Bradley Ruderman is currently in a federal prison serving his 10-year sentence for operating a ponzi scheme (an illegal investment fraud). Apparently, he lost nearly $25 million of his investors' money, who are now trying to regain some of it. Through the Trustee of his company, Ruderman Capital Partners (which is currently bankrupt) Ruderman filed a complaint against Tobey Maguire to return his $311,200, which he won in illegal game, to pay some of his investors back. Since the arranger of such home games, Molly Bloom Inc, is not a licensed poker provider in California, the games were illegal, therefore the winnings are illegal as well.
Other Hollywood celebrities like Matt Damon, Ben Affleck, Nick Cassavetes, Leonardo DiCaprio and many others might also be in trouble, they also played at the supposedly illegal home games in Beverly Hills hotels and private residences. They can face up to 6 months jail time if proven guilty.
However, the accusations seem rather far-fetched, and there seems to be no evidence that either Maguire or his fellow players know anything about the illegal nature of the games. We'll see how this will work out.
You can read the whole court document if you are interested in the case.
