Tobey Maguire’s inscrutable smirk, so useful in making others underestimate him in Spider-Man, has also made him plenty of money at the poker table, apparently. The actor is at the center of a high-profile lawsuit involving incarcerated hedge fund manager Brad Ruderman, who orchestrated a massive Ponzi scheme then blew $25 million of his ill-gotten gains in poker games with actors like Maguire, Leonardo DiCaprio, Matt Damon, and Ben Affleck, and their fellow teen heartthrob, Welcome Back Kotter’s Gabe Kaplan. An FBI investigation into Ruderman’s finances uncovered his connection to the Hollywood poker ring, which met frequently between 2006 and 2009 in secret locations all over Los Angeles, in rooms protected by armed, bulletproof vest-wearing guards who demanded secret passwords to enter. And while underground gambling is illegal in California, particularly when it's so intense it involves hiring big guys with guns, it’s rarely prosecuted. However, Ruderman’s victims would definitely like their money back.
Fortunately for them, Damon, Affleck, and DiCaprio are not named in the suit, because they suck at poker. But Maguire is such a high-roller, he personally took Ruderman for around $311,300—though that’s just a drop in the bucket compared to the estimated “$1 million a month over a period of three years” one fellow player believes he made overall. So yeah: Do not play poker with Tobey Maguire. That boyish smile is just the prelude to a stab in your heart. Matt Damon, on the other hand, reportedly “never won,” which only makes that Rounders sequel idea seem even sillier.