You’ve seen them in the movies Rounders, Oceans 11, Spiderman, The Town, and even Titanic. Now, you might be seeing them in gambling-related news for some time. A-list celebrities Matt Damon, Ben Affleck, Leonardo DiCaprio, Matt Damon, and Tobey Maguire are among more than a dozen named in a law suit by a jilted poker player, now-jailed hedge fund manager Brad Ruderman, who is trying to recoup his losses from playing in illegal private cash games.
Ruderman, the CEO of Ruderman Capital Partners, apparently a consistent loser in both financial markets and Texas Hold ‘Em, is suing specifically Tobey Maguire to whom he lost more than $300,000. Ruderman is currently serving a jail sentence until 2018, for embezzlement of funds and investment adviser fraud. He reportedly lost $25 million in investor money in private Beverly Hills poker games and put together a desperate Ponzi scheme in an attempt to pay off his debts. “As part of the scheme, funds invested in (Ruderman) were transferred to persons such as Defendant (Maguire), who received the funds on account of Ruderman’s gambling losses and on account of Defendant’s gambling winnings.” The lawsuit clams that Maguire is “not entitled to receive the transfers from the Debtor, which transfers were compromised of improperly-diverted investor funds.”
DiCaprio, Affleck, Damon, and Maguire reportedly played as regulars in private cash games with $100,000 buy-ins. The lawsuit claims that Maguire made as much as $1 million a month over three years, but this is likely exaggeration. Well-known poker commentator and longtime successful tournament player Gabe Kaplan also played in the games. According to the lawsuit, the games were “exclusive events, by invitation only, and that there was a regular roster of players consisting of wealthy celebrities, entrepreneurs, attorneys and businessmen.” Entry to these games was highly regulated, with secret passwords and a referrals system.
In California, unlicensed private poker games are illegal. In an interesting twist, Maguire has hired an attorney to fight the lawsuit and will argue that private cash games are not illegal. One of the regular players, Dan Bilzerian, informed media that while Matt Damon played irregularly, when he did play, he never left a winner.