The Star-Studded Past of New York Underground Poker

The term “underground” automatically implies intrigue, mystery and potentially illicit activity; throw in some luminaries from the entertainment, sports and business worlds and you’ve got yourself the makings of a seemingly scripted but very real slice of the history of poker in the Empire State.
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The term “underground” automatically implies intrigue, mystery and potentially illicit activity; throw in some luminaries from the entertainment, sports and business worlds and you’ve got yourself the makings of a seemingly scripted but very real slice of the history of poker in the Empire State.

As New York continues its push to legalize online poker, it bears noting that the allure of the activity is essentially as old as the game itself, an appeal that’s been immune to mundane things such as legality, safety, and in the cases of several prominent figures, even skill.

Molly Bloom and Her Famous Friends

Underground poker rooms have been a fixture in Manhattan and surrounding boroughs for decades, with a certain ebb and flow to their popularity and pervasiveness. Although they’ve largely flown under the general public’s radar at various points in time, they skyrocketed in popularity in the four-year period between 2003 and 2007, coinciding with the explosion in visibility for poker on a national level. A quirk in current New York penal law renders the actual players in these rooms susceptible to losing only the chips they have on the table at the time of a law enforcement raid, and not their freedom. The operators of any of these unlicensed “establishments” suffer a different fate, however, as their involvement in facilitating the operation does place them in legal hot water.

The wave of notoriety earlier this decade undeniably received a major assist from the rub of celebrities such as then-New York Yankee Alex Rodriguez and Cirque Du Solei CEO Guy Laliberte participating, as well as the well-publicized April 16, 2013 84-page indictment of hostess Molly Bloom and her ring of underground games that both gentlemen were associated with as players at various points. The wave of arrests were made at the federal level and ensnared a total of 34 people, with charges ranging from the actual facilitation of illegal gambling to the operation of a Ponzi scheme. The group included multiple reputed Russian mobsters and renowned East Side art dealer Helly Nahmad.

West Coast Success Leads to East Coast Expansion

When Bloom started running her original invitation-only poker games, the locale was Los Angeles and surrounding areas such as Beverly Hills that drew in Hollywood A-listers such as Toby Maguire, Ben Affleck, Matt Damon and Leonardo DiCaprio, along with prominent West Coast attorneys, real estate brokers and other that could easily swing buy-ins that typically began at $10,000. Often, the biggest names were far from the sharpest players, but their sizable bankrolls and willingness to see those take a hit now and then kept the games highly lucrative and therefore appealing.

Thriving on the Left Coast, Bloom figured more was better and dipped her toe into the New York underground scene in September 2008 with a high-stakes affair in a 4,300-square foot suite at the Four Seasons hotel in Manhattan. The event came complete with caviar, champagne and a bevy of models and masseuses that rounded out the first-class experience for the likes of Rodriguez and Laliberte, both of whom were in attendance that first night. Minimum buy-in was a whopping $250K, ensuring the exclusivity of the clientele at the tables.

Just as the California games had proven to be a magnet for perhaps the wealthiest industry in that area – entertainment – the Manhattan scene drew in plenty of Wall Street traders and hedge-fund millionaires eager for some high-stakes action alongside power brokers from domains outside of their circle.

While there was reportedly plenty of action to be had throughout the city at buy-ins that fit virtually any budget, Bloom’s games were considered the elite offering in this regard. With their invitation-only criteria and heavily-secured locales, the variety of problems that either plagued or served as a perpetual threats to other underground rooms such as the Play Station, Straddle, Diamond Club and Genoa – namely, law-enforcement raids and armed robberies – didn’t touch Bloom’s games until the aforementioned 2013 crackdown.

Rodriguez was one of the most prominent names known to consistently frequent Bloom’s games, as well as several other high-stakes affairs around the city. One such instance that was reported about openly in the New York Post involved Rodriguez utilizing a late-night game at a Union Square room in which he sat alongside renowned poker pro Phil Hellmuth as his way of unwinding following a Yankees victory over the Orioles. Eventually, gambling-sensitive Major League Baseball began an investigation in 2011 of Rodriguez’s participation in the underground scene, which reportedly led to him ending his involvement altogether.

Potential Impetus for Current Efforts

Underground poker’s rich and storied history in New York has been far from pretty at times, and certainly didn’t lead to happy endings for many who facilitated the once-vibrant scene. However, its once white-hot appeal did serve to corroborate the appetite that exists for poker, and likely helped ignite early momentum for legalization of an online version in what many hope will be 2017.

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