Born to Gamble Part III: Midnight Rider

I left Atlanta a couple of months after graduation, with a few grand in my pocket after a successful summer of poker and blackjack. I drove back to New York City without a job, nor a place to live. I really didn't have a clue to what I was going to do with my life. A few months earlier, I applied to NYU film school and I was quickly rejected. The previous summer, I was the ice cream man in Atlanta. I wrote a screenplay that was a taut psychological drama about an ice cream man who couldn't sell ice cream on the hottest day of the year. It was Do the Right Thing meets Taxi Driver and I figured that my cinematic gem was going to get me a scholarship to film school and a three picture deal with Miramax. My screenplay was rejected and so was my dream of going to film school to become the next Richard Linklater or Quentin Tarrantino.

The job market was at an all time low for the mid 1990s and I was one of hundreds of thousands of college grads migrating to NYC to find work. I took my LSATs and did extremely well. I figured law school was a distant option since I had not yet applied. I thought about getting my old job back at the Commodities Exchange, but I was reluctant. I wasn't ready to throw on a suit and tie and my four-year slacker lifestyle seemed more appealing. I took a menial job at the Metropolitan Museum of Art. Within a few weeks I met a sultry French chick with big brown eyes and I moved into her loft in Chelsea that was inhabited by rats and her two roommates, both drag queens. I was in a holding pattern until I figured things out, which meant I got shitfaced every night and followed the Grateful Dead around until Jerry Garcia dropped dead.

I grew up in New York City during my childhood, but the city is completely different when you were 21 years old and being reintroduced to it for the first time. I returned just before Giuliani cleaned up the city. There was still a slight edge to it and the cooler parts of town weren't overrun by hipsters, dotcommers, and the Starbuckification of America.

I ran rampant through the streets of my city like a horny Russian sailor on shore leave in Bangkok for 48 hours. I viciously tortured my brain cells and went on a year-long bender that would make Ted Kennedy proud. I spent many late nights getting trashed in dive bars in the East Village and in Brooklyn. I'd puke in between subway cars and pass out on people's couches that I had only met a few hours earlier. I was "young, dumb, and full of cum" and raising hell with some of my co-workers, who were an odd cast of peculiar painters, narcissistic actors, progressive musicians, understated sculptors, and hackneyed poets. They were what and who they wanted to be and didn't let a day job nor society define their existence.

I learned from their devout dedication to their crafts that it was going to be at least ten, possibly twenty years before I began to fully understand and master my craft. I had a life-altering decision to make: if I wanted to be a writer, I had to be willing to choose a life of sacrifice with the knowledge that what I was attempting had astronomical odds against what I was trying to achieve. Millions of people begin their careers trying to do something with their art and talent, but only a small percentage earn a living wage doing it and most of the time it's a sheer compromise that they have to endure in order to earn a living as a writer, painter, or musician.

I also discovered a group of hard-core gamblers at the museum. My friend Marco was a security guard in the Classical European paintings section. He introduced me to OTB's betting by phone feature. We set up and funded my account at the local OTB and then I was able to use their automated system to phone in bets on horse racing. I would do this during work hours! I worked with a lot of union guys who had mob connections. And everyone knows that horse racing is fixed. When we'd get word of a "sure thing," we'd bet heavily on our tip. It only had to hit 1/3 of the time for us to break even.

One day Marco had a tip but didn't have any money in his phone account. He had to go to the OTB and put in the bet directly, so he called his supervisor and told him that he was taking a ten minute bathroom break. He left his post in the Caravaggio Room at the museum, hailed a cab on Fifth Avenue and told the driver to take him to the nearest OTB 15 blocks away. He jumped out, placed the bet, then jumped back into the cab and ran back into the museum. He returned thirty minutes later dripping in sweat. When his supervisor wondered where he went, he explained that his trip to the bathroom turned into a nasty case of explosive diarrhea and was stuck shitting his brains out.

I met another guy who ran the football betting slips ring and sold dime bags of weed on the side. I'd gamble with the same parlay slips that my father had given me ten years earlier. I also worked with a bookie, and I bet on college basketball and pro football. I would classify my sports betting as moderate to low at the time. Living in NYC was expensive especially since I went out to party every night.

My buddy Stormy (who just won a seat in this year's WSOP main event) and I would organize poker games with some of the security guards. We'd play at Marco's apartment in Peter Cooper Village or at my apartment in Park Slope. I introduced Four Barrel to the home game and they were hooked along with other games such as Acey Deucey. The games started out low stakes and by the end of the night it would get ugly when we'd play Four Barrel. There was a group of seven or eight of us that rotated in and out of that game for over a year. I won more than I lost and the games were more social than competitive.

I also heard about the illegal poker rooms for the first time although I never played. I went to one once with Marco around Union Square. He went a few times with one of the ex-cops who worked security at the museum. It was a private club and you could not get in without being introduced by a member. Marco just got his membership card and was going to get me one. They only had one table running (Seven-card Stud) and we didn't want to wait. I never went back.

Around that time I started going to Atlantic City to play blackjack. It was a two hour bus ride from Manhattan and we'd arrive around Midnight. I counted cards and Stormy, Marco, and I would buy $25 roundtrip bus tickets to AC. They'd give us $20 in free play at the casino and we discovered a scam where we could cash it out at Sands, so the roundtrip would only cost us $5. We'd play blackjack all night and comeback the next morning.

I first sat down at a poker table at the Taj Mahal because I was down to my last $30 after getting seriously cold-decked at the blackjack tables. While I waited for the next bus back to the city, I sat down at a $1-3 Seven-card Stud table where I was about forty years younger than the other players. Since the Taj's poker room was close to the exit, I could step outside and smoke a couple hits off of a blunt and not miss too many hands. I'd joke around with the infamous Atlantic City hookers who mingled in the same area. That's when one lady of the night uttered one of my favorite phrases that I have ever heard from a hooker, "Honey, if you wanna fuck Big Momma, you better wear a space suit," as she lifted up her pink mini-skirt and pointed to her crotch, "Cause you ain't getting out of this black hole alive."

I had no clue what I was doing at the tables since I never read a poker book. I played by instincts. I had home-game experience where we played Stud frequently. With an excellent memory, almost photographic, I could easily memorize what cards were already out. I relied on my ability to read people and had no knowledge of advanced concepts. I played fairly tight because I didn't have much money to gamble with, so I didn't play too many pots.

At first I didn't understand the commonality of tipping poker dealers. Like blackjack, I would tip out a dealer when they left the table. Fortunate for me, the other players at my table were friendly and clued me in on the proper etiquette. Some of the WWII vets gave me free advice on playing Stud, like how I should always complete my bet with an ace out there and about not giving other players on a draw free cards.

After a year of heavy partying, I grew tired of living the hungover life of the village drunk from an Irish novel. I eventually decided that I wasn't willing to fight the overwhelming odds to try to be a writer. I was at a fork in the road, and took the easy way out. I became a suit and quickly found myself trading bonds for a brokerage firm located on Wall Street.

Part of that decision to head to Wall Street was due to the fallout over horrible relationships that I had with two particular women during my first year living in New York City. Frustrated, heartbroken, and lacking any self-worth, I needed something to take my mind off of the misery. Long hours in the trenches trading New Jersey sewer bonds provided that escape.

I always fall for the wrong women. I should know better, but I can't stop it. I have a weakness for emotionally disturbed women. I barely survived the hellish period when I lived with a self-hating, chain-smoking, French painter. Then I dated a strung-out, chain-smoking, Belorussian model. One despised men so much that I wondered why she wasn't a lesbian. And the other one was so fucked up in the head and mercilessly addicted to cocaine that she made me seem like Richie Cunningham to her Courtney Love. Of course we ran off to Jamaica together to live in Paradise but that didn't work out very well. You can read about that drama in my book Gumbo. Here's an excerpt:

"I massaged Natasha's smooth hair and she rushed in for a kiss. I brushed her left cheek with my hand and she took it and kissed my fingers one by one. She closed her eyes and inserted two fingers into her soft mouth and began slowly sucking them. When someone knocked on the locked bathroom door, she clamped down hard and bit me. I screamed and with my first impulse, I punched her in the head with my free hand and pulled my fingers to safety. She laughed as I inspected my right hand and saw teeth marks impressed into my flesh, but no blood..."

I was a scorned lover, dead broke, and my soul was bankrupt. I was a perfect candidate to be brainwashed and I quickly fit in. I was recognized as the best trader in my class and won Rookie of the Year at my firm. I don't think I was exceptional, rather I got lucky and put in rigorous hours, upwards to 80+ a week including Sundays.

The financial markets are a form of legalized gambling. You're speculating the future. I got paid to gamble... with other people's money. And it was tons of fun except when I was wrong which happened more often than not. The rush was overwhelming and the work was exhilarating. In many ways I miss those aspects of my day, when you get so jacked up on adrenaline that it feels like you are floating several feet off the ground.

The guys in my office were smug assholes. In many ways, they deserved that right to be cocky. What they did mattered much more than the other suits and skirts scattered in offices and cubicles all over Manhattan pushing paper, where a bad day for them was getting chewed out by their boss or blowing a sales presentation. In the trenches on Wall Street, a slip up could cost millions of dollars. People get whacked for those sorts of mistakes. An error in judgment by a rogue trader or broker could ruin an entire company or an entire country. Yeah, the guys I worked with were pompous snobs. They thought they were Gods among men. Big Swinging Dicks. Masters of the Universe. And I was one of them.

... to be continued


Editor's Note: If you have not read the first two installments, then visit Born to Gamble Part 1: Where It All Begins and Born to Gamble Part 2: Southbound. The fourth installment will be published later this week.