Born to Gamble Part II: Southbound

"Like most New Yorkers, my family did not believe that a glass of beer or a game of cards imperiled their souls, and there was something ugly and silly about those who insisted they did." - Edward Conlon, Blue Blood

When my internship at the NY Commodities Exchange ended in late May, I was offered a full time position with the brokerage house that I had been working with. At the age of 17, I made $500 a week plus overtime. That seemed like all the money in the world to me. (The sad part is that a decade later at age 27 as a struggling writer and artist, I'd make substantially less per week including inflation than when I was 17.)

I picked up at least $40 a day in prop bets on the floor of the exchange. For $20 a pop, I'd make crank calls to brokers' ex-wives and ex-girlfriends. I'd willingly say things like, "How would you like to make $14 the hard way?" or "How many cocks have you sucked today, you dirty slut whore?"

Most of the time, I pretended to be a doctor suggesting that one of their ex-lovers tested positive for the AIDS virus and that they should get tested immediately. It was a fucked up thing to do, but I was 17 years old and that was probably the least crazy thing I did. After work, I would go to the bars with the other brokers and clerks. Yeah, I wish I was 17 again drinking $1 mugs of beer at the Dugout in the East Village and trying to pick up rich stoner girls from schools like Fieldston or Chapin.

During my last week of work in August of 1990, the markets went completely crazy. The stock market and gold market were at new highs and oil futures went through the roof when some insane guy in Iraq named Saddam invaded an oil rich neighboring country. That was the first time I understood how international politics and war affected the financial markets. I saw it with my own eyes. During the seven months I worked on the floor, I never witnessed that much chaos as I did when Saddam attacked Kuwait. Everyone who had an account was gambling on the future. War is good for the economy and everyone was trying to position themselves to earn as much (or lose as little) money as possible during the impending showdown in the first Gulf War.

"You're lucky you're going to college," my supsenders-wearing boss with slicked back hair told me, "otherwise they'd be shipping your ass off to the desert."

* * * * *
Parts of college were a blur for me. I blame the mushrooms and Jim Beam, which caused partial memory loss. I didn't learn all that much in Atlanta while I dabbled in hedonism for four straight years. Although you can make a solid argument that 16 years later, I'm still caught up in my Dionysian lifestyle. The foundation of my intellectual knowledge was given to me by the Jesuits who taught me a classical education in high school which included learning four languages (Latin, French, Russian, and Greek), while studying Russian, Victorian, and early American literature, Advanced Calculus, Economics, and four years of theology.

Since my prep school was so rigorous academically, my classes in college were a joke. I took classes like Bowling, Stress Reduction and Flexibility, Social Problems in Modern Society, and the Presidency. No wonder I'd show up to class stoned, drunk, or both.

I wasn't challenged. College reminded me of watching Wheel of Fortune just after watching Jeopardy. It was a waste of time. I spent less time in classes and most of my time drinking in Atlanta bars, sitting on the porch of my fraternity house make cat calls at the sorority girls who jogged down Fraternity Row, or roadtripping to New Orleans or following the Grateful Dead throughout the South.

I also gambled in my late teens. Heavily.

My fraternity held a football pool and a March Madness pool, and I was in contention for both every year. I won the March Madness pool when UNLV beat Duke and guys in my house were verbally abusing Christian Laettner as they shouted homophobic references at the TV about his "close relationship" with point guard Bobby Hurley.

Most of us gambled on football every weekend. I had a bookie back home in NYC. Karate Tony started his own book during college and we used his services. My buddy Chicago Bob had a bookie in Atlanta and we'd phone up both bookies and go with the one who had the better spread. During my senior year, we had an amazing run and won seven weekends in a row. I have still yet to match that rush.

Sometimes on weekends when there wasn't anything going on, we'd roadtrip down to the riverboats in Biloxi, Mississippi to play blackjack. That's the first time I played poker in a casino, was on a riverboat. I was down to my last $30, so Chicago Bob and I played Seven-card Stud with a bunch of WWII vets.

During senior year, eight of us rented an RV and drove to Mardi Gras. We parked the large beast on Chartes Street in front of a church and went on a three day bender which included the consumption of massive qauntities of liquor, narcotics, and groping half-naked college girls from Texas. On the way back to Atlanta, we stopped off in Biloxi and headed to a riverboat casino. We needed to win enough money at the tables to pay for gas for the ride back.

My friends and fellow fraternity brothers started asking me to place bets for them. I would phone in their bets to Karate Tony or Chicago Bob's bookie. They lost more than they won and I started booking their action... myself. I stopped passing the bet along to Karate Tony unless it was so huge that I was afraid to cover it myself. Although I had one or two problems collecting money (and it was always from the rich kid who drove a nice car that refused to pay), I made enough scratch that I quit my part-time job cold calling alumni for donations. At best, I was a low level thug making a couple of hundred bucks of the degeneracy of the rich kids in my fraternity who would drop $100 on the Eagles because they were rooting for their hometown Philly team and betting with their hearts instead of their brain. All my bookie money went to pay my bar tab at Dooley's Tavern and to pay for tickets to Grateful Dead shows.

We played cards all the time in my fraternity house. There was a period of time when everyone played Spades and we even had a house-wide tournament. Spades is played with four players comprised of two-person teams. Rib was my partner and we were one of the best teams in the entire house. We would spend hours and hours playing and drinking cheap beer and smoking bad weed while listening to Widespread Panic bootlegs on the stereo in Rib's room.

We would play drinking games with freshmen girls who would wander down to the house. We'd try to get them hammered drinking Malibu Rum or some other conncoction that I came up with... lemonade and Southern Comfort. We'd play Asshole most of the time and some of the girls would be doing the "Walk of Shame" sometime around 8am.

We also played poker in college and the games were intense. We'd play in the living room of our fraternity house. One weekend we had a huge party where a band played in the formal room. After the party ended, we left the stage there for a week maybe longer. We threw green felt over one of the dinner tables and we started a poker game. That game lasted for a week straight as brothers and friends of ours would sit down and play rotating in and out. It was our version of the Big Game. Playing up on the stage under the bright lights with a small crowd gathered around made the players in the game feel like they were doing something extra special. We'd drink Jim Beam like it was water and chug Beast Lite, tossing empties into the fireplace or out the window. We made pledges go fetch us food, buy us more liquor, and clean out the gravity bong for us. Guys were afraid to go to class, take a nap, or have lunch with their girlfriends because they were worried they'd lose their seat in the game.

When it got too big we moved the game off campus. One of the dorky brothers in my fraternity complained that we were gambling in the open and that we could get our charter revoked for such aberrant behavior. It was just cards and not a big deal, but we got yelled at anyway. I thought it was a hypocritical decision since our other degenerate behavior was still allowed like the rampant drug abuse, giving our pledges alcohol poisoning, and the occasional date rapes.

My buddy Jerry lived off campus with Rib and his three-legged cat, Smooth, that was addicted to marijuana smoke. I guess if you were missing a leg, you'd get stoned all the time too. During the spring of 1994, two NYC teams were in the playoffs. The Rangers ended their 44 year drought and brought home the Stanley Cup. And the Knicks were bounced by the Houston Rockets in the NBA finals after John Starks went 1-87 from the floor in game 7.

Every night for a month straight, a NY team was playing in the playoffs so there was a different game to watch on TV. We'd be huddled around the TV and when the games ended, we'd play poker until sunrise. There would be 14-16 people playing with two tables going. The girls who lived across the hall got hooked. This went on all summer long.

We played dealer's choice with the emphasis on a four card guts game called Four Barrel where 4s and 8s were wild and flushes and straights don't count. Those games would get ugly and it would not be uncommon to lose a couple of hundred dollars in a Four Barrel pot. This was a lot of money considering we'd start out the night with nickel and dime antes. Even the sorority girls across the hall were hooked on Four Barrel. The second table would break around 2am when the people with "real jobs" had to crash. The first table would continue until sunrise when we'd go back to campus, pass out, then wake and bake and start the routine all over again.

I didn't work at all that summer. During Memorial Day, I went on a rush and won $2K playing two hands of blackjack at the same time at the Casino Magic in Biloxi. I made enough money to cover rent and food for the entire summer. I guess you can say that my first job out of college was being a professional gambler.

One guy in our game had spiraled into in a big losing streak. Dutch lost so much money that he had to use IOUs, which he scribbled on yellow Post-It notes. We nicknamed those IOUs "Dutch Bucks." They were as good as gold. My friends and I would use Dutch Bucks as currency. If Jerry bought me a twelve pack of Beast, I'd pay him with $5 in Dutch Bucks. At one point I had almost $200 in Dutch Bucks and I traded that in for a free round of golf (cart included) at Pinehurst, NC, a ticket to a Phish concert, and a big bag of mushrooms.

We'd all bring cash or jars of change to play in Jerry's homegame. Dutch would bring Post-Its. I still have a few Dutch Bucks to this day.

One night Teddy B (our version of G-Rob) got so drunk that he gambled away gift certificates that his girlfriend gave him for his birthday. She was still in school and didn't have much money. She knew Teddy B loved watching flicks, so she bought him $50 in gift certificates at Blockbuster. He was stuck pretty bad one night trying to bluff at a big pot in Four Barrel and "Zeke" got the best of him. He didn't have cash to buy back in and busted out the book of gift certificates. He promptly lost every single one. When his girlfriend found out she was furious. When we offered to give them back, she refused to accept them.

"Don't give them back. Let him learn this valuable lesson," she said. They broke up soon after.

... to be continued


Editor's Note: FYI, check out Born to Gamble Part I: Where It All Begins if you haven't read it already. Part III of the Born to Gamble series will be posted on Monday.