“Listen, here’s the thing: If you can’t spot the sucker in your first half hour at the table, then you are the sucker.”
– Matt Damon’s first line in Rounders

Damon’s classic line would soon be replayed in his head thousands of times over after a 15 hour Texas hold em’ poker binge with his buddies DiCaprio, Maguire, Affleck and one hell-of-a dodgy businessman.

So what makes an underground celebrity poker game so underground? Well, throw in a few pro poker players, some egotistical A-Lister’s and a financially corrupt hedge fund manager, and you’ve got a multi-million dollar high-stakes Hollywood house of cards waiting to come crashing down. We’ll also mention that Brad Ruderman, the hedge fund manager, used million’s of his clients’ funds to gamble. It wouldn’t be underground enough if he didn’t use other people’s money now would it?

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So who organised these underground poker games for the elite and famous?
You’re lookin’ at her – Molly Bloom.

Bloom would ‘supervise’ the games and organise the money be paid out to the winner over the coming days after games.

“One time Tobey asked me to bark like a Seal for a $1,000 chip.” Says Bloom. “I didn’t do that.”

Having played poker for a number of years, Maguire was the most egotistical of the four. Games usually took place at various mansions and hotels in LA as well as Maguire’s residence, however the big money tournaments were always in New York which involved other heavyweight Wall St power bankers wanting to hang with the stars. Maguire always demanded a Shuffle Master card shuffling machine worth $17,000 which he charged each player $200 to use per game.

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So what about Matt Damon? Well..

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And Leo? Probably remains the most respectable out of these lot.


It all came undone when Ruderman lost $110,000 in one hand to Maguire and couldn’t pay back the funds to his clients which then eventually lead to his arrest by the FBI. Molly Bloom was arrested for her involvement in organised crime syndicates and money laundering.

As for DiCaprio, Affleck, Damon and Maguire, well, let’s say they got lucky.