As ‘Rounders’ Turns 25, One Player Tells His Underground NY Poker Stories

Written By Hill Kerby on November 16, 2023
Image of a poker hand in front of the New York City skyline. One NY poker player looks back on his underground playing days and examines how

What poker player, gambler or movie lover hasn’t seen “Rounders”?

The iconic poker movie featuring Matt Damon and Edward Norton celebrated its 25th anniversary earlier this year. Think about that: its September 1998 premiere came five years before Chris Moneymaker won the 2003 World Series of Poker Main Event and set off the poker boom responsible for many of our entrances into the game, including mine.

“Rounders” portrayed New York City’s underground poker scene with Damon’s character, Mike McDermott, risking everything – on and off the felt – to beat NYC’s best and chase his dreams of going to Las Vegas and winning the WSOP Main Event.

The movie was mildly popular and played a role in poker entering the mainstream before the 2003 boom, well before online poker – heck, we’re still waiting on the legalizing of online poker in New York – hit the scene. It has since become a timeless piece of history with a cult following, showcasing an era of poker from before the boom that, in many ways, will forever be etched in poker’s past.

To commemorate the movie’s 25th anniversary, PlayNY spoke with David Paredes, who cut his teeth in the NYC scene. Paredes is a top cash game player today and has more than $2.7 million in live tournament earnings, including a WPT Main Event victory at Borgata in 2015.

Paredes shared some experiences and stories from the “old school” days and provided his take on how accurately the movie portrayed the games in real life. Let’s dive in.

How realistic were the scenes from ‘Rounders’?

Paredes remembered several other rooms throughout New York City, some even larger than Skylight. He said the operations were highly professional and legitimate despite being blatantly illegal.

“So, that was the club era,” Paredes said. “And when you ask how realistic were those scenes in ‘Rounders’? I would say very.

“You see those scenes, where like, is a Russian mobster eating Oreos? No. That’s Hollywood.”

But the overall portrayal of the games? Paredes said:

“It was unbelievably accurate. And there’s no way anyone could have written that if they hadn’t themselves been to underground clubs. There’s simply no way. And the thing is, I didn’t know how accurate it was because I had never been to the underground clubs in 1998. In 1998, no one had even heard of them.

“I really was pressing an unmarked buzzer on an unmarked door, and there were security cameras and you’d come in. Then, all of a sudden, you’re in this poker oasis. It was absolutely incredible, and it was completely real.

“It’s one of those movies where someone who wasn’t from New York City and never set foot in an underground poker club could tell that it feels real. And the only way to make it feel real is from actual knowledge [of the scene]. There’s an authenticity that you can’t fake. And I’ve seen a lot of poker movies that didn’t have that authenticity, but ‘Rounders’ really did.”

Who was the movie modeled after?

You know the story, with McDermott putting himself through law school with poker winnings before taking a shot and losing his entire bankroll. You know that he deals with relationship issues and drama with his best friend, “Worm,” played by Norton.

You know the cameos from Doyle Brunson, Erik Seidel, Johnny Chan and Phil Hellmuth. You know the other characters, like Teddy KGB and his classic sayings. (“Very agg-re-ess-ive!” “Pay that man his money!” “The kid’s got alligator blood!” The list goes on.)

Given how accurately the movie portrayed NYC’s underground scene, Paredes wonders if these characters were based on any person (or combination of people) from the games. Of course, it wasn’t him since he didn’t start playing these games until 2003.

Coincidentally, though, Paredes put himself through law school from these games. Unlike McDermott, who dropped out of law school, Paredes graduated from NYU Law School.

Getting into the NY poker scene

According to Paredes, NYC’s underground games peaked at the same time as the rest of the country. This was when he found out about them, too.

“Basically, I’m taking you to 2003,” Paredes said. “The heyday of New York City underground poker was from 2003 until roughly 2007-09. But it was really from ‘03 to ‘07 that the underground clubs were booming.”

Before that time, Paredes took buses from Chinatown to Foxwoods, in Connecticut, to play $10-$20 Limit Hold’em games. He met someone at Foxwoods who told him underground games existed in The City.

At first, Paredes didn’t believe it. He said that you would never know these places existed. But he trusted the gentleman, a novelist who wrote a poker book with a similar storyline to “Rounders.”

“He’s like, ‘Go to this unmarked door; press this buzzer,’ you know. ‘This guy’s going to be expecting you,’” said Paredes.

“So I’m like, ‘Okay!’” he continued. “The place was called Skylight. So I walked in, and again, you would never know these places existed. Like, literally, there were these doors that you’d just press a buzzer, look up at the camera, and they let you in.

“And it was like an oasis. I opened the doors, and there was candy set up front. Seven or eight tables. It was a beautiful room called Skylight because of the beautiful skylights in the ceilings. Everything was so pristine. And I was like, holy shit, I don’t have to take a bus for four hours to go play poker?!”

The NY poker games were great … until they weren’t

All of NYC’s underground games operated on a cash basis. Paredes said he always felt safe, never worried about cheating or had a problem getting paid as a customer.

Everybody who knew about these games knew someone involved in the scene, creating an organic vetting system that kept trouble at bay. But eventually, the scene grew too large to stay underground in a place like New York City.

“I think what happened was people saw how much money these clubs could make,” Paredes said, “and poker was really getting popular. I think when money comes, then you have greed. So then you have these newer clubs start popping up.”

Paredes recalled one of the more famous game-runners starting a club called Broadway, featuring “Bobby’s Room-style, high-stakes games.” One of which drew the attention of New York Yankee Alex Rodriguez, who was caught playing a game during the MLB playoffs. Someone took a picture of him, Paredes remembered, and sent it to the New York Post.

“That was the beginning of the end, I feel like,” Paredes said. “Because you’re basically throwing it in the cops’ faces that there’s an underground poker scene. It’s not so underground anymore when you have this on the front page of the New York Post.”

The end of a scene for Paredes – and poker

Police officers raided a number of games as they came into the public light. Paredes remembered an even worse encounter, which proved to be his last in the scene.

It all took place in 2007 at a small club known as Genoa. Paredes said ownership must have changed, because a new security guard was posted up during a dark and stormy night. While Paredes was playing poker, some individuals burst onto the scene with guns.

“They were like, ‘Everyone, get down on the ground underneath the tables!’ And they flipped the tables over,” Paredes remembered. “We were on the ground, and they went person by person, robbing us. I had a Rolex that I put in my hoodie pouch. We gave them our wallets and stuff, and the crazy thing was they mailed everyone’s licenses back to them.”

Paredes wondered why this group would do such a thing, something almost … chivalrous. Although, he argued, perhaps they were proving to the people they robbed that they knew where they lived. Paredes joked with his friend that perhaps they were well-aware of how bad it was to wait in line at the DMV.

“But I’m in law school, right? I’m about to take a job as a lawyer making $180-something K a year,” Paredes said.

“What am I doing grinding in a game where I had a gun to my head? It was a real wake-up moment, and at that point, the games started shifting into these Molly’s Game-type places where it would be like one table, maybe two tables max, in a super high-end hotel with catered food and everything. It had moved away from the Rounders-style games in tiny places and stuff like that.”

Paredes’ time in the heyday of New York City underground poker came to an end. He played clubs all around Manhattan, not to mention a few uptown and in midtown. Most, he said, were situated below 34th Street.

“It was really amazing for a while. It was unbelievable,” Paredes said. “And like I said, you would never know any of these places were there. The average person would have no clue.”

Photo by PlayNY
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Hill Kerby

Hill Kerby is a contributing writer for PlayNY who, above al else, emphasizes safe and legal betting, all while remaining grateful to be able to contribute to growing the gambling industry. His background includes poker, sports and psychology, all of which he incorporates into his writing.

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