New York City’s Underground Poker Scene

A former player says it’s time to bring the game out of the shadows

Illustration by Adolfo Valle
Illustration by Adolfo Valle

There was a time in New York City, not so long ago, when men and some women, myself included, played in underground poker games all over the city. “Underground” makes it sound glamorous, like all the women wore ball gowns and red lipstick while the men smoked cigars and threw their Rolexes on the table when they were low on cash. (Despite what you see in movies, no halfway-legitimate game would ever let you gamble more than the money you have on the table at the start of a hand.)

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Actually, it wasn’t like that at all. We’d duck into the most nondescript buildings. Instead of ball gowns, I wore hooded sweatshirts and headphones in my ears, and walked into mini casinos. They had cameras at the doors, sometimes burly security guards. Some places issued I.D. cards. In retrospect, it was security theater. The measures were meaningless, practically funny. They didn’t stop the cops and they didn’t stop the robbers.

There was Genoa, the small one downtown. It was the oldest poker club in the city, with only three tables and an old Italian man cooking up the best pasta with red sauce you’ve ever had for five bucks. The busy one, Straddle, in Midtown East, which had inexplicably never been raided so everyone whispered they had someone big on the take (they would eventually, like all the clubs, be raided and shut down). There were dozens of others. Upper East, Midtown West, all over Brooklyn and Queens.

I was entry-level in PR at the time, starting over in my late 20s in a new career after an expensive graduate school experience. The other people at the tables did all kinds of things.  There was a guy who said he was mayor of a small town in northern New Jersey (I had no reason not to believe him, but anything that is said at a poker table should be taken with a large grain of salt), filmmakers, bankers, housewives, Juilliard students and many, many lawyers. I played poker with famous actors, musicians, judges. No, I never saw A-Rod.

The players didn’t worry about cops. We knew it wasn’t going to lead to arrest. There was some weird quirk in the law in New York where apparently it’s illegal to facilitate gambling but it’s not illegal to actually gamble. Or so we heard from, again, the many, many lawyers who played in the games. I’m not a lawyer so I can’t confirm the law but I was present during a raid once and it went down exactly as they said it would: the cops burst into what was my favorite game in the city—the All-In Club in Midtown West. They kept the players at the tables and ran all of our I.D.s. Anyone with a warrant, which turned out to be only one guy in a room of many, was arrested. The rest were free to go. We lost all the money we had on the table, which sucked, especially for the people who had been playing all day and built considerable stacks, but at least it wasn’t jail. Someone I know left with a pocketful of the branded chips so that if that poker club ever reopens in New York City, he’ll be ready to cash them in. This was in 2007 and he still has a stack. The staff wasn’t so lucky. All the dealers and front desk staff were arrested. They let the woman who made sandwiches go, as well as her teenage daughter.

We did, however, worry about robbers. I had a friend who was a dealer at Genoa, the old downtown place. It had been robbed and he said the scariest part was that the guy pointing the gun at him was scared and shaking so hard that my friend feared he would accidentally shoot him. This turned out to be prescient. In November 2007, Frank DeSena, a schoolteacher from New Jersey, was at the City Limits club in Gramercy when robbers busted in. They ordered everyone onto the floor and one of the nervous gunmen dropped the shotgun he was carrying. The gun went off, killing DeSena.

The boom time of the clubs pretty much ended there. I never went again and many others I know didn’t either. No longer able to ignore they were there, the police began raiding and closing clubs. When Genoa closed, it really felt over.

But my poker life went on. I played in a few home games and was still playing often enough online. I heard that some new places had opened but after that killing I had no interest in ever going again. I never wanted to be doing something cool and dangerous. I played poker because I loved it and because I was pretty good at it and the only reason I chose the clubs was proximity. I couldn’t exactly dip into Atlantic City after work, though that wasn’t unheard of every now and again. My day job in my new career was entry-level, so my after-hours poker-playing paid my bills. I kept an Excel spreadsheet with all of my wins and losses and would record them even if they were “-$3” or “+$6”. I knew one of the biggest traps for people who play a lot was to feel like you’re always winning even if you weren’t.

I played with a lot of people who considered themselves great players but went home losers much more often than winners. I didn’t want to be the kind of player who swagged with my amazing skills; I just wanted to make the money.

The skill level in the clubs was extremely varied. I saw some incredible players there, much better than I had ever seen in Vegas or Atlantic City. I stayed as far away from them as I could. I knew the targets; we all did.

As successful as I was at live poker, I was not a winning player overall online. I did O.K., and I did well during a time in my life where I was playing to eat, but Internet poker wasn’t my thing. I needed to look at the other players at my table, and them at me, to play well. Being one of the few women playing the game was always an advantage for me in live play.

Men have a preconceived notion about how women play—weakly—and I fed into it. I often wore my hair in two braided pigtails. Would someone this innocent lie to you about her hand?

With limited options for live play, I started playing online more often. I got married, to a poker player, and got pregnant shortly after our wedding. As motivation dwindled to leave the house, online play became a regular part of our evenings. The night before I gave birth to my daughter, I won a large online tournament. During her newborn year, as motivation to go out may have gone up but opportunities went down, we played online constantly.

Then suddenly, that was over too. While the Unlawful Internet Gambling Enforcement Act (UIGEA) of 2006 crippled online play, it was actually April 15, 2011, a day dubbed “Black Friday” among online poker players, that online poker in the U.S. ended. The Department of Justice seized the domain names of three major poker sites and essentially ended real money play in America.

Our laws against poker are some of the most backward around. It’s been four years since “Black Friday” and three states have brought back online poker: Delaware, New Jersey and Nevada. If there are two states that don’t need online poker, as they have an abundance of casinos, they would be New Jersey and Nevada. Only people in those states may play on the sites. It’s all ridiculous.

In the last year there has been an online gambling boom of a different type. Fairly suddenly, sites like DraftKings and FanDuel have sprouted to let people pick a fantasy sports team and gamble real money against their opponents. This kind of gambling is exempt from UIGEA (though as we go to print, Democratic Congressman Frank Pallone Jr. of New Jersey is calling for a congressional hearing into the legality of the sites) because fantasy sports knowledge is considered “skill.” I don’t doubt that it does require skill to keep track of hundred of players and utilize them on your “team” at just the right time. The implication there, though, is that poker is not a game of skill when it so clearly is.

My favorite poker club, All-In, the one in the raid I mentioned above, had a sign up that read “No Rounders quotes.” The poker movie lends itself to quoting it around a table and it could get old fast. There’s a line in it, though, that really sticks out: “Why do you think the same five guys make it to the final table of the World Series of Poker every year? What are they, the luckiest guys in Las Vegas?” As poker has grown, it isn’t the same five guys anymore (and the prize isn’t an adorable million dollars as it was in 1998 when the film was released), but every year it’s the same faces who do well at the World Series; every year it’s the same poker heroes on TV.

Poker has a long and storied history, in New York and across the country. It’s well-known that President Obama, when he was a senator in Illinois, had a popular poker game attended by other prominent politicians, but the fact is his game was likely illegal. Illinois prohibits all forms of gambling outside of sanctioned casinos, including home games where any real money is involved. Similarly, President George W. Bush is said to have played a lot of poker, and been quite good at it, while at Harvard for his MBA. At least poker home games are allowed under Massachusetts state law.

We see poker skills as strengths in presidents; in theory it means they will be better at money management, have negotiating and bluffing skills, and ability to see the angles that a non-poker player may not. And yet we also regard poker as something illicit, grouped with games of chance like three-card monte, instead of games of skill like chess. As in Massachusetts, home games are legal in New York so long as no one is making money on the game (such as charging an entry fee or taking part of each pot as commission called a “rake”) but if you facilitate a game and get paid for your trouble, so that you’re not playing with the same half-dozen dudes every Friday night of your life, you’re breaking the law.

In 2011, after years of debate, New York City finally got a casino. Sort of. It’s in Queens and it’s all automated games, almost entirely slot machines. In other words, the people who deem poker to not be enough of a game of skill to legalize it have decided that a room full of machines, where people lose their money by pressing a button or pulling a lever in a monkey-like manner, is worth legalizing. In their infinite wisdom, even the table games such as blackjack or roulette are automated so as not to add any additional jobs to the area. If it all seems extremely convoluted, it is. After all, the state lotto, where you pick numbers at random and hope they hit, as well as horse-racing, where you bet on which horsey will cross the finish line first, are always exempt from gambling laws.

It doesn’t have to be this way. New Yorkers deserve to be treated as adults. Poker rooms can flourish in our city and with them a new culture of playing. No more will we have to play in unmarked office buildings, afraid of raids or robbers. Poker can be out in the open, where it belongs. It can bring jobs for card dealers, food service providers, room managers, etc. It can be somewhere stripper-squeamish guys have their bachelor parties. It can have day games for senior citizens. We don’t have to become a gambling mecca; we can identify that not all gaming is the same and legalize this particular game of skill. It can be even be tuxes, gowns and red lipstick if people want it to be. But the Rolexes stay off the table. 

New York City’s Underground Poker Scene