Tobey Maguire, Others Named In Gambling Ring Sting

By Vanessa Beatriz Soto

Oh my god, you guys. News is coming in over the PR wire that a clutch of A-list celebrities including Ben Affleck, Matt Damon, Leonardo Di Caprio and Tobey Maguire, as well as entrepreneur/smut peddler Rick Salomon and director Nick Cassavetes and many many others have been named in a lawsuit and potentially even criminal charges (for receiving stolen property) resulting from winnings derived from unlicensed gambling.

Here's the scoop. It all started when Bradley Ruderman, CEO of Ruderman Capital Partners, was convicted of several charges of wire fraud and investment adviser fraud in relation to a Ponzi scheme he rigged to dupe his clients, friends and family, out of over US $25mm. It seems that  Ruderman, age 46 at the time of his sentencing (he will sit in a Federal prison cell until 2018), had promised annual returns in the neighborhood of 60% to many in his inner circle, only to use a lion's share of the more than $44mm in funds he collected to pay his own expenses. This is where it gets seriously messed up.

"His own expenses" turns out to be a list of embarrassingly obvious rich-guy stuff, culminating in some pretty massive gambling debts. And those gambling debts aren't linked to any licensed casino... From the FBI's press release on Ruderman's sentencing:

"An investigation by the FBI revealed that during the course of the fraud, Ruderman spent at least $8.7 million of investor money on personal expenses, including $200,000 each summer for a rented beach house in Malibu, two Porsches, $53,930 on sporting events, $896,000 in credit card charges, and $327,000 in cash expenditures. Ruderman further admitted that he lost $5.2 million of investor money in clandestine poker games held on a regular basis in a suite at a luxury Beverly Hills hotel."

This guy is such a cliche! But wait:

"As part of his plea agreement, Ruderman admitted that he failed to report income every year since 2004. He has agreed to file tax returns for those years and to resolve all taxes, penalties and interest due to the government. In addition to the 121-month prison term, Judge Walter also ordered Ruderman to pay $27,585,849 in restitution. Ruderman was ordered to surrender to begin serving his prison sentence on February 1."

Are you starting to get a bad feeling? I'm starting to get a bad feeling.

So back to those clandestine poker games. We know Ruderman was involved in a ring of swanky but unlicensed gambling that seems to have involved many of Hollywood's leading lights. You may already have guessed that Ruderman was also a terribly bad poker player.

Well, now that his firm is in bankruptcy, "trustees" are going after money to pay off "victims and creditors." And that's where Hollywood's leading men and enter, stage right.

California law forbids unlicensed gambling, making all winnings from those games "ill-gotten." And that means that those winnings can be seized right out of the pockets of the big winners from those invitation-only five-star hotel casino nights. So who are the big winners? Well, allegedly the big one is going to turn out to be none other than Mr. Peter Squeaky-clean Parker himself, Tobey Maguire.

Guys, they are suing Spiderman!

Here are some seriously stress-inducing details, and some juicy nuggets for you to mull over:

1. The games had a stake or buy-in of $100,000. That's right. In order to play, that's what you had to pay.

2. Over a period of three years, Tobey Maguire was allegedly winning around $1mm US/month, meaning that he could be asked to cough up $30-$40mm if things go very badly.

3. Leonardo DiCaprio is a little stingy. Apparently he lost a hand of poker that cost him 50 grand and had enough. He quit the games after that...

4. Or, quite possibly, Leo DiCaprio had better things to do... Another source claims Leo quit the game after he started dating Israeli bikini model Bar Rafaeli.

5. Tobey Maguire took up tournament poker in 2007 and took almost US $40,000  in winnings in that year's World Series of Poker, although he was eliminated in 292nd place after a couple of days. Did I mention Ruderman was bad at cards?

6. Tobey is married to jewelry designer Jennifer Meyer, daughter of the President and COO of Universal Studios. Oh God, she must be so pissed.

More as soon as news comes in! Tell us what you think in the comments.

Tags Bar Rafaeli, Ben Affleck, blogger: Vanessa Beatriz Soto, Bradley Ruderman, Jennifer Meyer, Leonardo Di Caprio, MAtt Damon, Nick Cassavetes, Tobey Maguire