The Secret World of Hollywood Poker

 

They are among the highest of the high-stakes players in this moneyed town: A-list actors, Hollywood hangers-on and businessmen who can shell out $50,000 just for a seat at the table. With eight or nine gathered, they play no-limit hold 'em into the night at one another's multimillion-dollar homes in Beverly Hills, Bel Air, Brentwood or Malibu. Hundreds of thousands of dollars are won and lost -- sometimes in a single hand. They order in dinner from Matsuhisa or Madeo or tuck into filet mignon prepared by private chefs. They catch up on their busy lives, maybe discuss a business opportunity. All the while, the cards keep coming. When they tire, masseuses dole out massages. And at this level, the game is no longer simply about a group of buddies getting together for friendly bonding over cards. Indeed, this game -- and much of the world of high-stakes Hollywood poker -- is an intoxicating mix of competition, power and ego.  

Nick Cassavetes and Gabe Kaplan are players, joined in the past by Leonardo DiCaprio, Matt Damon, Ben Affleck and on occasion, New York Yankees star Alex Rodriguez. But the star of these testosterone-fueled games, the celebrity who stands out in a group of millionaires and A-listers, is Tobey Maguire -- careful, conservative, effective.

It's a secretive gathering, one to which outsiders are typically denied entrance. Discretion is of paramount importance; trust is vital. But after several years of successful operation, that collective trust was breached. In March, players' names started appearing in court filings alleging that unbeknownst to them, they had been pocketing stolen money.

DiCaprio, Affleck, Damon and Rodriguez have never been mentioned in connection with the litigation, and most of the high-stakes players who were have settled. But two high-profile cases are pending. A court-appointed bankruptcy trustee is seeking the return of $311,200 from Maguire and $73,800 from Cassavetes -- plus interest. Both have retained counsel, and Maguire's attorney has vowed to fight.

The trouble began one day in summer 2006 when a hedge fund manager named Bradley Ruderman wandered off of exclusive Carbon Beach in Malibu and talked his way into the game. He appeared to be rich, affable, out for a good time. It would take years for the others to learn to their chagrin that he was not what he seemed.

In the meanwhile, they let him play and lose -- a lot. No-limit means that a player can wager any amount at any time. The most popular game in a town that has had a long love affair with poker in its many forms, no-limit hold 'em delivers the biggest highs and lows for those whose wealth and ennui leave them hungry for thrills. And it demands total concentration, making it a distraction from the day's anxieties. "You get in front of that green felt, and that's all you can think about," says one regular player.

All manner of Hollywood heavyweights are poker players, from former Warner Bros. chairman Bob Daly to Titanic and Avatar producer Jon Landau. Jeffrey Katzenberg has been known to turn up on a Sunday morning at the Commerce Casino outside Los Angeles for a game. But only a select few have the means and desire to play at the highest levels of wagering. "This Texas hold 'em stuff can get pretty serious," says former Warner Bros. president Alan Horn, who hosts a far less intense poker game -- dealer's choice -- at his house. "It's another animal. I mean, we're all animals, but we're playing the gazelle version and the guys across the watering hole are playing the lion-and-tiger version."

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By most accounts, Ruderman was prey, a "fish," in poker parlance, who obliged his fellow players by losing. "A fish is somebody that just regularly donates," says one of Hollywood's veteran poker players. "Believe me -- these guys want patsies. … It's not easy finding players at this level."

Ruderman may have been a bad player, but he must have been a pretty good actor because the wealthy hedge-fund manager turned out to be a con man, a mini-Madoff who was charged with running a $44 million Ponzi scheme that targeted his friends and family and bilked investors out of more than $25 million. Since his 2009 conviction, he has been serving a 10-year sentence in a Texas prison. But once his company, Ruderman Capital Partners, was forced into bankruptcy, his Hollywood friends -- some of whom had pocketed easy winnings from him -- suddenly found themselves on the receiving end of litigation. A court-appointed trustee has moved to claw back the ill-gotten gains that Ruderman had lost at the poker table. The whole ugly mess has brought with it unwelcome publicity and raised the specter of something darker than a simple night out with the boys.

 

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