Hedge Fund Manager Didn’t Know You’re Not Supposed To Gamble And Lose Investor Money To Tobey Maguire, Paris Hilton’s Sex Tape Partner, Et Al

By Bess Levin

You’re a hedge fund manager running a Ponzi scheme in Los Angeles. You’re pretty into poker and attend bi-weekly games with various actors who, as it unfortunately turns out, aren’t half bad at cards. The buy-in’s $100,000 but you don’t have the cash. What do you do? If you’re Brad Ruderman you use some client funds to cover it, as well as the money you lose to Spiderman and Co.

An FBI investigation into Brad Ruderman, the CEO of Ruderman Capital Partners, uncovered how he lost $25 million of investor money in clandestine poker games held on a twice weekly basis in suites at the luxury Beverly Hills hotel, Four Seasons, and the Viper Room on Sunset Boulevard. Tinsel town A-listers Leonardo DiCaprio, Ben Affleck and Matt Damon also played in the no-limit Texas Hold ‘em games which had a buy-in of $100,000, multiple members of the ring told Star. DiCaprio, Affleck and Damon are not being sued. Others who were part of the secret society and are facing hefty lawsuits include billionaire businessman Alex Gores, The Notebook director Nick Cassavetes, Welcome Back, Kotter star Gabe Kaplan, Paris Hilton’s infamous sex tape partner, Rick Salomon, record label owner Cody Leibel and Las Vegas nightlife entrepreneur and real-estate developer Andrew Sasson, among others.

The games were “exclusive events, by invitation only, and that there was a regular roster of players consisting of wealthy celebrities, entrepreneurs, attorneys and businessmen,” according to the lawsuit filed against Maguire in the United States Bankruptcy Court, in Los Angeles. Ruderman lost $311,300 to Maguire, including one losing hand of $110,000, on July 30, 2007, it’s claimed. The Ponzi mastermind used clients’ money to “pay for gambling losses at clandestine, high stakes poker games that were operated without any licenses or permits,” the suit said.

In their attempt to win back Ruderman’s losses, the trustee has claimed Maguire is “not entitled to receive the transfers from the Debtor, which transfers were compromised of improperly-diverted investor funds.” In a deposition of the alleged ringleader of the operation, which took in tens of millions of dollars beginning in 2006 through 2009, Maguire is described as a “very, very frequent player,” in the games, which ended in 2009. Maguire won as much as $1 million a month over a period of three years, one source told Star… “That means he could have made up to $30 to $40 million from these games,” the whistle-blowing card shark predicted.

Tobey Maguire Sued Over Multi-Million Dollar Illegal Poker Game; DiCaprio, Affleck & Damon Involved [Radar via FINalternatives]

Comments (36)

  1. 1
    Posted by Short Stack | June 22, 2011 at 6:12 PM

    DiCaprio, Affleck, and Damon? Talk about a rainbow flop…

  2. 2
    Posted by PasteSpecialFormats | June 22, 2011 at 6:20 PM

    Listen, here’s the thing. If you can’t spot the sucker in the first half hour at the table, then you are the sucker.

    -Mike McDermott

  3. 3
    Posted by Texashedge | June 22, 2011 at 6:21 PM

    I heard at the Viper Room he just got killed on the River

  4. 4
    Posted by F A G | June 22, 2011 at 6:21 PM

    Maaat Daaaamon.

    I’m Maat Daamonn.

  5. 5
    Posted by Worm | June 22, 2011 at 6:28 PM

    Keep grindin’ out that rent money Spidey.

  6. 6
    Posted by Kghasoa | June 22, 2011 at 6:29 PM

    omg how do i get in on these games. i will give 60% of profits for access. anyone?

  7. 7
    Posted by Joaquin | June 22, 2011 at 6:30 PM

    Real funny, smart guy. 

  8. 8
    Posted by Kevin Federline | June 22, 2011 at 6:35 PM

    Just do something anyone cares about, then you’ll get an invite.

  9. 9
    Posted by Hey Dumbass | June 22, 2011 at 6:39 PM

    “I don’t have to see “Jackass”…I’ve lived it…”

    -Ruderman

  10. 10
    Posted by David Einhorn | June 22, 2011 at 6:42 PM

    Hey Brad, if they start looking at Greenlight Capital’s finances, you and I are going to have a problem

  11. 11
    Posted by Guest | June 22, 2011 at 6:43 PM

    Tobey,

    Respect. 

  12. 12
    Posted by Rhianna | June 22, 2011 at 6:46 PM

    Texas Hold ‘em  is for sell side pussies.   Real ballers play Caribbean Stud.

  13. 13
    Posted by Ryan Dunn | June 22, 2011 at 6:54 PM

    You haven’t lived Jackass untill you hit 130 in a Porsche at 1am.

  14. 14
    Posted by Texashedge | June 22, 2011 at 6:59 PM

    Also a great game if you have no friends

  15. 15
    Posted by Harrybalzer | June 22, 2011 at 6:59 PM

    holla

  16. 16
    Posted by Ryan Dunn's Passenger | June 22, 2011 at 7:01 PM

    Or….  until you hit a TREE at 2:30 while doing 130 with a blood alcohol level of .23….  too early?

  17. 17
    Posted by Ryan Dunn's Passenger | June 22, 2011 at 7:01 PM

    Or….  until you hit a TREE at 2:30 while doing 130 with a blood alcohol level of .23….  too early?

  18. 18
    Posted by guest | June 22, 2011 at 7:07 PM

    Dear DealBreaker

    I imagined myself as a hedge fund manager running a Ponzi scheme in LA and it gave me a stiffy. Now I feel guilty. Is that normal?

    Sincerely,
    Curious in NYC

  19. 19
    Posted by 25th Hour Trader | June 22, 2011 at 7:08 PM

    After Spidey takes Madoff in training for six figures…

    Bradley: Did you have it?Tobey: I’m sorry Brad – I don’t remember. 

  20. 20
    Posted by Dennis Kneale | June 22, 2011 at 7:09 PM

    I had sex with a shrub trimmed like a dog once, does that count?

  21. 21
    Posted by Brooklyn Bully | June 22, 2011 at 7:36 PM

    So I more than lived 130+ down Park Ave at 2am… The street are completely empty mid-week after 1am in the upper numbers.

  22. 22
    Posted by Guest | June 22, 2011 at 7:39 PM

    No madam, it isn’t.

  23. 23
    Posted by EveryMan | June 22, 2011 at 8:08 PM

    No, you didn’t.

  24. 24
    Posted by Brian_Hunter | June 22, 2011 at 8:08 PM

    So, so true!

  25. 25
    Posted by Hey Now | June 22, 2011 at 8:30 PM

    Go fish!!

    /Stamford Quant for Hire

  26. 26
    Posted by Lord Humongous | June 22, 2011 at 9:22 PM

    too soon

  27. 27
    Posted by Guest | June 22, 2011 at 9:40 PM

    I’m shocked that Spidey’s a poker shark. Other than that I have no concerns.

  28. 28
    Posted by Guest | June 22, 2011 at 9:41 PM

    Quality video your ex put out today. She clearly has a type.

  29. 29
    Posted by Guest | June 22, 2011 at 9:41 PM

    Welcome to DealBreaker, Mr. Ebert.

  30. 30
    Posted by Anonymous | June 22, 2011 at 10:22 PM

    I’ve made a few gambling mistakes in my day. Thank god for my uncle Sam, he always gives me a bit of cash when i’m taking a few hits.

  31. 31
    Posted by Anonymous | June 22, 2011 at 10:45 PM

    No problem, bro.

    - B Bernanke

  32. 32
    Posted by Mexi-Cant | June 23, 2011 at 4:40 AM

    Yer name is Tobey, it is a good name!

    -S. Master

  33. 33
    Posted by Guest | June 23, 2011 at 5:17 AM

    Probably the juiciest game in the world. Rumor has it Jamie Gold still owes the game ~$3M (down ~$10M total). Also, how is this illegal if there’s no rake?

  34. 34
    Posted by Guest | June 23, 2011 at 5:22 AM

    Gives new meaning to:
    RS_Hustla: HOW THE $&$ DID U THINK J HIGH

    WAS GOOD?

    RS_Hustla: I WANNA KNO?

    RS_Hustla: HOW

    RS_Hustla: ?
    …
    RS_Hustla: HOW DID U THINK U WERE GOOD

    ??

    RS_Hustla: PLZ EXPLAIN

    INTERNET POKERS: spidey senses

  35. 35
    Posted by fsm | June 23, 2011 at 6:37 PM

    2 7 suited into a rainbow flop?!

  36. 36
    Posted by guest | June 23, 2011 at 8:19 PM

    I have the weirdest boner right now..

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