Report: Tobey Maguire Named in Illegal Gambling Lawsuit

By Kiki Von Glinow Posted Jun 22nd 2011 10:40AM

No, this isn't the premise of the next 'Ocean's 11' flick. Tobey Maguire, Leonardo DiCaprio, Ben Affleck and Matt Damon (the list goes on) are all among the Hollywood A-listers who are being named for their involvement in an underground, illegal gambling ring, according to Radar Online.

The group reportedly used secret passwords and unmarked rooms to keep their extra-curricular activities on the down low -- playing behind closed doors manned with armed guards in bullet proof vests. Members would often meet for games at the Beverly Hills hotel or the Viper Room on Sunset Boulevard -- details learned after the FBI investigation into CEO of Ruderman Capital Partners, Brad Ruderman, whose loss of $25 million of investor cash led officials to the Tinseltown 12 plus gamblers. Ruderman, is currently serving time in a Texas jail until 2018.

The multi-million dollar ring reportedly landed Maguire -- who is under a bit more water than the rest of his pals -- $300,000 over the span of several games. Only problem was that his winnings came at the expense of hedge fund manager, Ruderman, who dipped his hand in his investors' cookie jar to buy-in (buy-ins generally started at $100,000) and allegedly created a Ponzi scheme to pay off his debts.

Ruderman's clients are now going after those that won what was supposed to be their investment capital. From just trying to blow off some steam to being the only man left standing after the fog cleared from Ruderman's smoking gun accounting, Maguire could be looking at some major losses if he is forced to give up his dirty money winnings.

Although DiCaprio, Affleck and Damon were involved in the poker ring, they are not yet the target of any of these civil suits. According to a fellow player, "Matt never won" and "Leo is a tight ass. When he lost $50,000 the look in his eyes was obvious, he was crazy."

In documents filed against Maguire in LA's Bankruptcy Court, the underground gambling meetings were "exclusive events, by invitation only ... there was a regular roster of players consisting of wealthy celebrities, entrepreneurs, attorneys and businessmen."

Maguire was described as a "very, very frequent player" in the exclusive gambling ring which ran from 2006 to 2009 and reportedly won close to $1 million per month during the three year span -- translating to potentially more than $36 million.

Although, at this point, Maguire is only involved in civil suits, it is illegal to gamble for money at unspecified gambling establishments in California -- although the law is generally not strictly enforced. Maguire is not under any criminal investigation at this time.

According to the civil suit, Maguire is "not entitled to receive the transfer funds from the Debtor, which transfers were comprised of improperly diverted investor funds." But Maguire, who has hired a lawyer, will argue that his poker face winnings are not of the illegal variety.

Although Maguire's involvement doesn't bode well, for Hollywood's other gambling guys, it can only add to their method acting repertoire.

Tags: ben affleck, leonardo dicaprio, matt damon, tobey maguire

Comments

(29)

Wednesday 22 June

By JC

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It seems that the one who should really be hot water is this hedge fund manager. He was playing with other people's money.

By Ed

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Not good, I hope any of the winners reported their winnings to the IRS or jail time. Can you see these liberal nitwits doing jail time.

By mdf0220

What does there liberalism have to do with anything, you teabagging hack?

By RJ

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...yup Ed, are you sure you know who the "idiot" is???

By Miles

I agree mdf0220, but being a member of the tea party I really must ask you to keep this discussion civil. No reason to call someone names.

By Paul

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Nit wit!
Liberal? Sure Vegasis loaded with liberals and conservatives go
to Lourdes!
Idiot

By teri

Point being--If you are member of the limosine liberal crowd, you can say and do anything and get away with it. teabagging hack???? get off the kool-aid. Libs are using you. What have they done for you?

By EmmBee

Right, because liberals are really known for their campaigns against gambling. Stop trying to make everything into a left-right issue. This is just a bunch of rich guys (including some bankers, whom I'm doubting were all card-carrying liberals) getting off on being rich and being able to throw their money away. This has more to do with the male mentality than the liberal one.

By Kimberly

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"Maguire's involvement doesn't bode well, for Hollywood's other gambling guys, it can only add to their method acting repertoire." Seriously? I take it the author of this article is NOT a Tobey Maguire fan? Tobey has just as much acting staying power as the others!

I'm sorry the investors lost their money, but that has nothing to do with Toby Maguire's Poker winnings! CEO of Ruderman Capital Partners, Brad Ruderman is responsible, not Tobey! Ruderman took the money, he should pay the price as he currently appears to be doing!

I'm on team "Tobey Maguire!"

By clmail10

"Matt never won"...But wait! Wasn't he the one who eventually took down Teddy KGB after spotting his Oreo-eating tell? You mean his portrayal in Rounders was totally bogus? I'M VERY DISAPPOINTED

By ttrexxx

if they don't go to jail the irs was paid off..i have an 2 level insider in the irs i'll keep you posted

By oommma

Puleez. This is ultimate in ridiculous. The people that unwisely invested with Ruderman of SOL. If the scam artist investor had lost the money in a casino they couldn't get it back. If he had purchased some perishable items they wouldn't get it back. Ruderman's clients should realize they gambled (legally) by investing in a crook and they lost. When will people get it...investing is the ultimate gamble and investing through a third party amplifies the risk.

By Rebecca

I agree totally. Unless he KNEW that it was not the guy's money and took it anyway, then what the heck?

By stu

How is Toby in trouble? Did he steal anybody's money? Peoploe will sue anyone for anything. I get it sucks, but Toby didn't steal their money and these people need to accept that they left control of their cash in the hands of a jerk.

LOL.... me thinks Jackie is an emotional wreck. Another hissy fit by screaming, card carrying li.....

By John Beaulieu

Hey Boy,

You do not call anyone Teabagging Hack you filthy Un-American liberal. You will get teabagged if I find you. Please leave the country immediately dirtball.

You're right, sir. I apologize for that statement. It was rude and I deserved that verbal spanking.

By Ron

Gambling should be legalized!

By Carl

Are the winners required to return the money because the gambling was illegal or because they won money that was stolen from investors from one of the players? In legal gambling establishments all over the country people are winning money from people who got their money illegally. What about people who stole money and then lost it in casinos. Are the casinos going to return the money?

By Sue

Tobey can and should write the check. He has plenty of Spiderman money. These knuckleheads can't just go to Vegas? And I'm a fan of their movies.

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