked like a movie star, but inside beat the heart of a badass, Mexican American brawler. Oscar and Ike traded bombs for 12 rounds, with a split decision ultimately falling in Oscar’s favor.

As we hit the town, you would’ve thought Rudy predicted Pearl Harbor. Jackie lavished Rudy with praise and spiced it up with his most brutal name-butchering yet.

“Fuckin’ Rudy called it. He fuckin’ told me and told me, ‘De La Hoya ain’t gonna run from shit.’ Rudy was right, man. That fuckin’ Koontay threw everything at him, pounded on him all night, and De La Hoya took it all and gave it right back. What a fuckin’ fight. Goddamn. That’s two tough motherfuckers, man.”

“It really was an awesome fight,” Rudy replied. “Two great fighters for sure. I’ve just seen too much of Oscar to think he’d back off.”

“You called it, Rudy,” Jackie said. “You fuckin’ called it. And how ‘bout that fuckin’ Koontay?”

“I know, man” Rudy said. “That guy just wouldn’t stop.”

“That motherfucker was ahead for sure. For sure.” Jackie said. “But he just kept comin’, Rudy. What the fuck? That fuckin’ Koontay. Goddamn. He didn’t sit on shit.”

Jackie carried on all night calling Quartey “Koontay.” We just let him go.

Jackie was right. Quartey held a clear lead—or at least we thought he did—and likely could’ve danced and clenched his way to victory. It certainly would’ve been the optimal path. But optimal didn’t interest Jackie. He was a fighter in every sense and thrilled by Quartey’s doggedness.  

The post-match talk illustrated another trait of Jackie’s I admired. Outspoken and opinionated, he’d shift his stance if shown a compelling counter point. Or, as in the case of De La Hoya, offered live, televised evidence.

And being resolute, but remaining flexible, is mandatory in gambling. In a poker game or horse race, a gambler backs his opinion with money. That takes courage. But if unable to recognize, then adjust to, mounting evidence to the contrary, he’ll be bravely rushing towards ruin. It’s a fine line that I became more adept straddling in poker.

By late 2001, I’d been a consistent winner in the limit hold ‘em games. Not that I could get rich grinding those games, but there was money to be made. The way most players approached the game astounded me.

Poker is a ruthless enterprise with one objective: get the other guy’s money. Yet a shockingly large percentage of players treat it like a slot machine. Calling an opponent’s raise with a ridiculous hand, they may as well go pull the arm and pray for a miracle.

“Come on, baby. Papa needs some spades.”

Ultimately, and especially at the lower limits, poker provides entertainment like dinner and a show. The average asshole counts on leaving with less than he brought to the table. The studious and disciplined sit, wait and stack the money. 

By June of 2002, I’d decided to call an audible: leave the Xanax-assisted safety of the Queen and pursue poker. I was young and unattached and looking for adventure. Prepared or not for the plunge, I put in my two weeks’ notice.

Just like Jackie, I’d be setting my schedule and calling the shots. I never had any desire to be rich or famous but wanted a life that’s my own. Poker would serve to disentangle me entirely from the politics and professional ass-kissing of the straight world.

In the meantime, we got the crew together for a fight night. On the card: the well-past-his-prime Mike Tyson versus then-current champion Lennox Lewis.

Like Jackie, Tyson’s ferocity had been forged in the back alleys of Brooklyn. Washed up or not, Jackie adored Iron Mike.

And Jackie was in attendance the night that Tyson’s star had shone the brightest. In June of 1988, Tyson savaged St. Louis legend Michael Spinks in 91 seconds. Held at Convention Hall in Atlantic City, Jackie got jammed in the beer line and missed the knockout.

Fourteen years later, we were gathered at the studio apartment Rudy shared with his girlfriend, Val. Jackie brought Racanelli’s, everyone’s favorite New York-style pizza. In typical Jackie fashion, there had to be a hustle involved. He’d convinced the cashier to put the pies on pans to preserve their quality. He promised her he’d return them the next day. Rudy has the pans to this day.

Lewis easily beat back a frantic and finally tired-looking Tyson. The inevitable knockout came in the eighth, Lewis having drilled Kid Dynamite’s career deeper into the abyss.

With Tyson’s ass kicked, Jackie and I prepared to hit the town. The crew sliced in two, we cut out of south city and made a cameo at Gene Lynn’s. As last call neared, we pondered the next stop.

"Wanna go over to Illusions?" Jackie asked.

Club Illusion sits squarely in East St. Louis. I'd never been there but knew that Jackie sometimes paid his respects.

"Seriously?" I asked.

"Yeah, fuck it,” Jackie said. “Why not?"

Let's get something straight: people don’t gallivant into East St. Louis, Illinois at 2 AM—not on purpose, anyway. I don't care who you are or what you look like. You could be white, black, red or teal. But Jackie tempted people to sling caution aside; me included. Besides, with Jackie riding shotgun, it felt like we were big favorites to dodge serious trouble.

Pointed for the Poplar Street Bridge, Jackie wanted to hear his song.

"You got 'Distant Lover' in here?"

This scene played out nearly every Saturday night. Once Jackie had had a few, he'd request his favorite Marvin Gaye tune. I gave him the same answer every time.

"It's back there somewhere. If you can find it."

Compact discs littered the backseat like plastic confetti. It cracked me up every time, Jackie cussing his way through the mess. Finally, he spotted Marvin and we spun the song. Just like always, Jackie sang along.

“D-iiiisT-anT l-uuuu-VER.”

Rudy often said that Jackie’s singing sounded like Phil Hartman’s over-the-top imitation of Frank Sinatra on Saturday Night Live.

It was business as usual when we got to the club. Even on the East Side, we skipped lines and escaped cover charges. Jackie couldn’t, however, keep us from a pat down and a cruise through the metal detector. Welcome to East St. Louis nightlife.

Club Illusion was dimly lit and loaded with people. The low-slung ceiling gave it the feel of a high school party in your parents’ rec room that’d veered completely off the rails. “Hot in Herre,” by St. Louis’s Nelly, thundered through the crowd. We ordered a couple cocktails and somehow commandeered a booth. Jackie and I were the two lightest-skinned customers by about three shades.

"Okay, man, seriously,” I said. “Is this even safe? I mean, this seems pretty sketchy to me.”

Rudy and I were regulars at North St. Louis basketball games, the only two white guys within 10 blocks. We hung out at Gene's all the time. It wasn’t some irrational fear of the different. This was East St. Louis at 2 AM.

"Get the fuck outta here,” Jackie said. “Two white motherfuckers just walked in the joint. If anybody's scared, it's them."

I shot Jackie a confused look.

"Think about it, man. How fuckin' nuts do we gotta be to walk in here? We gotta be some crazy-ass motherfuckers. Know what I mean?”

“Yeah,” I said. “I guess that’s true.”

“Fuckin’ right it’s true. Don’t you worry, sir. Ain’t nobody fuckin’ with us.”

I must admit: his reasoning made a lot of sense.

Two dudes in Technicolor suits stopped by our table. Their identities weren’t clear, but they were somehow tied up in boxing. Apparently, Jackie had jumped into that business, too. I couldn’t begin to count all the balls he had in the air.

Later, just the two of us, Jackie got talking about Tyson and Brooklyn. Jackie grew up in Bensonhurst and Tyson in Brownsville. He talked about where Tyson came from and just how tough it is.

"You gotta be a bad motherfucker just to live long enough to get the fuck out."

And apparently, Tyson and the vodka tonics put Jackie in the mood for memory lane.

"Did I ever I tell you about my Puerto Rican buddy, Tito?"

"I don't think so," I said. “From back home?”

"Yeah-yeah, guy I knew back in the day. I dunno—I was young. Anyway, Tito knew all the Dominican drug dealers, right? I mean all of 'em. Spoke the language, too, you know. Well, we went into business robbing every one of those motherfuckers."

“Wow,” I said. "I guess that’s pretty profitable if you can live through it.”

Jackie laughed.

"Yeah, no shit. Fuck, man, one of the first ones we did was a real fuckin’ jam. Four of us. Tito drivin', two guys in the backseat, and me ridin' shotgun with a fuckin' shotgun like this," Jackie said, showing me how he’d held the gun across his lap, pointing towards the passenger side door.

"I dunno know what the fuck happened,” Jackie continued. “We hit something pulling into the parking lot or some shit—pow! Fuckin' gun goes off and I blow the fuckin' door right off. Blasted the fucker clean off. Can you fuckin' imagine, Chris?”

It was obviously a scary situation, but I busted up laughing. Of course, Jackie roared right along.

"Nuts, huh? Crazy. Best part—Get this shit. Best part is we were gonna rob ‘em and go out after. So, I’m wearing my goddamn dancing clothes, you know? My fuckin' platform shoes with goldfish in the heels.”

Were they live goldfish? The heels doubled as aquariums? And on second thought, maybe Jackie riding shotgun didn’t provide the security blanket I originally thought.

Jackie said he and the crew quickly cut bait after the door got blown off, and added, “Lemme tell you: that was a pretty fuckin’ windy ride home, sir.”

Of course, I’d heard and read about Jackie’s RICO conviction and his father’s foul history. This was different. This was Jackie himself doing some seriously violent shit. And it came straight from his mouth.

When the alcohol kicked in, I’d known Jackie to cut loose with details. But running armed robberies on drug dealers? That sort of detail slapped me across the face. It shot to the top of his colorful, criminal past. Why tell me, I wondered.

Try to put yourself in my spot. How would you respond to a story like that?

Anyway, the joint jumped to another level and the Tito talk faded. It got tough to move or talk in there. By 3:30, Jackie’s boxing buddies had returned with a string of sweet-smelling mocha cuties we somehow shoehorned into the booth.

By 4:30, our table overflowed with baskets of chicken fingers and fried shrimp. Like Jackie, Club Illusion had every angle covered. We didn’t stagger out until well after 5.

Are you looking for fun? No, I wouldn’t advise a small hour rip through East St. Louis. But I do suggest an occasional jaunt beyond comfort’s city limits. You might even find yourself a story to tell.

And comfort—a steady paycheck—is precisely what I tossed in the river when I left the Casino Queen. I still saw the junkies every day, slotting away their social security for a score that wouldn’t come. No longer, though, was I headed to a blackjack table. I reported to the poker room.

Poker captured almost total control of my life. It wasn’t just about money, either. I wanted to make optimal plays out of a sense of pride. Misplaying a pot dealt me a double shot of misery. Some donkey stacking my chips not only lightened my bankroll but bruised my ego. Gotta be fucking better than that, I’d tell myself.

During the first year or so of playing full time, I logged upwards of 70 hours a week. Rarely did I play fewer than 50. Most days saw me in the poker room between eight and 10 hours, followed by 90 minutes of reading and replaying hands at home. I was exhausted by the time I laid my head down—the good exhausted. Closing my eyes triggered colorful visions of black Jacks, red Queens and an ocean of green felt.

July 2003: Saturday Night Safari

St. Louis’s summer menu is a limited one. Like twin chefs from hell, heat and humidity team up every June for a three-month cook-off: one bakes your body while the other boils your soul.

On this Saturday night, the heat lingered long after dark. Brian, Rudy and I had met Jackie at Churchill's to jumpstart the evening, and, after downing a few beers, we skipped across the West End to check out the scene at Gene’s.

Around 12, I leaned over the bar with my jazzy boxer buddy, Joe. Near Gene’s spot by the end of the bar, Rudy and Brian worked out the world's problems with Lenny and Freddie. Jackie, meanwhile, was cozy at a cocktail table with what looked to be two good-looking brunettes. From across the dark, smoky club, it appeared one was quite older than the other.

Joe’s curfew struck so I floated over to investigate. I've always had eyes like a fighter pilot and indeed found both ladies attractive. One looked to be about my age and the other maybe 20 years older. Jackie introduced me to Lisa and her mother, Kathy.

It turned out Jackie had known Kathy for some time and said I'd met her and Lisa before. I couldn't recall meeting either, but Lisa confirmed we'd crossed paths about a year prior. Okay, Lisa, whatever you say.

I helped myself to the seat next to Lisa.

Here we have a perfect example of the power of alcohol. Without an agreeable amount of Anheuser-Busch product on board, I would’ve never walked over there. Forget sitting down. When I’m among family or friends, my mouth runs like a marathoner doped on tangent juice. In the company of strangers, I may as well be hidden behind the flowers on the wall. Beer was created for me to meet women. Especially women like Lisa.

Everything about her was arranged just right: long, dark, almost black, hair; some make-up and jewelry, but not too much. And when she strutted to the Ladies room, her well-developed derriere stole the show. At a curvy 5’4”, she could’ve been a long-lost Kardashian sister.

Jackie carried on with Kathy, so Lisa and I got to know each other. I shot her the short version of how Jackie and I had come to know each other. However, I decided it best to not delve into my gambling venture just yet. I told her I was at “loose ends” or some shit and left it at that.

Lisa told me her mom had known Gene for years and lived just up the street. Kathy had gotten to know Jackie through living and playing in the West End. Then, Lisa spilled the skinny on her personal life. Married with a young daughter, she was heading for separation and destined for divorce.

Trouble, right? If the situation sounds too messy to pursue, please consider the warm, hazy glow that comes with drinking beer in the summertime with a beautiful woman. Toss in the jazz at Gene’s, and solid decision-making was an odds-on favorite to disappear.

So, I complimented Lisa on her brilliant blue-green eyes.

“Thanks,” she laughed. “Too bad they’re color contacts. But you sure have pretty blue eyes.”

“Thank you,” I said. “And get this shit: they’re real."

Not long after Rudy’s gal, Val, arrived, we needed a plan. Jackie suggested a new place downtown that’d recently opened: The Pepper Lounge. Lisa and Kathy said they were game. Good, let’s go.

Still an unknown spot, Pepper didn’t have a line. The deserted front room featured a small bar and several tables for dinner. After drifting down a short hallway, we came upon the hub of after-hours activity. Well, it was designed for activity. I could’ve rolled a bowling ball across the main floor and not come within four feet of a body.

Behind the bar, about two dozen antique lamps adorned the wall. On another wall, a muted classic movie played from a projector. We all crammed into a corner booth and ordered drinks.

Lisa had squeezed in on my immediate left, nearly in my lap. She smelled delicious.

“What’s this perfume you got going here?” I asked.  

“For real?” Lisa said. “It’s Chanel No. 5."

“Well, then, please excuse my ignorance. I’ll admit the truth. I’m not exactly an expert on perfume.”

Lisa laughed. 

“You’re kind of a smart ass, aren’t you?”
 
“If you say so,” I said. “But you know, if you didn’t douse yourself with that shit, I probably wouldn’t’ve said anything to begin with.”

“Jesus Christ. What an asshole. You know, maybe if you smelled a little better you’d have a fucking girlfriend.”

I shot her a wide-eyed look and she smiled.
 
“Never thought of that, huh, smart guy?” 
 
“Look at you,” I said. “Well played, woman.”
 
“What, you think I’m just gonna sit here and take your shit? Jackie, is your friend here always such a jerk?”
 
“Don’t pay no attention to him, honey,” Jackie said. “Fuckin’ cuckoo Chris over there.”
 
We sparred like this for the next hour or so. Lisa countered every jab with something stronger. I liked her style.

With last call looming, Kathy told the table of an impromptu after-party at her place.

"You gonna come over?" Lisa asked.

I am now, I thought.
 
Brian, Rudy and Val said they’d had enough and took off.
 
"I guess let's go," I said to Lisa.
 
"Hey, you crazy cocksucker,” Jackie said. “Don't leave without me."

Jackie knew where Kathy lived, so we settled the tab and scooted out. Lisa said she'd see me there and left with her mom.

Located on the west side of the Central West End, Kathy’s building overlooked Forest Park. I parked on the street, near the main entrance, and the mother-daughter team arrived right behind us in Kathy's turquoise convertible. So, the four of us walked in the front door and hopped on the antique-looking elevator.
 
A few floors up, we stepped into Kathy’s spacious apartment. After 3, and having had five-too-many beers, I could've gotten lost in there. The place was spotlessly clean and decorated with care. I know even less about interior design than perfume, but the furnishings alone had to cost a fortune.  

"Wanna take the tour?" Lisa asked me. 

Here’s where details get sketchy. I trailed Lisa around for a bit, but don't recall the route; only the destination: the safari room. Say what? The fucking safari room?
 
"Look,” Lisa said. “See the tigers and leopards on the wall? The curtains? All the plants and flowers?"  

Where I come from, we refer to rooms by their utility; the bedroom, or the living room, for example. Sure, though, the safari room works for me. We got cozy on the couch.

"So, Christopher. You’re telling me you've never had an actual girlfriend?" 

I got a kick out of her calling me Christopher.

"Like how long we talkin’ here?"

Lisa laughed.
 
"Like, you know. Where you're in an actual relationship. Like, not seeing other people."
 
It was my turn to laugh.  

"Oh, fuck no," I said. "I just don't think that's for me."
 
"What? You mean you don't wanna get married or anything? Ever?"

"Yeah, no, I don't think so.”

"Wow,” Lisa said. “Okay, glad we got that straight. Let's find a movie, want to?"

Not really, I thought.

"Sure," I said.

Lisa turned on the TV.  
 
I haven't a clue if we found a flick before I grabbed her. Our tongues were attached for the next few minutes, then I tore off her shirt and she removed mine. I fiddled with the zipper on her skin-tight jeans far longer than I would’ve preferred, but, eventually, I was able to manage. You can figure out the rest.
 
We finally fell asleep about 6.
 
Around 8, we came to and resumed the boy-meets-girl routine. I moved my mouth below her belly for a most intimate exercise—then the door opened. 
 
"Oh shit! Sorry."

Who the fuck is that?

"Mom,” Lisa yelled. “What the fuck?"

Cardiac arrest set in. Then the door slammed shut.

Kathy had strolled smack-dab into a dandy shot of my ass—my face between her daughter's legs. The safari room had been equipped with a name, but not a lock. How lovely.
 
Once we regained our composure, what could we do but laugh? I pulled on my T-shirt while Lisa searched for her scattered underthings.
 
“So, is Jackie still here?” I asked.

“Oh, Jesus,” Lisa said. “I don’t know. Not even sure I wanna know, you know?”

“I hear that,” I laughed.

Lisa pulled on a pair of short shorts from an overnight bag and collapsed onto the couch. Together, we sat and stared at the silent TV. She’d started to drift asleep on my shoulder when the safari door swung open—again.

“There they are,” Jackie said.  
 
“What the fuck?” I said. “Sure, come on in.”

Lisa’s head darted up to drink in the sight: Jackie wrapped neck to toes in a white bed sheet, apparently buck-naked underneath. His gelled hair stood straight up, forming a spiked helmet of sorts, and, as if the cape and headgear weren’t enough, his face was splotched in cherry red. About eight perfectly puckered kiss marks trailed from forehead to chin.

Lisa threw her head back in a laughing fit. Jackie just smiled and flopped onto the couch.  
 
“Fuck, dude,” I said. “You couldn’t put some clothes on?” 
 
“Or knock,” Lisa added. 

Jackie laughed.

“Kathy told me she got you two a little, u-hhh. A little fuckin’ jammed up.”

“Oh my God,” Lisa said. “I’ve heard enough. I’m making coffee.”

Lisa lit out of the room and down the hall.

“Good idea, honey,” Jackie said.

“That’s a good look you got going with the lipstick,” I said.
 
“What? Oh, I got it on my face?”
 
“Just a tad,” I laughed, as Jackie swiped at his cheek. 

"Fuck it,” Jackie said. “I'll get it off in a minute." 

We sat quiet for about 30 seconds.

“Welp,” I said. “This is quite a scene we got here this morning. I mean, what in the fuck, man?”

“O-hhh,” Jackie groaned, rubbing his eyes. “This is what we do, sir. This is … what … we … do.”

I laughed. I hadn’t a goddamn clue what it meant, but it cracked me up.

Pretty soon, I decided it was highway time. I stood up, pulled on my jeans, and started buttoning up my ratty '70s shirt.

“Look at you,” Jackie said. “You got a hole in your T-shirt and what, what the fuck’s this other shirt here?”

“Come on, now,” I laughed. “This is a Rag-O-Rama special.”
 
“Oh, it’s special alright,” Jackie said. “Looks like something I wore in about 1977. You know, though, I tell you, I gotta give you credit. Lisa’s a great-lookin’ broad.”

“Yeah,” I said. “She is. And I gotta say, I kinda like her.”

“Do you know how many broads would talk to me if I had a fuckin’ hole in my shirt?” 
 
I laughed.

“Clothes don’t matter for you, though, huh?” Jackie said.

“I don’t know, man. I just think girls are weird. You never know what’ll catch their eye, you know?”

“That’s true,” Jackie said. “That is true.”
 
“Fuck it,” I said. “I gotta find Lisa and get the fuck outta here.”
 
I left the safari room to look for Lisa. I found her leaving the kitchen.

“I gotta get going,” I said.
 
“Yeah, me too. Let me grab my stuff and I’ll walk out with you.”

We said our goodbyes to Kathy and Jackie, then stepped into the muggy Sunday morning. Not even 10 yet, but it had to be close to 90 degrees. Lisa gave me her cell number and hopped in her car. She looked up with a pretty smile.

“I had fun, Christopher.”

“Me too,” I said. “I’m gonna call you.”
 
“I hope you do."

"By the way,” I said. “What's with the 'Christopher' shit?"

Lisa laughed.

"What, you don't like it?"

"Actually,” I said. “I kinda do. Nobody really calls me that. Not even my mom."

"Then good," she said. "That's what I'll call you.”

The window went up and she disappeared down the street. I'd made it to 27 and hadn’t been gobbled up by a girl yet. Despite what I said, I knew goddamn well I’d no intention of calling. Just in case, I slid her number into my pocket.

Over the next few days, my mind drifted back to the safari room and that night. Lisa had slivered inside me. She not only looked nice but threw me off-balance in a good way. I loved her zing for verbal ping-pong. Or maybe I’d changed. Was I ready to run for something beyond the casual? Maybe I will call her, I thought.

I didn't. Everything about Lisa and her mother smacked of dysfunction. Jackie later told me Kathy had been married a few times. Her last husband had died a couple years prior and left her a few million bucks.

Above all, Lisa was still married, with a daughter. Painting the town with her mother seemed strange to me, too. That's not even to speak of the safari scene. I put her out of my mind and sailed through the summer.

 

Each year, the onset of autumn saps my spirit. It smacks of three o’clock football games ending in total darkness, followed by the ticking of 60 Minutes and me plumb out of excuses to put off my homework. The one plus is baseball’s postseason, and the 2003 playoffs turned out as pleasant as they did profitable. Pleasant because the Cubs' year ended in nationally televised torture; profitable thanks to the Florida Marlins. 

On Halloween Friday night at The Pepper Lounge, less than a week after the World Series, I met Jackie to collect $1,200. As Jackie peeled off the C-notes, he told me how Martin moaned when Florida closed out the Yankees.

“You oughta hear Martin,” Jackie said. “Oh, is he cryin’. On and on. ‘Who is this fuckin’ kid? How the fuck does he bet the Marlins? Nobody bets the fuckin’ Marlins.’”

I was no baseball-betting wizard. I stabbed at what I figured were nice odds and made a little score. Randomness is the long shot backer's best friend. To be clear, he doesn't expect the underdog to come in. If laid a big price, however, lightning needn't strike often to turn a long-term profit.

With Martin’s crispy cash lining my pocket, I ducked into the bathroom. Coming out, I nearly knocked Lisa over. I hadn't seen her since we left the safari room.

"Well, well, look who it is. Hello, Mr. Christopher.”

She had a black fedora perched on her head and her hair pulled into a ponytail. The hat perfectly framed her pretty face. Yikes. I do like a lady in a hat.

Pepper's popularity had exploded since summer. We grabbed a drink and waded through the crowd, carving out a spot between Austin Powers and a pair of naughty nurses. After she gave me a good-natured lashing for not calling, we picked up where we'd left off. The conversation flowed as easily as the drinks.

Getting her back to my apartment took some top-notch talking, but Lisa finally relented.

"Okay, fine, let's go," she said. "But I'm not gonna keep doing this, Christopher."

She stayed the night and we danced a full card of half-drunken debauchery. I woke up around 9 to the sight of her naked ass sashaying to the bathroom—a miles better jolt than any alarm bell.

Lisa told me she had to pick up her daughter from her mother's. I wanted her to stay.

As I walked her out, she reminded me of the previous night's warning. I told her I'd call in a few days and, this time, kept my word.

She's fun, I thought. It doesn't have to be serious. Why not give her a call? Over the next several months, more calls begat more time together. Lisa soon emerged as a Saturday night regular with Jackie and company. By the spring of '04, she'd separated from her husband and begun crawling towards divorce.

I did continue to see other women. I didn't advertise this to Lisa, but there wasn't yet any expectation of commitment. She was still married, anyway. Not to mention, she’d planned to pursue divorce before the safari session. In other words, she wasn't leaving the marriage for me.

Save about six nights a month with Lisa or the odd random, my life still revolved around poker. I had no expectation of fame or real riches. If I could pay the rent and lead a middle-class life, whatever that is, I’d be happy.

Late on a Saturday morning in April of 2004, I was in a dead-to-the-world sleep on the living room couch. The day before, I'd cashed into a poker game around 2 PM and played until 5 AM, Saturday. I got home a little before 6 and watched a Cagney flick on Turner Classic Movies until finally drifting asleep.

But then the godawful ringing phone got me stuck somewhere between sleeping and not. Once roused upright, I checked the caller ID and saw “Jackie Messina.” He'd called no fewer than five times since early Friday evening. That’s not like Jackie. I figured I better call him back.

"Where the fuck you been?" Jackie said. "Been callin' you since yesterday, you cocksucker."

"Yeah, I saw you called a bunch of times,” I said. "Put in a long one at the boat last night. Was still sleepin' when you called."

"Ah, right, okay," Jackie said. "When you gonna get a cell phone, you crazy fuck?"

"Fuck that,” I said. “You know I like to stay off the grid. Anyway, what's up?"

"Well, I don't know. I'm not sure, you know? Me and Freddie went bouncin' on Thursday and we ran into Kathy at Churchill's after dinner."

"Okay?” I said.

Jackie explained that talk of Lisa and I came up. Kathy scoffed when Jackie said that it looked like we might be getting serious. Lisa was just having fun, she said. Lisa had no plans to leave her husband. In fact, they'd just moved into a new home.

Jackie wrapped his Thursday-night replay, but I didn’t respond.

I hadn’t been all-in on Lisa, but the news stung. More all the time, I could picture us together once the divorce was finalized.

"You there?" Jackie asked.

"I'm here," I said. "I’m just thinkin’.”

"Yeah, okay," Jackie said. "Crazy though, no? You thought she was separated, right?"

Lisa told me they'd separated. She said her husband had moved into a newly built home, while she rode out the lease on the previous house.

Whenever we got together, she came to me. Her reason struck me as logical enough. It'd be difficult introducing her daughter to a new man in her life. She wanted to delay that delicate maneuver until the divorce went final, at the earliest.

"What the fuck, Chris?" Jackie said. "You there?"

“Yeah, I'm here," I said. "I'm just trying to figure what your angle is in all this, you know?”

It spilled out of my mouth. Almost like it’d been said by someone else.

"What?” Jackie hollered. "My angle? What the fuck you talkin' about, my angle?"

"I don't know, man. Forget it. I’m just thinkin' out loud."

"Chris, come on now. I got no angle here. You crazy?"

"Okay," I said. "Then what's the point of this fuckin' phone call?"

"The point is that you're my fuckin' friend. What the fuck, man? How long I known you?"

"Fuck, I don't know. Going on eight years, I guess."

"Eight years, okay," Jackie said. "All that time, how many times I seen you with the same broad more than like, I don’t know, twice?”

I laughed.

"Okay, then," Jackie said. "You see what I'm sayin'."

"No, not really," I said. "I don’t.”

"Well, I don't know, man," Jackie said. "I don't know where you're at here. Not for nothin', but seems like you might be fallin' in love with this broad a little bit."

I hesitated.

“Maybe,” I admitted. “I don’t know.”

"Yeah, look,” Jackie said. “I get it. Fuck knows I get it. Listen, that’s your business. Women are a real motherfucker, man. But I just thought you oughta know, you know?"

I thanked Jackie for the heads up and told him I needed to talk to Lisa.

“Okay,” Jackie said. “I gotta get goin’, too. You comin’ out tonight?”

“I don’t know,” I said. “Maybe.”

I clicked off the TV and sunk into the couch. Except for the faint sound of weekend traffic, I sat in silence.  

Jackie’s right. I might be in love with this broad a little bit. How’d that happen?

Relationships, and how they grow, defy all logic. They’re immune to the most rigorous post-hand analysis. I hadn’t considered the depth of my fondness for Lisa until Jackie mauled me with the news.

Halloween changed everything; or, at a minimum, allowed for everything to change. Though I'd held onto her number, it's unlikely I would've ever called. Randomness: bitch or blessing? In life, unlike gambling, you can't always tell right away.

And I blindsided Jackie with the angle remark. It shot from my gut like a thoughtless geyser. Jackie wasn't bashful about his love of Lisa's look. He ogled her ass more than I did. Might it be a ruse to get me off Lisa’s trail? Does he have his mind on a mother-daughter double?

Jackie’s iron stomach for stealing, cheating and violence played in my head. At Sam’s Wholesale Club to load up on supplies, Jackie would hide a 10-pack of bubblegum inside a case of snacks. The total might ring $600, yet he’d steal an $8 box of gum. Why? Why risk a huge headache for such little reward? Because he needed to get over on Sam’s somehow—he fucking needed it.

But since the early dispute over football bets, Jackie had done me no wrong. Every workday, he sprang for lunch and paid me in cash. He picked up every dinner check, spent a crazy sum on Derby night, and honored every bet. He once threw me 40 bucks just for driving him to the airport. Yet still, my instinct screamed “bullshit.”

I let it marinate in my mind and called Lisa the next day. She confirmed half of Jackie’s story. She told me the new house had been in the works since well before she wanted out of the marriage. Living in the new home, Lisa hoped to soon settle into an apartment and proceed with divorce. That’s the part her mother hadn’t been privy to. Lisa told me she hid the truth for fear of chasing me away.

At least I knew the score. What could I do but wait and see? In the meantime, I parked any thoughts of a proper relationship with Lisa.

So much for gut instinct, I guess. I felt foolish for ambushing Jackie. Why not speak with Lisa before accusing him of mischievous motives?

Over the next week, I burned valuable brain power trying to get a read on myself. That’s the sort of shit that happens when you live mostly inside your own head. But as well acquainted as my brain and I are, I couldn't dig up a decent reason to have not believed Jackie.

Merriam-Webster defines instinct as "a natural or inherent aptitude, impulse, or capacity” and “behavior that is mediated by reactions below the conscious level.”

The former makes me think of a mother diving before an oncoming train to save her baby. The latter happens in poker. The mind sharpens from weeks and months, hour after hour, of seeing every type of opponent and situation. After a while, even semi-tough decisions become routine. It springs from the subconscious, sure, but it’s been drawn from a deep, inner log of data. My Jackie instinct misfired despite having collected eight years’ worth of data.

I called him a few days later with Lisa’s side of the story.

"See?" Jackie said. "I told you, man. I mean, not that I was sure, you know. Just that it's what Kathy said."

"Yeah," I said. "I'll guess we'll see about the rest."

The following Saturday, we bounced into Churchill's about 9:30 to meet Jackie and Freddie. Rudy and I settled onto a small couch and Freddie wandered over. Brian stood at the bar, chatting with Jackie.

"What's new, guys?" Freddie asked. "No Val tonight, Rudy?"

Freddie loved Val. He treated her, like all the ladies, with an old-school respect. He'd open doors, pull out chairs and offer his seat in a crowded bar. And Freddie loved to dance. Even in his mid-60s, Freddie could tear up any floor. He danced with Val and any other willing women, but nothing creepy. Freddie classed up everything in his orbit.

"Yeah," Rudy replied. "She's gonna meet us up here later or over at Gene's."

"Good," Freddie said. "She's a good one, Rudy. What about Lisa?”

"Nah," I said. "She's not comin' out tonight. Guess we're gonna have to see how that goes, you know?"

"Yeah," Freddie said. "I was here when Kathy told Jackie about that whole thing."

"Jackie told me," I said. "I kinda went haywire on him when he told me. Really fucked that one up."

I assumed Jackie had filled Freddie in on our phone calls.

"What do you mean?" Freddie said.

"Well, I just wasn't sure what to make of it, you know? I jumped on him like, I don’t know. Like maybe he was fuckin’ with me."

"What?"

"I don't know," I said. "I don't wanna get into it. I just—I guess I didn't think he was being straight up with me. I don’t kn—Fuck it, whatever. It was stupid."

"Jesus, Chris,” Freddie said. "He wouldn't do that to you. Do you have any idea what he thinks of you?"

"I don't know," I said. "What do you mean?"

"He loves you. You too, Rudy. And Brian up there. He really loves you guys."

Rudy and I laughed.

"I'm serious,” Freddie said. "Lemme tell you guys something. Couple months ago, we were out to dinner and got talking about you guys. He said to me, 'You know what's so great about those guys? They don't want nothin' from me. They wanna go out and have a good time. That’s it. You always know where you stand with those guys.' He started talking about guys from back home who you thought were friends, but … Well, you know the kinda guys he means. Everybody trying to get something, you know. He told me you guys are about the best friends he's ever had."

A curious cocktail—one-part flattery, one-part depression—flooded my brain.

It depressed me not because I didn't think of Jackie as a friend. I did. But it brought visions of guys who’d made a million friends yet hadn’t a friend in the world. I'm the opposite. I've never called many people my friend, but the ones I have could be trusted in a tight spot. At the same time, it’s flattering to discover you’re held in high regard; more so by someone so radically different than yourself.

Jackie cut his teeth in a world contrary to ours. No matter how hard you try to imagine life in the other guy’s shoes, you don’t know what it's like. He’d lived over 40 years with his head on a swivel, wary of every smile.

Jackie had played the part of a real friend and I appreciated it. He harbored no animosity over my ill-conceived accusation. He never mentioned it again.

So, just in case I hadn’t already felt like a first-class jerkoff, Freddie’s heartfelt speech sealed it.

I looked at Lisa with a more cautious eye, but we continued to see each other throughout 2004. True to her word, the divorce ink had dried by early ‘05. She and her daughter took an apartment in south city, not far from Rudy and Val.

The proximity to Rudy and Val came in handy. With the poker boom offering peak earning potential, Rudy had begun playing full time, too. Most days, we’d roll to one of the area’s poker rooms together and play into the evening. I’d drop him at his apartment, then drive to Lisa’s a few blocks away. Closing in on 30, I’d locked myself into a committed relationship for the first time.

March 2005: It’s Not About the Money

It was a Saturday and the NCAA basketball tournament had swung into its third day. I trekked across town to pick up Rudy around 5.

Cruising back to my neighborhood, we stopped at a deli to pick up dinner. As Brian liked to say, "Gotta get a good base. Never wanna do any serious drinkin’ without a solid base." We planned to eat, drink a few beers and watch some hoops before hitting the town.

Brian and I lived on the top floor of an old place we loved. The living room ceiling vaulted to about 20 feet, and a talented, troubled crew—Babe Ruth, Stuey Ungar, Miles Davis, Jimi Hendrix and James Brown—kept close watch from the walls. Brian’s girlfriend once said, "It’s such a weird vibe in here. It's like this real classy place, but then someone dropped in grandpa's furniture and turned it into a frat house." She made a solid read.

Sweating the ball games, we slammed our beef and cheddars and cracked open the beer. We’d all invested money in various pools. If my brutal bracket history held, I'd be setting mine ablaze before the buzzer sounded on Sunday's games.

Well before 9, I'd tired of hearing myself whine. With shots dropping from the third deck, every game looked like a reprise of the movie Pleasantville. Nailed by teams I needed to lose, of course.

"Fuck this," I said. "I feel like playin' cards."

"I'll play," Brian said.

"I'll always play," Rudy chimed in. "Kinda blows with only three of us, though, you know?"

We called a couple of usual suspects but couldn't find anyone on late notice.

"Fuck it,” Brian said. "We oughta call Johns."

We never called Jackie "Johns" to his face, but it'd become something of a running joke. The name cracked us up. It seemed unbefitting of such a proud paisan.

"What the hell," I said. "He might play. Call him, B."

“It’s barely 8:30,” Rudy said. “Maybe we snag him before he gets to Churchill’s.”

Brian flipped his cell open, 2005-style, and bounded away to grab a beer. Just as he returned, he snapped the phone shut.

"He just got done with dinner at Bar Italia,” Brian said. “Said he’s gonna finish a glass of wine and head over.”

"Nice," I said. "I guess let's haul in the table and set the shit up."

Brian and I didn't own a proper poker table. We lugged the kitchen table into the large living room; better to hear Hendrix and bitch about basketball. A closeted, devoted masochist, I craved the misery.

We'd about chopped up the chips when a soft knock struck. Jackie didn't wait to be let in.

"Hey,” Jackie said. “There they are.”

His suit smacked me upside the head: white jacket, black shirt, black tie, black slacks and two-tone, white-on-black loafers. Even accounting for Jackie’s closet, the ensemble soared to the top of the what-the-fuck charts. Whatever. Ten shirts hung in my own closet at a total cost of about 50 bucks. Who was I to judge?

Jackie clinked a bottle of red wine down on the glass-top coffee table.

“Okay,” he said. “What are we playin'?"

I grabbed a glass for Jackie's wine and a beer for myself.

I never drank anything stronger than sugar-free Red Bull when playing for real money. I might've been a small-time grinder, but friendly $20 freeze-outs didn't qualify as serious business even by my low-rolling standards.

In a freeze-out, each player ponies up a predetermined amount and starts with a set number of chips. Play continues until someone collects every chip on the table. With a modest prize pool of $80, the winner would receive $60 and the runner-up his entry fee back.

A 25-year-old, neon Busch beer sign and a reading lamp lit the room. Jackie removed his jacket and got comfortable. I sat facing the TV, across from Brian; Jackie to my left and Rudy to my right. Brian won the deal and the cards were in the air.

A pitching coach, Brian didn't spend much time in casinos. He'd been playing poker since his early-teens, though, in home games and baseball road trip hotels. Jackie? All the time I'd known him, we'd never played together.

The first few hands were uneventful; a couple of raise-and-take-it pots and a flop bet winner for Rudy. Jackie took his turn to deal. He looked a little awkward gripping the deck; his shuffle wasn’t any better. Toss in a tad clumsy with his chips and it looked like he hadn’t played much.

Another orbit and Jackie again held the deck. Dealt two Jacks, I raised three times the big blind. Jackie called, but Brian and Rudy surrendered their blinds. Jackie spread a rainbow, 8-high flop—not bad for a pair of Jacks. I cut out a pot-sized bet and Jackie called. The turn paired the low card on board and I bet again. Jackie called. A 10 turned up on the river and, exercising caution, I checked. Jackie hadn't yet shown down a hand, so I planned to call any sane bet he slid to the middle.

He bet about half the pot.

"Okay," I said. "I call."

"Full house," Jackie said, flipping over two 8s.

"Fuck," I said. "Good hand."

I didn't think I could beat much he'd bet, but I couldn't fold an over-pair versus an “unknown” opponent. Poker is a game of incomplete information. I’d gleaned a little more on Jackie, at least.

The World Series of Poker uses the freeze-out format and plays out over several days. We'd designed our contest to reach a quicker conclusion. The stacks started shallow, so the Jacks left mine ready for the kiddie pool.

Jackie strung a few winning hands together and jumped to an early lead.

Jimi’s "Foxy Lady" filled the room.

"I hate this fuckin' song," I said, clicking ahead to the next.

"I never really got into Jimi Hendrix or any of that," Jackie said. "Rolling Stones, The Doors. No Woodstock shit, you know?"

"Pretty sure the Stones weren't at Woodstock," Brian said.

"Neither were The Doors," Rudy added.

"Oh, fuck you guys," Jackie fired back. “I just mean all that drugged-up, hippy shit. You guys know what I mean."

Everyone laughed.

"Doo-wop and soul music was all I listened to growin' up." Jackie said. 

"I got some Dion over there," I said. "Little 'Runaround Sue' make you happy?"

"Nah, no, no,” Jackie said. “Play what you want. Was just sayin’. And Dion’s Italian you know.”

“DiMucci’s Italian?” I asked. “No shit?”

Jackie's phone vibrated and volleyed off his chip stack. I could see the caller ID: "Martin."

"What's up, sir?" Jackie said, answering the phone.

We stopped the action, so Brian took off to take a leak.

"Yeah, yeah, I'm over at cuckoo Chris's,” Jackie said. “You remem—yeah, right, the Marlins motherfucker.”

Rudy and I looked at each other and laughed. Over a year later and still crying? You would’ve thought I beat him out of 12 grand instead of $1,200.

"I'm playin' cards with him and his brother and Brian. Yeah. You met those guys, right? Yeah, Chris and Brian live together. We're just playin' some cards before we go to Pepper Lounge."

"What's that?" Jackie said. "Huh? Oh, yeah-yeah, right. Martin wants to know if you been shootin' dice down at Churchill's lately," Jackie said to me.

The first time I met Martin, I'd joined he and Jackie at Churchill's on a summer night. We hit it off right away, talking sports and horses on the patio.

Martin dressed sort of like Jackie, but not as loud. He somehow seemed more refined, too. He spoke with a faint, but discernible east coast accent; his deep, I-got-a-nice-life tan earned on the beaches and golf courses of Sarasota-Bradenton. "Near my father," Jackie later told me. 

When Martin popped up to use the bathroom, Jackie hit me with the backstory.

"Whaddya think of Martin?" Jackie asked.

"He's a nice guy," I said.

“Yeah, yeah. Good guy. From Boston.”

“Okay,” I replied. “Was tryin’ to make out that accent. He seems really fuckin’ sharp to me.”

"Oh, yeah," Jackie laughed. "That's a smart motherfucker, Chris. You wanna how sharp he is? Back home, in the clubs, Martin dealt craps for a while. Fuckin' guy could run a whole table by himself."

"Wow," I said. "I made a good read, then. That’s pretty impressive.”

"No shit,” Jackie said. "Fuckin' solo, man. He calculated the shit so fast, it'd blow your fuckin' mind."

Later that evening, Martin and I saw two kids shooting dice about 60 feet from Churchill’s patio. We wandered over and tossed in 10 apiece. We took a couple turns with the red cubes, then left our stake with the promising, young action freaks. The score prompted big smiles from the boys and was easily the best 10 bucks I spent that night.

"Yeah," Jackie laughed into the phone. "Okay, yeah, I'll talk to you."

Jackie hung up with Martin just as Brian rejoined the table.

The break did nothing to cool Jackie’s heater. Before long, his soaring chip tower looked unbeatable. Short-stacked and desperate, I shoved all-in with a modest holding. Brian called and bounced me from the table when my hand didn’t improve.

“Okay,” I said. “I’ve had enough Jimi.”

I rummaged through the CDs and settled on the Dead Presidents soundtrack—a nice mix of old-school soul that’d keep everyone happy.

Rudy joined me on the rail when his ace-10 couldn’t outrun Jackie’s two Queens.

“Jesus fuck, Jackie,” Rudy said. “You’re a hand-makin’ machine tonight.”

“I know,” Jackie said. “Crazy, huh, Rudy? Never got dealt so many pocket pairs in my life.”

Rudy cracked a fresh beer and kept me company on the couch.

“You know,” I said. “I gotta quit getting in these fuckin’ pools. Am I the unluckiest motherfucker around or am I the fish? Either way, I’m tired of spraying the money hose. How the fuck did you do it?”

Rudy had had a four-figure score the year before and could only laugh. He had no desire to entertain my musings on tourney mishaps. Nothing tilted me like the annual March massacre.

Brian hunkered down, hoping to ride a wave of hot cards to a comeback. It didn’t happen. Jackie secured the $60 first prize and we agreed to run it again.

The new game did nothing for my luck; I limped around like a three-legged donkey. Jackie, though, blazed along like Secretariat in the ’73 Belmont.

“Goddamn, Jackie,” I said. “What the fuck? I never seen anything like this.”

“I know,” Jackie said. “Nuts, huh?”

A bit later, Jackie ripped off another pre-flop raise. Rudy cut out chips for a call to make it heads-up. The flop turned up Jack-high. Rudy checked, Jackie bet and Rudy called. The turn and river brought two babies and Rudy check-called all the way down. Jackie rolled over two Queens, topping Rudy’s ace-Jack.

“Wow,” Rudy said. “What a show.”

Wait a fucking second. Jackie dealt that—again. How many of these hands has he dealt? Okay, wait, let’s think about this. He’s been hitting cards all night; dealing or not, right? Yeah, he’s been hot, but sure seems like a helluva lot hotter on his deal.

I studied Rudy to gauge his reaction; maybe catch his eye. But he didn’t see me because his gaze was glued to Jackie.

Brian, Rudy and I had been tearing through the beer for some time. Low stakes with a friendly line-up or not, I needed to pay closer attention.

Hoping to get lucky, I splashed around in too many pots and again took the dreaded F.O.—first out. I’d screwed my concentration tighter, but not on playing good poker.

The basketball games had ended, so I stayed in my seat to sweat the action—and Jackie. Jackie again had the deal and slid out a standard raise. Brian called and Rudy folded. The flop came ace-high and Brian checked. Jackie bet and Brian reached for his bullets, counting out a raise. Jackie paused for a few moments.

“Okay,” Jackie said. “I’m all-in.”

Jackie’s stack covered Brian’s, but Brian quickly called. Jackie turned up two aces to make three of a kind.

“Ha,” Brian hollered. “You gotta be fuckin’ kiddin’ me, dude.”

Brian flipped his ace-King. Drawing dead to running Kings, Brian missed the miracle and busted out. As Jackie raked the pot, I looked across the table. About five seconds later, Brian stared me dead in the eye and tilted his head back.

 “Welp,” Brian said. “I think I’m due for a beer after that.”

 Brian got up and walked towards the kitchen.

“Yeah, me too,” Rudy said. “Jackie, you mind if we stop for a minute? I gotta piss.”

“Nah,” Jackie said. “Go ahead.”

“I gotta call Lisa real quick,” I said. “Told her I’d holler before we head out.”

Past the kitchen, I turned the corner to take the couple steps to my bedroom. I found Brian and Rudy whispering to each other, outside of the bathroom. Rudy waved me over.

“Dude,” Rudy said. “This is total bullshit.”

“His dealing?” I asked.

Rudy and Brian both nodded yes.

“Yeah,” I said. “It’s really fuckin’ fishy.”

“Nothing fishy about it,” Brian said.

“Fuck, no,” Rudy said. “I thought the way he gripped the deck was shady right away. And that jacked-up shuffle? Fuck off.”

“I know,” I said. “It’s really screwy.”

“Rudy,” Brian said. “You’re so short, just shove all-in every hand ‘til you lose or get lucky a few times. Then, I say we start another.”

“Why?” I asked. “Let’s just call him out.”

“I was kinda thinking like Brian,” Rudy said. “Fuck the money. I wanna see how ridiculous he gets with it.”

“Exactly,” Brian said.

“Okay, whatever,” I said. “I gotta piss. Get back out there before he comes back looking.”

I’d hoped they hadn’t seen it the same as me. I called Lisa, as promised, but didn’t tell her about Jackie’s full house fiesta.

I returned to the living room and saw the guys divvying up the chips for round three.

“Guess you polished it off, Jackie?” I asked.

“Yeah,” Jackie said. “He went all-in first hand. I called with ace-high and held on.”

I nodded.

“He was so low,” Jackie added. “Had to call, you know?”

The first few orbits of game three didn’t bring much action. Jackie’s third deal, though, set Rudy steaming. 

Jackie raised, Brian called and they took a two-way flop. The disjointed board ran out 10-high and Brian check-called all the way. Jackie tabled two Kings.

“You got it,” Brian said, giving us a peak at his pair of Jacks.

“What’d you have?” Jackie asked.

“Not much,” Brian said. “Just a pair.”

As Brian scooped up the cards to shuffle, Rudy cut loose.

“Jackie, do you really think I don’t know what’s goin’ on here?”

I knew what was coming as soon as Rudy said “Jackie.” I’d fixed my eyes on Jackie before Rudy even finished.

“Whaddya talkin’ about?” Jackie asked, looking confused.

“Oh, fuck, dude,” Rudy said. “Get off it. How fuckin’ stupid do you think we are?”

“Rudy, what?” Jackie said.

“Jackie, the set-ups on your deal are fuckin’ unreal. I mean, how many coolers’ve been on your deal?”

“What the fuck, Rudy?” Jackie said, raising his voice. “I don’t know what the fuck you’re talkin’ about.”

“Jesus Christ, Jackie,” Brian said.

“I really don’t know, Brian. Whaddya want from me? I been hittin’ hands all night, no matter who’s dealin.”

“Oh, you were,” Rudy said. “Way more on your deal, though. And it’s not so much the hands as the fuckin’ set-ups. The three aces vs. Brian’s ace-King, that last one, the one on Chris early. That’s not even half of ‘em.”

“Guys, c ‘mon now,” Jackie said. “You really think I’d come in here and cheat you? Really?”

“Jackie, c ’mon,” I said. “Let me ask you this. You think we’re just pissed about losing and pulling this out of our ass?”

Jackie looked at me but didn’t reply.

“Dude,” I said. “We all thought it without even talking. You think we all just came up with this outta the blue? I mean, what the fuck? Like we’re makin’ this shit up?”

I popped up and left the room without knowing where I was going. I walked into my bedroom and could still hear them going at it. I used the bathroom, then picked up a beer and a baseball bat—a Louisville Slugger Darryl Strawberry model—on my way back.

The Strawberry bat was a relic from Brian’s childhood. Knowing my long-running love of all things Straw, Brian had gifted me the bat. I’d no intention of using it; I’m not even sure why I picked it up. Instinct for self-defense, maybe.

“He admitted it,” Rudy said, as I got back to the living room.

“What?” I said.

“He was fuckin’ with the deck from the get,” Brian said. “Just like we said.”

“You motherfucker,” I said. “What the fuck is wrong with you, man?”

Even though I’d been near certain, I seethed at the admission.

“Chris, listen to me, man,” Jackie said. “I was tryin’ to tell these guys. I was just workin’ on my game, that’s all. Me and Martin gotta game in Memphis in a few weeks.”

“Jesus Christ,” I said. “You’re so full of fuckin’ shit. What the fuck are you talking about?”

“We gotta a game with some guys in Memphis, me and Martin. You ‘member when he called earlier? Chris, I told him—I told him I was playin’ cards and he said, ‘You workin’? You gettin’ ready?’”

“Oh, fuck, dude,” I said.

“Pretty neat,” Brian said. “Gettin’ ready for the big game by cheating your friends.”

“C ‘mon, Brian. Guys, listen. I’d never fuck you guys over.”

“You been doing it all night, Jackie.” Rudy said.

“Rudy,” Jackie said. “Guys, I didn’t even know if it’d work, you know? That’s why I needed to work on it. You know, my shuffle or whatever. If I won, I was gonna cover everybody at Pepper.”

“I mean,” I said. “This is just fuckin’ unreal, man. Really, just flat out fucked up. You come in here and pull this shit?”

When people say, “it’s not about the money,” it’s almost always about the money. If we’d played with no money on the line, and Jackie pulled the same antics, would we have been so upset? No way.

At the same time, not so much as a snack would be missed over the amounts contested. Then what, then? Was it really about the money? No way.

I stood up, bat in hand.

“Jackie,” I said. “Why don’t you just get the fuck outta here.”

“Chris, Chris, c ‘mon, man. You wanna leave it like this?”

“What else is there?” I asked. “Like a scumbag, you came in here and cheated your friends. You got your money. So, that’s it, I guess.”

“It’s really horseshit, Jackie,” Rudy said. “Who does that?”

“Rudy, guys, c ‘mon. I’m tellin’ you, it’s not about the fuckin’ money. A hundred somethin’ fuckin’ bucks? C ‘mon now, guys, you really think I give a fuck about that money?”

The question ramped up my anger.

“It sure fuckin’ looks like you do,” I shot back.

Brian and Rudy arose from the table, as well.

“Jackie,” Brian said. “I think you gotta go, man.”

Jackie shifted into self-preservation mode.

“Guys, guys, c ‘mon now,” Jackie said.

He scooted his chair back and popped up, then backpedaled for the door.

“Look, look,” Jackie said, pulling a wad of cash from his pants pocket. “Let’s make this right. What is it? A hundred ‘n twenty, right?”

He feared it might get physical. Three guys in their mid-to-late 20s—one of whom held a Louisville Slugger—versus the graying gangster in his mid-40s. Brian, glaring down from his lofty 6’5” perch, only added to Jackie’s unease. The math made him a big underdog and he knew it.

It gave me the best peek ever at what Jackie’s life had been like. The block he comes from, guys get busted up over money no matter how small the amount. That much was clear.

“Keep the money,” I said. “You obviously fuckin’ need it.”

“No-no, here, Chris, take it,” Jackie said, leafing off the 20s. “And, and like I said, I got you guys at Pepper.”

Scrambling now, Jackie had never seemed so small—in every sense.

“Keep the fuckin’ money, dude,” I said.

“Chris, what the fuck, man?”

I shrugged.

“Okay, fuck it—fine.” Jackie said, slipping the cash into his slacks. “You guys still comin’ to Pepper? C ‘mon, c ‘mon down there. I gotta make this right.”

“I don’t know,” I said. “I’ll see you around, man.”

I set the bat against the wall and walked away. Two seconds later, I heard the door shut.

July 2013: Seven Years Gone

“Hey dude, what’s up?”

It was Julie calling from home. No longer 24, she was still tomboyish and still blonde. And despite the curtain having fallen years prior on our long, distinguished Sammie's careers, we'd never lost touch.

“You’re leaving tomorrow, right?” Julie asked.

My dad and I planned to leave on a road trip the next day, bound for Saratoga Springs, New York. For seven weeks every summer, Saratoga Race Course hosts the finest thoroughbred race meeting in North America. Since the Civil War, the best horses, trainers and jockeys, not to mention droves of gamblers, descend on Saratoga. And everyone’s looking to make a score.

My dad had suggested the trip after I'd strung together several winning weeks at the poker table. When he offered to cover the outrageous hotel costs, it was a no-brainer. There is no place on earth I’d rather be than Saratoga in the summertime.

Julie asked that I swing by that afternoon before I hit the road, and I agreed.

I climbed the steps to Julie’s second-floor apartment and let myself in. Immediately, my ears were greeted by the awful clatter of cable news booming from the TV. And then I saw, sitting on the couch and scrolling through his phone, none other than Jackie Messina.

“Look at this guy,” Jackie said.

Julie played only a bit part in the Saturday night Jackie story, but she dated Jackie’s buddy, Black Bill, for a while, and got to know Jackie better in the process. In town for a few days, he’d stopped in to say hello.

I hadn’t seen Jackie in almost seven years. Though he’d retained nearly all his hair, the black and gray had turned silver and even white. Reading glasses sat on the end of his nose.

Things between us had never been the same after the poker game. We did still see each other at the Pepper Lounge, talking sports and sharing a few laughs. No longer, though, did we make definite plans to meet up. No more boxing matches or dinners, and certainly no more poker games.

The Saturday-night crew slowly splintered off. By six or seven months after the poker game, Brian had moved in with his girlfriend, and Rudy and Val were moving towards marriage. A night out for me meant Lisa and I going to dinner and finding some live blues music.

“Hey, man, what’s up?” I said. “Julie told me you were in town.”

I hadn’t, however, expected to see him and wished Julie had shot me a heads-up. She loves surprises. I fucking hate them.

Julie had been in the kitchen, on the phone with her mother. She joined us for the Chris-Jackie reunion soon after she heard me walk in.

“So Julie says you’re going to Saratoga, huh?”

“Yep,” I said. “Leaving tomorrow.”

“Nice,” Jackie said. “You been there lots of times, right?”

“Yeah, but it's been a few years. You been there, right?”

“Oh yeah,” Jackie said. “Yep. Went a few times back in the day. Lotta fun up there.”

“What’s the ‘C’ stand for?” Julie chimed in, gesturing to my Cleveland Indians baseball cap.

“Stands for ‘Chris,’ you silly bitch,” Jackie laughed.

The more things change … Never mind. Shit changes but people don’t.

Jackie turned his head and pointed to the TV.

“Lemme ask you something, Chris. Whaddya think about all this fuckin’ terrorist shit? The Middle East? You know, all that shit.”

Nothing like a little light-hearted conversation. We bounced a few opinions back and forth, but not much else. Jackie summed it up nicely: “Lotta crazy motherfuckers in the world, huh?”

After about 30 minutes, I’d had enough. I told Julie I still had to run some errands and pack for the trip. Jackie had a business meeting to get to, so we walked out together.

“Alright,” I said. “Good seeing you, man.”

“Yep. You, too. And good luck at the track. Hope you get all the money.”

“Thanks,” I said. “Already got the Brinks reserved.”

Jackie laughed.

“I’ll see you,” I said.

“Yeah,” Jackie said. “Take it easy, man.”

Car doors pulled shut, we both went on our way.

The day after I got back from Saratoga, Julie called and I brought her up to speed on the trip. She asked if I wanted to grab some dinner and watch a movie.

I picked her up early in the evening and we took off to pick up Chinese.

“So, anyway,” Julie said. “I was talking to Jackie before he left town and your name came up. He says you’re way too smart to still be scraping around in poker. He said, ‘Chris oughta be doing something more constructive.’”

“Now that’s pretty sweet,” I said. “Gotta love some career advice from Jackie.”

“Oh, dude, stop. I thought it was nice. And by the way, you never really said. What’d you think about seeing him? It’d been a long time.”

“Hell, I don’t know. Kinda shocked at first, I guess. But then, I don’t know. It’s weird. It’s like we just pick it up like old times, you know?”

“Yeah,” Julie said. “Cracked me up when he went into the terrorist stuff.”

“You know,” I said. “One thing I’ll say: I was blown away how old he looked. Kinda hit me how long it’d been when I saw him. He seems way older to me.”

“No way,” Julie said, bursting into a fit of laughter. “That’s hilarious.”

“What the fuck’s so funny?” I asked.

“It’s funny,” Julie laughed. “Because he said the same thing about you.”

EPILOGUE
 

September 2013: Facts Are a Real Motherfucker, Huh?

Jackie killed the boxer.

Well, I guess I can’t say for sure. But I’d bet every buck I could raise that Jackie either killed him or paid the guy that did. Jackie’s father was likely involved, as well.

Do you remember the boxer, Eric Miller? Thanks to a Google search, news of his still unsolved murder landed on my laptop screen at 5 AM Yeah, him. And a Google search, by the way, that came about a month after seeing Jackie at Julie’s apartment. The power of suggestion is real.

On August 31, 2013, the Hartford Courant ran the story following the death of Jackie’s dad, John “Sonny” Castagna. The investigation into Miller’s 1988 murder had recently been revisited. As they had all along, Jackie and his dad topped the persons-of-interest list.

According to the Friday, December 30, 1988, edition of the Courant, Miller “was found slumped over the wheel of his 1988 Chevrolet Blazer … early Wednesday with gunshot wounds to his head and neck …”

Miller was a low-level professional boxer living in Hartford, Connecticut. In addition to fighting, he managed a boxing gym and piled up extra cash selling cocaine. Always hustling, Miller moonlighted as a sometimes debt collector, driver and bodyguard for Jackie and his dad. Jackie even became a regular at Miller’s gym. In September 1988, less than four months before his murder, the beginning of the end of Eric Miller’s story was likely written.

Miller pulled up one afternoon at Franco’s, a popular South End spot for lawyers, gangsters and politicians, to meet Jackie and his dad for lunch. He found Jackie, who owned a landscaping business, laying sod in front of the restaurant. Miller asked what the badass gangster was doing on his knees, working in the grime. What followed was no different than the good-natured bomb tossing I saw between Jackie and The Jews. With a few people looking on, the two men laughed and traded insults of “guinea” and “mick.” One onlooker was Jackie’s dad. Another was William “The Wild Guy” Grasso, then underboss of the Patriarca crime family.

The Patriarca family had long reigned as the Mafia’s faction in New England—based in Providence, Rhode Island, but also strong in Boston, Massachusetts and Hartford. His dad was a full-time wiseguy and Jackie was on his way. Befitting his nickname, Grasso became enraged at Miller’s disrespect toward a rising member of the outfit.

Grasso grabbed a shovel and a gardening knife, then moved in on Miller. The men stood toe-to-toe when Jackie and his dad stepped in, trying to separate them. But tensions rose, obscenities flew and Miller finally had enough. The prizefighter cocked his arm back and let it go, landing a punch that knocked Grasso to the pavement, out cold.

Laying your hands on a made man is bad shit, and almost certainly spelled Miller’s doom. Five days before Miller’s lifeless body was found, a safe, containing drugs, valuables and cash, got lifted from the apartment he shared with his girlfriend.

According to Miller’s girlfriend, Jackie called their home on the night of December 27, 1988, and spoke with Miller. Soon thereafter, Miller left and she never heard from him again.

The discovery that a once good friend is a killer, or, at a minimum, neck-deep in the plot, delivers quite a punch. It’s sort of like driving down a quiet, country road and suddenly having a brick blast through your windshield. But there’d be time for perspective later. I needed to know more; namely, the details regarding Jackie’s entry into the Federal Witness Protection Program.

Back to the Google machine for more on Jackie.

On March 26, 1990, the Associated Press reported: “FBI Nabs Reputed Top Crime Figures, Tapes Mafia ‘Blood’ Rite.”

Twenty-one alleged New England mobsters were named in the 113-count indictments, including “reputed boss Raymond ‘Junior’ Patriarca, who is the son of the region’s late reputed mob leader…”

According to the AP:

FBI agents fanned out Monday over Massachusetts, Rhode Island and Connecticut to arrest the alleged criminals on a range of charges including murder, racketeering, kidnapping, drug trafficking, gambling, obstruction of justice and witness intimidation. 15 of the 21 were in custody Monday afternoon … Lawyers said three suspects, Gaetano J. Milano, 39, of East Longmeadow, Mass, John F. Castagna, 49, and his son, Jack Johns, 29, both of Hartford, were expected to surrender Tuesday.

Surrender? Not the Jackie I know. Then again, a federal jam is no ordinary jam.

The indictments were the culmination of a five-year investigation. Authorities even obtained recordings of the Mafia’s blood initiation ceremony. Given the tapes, it’d be tough for the suspects to deny their organization’s existence.

Fast forward more than one year later, to May 4, 1991, and Jackie had landed in The New York Times. The headline read: “Mafia Trial in Hartford Opens with Guilty Plea.”

According to The Times:

The murder and racketeering trial of nine reputed members of New England’s largest organized crime family began in Federal District Court here this week … The case will include testimony from two former Patriarca associates, John F. Castagna and his son, Jack Johns, both formerly of Hartford.

In return for reduced sentences, they are expected to testify about the 1989 murder of William Grasso of New Haven, the underboss of the Patriarca family. The two have pleaded guilty to racketeering and are now protected witnesses. They are expected to testify that the killing was part of a feud between family factions, and to implicate four defendants: Gaetano J. Milano, Frank A. Pugliano, Louis F. Pugliano and Frank Colantoni Jr.

There it was in black and white: Jackie and his dad had cut a deal. And that’s the same Grasso that slumped to the sidewalk, unconscious, courtesy of Eric Miller’s pro-style punch. He’s dead, too?

On June 18, 1989, The New York Times chronicled the “murder of the man reported to be the most important mobster in Connecticut,” William “The Wild Guy” Grasso. His body was found near a bank of the Connecticut River in suburban Hartford, half-submerged in water.

And so, father and son were the federal government’s star witnesses. Courtesy of the Hartford Courant, snapshots of the trial:

June 3: Jack Johns, Castagna’s son and the second half of the father-son informant team, takes the stand. He tells about three attempts to kill Grasso, and about finally watching as Gaetano Milano, one of the defendants, shot Grasso in the neck.

As part of their plea agreements, Jackie and his father had told authorities of their involvement in Grasso’s death. They both testified to being part of a “renegade mob faction” in an ongoing family power struggle, and Grasso was a key target. After three failed attempts on his life, Grasso finally went down on the fourth.

According to Jackie’s testimony, Milano fired the fatal bullet as the gangsters traveled along I-91 in a customized van. Jackie was hidden in the back, charged with shooting anyone that may have interfered with Grasso’s execution. Once he heard the shot, Jackie said he popped out, and, after grabbing Grasso by the hair with his free hand, pulled him into an upright position. In the other hand, Jackie gripped a pistol. The defense lawyer asked Jackie which hand held the hair and which hand held the gun.

“I dribble with my left and shoot with my right,” Jackie said.

What did Jackie see after Grasso was shot, the lawyer asked.

“A dead guy,” Jackie replied.

Any shred of doubt I might have had that I’d found the right Jackie …

And that wasn’t all. The jury listened to a recorded conversation between Jackie and Louis Pugliano, one of the defendants charged with plotting and carrying out Grasso’s murder. Just weeks removed from his decision to cooperate with authorities, and strapped with a body microphone, Jackie spoke with Pugliano on August 16, 1990. No one had yet been charged with Grasso’s murder.

Jurors heard Jackie move the conversation toward Gaetano Milano, also a defendant in the Grasso murder wrap, and, according to Jackie’s testimony, the trigger man.

"You think he [Milano] told them that he shot Billy [Grasso]," Jackie asked, "and he's looking to make a deal?"

"No. Course not," Pugliano replied. "You gotta be (expletive) whacky to do a thing like that."

Eventually, Pugliano would learn the unwelcome news: Jackie was the “whacky” one.

Judging by Jackie’s dad’s testimony, it’s safe to say he didn’t miss The Wild Guy’s company. Regarding Grasso, he said, “… He had a big ego. He treated everybody harshly. Old women. Kids. Everybody. He would threaten people over money, anything. It depended on how he felt when he woke up. If he was in a good mood, he would be all right. If he wasn't, he'd be nuts.”

June 18: Dr. William Rodriguez, a forensic anthropologist with the U.S. armed forces medical examiner’s office, uses a pointer to identify tiny bone fragments mounted on white posterboard. The bones, from three men, were taken from a mob grave in Hamden where Johns said he, Grasso and defendant Salvatore “Butch” D’Aquila Jr. buried the body of a Boston man in 1986.

The makeshift cemetery, in Hamden, Connecticut, belonged to a man once associated with a New Haven bank robbery gang. The location? A garage behind the bank robber’s locksmith shop. Grasso had rented the space for some time to bury mob victims. As part of Jackie’s deal, he led authorities to the site. The grave had clearly been disturbed and any bodies removed, but bone fragments did remain. That was good enough to identify at least one victim.

Jackie testified that he’d helped bury the body of Boston-area hotel executive, Theodore Berns. A portion of the remains were positively identified as those of Berns. And why did Berns meet such a brutal end? He’d been having an affair with a mob associate’s wife.

Grasso’s murder and the garage-cum-grave highlighted Jackie’s testimony, but there was more. He recounted a lengthy criminal past that included robbing drug dealers and beating people with baseball bats.

Of course, I hadn’t known about a murdered boxer, The Wild Guy or Patriarca burial grounds. But drug-dealer robberies and baseball-bat beatings? Now those sounded familiar.

Hartford Courant July 9, 1991: “Defense Sets Out to Counter Prosecution Case”

Nearly all the government evidence concerning the Grasso murder came from informers John F.“Sonny” Castagna and his son Jack Johns … Defense lawyer Jeremiah Donovan used five of the government’s recordings in an effort to weaken the prosecution claim that his client, mob soldier Louis Failla of East Hartford, conspired to murder his son-in-law, Luis “Tito” Morales.

Prosecutors have charged a murder contract was placed on Morales because he was disrupting mob rackets on Franklin Avenue in Hartford, in particular a card game Johns ran in the Roma Café. In addition, Castagna and Johns were convinced Morales arranged to have Johns beaten with a lead pipe late one night in September 1989.

Tito? I know about a Tito.

Tito Morales lived for a while on Adelaide Street, which then was also the address of John “Sonny” Castagna, an associate of the Patriarca crime family and one of Hartford’s most notorious gangsters. Morales became friendly with Castagna’s son Jackie Johns, and the two men went into business robbing drug dealers, according to law enforcement sources and court records.

Jesus Christ, it’s him. Tito “knew all the Dominican drug dealers … We went into business robbin’ every one of those motherfuckers,” Jackie once told me. Unreal. Not that I didn’t believe Jackie’s story … I don’t know. I guess I never expected it to be confirmed via newspaper.

Anyway, Louis Failla was a sworn Patriarca soldier and one of the defendants. Among other crimes, Failla was charged with conspiring to murder Tito, the father of his grandson. Failla’s attorney, Jeremiah Donovan, argued that Failla was the only reason that Tito (by then, in prison; he’d been nabbed selling eight ounces of cocaine at a mall) was still alive. Failla knew about the plot, sure, but it was Jackie and his dad that wanted Tito dead.

In his book, Storytelling for Lawyers, Philip Meyer chronicled Donovan’s trial tactics:

“Donovan employs sequences of scenes depicting the characters through their actions … First a sequence of scenes displays the bad blood between Morales and the mob henchmen (Jackie and his dad). In one scene, Morales, who had once been a partner with young Jackie Johns in various Hartford crime activities, was arrested. In another scene, the dialogue between Castagna and Johns reveals their belief that Morales thought they had turned him in to police. In another scene, again reenacting transcripts from recorded surveillance tapes, Johns and Castagna tell Failla that Morales can implicate them both in the murder of a young boxer named Eric Miller … ‘Tito Morales, who knows about what happened with the other kid [Eric Miller], can get Sonny and Jackie into some pretty serious trouble.’”

Donovan told jurors about an emergency call Jackie had received from his dad. The call came shortly after Jackie’s dad spotted Tito strolling into the federal building. Donovan addressed what may have been the reason for the call:

“…They’re worried Tito Morales is going to go in and spill the beans that these were the guys who murdered Eric Miller [on the order of Billy Grasso]. They’re scared that he’s going to go in and tell them all about … Jackie Johns’s counterfeiting and drug activity …”

In closing arguments, one of the defense attorneys called Jackie and his dad a “kind of cross-genetic horror show” that shouldn’t be believed. Sarcastically referring to father and son as “the dynamic duo,” the defense argued that they’d fooled the government with fairytale stories.

I can’t speak for jurors, fairytales or the federal government, but I know all about being fooled. And yet, it all seems so obvious now. Not the dirty details, but …

Recently, a friend asked if I’d been a doubting Thomas and I replied, “Yeah, probably, but what kind of badass New York gangster lives in fucking Missouri, selling cars?” After staring at me for a few seconds, waiting for me to answer my own question, he said, “U-hhh, one that’s in the witness protection program?” Good point, smart guy.

I guess Steve had it right from the start. Jackie was locked up before moving to the Midwest? Check. Baseball bat beatings? Yep. Jackie was told to leave New York? Not exactly, but close enough.

The extent of Steve’s knowledge, though, remains unclear. He never returned to Sam’s, and I haven’t seen or talked to him. His friendship with Jackie cooled considerably, and Steve rarely came up in our conversations.

Long before any revelations of the “real” Jackie, I figured my friends and I got screwed on the football bets. Steve grew up in the Italian enclave of the St. Louis Hill. Since meeting Jackie outside of that nightclub, he’d shifted from a “fruity, pink Polo sweater, tied ‘round his neck,” to a hideous collection of suits and ties. It’s not hard to imagine Steve dancing to Jackie’s tune, just dying to show Jackie how agile he’d become. Steve wouldn’t have won any IQ competitions, but there’s little chance he screwed up the bets that bad. Most importantly, the missing bets clearly fit Jackie’s M.O.

And what about my Johns-as-alias theory after the casino arrests? Could it have been any more ridiculous? The St. Louis Post-Dispatch reported “Jackie Johns” had been convicted on RICO charges in 1990. Obviously, official police records aren’t filed under an alias. What do you want from me? I was 22. It’s a terrible excuse, but the only one I have. I still don’t know how the paper got their real identities. Shouldn’t “Johns” and “Castagna” have been wiped off the grid?

But perhaps the casino affair’s biggest red flags arose in its aftermath. Given his record, how did Jackie wiggle out with probation alone? How did he afford the high-flying lawyer? And his father, the manslaughter convict, shimmies back to the beach? C ‘mon. I didn’t ask these questions at the time. Remarkably, it never occurred to me to ask them. And speaking of Jackie’s dad, his violent rap sheet reeked of trouble, but his warm-weather retirement should’ve been the tipoff. Wiseguys don’t simply hang ‘em up and sail into the sunset.

Finally, there’s one minor footnote. In the summer of 1997, a book appeared on Jackie’s desk: Underboss: Sammy the Bull Gravano’s Story of Life in the Mafia. Gravano climbed to second in command in the Gambino family, serving under John Gotti. Gravano testified against his former boss in the early nineties, then began a short stint in the program. When I spotted the gangster’s autobiography, I clocked Jackie as a wannabe wiseguy reading about the genuine article. I couldn’t have been more wrong. Again.

Individually, none of the above could reveal Jackie as a full-blown Mafia foot soldier. But add ‘em all up. What do you get? I horribly misread Jackie’s hand. I committed a cardinal gambling sin by getting locked into an early read.

Most guys, given my age and fascination with gangster movies, would’ve had Jackie as the godfather, come to the Midwest. Not me. Hell, I was the opposite. Maybe I was open to the truth, but too close to see it—like getting flattened by 10 cars hid the fact I was playing in heavy traffic. Or, maybe, I simply refused to believe it.

A Hazy Glut of Gray

I never did get the truth about Jackie using our home game as a Memphis test run. Not that it’d be any more acceptable, if true; more understandable, maybe, but not acceptable.

And we did hit The Pepper Lounge that night after the poker fiasco. Pepper was our spot, too, and we decided Jackie wouldn’t screw up our Saturday night plans any further. As promised, he paid for everything. When we ordered the first round, the bartender said, “You’re good. Jackie said he’s got it all.” We said little more than hi to Jackie; we mostly stuck together and away from him.

Like I said, things were never the same after that. Always gregarious, Jackie goosed it up notch in hopes of restoring himself to our good graces. But aside from a few hours a week at Pepper, it didn’t happen; soon enough, that faded away, too. There’d be no reunion tour.

Our paths had strayed still further apart when Jackie found himself in trouble—again. This time, for paying a car lot employee under the table. Someone was keeping close tabs on Jackie, waiting for the slightest misstep. He got a six-month sentence that required him to report to jail by early evening and didn’t allow him to leave until 7 AM.

Once free of legal problems, Jackie partnered with Freddie to buy Churchill’s. They remodeled the place and, in November 2006, unveiled Posh. By then, Jackie and I rarely even spoke by phone. I never once dropped by the joint. Once upon a time, not being a regular at Jackie’s club would’ve been unthinkable. Shit happens, you know? I didn’t much care for barhopping anymore, anyway. I played poker, bet on football, and, in my spare time, I read books about playing poker and betting on football. And I always found time to hang with Lisa.

Yeah, about Lisa; we lasted until late August 2007. That was a curious ride. I think the thing that brought us together was, ultimately, what made “us” impossible. We both enjoy verbal warfare. However, neither one of us knew when, or perhaps even how, to wave the white flag. Throw two people like that together? Man, we battled through some doozies. Still, we loved each other. We’d been recently reunited after another break-up when Lisa asked the inevitable.

“Christopher,” she said. “What are we doing? It’s time to figure this out. Are we ever getting married?”

I did us both a favor when I replied no.

Around 2009, Jackie returned to the Northeast; New York, supposedly, but who knows? He always said he was from Bensonhurst, Brooklyn. In all the news coverage, I never saw a single bit that tied him to Bensonhurst or Brooklyn, or even New York.

Wherever it might be, I know Jackie wanted to be near his kids. He missed most of their childhood and it killed him to be so far away. And hell, he’s even got grandkids now. Julie keeps in touch with him by text message and his occasional visits back to St. Louis. It’s not clear to me what he does for money. I haven’t seen or talked to Jackie since the surprise encounter at Julie’s.

And so, I guess that’s the story. That’s it and that’s all. All I got, anyway.

Jackie’s definitely a thief and maybe a killer—a gangster. The genuine article. Yet he was so much fun, and, for most of nine years, he was a real friend. What am I supposed to think of him? Like so much else in this story, I’m not sure. If I’ve learned anything in almost 42 years, it’s that I don’t know much. I’m not afraid to say, “I don’t know.”

Put yourself in Jackie’s spot. Your father’s a full-blooded Mafia badass and it’s all you’ve ever known. One fine day, a guy mistakes a little banter for ultimate disrespect and gets decked. Now, the guy orders you to mete out his revenge. What are you gonna do? Before you consider, please know the man ranks well above you. He’s also certifiably insane and would kill you just for kicks.

If you reached a quick and easy answer, perhaps you need to reread the last paragraph.

I’m not absolving Jackie of anything; I’m not even attempting to explain it. It’s meant only for perspective.

Okay, you say, then what about the football bets and the poker game? I think, like everything else in Jackie’s warped reality, it’s complicated.

He blew more than $2,000 celebrating the Derby score; most of it on “about the best friends he’s ever had.” But then he cold decked us for about a hundred bucks. Why? Why cheat your friends? Because, like swiping soda and bubble gum, the card game was business. If money hangs in the balance, either to be saved or swindled, then Jackie’s taking a swing—period. If you ain’t cheatin’, you ain’t tryin’. You just know Jackie was the shifty little bastard that stole from the Monopoly bank. The Derby was different; the spoils were his to do as he pleased.

I do believe one part of Jackie’s poker game spiel. That night, he said, “… If I won, I was gonna cover everybody at Pepper.” Even before we discovered his dirty dealing, I believe he fully intended to foot the bill at Pepper. Then, he could square it in his twisted head: “We’re even.”

Either way, does it really matter? How could I ever trust him after that?

I don’t, however, regret a single minute I spent with him.

Hall of Fame basketball coach and New York City native, Al McGuire, was a street-savvy quote machine. I’m not old enough to remember when McGuire was coaching, but it was not long after I learned to read that he became known to me. It happened in my childhood barbershop. The place played country music and sold soda from a glass-bottle Coke machine. Opposite the barber chairs, dozens of quotes adorned the wall; one, courtesy of McGuire:

“I think everyone should go to college and get a degree and then spend six months as a bartender and six months as a cab driver. Then they would really be educated.”

Of course, a little kid couldn’t possibly understand what McGuire meant. I reread it every visit, though, and, eventually, I learned.

I went to college (for a while, anyway) and then randomness threw Jackie and I together. I worked for him for a couple years and we tore up the town for several more. It sure beat the hell out of tending bar or driving a cab. I met people—Harry and Darwin, the Other Jew, Gene Lynn, Jazzy Joe, drug-addled Jeff, the Club Illusion crew and countless more—the best fiction writers couldn’t craft on their finest day. Talk about an education.

And if Jackie wasn’t a teacher, then, surely, he was a guide. In The Color of Money, Tom Cruise portrays a talented, young pool player. But instead of hustling the circuit and stacking up the cash, he’s stuck at a toy store. As Paul Newman tells him, “You couldn’t find big time if you had a road map.”

So, Newman takes Cruise by the hand and teaches him to use that talent to make money.

“You got to be a student of human moves," Newman says. "See, all the greats that I know of, were students of human moves.”

Well, Jackie Johns was, and I’m certain still is, a student of human moves. Jackie showed me the importance of a continuing education. That class—whether you know it or not—is never really dismissed.

And I think that’s it. That’s what I took with me when I left Jackie University:

Heads up, motherfucker—shit comes fast. Pay attention. Be a student. And always cut the cards.