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How to Handle Yourself in a High-Stakes Poker Game

Badlands of Dakota (1941) Photo: Courtesy Everett Collection

The first hand of poker I ever played against hip-hop mogul Irv Gotti, in December 2006, was one I played like a total idiot.

Just before the hand – at a game in the offices of the Lotus nightclub, owned by Gotti’s brother-in-law David Rabin – Gotti and I were chatting about PokerStars. Back then, the superstar music producer liked to play the Sunday Million tournament (a $215 buy-in with thousands of entrants and $1 million guaranteed prize pool) each week. He had gotten deep the day before.

“I can’t play those things,” I said. “They always take too long. I don‘t have the patience.”

“Yeah, but it’s all good,” Gotti replied. “I have my laptop. I’m watching football, cooking dinner, hanging out with my kids. And anyway, you just fold, fold, fold most of the time. You just wait for queens, kings or aces and don’t get involved that much.”

So, okay. I learned that Irv is capable of playing tight and isn’t just a crazy gambler.

And then this happened a couple hands later.

Irv straddled. A straddle is a blind bet made to induce bigger action. Somebody re-straddled, doubling Irv’s bet.

I looked at my cards, saw ace-queen and raised. Everyone folded except for Irv, who quickly made a big re-raise that basically committed me for all my chips if I decided to continue.

Even though I knew you’re supposed to raise or fold in a situation like this (and folding was probably the best move given that Irv and I just met and my only read on him was that he was capable of playing tight), I called like a rank amateur.

An ace and two small cards landed on the flop. Irv checked. I went all-in for my remaining stack, which wasn’t even half the size of the pot. Irv seemed a little annoyed. “I don’t know you, kid,” he said. “You could be crazy.” He called my bet and turned over pocket kings. I got lucky, flopping an ace. Never has a winning hand left me feeling more like a loser. He was more than a 70 percent favorite to win when I’d called his re-raise. Irv had gotten me to put most of my chips into the pot when I was a huge underdog, only to see me get rewarded at the end for being a fool.

Irv laughed when I took the pot. I wasn’t sure if I had pissed him off or would ever get invited back to the game. But the laugh really didn’t mean anything.

It was just one hand, one of thousands I would end up playing with Gotti and assorted billionaires, actors, filmmakers, musicians, celebrity chefs, athletes, and serial entrepreneurs. These late nights at the card table have taught me a lot about self-control and etiquette and being a better man. If you ever find yourself in a similar situation, here’s how to conduct yourself properly at a private high-stakes poker game.

Stay until the end of the game.

This is the most important tip I have: You are not in a casino, so don’t behave like you are. You can’t win a big hand and leave for dinner. People who come to quickly take cash from the game and bolt won’t get asked back. I wasn’t at my regular New York poker game on the night when a Law & Order actor doubled his chip stack, took a phone call, and then said he had to depart because of an “emergency,” but I’ve heard the story many times. Nobody at the table believed him or wanted him back.

Several years later, my wife and I were with our children at Coldwater Canyon Park in Beverly Hills and she spotted this actor hanging with his kids. She recognized him because she knew that the entire poker game still, after all this time, thought of him as a huge dickhead.

It’s not about the money, so be cool.

When men with unlimited bankrolls play poker, it’s about the action and the competition, not the money. So if some billionaire makes a dumb all-in call on the flop, hits his two-outer on the river and ends up taking your whole stack, giving him a hard time can get you banned from the game. (Again, private games are not like casinos.) Don’t taunt the independently wealthy globe-trotting DJ when he gets upset about losing a huge pot. Be a good guy, even when you’re losing. Tip the dealer well – $5 for each hand you win is pretty standard in games I’ve played in – even when you’re down. Participate in ridiculous side bets, whether they’re about who will miss the most shots in the basketball game you’re watching or just the equivalent of flipping coins for big money at the end of the night. It’s all part of the game.

Don’t make the stakes of the game public.

I remember poker pals e-mailing me about how much of a fuckwad they thought James Altucher, not even a regular in our game, was when he wrote this. The piece wasn’t even about cards, really. And despite Altucher’s greater message, the opening part about how he lost his “last $2,300 in a brutal hand of poker to Irv Gotti” at our game just seemed like the worst kind of brag, what years later we would all know to describe as a #humblebrag.

Don’t pitch anything.

You’re not here to hustle. This is absolutely the worst place to ask somebody to read your screenplay or introduce you to a venture capitalist or consider hiring you for their real-estate listing. If you become friendly with someone at the game, invite them to lunch or drinks and then decide if it makes sense to talk business.

Talk a good game.

A lot of people think they have absolutely nothing in common with celebrities and billionaires, that A-listers might as well be space aliens. But really, beyond multiple vacation mansions and private planes, there’s a lot that a boldface name has in common with, say, a discerning New York Magazine reader.

Yes, the dude on your right might be a hedge-fund billionaire getting a massage while he emails about a political fundraiser he’s hosting. Yes, the guy on your left might have explained the economics of litigation finance to you just a few weeks before Peter Thiel’s battle against Gawker was revealed. And yes, that might be Hank Azaria, Bobby Flay, and Don Cheadle, all invited to the game by Rabin, who’s since gone on to open the Lambs Club, Cafe Clover, and the Skylark.

But guess what: Rich guys like to eat and drink and party at the same places you probably do on your most baller nights. They might live in L.A. but go to Carbone whenever they’re in New York. They like to hang out in Vegas and Miami. They invariably know Noah and Jason at Marquee, Eugene and Mark at Catch, Richie at 1OAK. So feel free to talk about those kinds of places and people even if you’ve only read about them on “Page Six.”

But you don’t even have to bluff. Safe, lively topics of discussion that lots of other players will relate to include: your kids and any nightmares you’ve had getting them into a good school; HBO shows; the real-estate market in Brooklyn; the relative hotness of various models and starlets; the best kind of Trader Joe’s candy.

Find the sweet spot.

Poker games have taught me that even the wealthiest of the wealthy are suckers for Trader Joe’s chocolate. You know what else you can bring to a game full of men who have everything? Fancy doughnuts. New-school ice cream. Sweets they haven’t tasted before but may have read about. (An L.A. game I play in might be the biggest purchaser of artisanal pastries in the city.) So go to Dough or Blue Marble or Dominique Ansel if you want a gift for your poker host. Don’t feel like you need to do this every week or even every month, but occasionally showing up with sweets or a nice bottle of liquor, especially around holiday time, is appreciated.

Laugh when you get lucky.

When Irv laughed, I laughed too.

How to Handle Yourself in a High-Stakes Poker Game