Beneath the glamorous facade of red carpets and blockbuster premieres of early 2000s Hollywood, a high-stakes poker game was quietly unfolding that would eventually expose some of the entertainment industry’s biggest names. What started as weekly Tuesday night gatherings between A-list celebrities would spiral into a scandal involving FBI raids, a $100 million money laundering operation, and a web of deceit that Hollywood’s elite never saw coming.
At the center of this underground empire was Tobey Maguire, fresh off his Spider-Man success and armed with nearly $200 million in today’s money from his superhero franchise deals. But behind his clean-cut public image lay a darker personality. He was described by industry insiders as difficult, rude, and someone who “enjoyed crushing other people.” This wasn’t the friendly neighborhood Spider-Man the public knew.
The poker ring began in 2004 when Maguire, frustrated with the casino environment at the Bellagio, partnered with TV producer Houston Curtis to create an exclusive game. Curtis wasn’t just any card player—he was a “card sharp,” skilled in the art of cheating through sleight of hand and deck manipulation. Their strategy was simple: use Maguire’s celebrity connections to attract wealthy “fish” they could profit from.
Initially hosted at Maguire’s home, the game quickly moved to the legendary Viper Room after Maguire grew tired of “degenerates” bringing meat, alcohol, and tobacco into his germaphobic, vegan lifestyle. The operation was handed over to a young assistant named Molly Bloom, who transformed the weekly games into five-star events complete with gourmet catering and top-shelf liquor.
The roster read like a Hollywood phone book: Leonardo DiCaprio, Ben Affleck, Matt Damon, and directors like Todd Phillips joined tables where buy-ins started at $10,000 and eventually reached $50,000. According to Houston Curtis, DiCaprio was notoriously cheap, requiring Maguire and Curtis to “stake” him—essentially providing him with money to play despite his massive wealth.
As the games grew more elaborate, so did the money involved. Players would mark their buy-ins on sheets, with each “X” representing $20,000 in chips. Molly Bloom’s tips escalated from reasonable amounts to astronomical sums—sometimes $15,000 to $30,000 per night. She arrived at games in a cash-purchased Bentley, living a lifestyle that began to concern the game’s organizers.
The tension between Maguire and Bloom reached a breaking point when he allegedly offered her $1,000 to “get on the table and bark like a seal”—a humiliating power play that signaled his desire to remove her from the operation. According to multiple sources, Maguire had grown frustrated with Bloom’s increasing tips, viewing them as money taken away from the players’ pots.
What the celebrities didn’t realize was that their exclusive club was built on increasingly shaky foundations. The games had attracted players like Brad Rudderman, who appeared to have endless wealth but was actually running a massive Ponzi scheme. When his operation collapsed in 2011, investors filed lawsuits against players who had won money from him, including Maguire, who eventually settled for $80,000.
Meanwhile, Bloom had moved to New York and started taking an illegal “rake”—a percentage of each pot that crossed the line from legal private games into illegal gambling operations. The Russian mob attempted to infiltrate her games, leading to her being beaten and robbed when she refused their “protection” services.
The house of cards finally collapsed when the FBI raided Bloom’s New York game in 2013. She was arrested alongside 33 others in a $100 million money laundering investigation. The raid was part of a broader crackdown on illegal gambling that had already targeted major poker sites like PokerStars, whose founder ended up on the FBI’s most wanted list.
The scandal’s reverberations reached Hollywood’s highest levels. When Aaron Sorkin adapted Bloom’s story into the movie “Molly’s Game,” Sony executives’ hacked emails revealed their frustration with the project, with one executive writing, “I don’t care if Aaron’s sleeping with the girl or not… They’re treating us like s**t.” The film notably avoided using Maguire’s real name, instead calling him “Player X”—likely due to legal concerns given his history of aggressive litigation.
The celebrity poker ring’s downfall exposed more than just illegal gambling—it revealed the entitled, often cruel behavior of Hollywood’s elite behind closed doors. What began as wealthy celebrities seeking higher stakes than casino games could provide ultimately cost them millions in legal fees, settlements, and damaged reputations.