Tao of Poker

The Wall Street Game

"You have to decimate before you get decimated." - Jeff Spicoli

The Tao of Spicoli is how I lived my life in the trenches on Wall Street. Who would have thunk that the half-baked wisdom of a California surfer could keep me focused? I took note of his acute assessment of relating Pac-Man to surviving in everyday life. I reminded myself his words before I showed up at the infamous "Wall Street Game."

I walked in the game expecting a fight. That was my mind set. I was ready to get jumped. It wasn't going to be a fun night of drinking and cards with the boys. This wasn't going to be a low-limit table on the Strip in Las Vegas with sunburnt tourists. I was playing in one of the biggest games in New York City and going to battle against some of the most talented minds in the financial industry.

Those guys were wealth personified. They shit Gucci cufflinks. They all had memberships at exclusive country clubs that still don't allow women and minorities on the links. These are the rare breed of suits that have people mercilessly killed. They rig elections and prop up puppet governments. They buy off the cops. They bring rival corporations to their knees. They pay $800/hour to have their testicles shaved by dominatrixes. They'll sell their own children into sexual slavery if it was feasible.

This encounter was not going to be just a fight, but a dirty street brawl with biting, kicking, and junk stomping. And I was completely alone. I was not going to be judged on my poker acumen, rather it was going to be one of those gut-check moments in life. The game would be a test of my mental and physical toughness. I lost part of that hardened shell that I developed when I worked on the Street two or three lifetimes ago and I secretly wished I had it back.

Several months ago, I ate a $300 sushi lunch with Briana and her father, Harry Buttons. He's a tall and lanky man with grey hair dominating 90% of his head. He looked a little bit like Harrison Ford (during his Jack Ryan days) but in personality he reminded me of Jimmy Conway's character from Goodfellas. He's a guy that "didn't take shit from nobody." Instead of going into the family elevator button business, Harry Buttons carved out his own path. He headed to Harvard Law and eventually settled into investment banking in the late 1970s. He married into a very influential family, one of New York's oldest and elite. Briana's parents have a hate-hate relationship with each other. And her mother hates me with a passion because she thinks I'm trying to steal her families money. That was enough for Harry Buttons to take a quick liking to me as he shook my hand and paraphrased Sun Tzu's Art of War, "My enemy's enemy is my friend."

When Harry Buttons found out that I went to a prep school around the corner from his palatial Park Avenue penthouse, his interest in the guy who was sleeping his daughter and secretly plotting to steal his wife's inheritance increased twofold. When he discovered that I wrote poker for Fox Sports, he nearly jizzed in his pants.

He quickly told me about his homegame. It's not really a homegame, but several friends of his broke away from an exclusive ivy league club where they frequently played cards. They had a dispute with one of the trustees and decided to start up their own game. They are in the process of finding a permanent property. Three times a month they rented out a suite in a hotel. The location always changed, but they always have a place to play. This is not an underground card room run by the Ruskie mafia, rather it's a bunch of rogue white rich guys who got sick of dealing with their stuck up blue blood cronies. Suits on the fringe. My kind of guys.

Harry Buttons is a stud player and got killed playing in the NL Hold'em cash game. That's when he hatched a plan to get me involved. Even though I told him I wasn't a NL cash game specialist, he ignored me.

"I can't keep up with these kids. These fuckin' sharks!"

When I asked him how much he lost in the game he shook his head and said, "Let's just say I could have bought Daddy's Little Princess a 2006 s350 (Mercedes) and instead I lost it all playing Hold'em."

After that conversation, I convinced him to play to his strengths, which was Seven-card Stud. Alas, he was livid that he couldn't crack the Hold'em game. Harry Buttons is an A-type personality. He's been successful at everything he did over the past 35 years, with the exception of his first marriage and poker. He wanted tips and I suggested that he read poker books and DoubleAs' blog.

"I'm a busy man!"

He wanted me to read the books and then give him a twenty minute summary. I told him that if he was serious about improving his game, he'd make the time. He decided that it would be better to get me in the game now while he took my advice brushed up on his NL game. He even downloaded Party Poker using my bonus code and learned how to play different styles from a rock like Dan Harrington to a loose cannon like Layne Flack to a cagey mofo like The Rooster.

I had been on the road for the first 1/3 of the year so I never had the opportunity to play in the Wall Street Game. When I got sick, one of the things I regretted not doing was taking shots at higher stakes poker games. And if didn't want to risk my bankroll, then I'd have to find backers and investors with disposable income. I found two backers for the Wall Street Game; Briana's father and my old mentor Mack, the guy who trained me and was my original jungle guide on Wall Street. They both loaned me $2K each for a month. I agreed to play in at least two games and at the end, they'd decide if they want to do... either cash out or let it ride or cut the losses. I had to sell off 60% of my action... 30% each of them. They wanted 35% each and actually Mack wanted 40%! I wanted to sell off 25% each and we negotiated to 30%. Heck, I'm not going to complain. If I can double up my $2K buy-in, that would be worth an $800 for me considering I don't absorb any of the liability if I get busted and lose my stake.

I brought $1K out of my own bankroll just in case. I met up with Mack first down on Maiden Lane and he made me sign a contract. Then I had to head to midtown to pick up some more money from Harry Buttons before I headed to the suite with $5K. That's the most money I ever took to the tables. When I rode the subway to the hotel, I looked around at all the stiffs on the train. The evening commuters had that wary Wednesday look on their faces. I used to be like them... barely awake as I shuffled through life. I had more money in my pocket than they made in an entire month. I was about to gamble the equivalent of their monthly paycheck, while they were rushing home in time to grab a slice of pizza before Lost came on the boob tube and they wasted a few hours before they had to so to sleep and get up to go back to work.

I thought about that old saying, "If you ain't living, then you're just waiting to die."

That fired me up to play even more. I found Briana's father in front of the hotel fifteen minutes later. He insisted that he take a taxi from his office in midtown. I took the subway, made two calls, then grabbed a calzone from a fake Original Ray's Pizza. I still beat him downtown.

We took the elevator up to one of the top floors. The entrance to the suite had double doors, and a six-foot tall woman wearing a tight black cocktail dress with flowing dark hair answered thirty seconds after we rang. I assumed that she was the hostess. The jewelry around her fingers and neck looked fake. I couldn't tell because I'm a straight guy and I kept staring at her breasts. But she wore Manolos. I know they distinct brand well after Briana and I once got into a fight and she tried to bash my head in with one of her shoes. I can't tell you if Manolo Blahniks are comfortable shoes, but they hurt like a motherfucker when malcontent blondes chuck them at your head like John Elway hitting Rod Smith in the numbers on a slant pattern.

The hostess' distinct Middle Eastern features stood out and I wanted to run my fingers over her shoulders and feel her smooth tanned skin. She could have been Greek, Israeli, or Syrian. I was dying to know as I came to conclusion that both her tits were fake.

She took Harry's jacket as we walked into a small room where two guys smoked cigars. They both wore dark grey pants, blue shirts with white collars, and suspenders. Harry stopped to talk to them as the hostess led me into a big room with two leather couches and two poker tables. A small bar sat in the corner and opposite the bar, the Yankees game was on in the background. Jaret Wright was pitching a one-hitter.

"Everything's free. Booze and food. Whatever you want," Harry said before he paused a beat and elbowed me. "Except for the women of course."

A guy with a funny accent came over and asked to see my driver's license. He looked like Alan Cumming and he smelled like cheap cologne. He gave me a weak handshake then asked for $100. Harry forgot to tell me that there's no rake, but they take $100 up front. That helped covers the cost of the suite, food, and liquor.

A buxom blonde who was about a foot shorter than the hostess walked over to me. She wore heavy concealer to cover up the rings around her eyes. The runny nose was a dead giveaway that she was on the sauce.

"Do you vant a drink?" she asked me in a thick Russian accent.

I declined. I was worried that they were going to lace my drinks and I'd wake up with my asshole the size of the Lincoln Tunnel and find my bankroll and both my kidneys missing.

I sat down at the NL table while Harry took a seat in the 20-40 Stud game. His table had 5 players all guys in their 50s and up. I was the only non-suit in the room besides the two hookers.

Here's my table:

Seat 1: Bertrand the Venture Capitalist... it's natural that a venture capitalist would be a loose poker player. They liked to spread their money around especially on long shots because they know it's gonna be a huge payday if the investment hits. Bertrand had a funny accent. I think he said something about being half-Welch and half-Belgium, but he grew up in Connecticut.

Seat 2: Palmer aka the Former Master of the Universe... at one point this guy was the Phil Ivey and Tiger Woods of his industry. When I was a rookie on Wall Street, he was the most successful fund manager in the world who used to date models and snort coke off their tits. Now he's a vegan health nut who's broke, yet addicted to poker and has two alimonies to pay.

Seat 3: Pauly... Your hero was originally a bond trader. The former rookie of the year left the industry abruptly in the mid 1990s before ending his retirement in late 2001 by accepting a position with JP Morgan as a stockbroker focusing on the pharmaceutical industry.

Seat 4: Drunk Guy.... Didn't get the broker's name. I think it's Steve or Sam or something with an S. He's the only guy who didn't give me a business card. He showed up drunk and knocked back Scotch all night. At one point I nicknamed him "Shakes the Clown" because his hands shook so much when he moved all in.

Seat 5: Larry Hedge... Hedge Fund managers are the boring in nature. He ran an Asian stock market hedge fund in the late 1990s and now is working with a major firm hedging currencies. Hedge funds are basically a way to reduce volatility and take smaller risks in an attempt to preserve the capital in the fund. That way they can deliver a positive return under any condition. Tightest player at the table. His wife also picks out his ties.

Seat 6: Vince Vaughn... Vince Vaughn didn't really play in the game, but this guy looked and sounded just like my boy VV. He's a cocky investment banker who makes more money in a year than A-Rod, and he had a much better season. He has houses in Westport, in Colorado, the Hamptons, and in Bermuda.

When I walked in that room that maniacal feeling quickly came back. I was ready to inflict pain. If anyone punched me, I was going to punch back twice as hard. The stakes were 5-10 NL. The buy-in ranged from 1K to 2K max. Since everyone had 2K in front of them, I bought the max. Harry told me that guys rebuy for as little as $500 and usually half of them will go into their pockets two or three times over the night. The most he won was 4K in one session and he's lost 8K in a night twice. Harry was the biggest fish in the room and he wasn't even sitting at my table. No wonder the guys were pissed I took his spot.

I had to choose one guy out of the five that I was going to pick on all night, otherwise I was going to be everyone's bitch. I focused on the drunk guy, but I had a feeling that Vince Vaughn and I were going to get into some big pots together. I didn't bring anything to take notes with, so my post lacks a lot of details. I took a few smoke breaks and went downstairs and called my voicemail to leave messages on my progress, but that was the extent to my documentation of the game. I also did not bring a camera either.

On the second hand I found the Hammer and raised to $30. I figured 3x would be a standard raise. Nope. I quickly got reraised to $100. I folded. I discovered that the standard raise was $50 preflop. The re-raise would be about $150. There were usually four players to a flop which meant that $600 was in the pot before we ever saw a flop. Talk about action!

I didn't catch any cards and folded almost every hand in the first hour. I tried to study the players and pick up on tells as they stole my blinds.

Harry would check up on my every ten minutes or so. He told me to get some food every time. I finally got a drink and the hookers would walk over and brush their breasts up against my shoulder as they brought over my beer.

During the second hour I grew frustrated. I got blinded down and waited for a hand that I could see a flop for $150 with but was card dead. VV amassed some chips early with some wild play until he lost a big pot and most of his stack against the drunk guy who beat him with bottom pair. VV tried to bluff with just a gutshot and drunk guy pushed. I kept having those moments where I wished I played in more pots. I'd fold marginal hands that would end up being winners.

When I finally found a hand and reraised to $150 with Q-Q, I got three callers. The flop had a King of spades and two baby clubs. VV moved all in UTG for almost $1K. I called. He had 9-9. One of them was the nine of clubs and both of my Queens were red. The turn and river were clubs. Flushed out by the table asshole. My testicles shrunk to the size of peanuts. I was down to like $525 in chips.

"Rebuy!" I shouted as Harry slouched in his chair.

The guy with the cheap cologne ran over and sold me $1500 more chips. I had $1500 more in cash on me, but if I had to rebuy one more time, I'd be using my own money.

"Good call," Palmer said as VV stacked his chips "Shitty river. You'll get it back."

"If I win a few more pots, I can afford both of you lovely lades," VV taunted the hookers.

Since the drunk guy to my left kept slurring his speak, I couldn't understand him. I ended up talking to Palmer most of the night. I doubt that he knew that I knew who he was. And deep down I hoped that no one read my blog, especially Palmer.

VV routinely teased Palmer about his mental breakdown seven years ago and his subsequent trip to rehab. He lost his job, his penthouse, his model wife, his limo and driver, and he lost his dignity. He also discovered that his mistress was pregnant with twins. After the birth, when one of the kids looked like neither of them, he suspected something was up. Palmer looked like a husky Ron Howard but with more hair, and his mistress was a strawberry blonde. The twins were fraternal which meant they were two different eggs. And each egg was fertilized by a different father. Palmer was one and a shoesalesman at Macy's originally from Nigeria was the other. Palmer discovered the horrible truth when his mistress sued him for child support for the twins. Since he was the father of only one, the court ruled that he only had to pay half of what she wanted. It totally sounded like a bad episode of LA Law.

At some point the conversation got focused on me, part of the standard conversations that New Yorkers have when they meet you for the first time... "What do you do? Where do you live? Who do you know?"

I told them I used to work on the Street on two different occasions.

"I'm retired," I said.

"Smart man," added Palmer.

"Of course he's smart. He's banging Harry Buttons' daughter," VV said loud enough that Harry could hear. "She's got more money than Paris Hilton."

By the third hour I noticed that a few of the guys would leave the table for 15-20 minutes at a time and retire in the bedroom with one of the hookers, while the other one served drinks.

The buxom Russian came over and asked me if I was hungry. She handed me a room service menu. If she made the food, I was going to make sure she washed her hands. I ordered a club sandwich with double bacon in homage to Daddy.

I finally got used to the flow of the game. I could sense when players were weak or strong. Instead of guessing blindly in the first hour, I got a decent read on the table. I was still down almost $2K with $1500 on the table when VV bragged the new Porsche that he bought. That's when I raised his big blind with Snowman Tater Legs. He called. The flop was Q-8-4. He bet $400 and I raised to $1000. I smelled weakness even though he reraised me all in. I called as he whispered, "Shit."

He had A-4. The turn and river were both Jacks and my SMTL held up. I waited almost four hours to win a decent hand. I had over $3K in chips and became quickly energized with confidence. That's when I shifted gears. When someone would raise, I re-raised. I wanted to be in early position because I wanted to move all in on the flop before anyone else did. My aggression paid off because I had close to $5K within an hour. Harry's stud table broke and he went home while the other suits got their salad tossed before they caught their trains back to the burbs.

The Hedge Manager left after he lost his buy-in and the game was five handed. Including the hookers and the guy with cheap cologne who ran the game, it was just eight of us in the suite. Sportscenter played in the background as the venture capitalist took a phone call from his agitated wife. We'd lose him eventually and the game was down to four players. Me. Master of the Universe. Vince Vaughn. And the drunk guy.

The action picked up and everyone flop was four handed. Palmer scooped a pot from me when his A-J outkicked my A-10. I took a pot off of drunk guy when I flopped a set of 5s. I missed two big flush draws on consecutive hands and lost about 1/3 of my stack to VV. I got it back when I bluffed VV out of a pot that I thought he was going to fold. On the turn I had bottom pair and a gutshot draw and I re-raised VV about $1500. He thought about it for five minutes before he folded. I let him see one of my cards and he picked the 3 of diamonds. He said he put me on two pair. With Q-Js, I also rivered two pair on the drunk guy when he flopped a pair of Queens with K-Q.

Around 2am the game broke and I had a little over 4K on the table. I played too tentative in the first hour or so, but finally took control of the game at the right time. Overall, I made good decisions. I made the right laydowns and got a few lucky cards. The game had one or two decent players but the rest were loose maniacs and kamikaze gamblers. I'm lucky I didn't lose all my money.

I bought in for 3500 and I walked away with 600 or so. VV dropped about 4K, while drunk guy won 9K. Palmer broke even. The drunk guy passed out on the couch as VV threw his arms around the shoulders of both hookers and led them into the bedroom. He never said good bye. He was pre-occupied.