Poker Stories: The Biggest Game in Hollywood

Imagine sitting down at the poker table with stars like Leonardo DiCaprio, Ben Affleck, and Brad Pitt. Now imagine winning millions of dollars off them and another rich fish week after week in one of the most lucrative home games of all time. That’s exactly the situation that Tobey Maguire—aka Spiderman—engineered for himself in one of the biggest and longest-running underground poker games that Hollywood has ever seen.

Photo: The Hollywood Roosevelt

By teaming up with TV producer Huston Curtis and entrepreneur Molly Bloom, Maguire set up a game at his mansion that would go down in history.

Reeling in the Fish

At the Hollywood poker game, the scene is just as important as the cards themselves. Between wild booze-fueled parties, massage girls, and the chance to rub shoulders with Hollywood’s biggest names, people couldn’t resist the draw of Maguire’s poker game, even if it meant losing week after week.

There was even one point where they staked DiCaprio just so that he would play the game. Of course, he could afford to throw around some cash, but that’s not the point. The hustlers knew that the fish would flock to a game with DiCaprio in it, and they saw it as a worthy investment. By all accounts, it paid off.

The Darkness Comes

The boom days couldn’t last forever. When they found a whale who went by “Bad Brad” who knew nothing about poker but just wanted to keep playing with stars, things began to get ugly. Maguire didn’t mind taking his money, but he wanted to do it ethically, so he bought him books and DVDs on poker strategy. But Bad Brad just kept losing.

The games became darker and dirtier with contraband and girls. That’s when the crud hit the fan. Unable to pay for his losses one night, Bad Brad assured them that it wouldn’t be a problem and that he’d pay them in a week. And that’s when the feds came calling.

It turned out that Brad was embezzling money from his hedge fund and that he was actually gambling money that belonged to his investors. When the FBI got involved, they issued legal notices to everyone who Brad had lost money to, saying that because the money was never his, it wasn’t his to lose. Of course, Maguire had taken a substantial portion of this money and ended up settling in court, but this scandal still spelled the end of Spiderman’s hustle to take Hollywood for all it was worth.