Report: Boston Natives Ben Affleck, Matt Damon Attended Underground Celebrity Poker Games Where Tobey McGuire Won Millions

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Jun 24, 2011

Matt Damon and Ben Affleck are as synonymous with Boston as Spike Lee is with New York or Jack Nicholson is with Los Angeles. The duo's feisty personalities on screen completely embody the Boston culture in which they grew up. Despite Damon playing a corrupt Boston cop in The Departed and Affleck playing a longtime Boston thief in The Town, we can assume that the majority of the duo's wrongdoing takes place while they're cursing out Yankee fans. Yet a report on Friday may prove the contrary.

Business Insider reports that Damon and Affleck reportedly attended underground celebrity poker events in the California area. Also participating in the games was Beverly Hills hedge fund manager Brad Ruderman, along with celebrities like Leonardo DiCaprio and Tobey Maguire.

The games featured a $100,000 buy-in, and Ruderman apparently lost more than $300,000 to Maguire. Ruderman used his investors' money to pay back the actor, and his former clients are now asking for their money back.

To make the story even more intriguing, Perez Hilton claims that cocaine and hookers were at the events. Armed guards stood close to the tables to monitor the millions of dollars that were being bounced around by people like Maguire who, according to Perez, was making close to $1 million a month from the games.

While Affleck and Damon were said to be at the games, there have been no allegations that the Boston fans were paid with money from Ruderman’s investors. Maguire is currently working with lawyers to deal with Ruderman's clients and to argue charges that claim the games were illegal.

Ruderman is currently in jail, and it’s unclear whether the money has been paid back. To force the corrupt hedge fund manager to pay back the money, someone should get Jason Bourne on the guy. Or Spider-Man. Or Daredevil — actually, let's forget Daredevil.

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