Tobey Maguire and Alec Gores sued over illegal high stakes poker winnings

Lesson of the day: If you want to play in illegal high stakes poker games, make sure the guys on the other side of the table are playing with their own money. Star and Radar have reported that Hollywood’s own Tobey Maguire and businessman Alec Gores are learning this lesson the hard way right now, while Matt Damon, Ben Affleck, and Leonardo DiCaprio have never been happier to have walked away from the table a bit behind.

Brad Ruderman (above, on the right)  is the problem. He was jailed last year on a 121 month sentence (that’s about 10 years to you and me) for running a Ponzi scheme that separated investors from about $25 million in embezzled funds. Now, some of those investors are trying to get their money back, and they claim that Maguire and Gores owe them.

^ Billionaire Alec Gores is also being sued for poker winnings

According to the lawsuit, when Ruderman lost a few hands to Alec Gores and Tobey Maguire in illegal poker games in California, the money he paid them off with was not his own. And, since the games weren’t legit, Ruderman’s investors are suing to get their embezzled money back from those who won it illegally. The suit against Maguire claims that he won over $300k of Ruderman’s embezzled funds. In Gores’ case, Ruderman’s investors allege that he owes $445,400 for winnings that he collected on 5 separate occasions. Damon, DiCaprio, and Affleck are not being sued, which suggests that the cards weren’t falling their way when they played Ruderman. Whew!

^ Tobey Maguire sued, Leonardo DiCaprio walks away (London Ent / Splash News)

Other notable celebs breathing a sigh of relief after participating in the $100,000 buy-in games but not being named in the suit include director Nick Cassavetes (The Notebook, John Q), actor Gabe Kaplan (Welcome Back, Kotter), record label owner Cody Leibel, the less famous half of Paris Hilton’s sex tape Rick Salomon, and Las Vegas “nightlife entrepreneur” Andrew Sasson.

Starcasm will be watching carefully to see what happens with this case. On the one hand, if Ruderman lost embezzled funds in an illegal game, then perhaps the winners in that game have some liability. We’re not lawyers. We don’t know. On the other, hand, this seems like a case set to test the boundaries of the gray area that private poker games currently exist within. Did the games in question have a paid dealer and did the house take a rake, or were they genuinely private games? Regardless of the stakes, most players assume that law enforcement isn’t interested in private games and only occasionally concerned about small, illegal gambling houses that keep a low profile. A few reckless guys gambling in a back room somewhere is far from a priority for most justice systems. It is a victimless crime . . . unless, I suppose, one of the guys at the table is an embezzler.

^ Card playing buddies Ben Affleck and Matt Damon attend the Ante Up for Africa celebrity poker tournament in 2009. (Judy Eddy/WENN.com)

However things turn out, you have to hate it for Gores, McGuire, DiCaprio, Damon, and Affleck. They aren’t the first guys to sit down at a poker table only to find out they were playing a different game than they bought in for, but this is still pretty rough. In case you’re not feeling the love yet, check out this back-in-the-day shot of young Leo and Tobey. How could you not trust those faces?

^ Tobey Maguire (left) and Leonardo DiCaprio’s gaming ways started early!