Tobey Maguire Poker Story – Learn The Full Backstory Of Molly’s Game

Tobey Maguire Poker

4 minutes

Last Updated: March 18, 2024

It's hardly a secret that many rich celebrities like to gamble and that some of them frequent private high-stakes games.

For the most part, details of these private games are kept on a need-to-know basis, and the general public rarely gets to hear what really happens behind the closed doors protected by armed and dangerous guards.

However, this had changed when Molly Bloom decided to publicly talk about private games she used to host for A-list Hollywood celebrities, first in her memoir and then in the poker movie called “Molly’s Game.”

If you’ve seen the movie, and especially if you’ve read the book, you probably know that many big names are mentioned in there: Leonardo DiCaprio, Ben Affleck, Matt Damon, Rick Salomon, etc.

One name, however, stands out from the rest – the name of Tobey Maguire.

Unlike the rest, who mostly came to these games to have some fun, play some big pots, and usually lose some money, “Spider-Man” was the driving force behind these high-stakes gatherings.

Molly Bloom could hardly do everything she did on her own. She needed help from someone with connections in the celeb circles. Tobey was that someone.

So, what’s Tobey Maguire poker story, and how big of a role did he have in the whole Bloom story? Why was he interested in setting up the games in the first place? Keep on reading to find out!

Tobey Maguire Poker Skills: Not Your Average Celeb

To understand the backstory of Molly’s Game and the role of Tobey Maguire, it’s important to make one thing clear.

In these private poker games, Maguire wasn’t one of the fish. On the contrary, he was the shark looking for blood.

Tobey Maguire Gambling

Since Maguire isn’t a professional Texas Hold’em player, it’s hard to say what his actual skill level is and how good he is at the game. But, according to all the rumors and stories, he did more than well for himself in this particular setting.

In fact, it was Tobey’s idea in the first place to put together a game consisting of rich Hollywood stars and help rid them of some of that excess wealth.

To achieve this, he partnered up with Huston Curtis, a TV producer.

Curtis testifies to this in his own book, “Billion Dollar Hollywood Heist.” According to Curtis, the weekly underground game kicked off in Los Angeles in 2005 was a sham of sorts right from the get-go.

There was no cheating going on, but Maguire was a far superior poker player than most of those who came to play, so it was quite literally like taking candy from a baby.

So, Molly’s game was more a Tobey Maguire poker game as he was the mastermind behind it all.

Only later, Bloom tried to break off from Tobey and go solo.

According to all accounts, both Maguire and Curtis made a lot of money in these underground games over the years.

In fact, at one point, Tobey was even hit with a private lawsuit from a group of unhappy investors who were defrauded by one of the game regulars.

The player in question proceeded to lose millions at the tables. When the dust settled, and he was convicted, fraud victims turned their eyes to Maguire to try and recoup at least some of the money. But, more on that later.

Tobey Maguire Molly’s Game Character

In the movie, producers were really careful with the names, so the player who clearly represents Tobey is referred to as “Player X.” In the book, Bloom often mentions Tobey, a “powerful and tactical” character, so it’s not hard to connect the dots.

But, neither portrayal is very flattering for Maguire, as he is shown as one of the “bad guys.”

In the movie, there are several scenes devoted to “Player X,” and not one of them shows him in a good light.

In one of the scenes, Maguire runs a big bluff against another player and gets him to fold the best hand by swearing on his mother’s life that he has the goods.

After a while, the player believes the story and mucks, only to be shown total air, followed by a vocal “fuck you” by Maguire.

Tobey Maguire Mollys Game

Another storyline in the movie sees “Player X” buy off a player’s seven-figure debt, but under really unfair circumstances – the indebted player has to give up half of his winnings until the debt is paid, but he alone is responsible for 100% of his losses.

This deal is described in the book as well, and according to Bloom, it was actually Curtis who got bought off by Maguire.

Curtis was one of the best players in the mix, but according to all accounts, those were crazy games with stakes of at least $200/$400, so losing $1,000,000 isn’t all that shocking.

What was somewhat shocking that Curtis, who wasn't as loaded as the rest of the regulars, agreed to the deal under these conditions. But, he wanted to stay on Tobey's good side, and he needed the money, so perhaps he didn't have that many good options.

Tobey Maguire and Molly Bloom Growing Animosity

When Maguire had first set the game up, Bloom was acting as the hostess. She was there to meet and greet the players and make them feel comfortable. And, apparently, she was doing a great job of it.

As time went by and stakes got crazier, her tips kept on growing – to the point where Maguire started to become really hostile towards Bloom.

It's a good place to mention here that these private games were operated on a tips' basis because taking poker rake in a private game is illegal in California.

It was largely due to Bloom's decision to break this rule and start taking rake that she got in trouble with the law.

But let’s get back to the main hero of this particular story.

Apparently, he felt Bloom was making too much money for what she was doing – after all, it was Tobey Maguire poker game, and she was just playing her part in it. This animosity between the two reaches its peak in a non-pleasant scene described in the book and the movie.

As the scene is described, Maguire shows Bloom a $1,000 poker chip and tells her this is “her tip.” But, as she reaches out to take it, he pulls it back and says that if she wants it, she needs to “earn it.”

Maguire then proceeds to loudly request Bloom to get up on the table and bark like a seal.

Bloom is obviously offended by this and refuses to do it, which further enrages already mad Maguire.

Because the scene is so distasteful, Bloom was asked numerous times about it, and she repeatedly confirmed that it really took place exactly as described.

Tobey Maguire Molly Bloom

With the Tobey Maguire and Molly Bloom animosity rising, it was clear that the partnership wouldn’t hold for too much longer. Sure enough, shortly after, Maguire decided to move the game and cut Bloom off completely, leaving her to her own devices.

How Good Is Tobey Maguire Poker Game?

In both books and the movie, it is Maguire who keeps the game going and makes sure the right people are invited. To put in all this effort into it, he must have had a significant financial incentive.

So, how big of a winner was he in these games?

As is often the case with private games, there is no official record of the Tobey Maguire gambling history. However, there are reliable hints and guestimates.

First of all, there were millions on the table every single week. With stakes being at least $200/$400, the game would have seen several six-figure winners and losers in every session.

Allegedly, Guy Laliberte, the billionaire Cirque de Soleil founder, lost more than $2,000,000 playing in these games.

But how much of that money ended up in Tobey Maguire’s poker bankroll?

According to Huston Curtis, Maguire's original partner in setting up the game, Tobey could have easily won $30 to $40 million in the span of few years. This number is quite impressive, albeit it's impossible to verify it.

However, accounts from others who participated in the game definitely corroborate the story that Maguire was the big winner – which is why he became a target of that civil lawsuit later on.

Tobey Maguire Gambling Winnings at Risk

The Tobey Maguire poker game gathered many high-profile players, and not all of them were high-profile actors.

Rich investors, hedge fund managers, and many others took their place at the table to rub elbows with Hollywood celebrities.

Brad Ruderman was a healthy hedge fund manager who regularly frequented the Tobey Maguire poker game. Reportedly, he lost millions over his time spent at the tables, with some of that money going to Tobey’s pocket as well.

Unfortunately for the players, it turned out Ruderman was running a Ponzi scheme, and when the FBI came knocking, things quickly fell apart.

During the investigation, the private poker game was mentioned as well, as Ruderman apparently lost some $25 million of his investors' money on the green felt.

In a bid to try and recoup at least some of the money, investors filed private suits against Maguire and several others who frequented the game (including Gabe Kaplan, Nick Cassavetes, Dan Bilzerian, and of course, Molly Bloom).

Maguire, however, was sued for the largest amount of over $300,000, which is another indicator that he was one of, if not the biggest, winners in the game.

Eventually, most of the players who were sued ended up making a deal and paying a fraction of the initial amount. Maguire's settlement was for $80,000.

So, Was It Tobey Maguire Poker Game After All?

The movie and the memoir may be entitled “Molly's Game,” but it seems like Tobey Maguire was the moving force behind the private game that's become anything but private after all the public attention.

Bloom and Maguire had different motives to keep the game going.

For Bloom, it was a source of income, and as long as the game was going and players were happy, she didn't care who won or lose.

Whoever was winning would probably leave more generous tips at the end of the night.

Tobey Maguire Poker Mollys Game

Maguire's interest in running the game was much different. He managed to set himself up with a line-up with virtually infinite bankrolls but very little poker knowledge. For any poker player, this pretty much describes the dream scenario.

Without his efforts, the game would probably never become as big, so it was Tobey Maguire poker game in many ways.

Unfortunately, some of the juicy details will probably remain a secret for the years to come. But, when the time is right, perhaps Tobey will come out with his own memoir, and we'll get to hear the story of Toby Maguire Molly's game from a completely different perspective.

I mean, with all due respect to serious poker coaching and training sites, who doesn’t love a good gossip story that involves crazy high stakes, table banter, and all the drama that comes with it?

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