Tobey Maguire Targeted Over Illicit Poker Ring: Are DiCaprio, Damon and Affleck Next?

Actor sued for unwittingly winning embezzled funds off a currently imprisoned hedge fund manager during Maguire's years of involvement in illegal, star-studded gambling group

By Gina Serpe Jun 22, 2011 9:06 PMTags
E! Placeholder Image

Funny, we always thought a good poker face is what kept you out of trouble.

Not so for Tobey Maguire, who's been sued after getting outed as one of the A-listers who allegedly took part in a years-long illegal gambling ring that saw millions of dollars change hands in a series of no-limit high-stakes poker games.

In addition to Maguire, Leonardo DiCaprio, Matt Damon, Ben Affleck and Notebook director Nick Cassavetes are among those who allegedly took part in the invitation-only marathon Texas Hold 'Em sessions.

Oh, what a tangled web. So, did the onetime Spidey simply overplay his hand? Here's what got Maguire singled out…

 Well, turns out, he's pretty good with a hand of cards. So good, in fact, that between 2007 and 2008, he managed to take $311,200 off of Beverly Hills hedge fund manager Brad Ruderman—with $110,000 of that coming in just one night.

Though these figures aren't noted in the lawsuit, a source told Star that over one three-month period, Maguire averaged $1 million in winnings.

Unfortunately for him, Ruderman anted up more than he had to spare, and as a result orchestrated a Ponzi scheme among his investors to pay off his debts, which included the money he owed to Maguire.

In other words: the actor inadvertently found himself on the receiving end of some hot cash and is now being sued by a trustee for the investors Ruderman embezzled from in an attempt to get back some of their stolen funds.

The suit—filed back in March but only recently uncovered—makes it clear that Maguire was not involved in Ruderman's scheme in any way and was completely unaware of how the businessman, currently serving a 10-year federal prison sentence after pleading guilty to five criminal counts, came up with the currency. However, the suit alleges that Maguire nevertheless wrongfully accepted the money and should hand it all back over, with interest.

According to the lawsuit, the games, which were held twice weekly at "luxury locations" like The Four Seasons, The Peninsula, the Beverly Hills Hotel and the players' own homes, were highly organized affairs. One woman, Molly Bloom, allegedly acted as the chief coordinator of the games, and scheduled the accommodations, amenities (massages and alcohol were heavy features), food, hired the dealers, kept track of the players' wins and losses and arranged for the financial settlements between players.

All of which, in addition to helping keep things civil and organized, made the card sessions "controlled games," which should then have been licensed or otherwise regulated by federal, state or local authorities. Which they weren't. And which is where that whole illegal ring thing comes into play.

So far, Maguire hasn't publicly commented on the suit, but is believed to have heavily lawyered up.

However, lady luck hasn't left the actor completely: as of now, he's not being pursued on any criminal charges—likewise Damon, DiCaprio or Affleck. Though should that change, the legal system may have just hit the jackpot.

—Reporting by Claudia Rosenbaum