Tobey Maguire was at the peak of his commercial fame in the late 2000s. The Spider-Man trilogy directed by Sam Raimi had grossed approximately two and a half billion dollars at the global box office between 2002 and 2007. The personal share of Maguire of the franchise was approximately fifty million dollars. He used a portion of the money to bankroll his second career as the highest-stakes recreational poker player in the Los Angeles entertainment industry.
Maguire was a regular at the private poker games organized by Molly Bloom at the Viper Room on Sunset Strip in Los Angeles. The games started with buy-ins of ten thousand dollars per seat and grew into hundred thousand dollar buy-ins by 2007. The other regulars included Leonardo DiCaprio, Ben Affleck, hedge fund manager Houston Curtis, and a rotating cast of approximately twenty other Hollywood and Wall Street figures. Maguire was widely considered the most aggressive and most successful player at the table.
Maguire studied poker more seriously than the other Hollywood regulars. He took private lessons from professional player Daniel Negreanu in 2006 and 2007. He read multiple books on game theory optimal play. He hired a poker coach to review his hands from the Bloom games on a weekly basis. He played in the World Series of Poker Main Event in 2004 and finished in 358th place out of 2,576 entrants, well above the typical celebrity finish in the event. His cumulative winnings from the Bloom games over four years were estimated at approximately ten million dollars.
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One of the regular losers at the Bloom games was Bradley Ruderman, a Beverly Hills hedge fund manager who ran a fund called Ruderman Capital Partners. Ruderman lost approximately twenty-five million dollars in the Bloom games between 2006 and 2010. The losses included approximately three hundred and eleven thousand dollars to Maguire over multiple sessions. Ruderman was widely regarded by other players as the worst player at the table. His losses were what economically sustained the games.
In May 2009, Ruderman was arrested by the United States Securities and Exchange Commission and the Federal Bureau of Investigation. He had been operating Ruderman Capital Partners as a Ponzi scheme since approximately 2003. He had stolen approximately twenty-five million dollars from his investors. Substantially all of the stolen money had been lost at the Molly Bloom poker games. He pleaded guilty in March 2010 and was sentenced to ten years in federal prison.
The bankruptcy estate of Ruderman Capital Partners filed lawsuits against several of the Hollywood poker players in May 2011 to claw back the gambling winnings under the legal theory that the funds were stolen and therefore the recipients had no legal title to them. The legal theory is well established in fraud cases under the doctrine of fraudulent transfer. The estate sued Maguire for three hundred and eleven thousand dollars. The estate also sued Leonardo DiCaprio, Ben Affleck, Andrew Sasson, and approximately twelve other regulars at the games for various amounts.
Maguire settled the lawsuit in February 2012 for an undisclosed amount that was reported to be approximately eighty thousand dollars, less than one third of the original demand. The other defendants settled at similar discounts. The settlement was paid to the bankruptcy estate, which then distributed the proceeds to the defrauded investors. The total recovery from all settled lawsuits was approximately one and a half million dollars across all defendants. The defrauded investors received an estimated six cents on the dollar from the combined estate distribution.
The lawsuits raised a legal question that had not been previously tested in California courts. Should poker winnings from a private game be treated as a fair exchange of value, in which case the winners had legitimate title to their winnings? Or should the funds be treated as the proceeds of fraud, in which case the recipients had a duty to return them regardless of whether they knew the funds were stolen? The settlements avoided a court ruling on the question. The legal theory remains untested in California as of 2026.
The Bloom games were investigated by the Federal Bureau of Investigation between 2011 and 2013 as part of a broader inquiry into illegal gambling operations linked to organized crime. Bloom herself was arrested in April 2013 and pleaded guilty in 2014 to operating an illegal gambling business. She was sentenced to one year of probation and ordered to pay one hundred and twenty five thousand dollars in restitution. None of the players, including Maguire, were charged with criminal offenses. The federal interest in the games was directed at the operators rather than the players.
The Maguire-Ruderman lawsuit became a case study taught in business school ethics courses on the doctrine of fraudulent transfer and the responsibility of recipients of stolen funds. Maguire has not commented publicly on the lawsuit since the 2012 settlement. He continues to play poker in private games but has not played publicly in any major tournament since the 2010s. His current recreational poker activity is reported to be substantially smaller in stakes than the Bloom era. He has not appeared in a feature film in a leading role since 2014, and has stated in interviews that the Spider-Man franchise produced enough income that further full-time acting work is not financially necessary for him.