In the glamorous world of Hollywood’s elite, where fortunes are made and lost with the turn of a card, poker games have become legendary. One such unforgettable night involved Leonardo DiCaprio, Tobey Maguire, and a $200,000 poker prank that left producer Houston Curtis both shocked and amused. Curtis, known for producing poker shows and his expertise in card tricks, recently recounted this wild story from the infamous Molly Games, where Hollywood’s biggest stars gathered for high-stakes poker.
A Plan to Rope in DiCaprio
Curtis and Maguire masterminded the idea of creating the ultimate high-roller poker game, and they knew that getting Leonardo DiCaprio to join would make it the hottest ticket in town. However, before DiCaprio played his first hand, Maguire suggested “sponsoring” the superstar actor. Maguire’s reasoning? When someone reaches DiCaprio’s level of fame, their life becomes one big “freeroll”—a poker term meaning they have nothing to lose.
“We sponsored him, and he did well. People were willing to lose $100,000 just to say they sat at a table with DiCaprio for a night,” Curtis shared in an interview with Poker.org. It wasn’t a huge risk either; DiCaprio’s ultra-cautious style meant he mostly played strong hands like pocket aces or kings.
A Tour of DiCaprio’s Lavish Lifestyle
Curtis shared another story of visiting DiCaprio’s home for a poker game. As Curtis waited for Maguire to arrive, DiCaprio offered to give him a house tour. Pointing to the luxurious furniture, DiCaprio said, “See that couch? See that chair? I have a deal with Giorgio Armani. All I have to do is wear one of their suits to three events, and Armani comes over and customizes all the leather furniture in my entire house.”
DiCaprio’s high-flying lifestyle was just one of the perks of being a Hollywood A-lister. But poker, it seemed, was a serious business for him and his close-knit group of friends.
The $200K Poker Prank
A year after their first games, Curtis found himself on the receiving end of an expensive prank orchestrated by DiCaprio and Maguire. During one high-stakes poker night, Curtis had $200,000 in chips in front of him and a meeting to attend. He didn’t want to lose his seat at the game, so he asked DiCaprio—a cautious player, especially when sponsored—to play with his chips while he stepped away for half an hour.
Feeling confident in DiCaprio’s conservative playing style, Curtis handed over his chips, assuming DiCaprio would avoid risky plays. But when Curtis returned, DiCaprio wasn’t at the table. Worse, he was told that DiCaprio had lost all his chips in a hand where he was dealt aces but lost to Bob Safai, a regular player who hit a flush.
The initial shock of the loss quickly gave way to laughter when Curtis realized it was all an elaborate prank, expertly pulled off by his friends, including “the best actor of our generation.” To add to the joke, DiCaprio had even offered to contribute $10,000 to the loss to make Curtis feel better. In the end, Safai slid the $200,000 worth of chips back to Curtis, and the entire table erupted in laughter.
Curtis took the prank in stride, admitting, “I just laughed it off—after all, I had just been pranked by Leonardo DiCaprio.”
The Infamous Molly Games and the Billion-Dollar Heist
This memorable poker tale is just one of many shared by Curtis, who authored the book The Billion Dollar Hollywood Heist in 2020. The book dives deep into the secretive and exclusive world of Hollywood’s high-stakes poker scene, where fortunes were won, lost, and sometimes even stolen—offering plenty of material that could easily inspire a blockbuster movie.
