Tobey Maguire’s Partner In Their High-Stakes Poker Game Explains How The Two Fleeced Hollywood’s Elite For Millions

Tobey Maguire Leonardo DiCaprio

Getty Image / Handout


I’ve always been very intrigued by that opening poker scene in Ocean’s 11 where Brad Pitt’s teaching Topher Grace and other celebrities to play high-stakes poker. There was such a sense of reality brought to that scene that I knew there must’ve been a much deeper story. As it turns out, there was.

On Tuesday nights from 2005 through 2009, actor Tobey Maguire and ‘a card cheat-turned-TV producer named Houston Curtis’ put together a weekly high stakes poker game that would regularly bring in players like Leonardo DiCaprio, Ben Affleck, Matt Damon, and others. This weekly game would go on to serve as the inspiration for the Molly’s Game film. Tobey’s partner in all this, Houston Curtis, is telling all of his real-life stories in a new book title Billion Dollar Hollywood Heist.

Some of the excerpts on a recent article in the New York Post dive into just how outrageous of a time it was in Hollywood. The way Houston Curtis tells it, they were fleecing people out of millions, ‘Molly’ was just a distraction, and celebrities were crossing paths with billionaires along the way. The story about Rick Solomon grilling Ben Affleck on Jennifer Lopez’s ass is particularly interesting as I think it’s easy to envision this is 100% something that would happen at a poker table.

Curtis claims Bloom (Molly) was not the mastermind she purported to be and that she was primarily there to deflect attention so that he and Maguire could win millions without spooking their pals.

“Molly had nothing to do with anything,” Curtis said. “Initially, she just served drinks and we gave her numbers to call the guys.”

“The guys” included billionaires who had everything but fame. Celebrities were brought in to add glamour and, occasionally, serve as collateral damage.

I don’t think anyone anywhere doubts that Molly’s Game was spruced up for the big screen. But this book from Houston sounds like it will likely lead to a much better movie down the line.

Rich men went home with their pockets light of cash but full of stories. Like the time film producer Rick Salomon — infamous for starring in a sex tape with Paris Hilton — grilled Affleck about Jennifer Lopez, the actor’s former fiancée.

“Did [her] ass have cellulite on it or was it nice?” Salomon asked.

The table was stunned into silence ­before Affleck replied: “It was nice.” (via NYPpost)

Houston claims he met Tobey Maguire in 2004 at a poker game in Los Angeles. Tobey was completely unaware that Curtis had a history of scamming Hollywood millionaires. Curtis says he was then invited by Tobey to play in a game and ‘played it straight’ to not raise any red flags:

When Maguire invited Curtis to the actor’s Hollywood Hills home for a game — in which players included lawyer Jon Moonves and billionaire scion Kevin Washington — Curtis played it straight and was careful not to win too much.

“Or else I’d never be invited again,” he said. “I dumped chips to guys who played badly and would lose them back.”

Serving as the dealer was Maguire’s then-wife, Jen Meyer. The actor pressed guests to tip Meyer, a successful jewelry designer who is also the daughter of Ron Meyer, a former Hollywood power agent and now the vice-chairman of NBCUniversal.

“He wanted to make her feel included,” said Curtis. “At the end of the night, she could count her profits alongside Tobey — who almost always won.” (via NYPpost)

If I’m him, I think I’m a little worried sharing these stories to be honest.

This is where the shift happened. Apparently, Tobey didn’t enjoy having people in his house. He didn’t like the germs and would make people leave their shoes at the door and wear Crocs (which he provided). I don’t blame the guy. THe last thing you want is a bunch of people leaving a mess in your house after you’ve lost $$$$ playign poker.

“Kevin Washington chewed tobacco and spit into a cup; Tobey hated that,” said Curtis. “And, since Tobey was a vegan, it really bothered him when people ordered pepperoni pizzas. He said to me, ‘Dude, I have to get these scumbags out of my house.’ ”
So in 2005, the game moved to The Viper Room, the Sunset Strip nightclub where River Phoenix fatally overdosed in 1993.
Maguire and Curtis arranged things with club co-owner Darin Feinstein.
“He said, ‘I’ll have a poker room set up downstairs and get a hot piece of ass named Molly to serve drinks,’” Curtis said of their introduction to Bloom, then an employee of Feinstein’s. (via NYPpost)

Now, things start to get interesting. Poker was blowing up. The World Series of Poker was airing on ESPN pretty much around the clock. Online poker was exploding. Tobey pulled Leonardo DiCaprio in to help him out with the game:

“Tobey said that he and I would have to stake Leo,” recalled Curtis, meaning they would put up cash for DiCaprio to play, covering his losses but also getting a share of his winnings.
“[DiCaprio] is a guy worth $80 million and he didn’t want to put up the $5,000 buy-in. But Tobey said, ‘Don’t worry. He only plays aces and kings.’ And he did. Leo was tighter than a gnat’s ass.”
One night, Matt Damon came as a guest of his buddy Affleck.
“He lost around $50,000 to me and didn’t have any money [on him],” Curtis recalled. “Affleck wrote the check.”
(Reps for Maguire, Meyer, Affleck, Damon and DiCaprio did not return requests for comment. Bloom had no comment.)
“Joker” director Todd Phillips was a regular.
“But when we went to $200/$400 blinds” — making it a no-limit poker game in which you could easily lose six figures per night — “Todd backed off for a while. Some people just didn’t have the stomach for those stakes.” (via NYPpost)

I hope you’re sensing the escalation here because the money that was about to exchange hands is wild. Sure, a lot of these guys were making fucking FORTUNES in Hollywood and they were mixing it up with independently wealthy millionaires and billionaires. But to put this all in a book seems pretty wild to me. Here he talks about easy money:

Two who did were Cirque du Soleil founder Guy Laliberté and hedge-fund manager Brad Ruderman. Curtis said that Ruderman was so inept and so rich that he was considered “a godsend.” Laliberté was also valued.
“The first time I won a quarter-million dollars was Guy’s first night in the game,” said Curtis, adding that the circus impresario invited the poker crew to fly with him to Hawaii.
“One morning, a bunch of guys took him up on it. They beat him for like $2 million [in Hawaii] and he flew them back on his jet.”
Curtis estimates he won around $15 million during the game’s four years. He, his wife and their two daughters lived in a $3 million LA home. He bought a dream house for his mother, a musical-instrument store for his dad and a dojo for his old karate teacher. (via NYPpost)

According to the Post, Curtis alleges Bloom was taking home around $30,000 a night in tips and Tobey Maguire hated seeing this happen, so much so that he tried to get Molly to bark like a seal for a $1,000 tip (which she didn’t) and the $1,000 tip was somehow an insult.

By 2008, things were going south for Curtis:

But by 2008, Curtis was enduring a trifecta of problems: The value of his $3 million home had dipped by two-thirds, a $4 million TV-distribution deal went south and he had lost $100,000 in Las Vegas. Then he suffered the biggest loss of his gambling career: $1 million in a single, terrible night at The Four Seasons.
That morning, heading home on autopilot, Curtis received a call from Maguire: “He said he wanted to make sure I wasn’t driving off a cliff. I walked into my house, my daughter ran up to me, and I literally broke into tears.”
Despite his earnings, the million-dollar debt was more than he could afford.
Maguire agreed to loan him $600,000. Curtis offered to pay back the principal and then give Maguire 10 percent of his winnings for the next year.
“I thought that was reasonable,” said Curtis. Maguire, who, according to unnamed sources in the book’s introduction, “could have made up to $30 to $40 million from the games” had ­reportedly earned $36.5 million plus back-end earnings on the “Spider-Man” franchise, thought otherwise. He wanted his principal plus 50 percent of Curtis’s wins and no downside. (via NYPpost)

Tobey Maguire’s starting to sound like he’s not such a sweetheart after all, at least according to these claims. Curtis alleges Maguire shouted “I own you now! And I’m gonna make sooo much f–king money this year at poker!” after their deal was in place. Of course, it didn’t work out that way at all.

The ‘godsend’ fish who was dumping money at the tables was busted in 2009 for his part in a hedge fund ponzi scheme, Molly was deposed, and everything unraveled quickly. You can read all about that here in the NYPost article or in the new book on Amazon.

BroBible Newsletter - The best sports and culture news directly to your inbox

* indicates required