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The Real Celebrity Stories Behind ‘Molly’s Game’

In Molly Bloom’s high roller poker games, Tobey Maguire was a big jerk, Leonardo DiCaprio wore giant headphones, and Alex Rodriguez just liked to watch

Getty Images/STX Films/Ringer illustration

When you name a character “Player X” in a “based on a true story” movie, as Aaron Sorkin does in his directorial debut Molly’s Game, it only invites speculation about who that character represents. And when your movie is based on the memoir of the same name by Molly Bloom, who ran a real-life underground poker scene for the wealthy elite in the late 2000s, it isn’t very hard to convert that speculation into something tangible. In her time running the game, Bloom crossed paths with A-listers like Leonardo DiCaprio, Ben Affleck, Nelly, and even Alex Rodriguez, so there are many sources of inspiration for Player X, played by a twitchy Michael Cera in Molly’s Game. Is he an amalgam of the poker players’ worst tendencies, wrapped up into one, smarmy character?

The truth is, Player X is less of a collection of stories relating to different celebrities, and more of a stand-in for one star in specific. In Molly’s Game, Sorkin narrows the focus of the book while letting its less impactful anecdotes fall to the wayside. But because those anecdotes are still thoroughly interesting, let’s go through all of the stories behind Molly’s Game—starting with Player X’s true identity, and then touching on the stuff that didn’t make it into the movie. For each section, we’ll include excerpts from Bloom’s book.

Reading the book and watching the movie, it’s pretty easy to determine that Player X is actually the OG Spider-Man, Tobey Maguire. Maguire’s poker prowess is already lore, but those who haven’t read Bloom’s book might just assume he’s a really good player who happens to be famous. That is true, but Maguire, as portrayed in the book and on screen by Cera, is more than that: He’s a sinister figure who takes pleasure in, as he puts it in the film, “destroying [the] lives” of his fellow players, and eventually Bloom herself.

It’s telling that in her book, Bloom is careful not to take shots at other celebrities—but she lets Maguire’s actions speak for themselves, and it’s all quite horrifying. Here are some of Bloom’s stories about Maguire that made it into Sorkin’s big-screen adaptation.

A Stone-Cold Bluff

How it plays out in the movie: Player X’s introduction in the film comes in the middle of a tense hand, during which he assures his opponent he’s not bluffing, swearing on his mother’s life. When the other player—a weak link on the table that others were feasting on—folds, Player X flips his cards over to reveal he had nothing, tossing in a very satisfied, “Fuck you.”

How it plays out in the book:

“I swear on my mother’s life I have you beat,” he had said, convincingly and earnestly. “I wouldn’t lie to you, man.”

His opponent had gotten confused. I had watched him stare at the cards he was holding, knowing full well he had the winning hand but suddenly unsure after Tobey’s performance. Tobey was incredibly convincing, and so earnest that the guy eventually, although reluctantly, gave in.

To add insult to injury, Tobey then victoriously showed his bluff. To me, his actions were in really bad taste.

An Impossible Deal With a Player

How it plays out in the movie: Sorkin’s film introduces Harlan Eustice (played by Bill Camp), one of the few players at the game with a finite amount of income. He plays well, but one devastating hand causes Harlan to unravel and eventually accrue over $1 million of debt. Player X agrees to cover the losses with an exceptionally unfair deal: He will get 50 percent of Eustice’s wins until the debt is paid off, and none of his losses. As Chastain’s Bloom points out, this is usury.

Eustice is an on-screen stand-in for television producer Houston Curtis, who had the same lopsided arrangement with the actor—though Curtis said Maguire eventually let the debt slide. “He told me, ‘Listen, I was never going to keep all those wins anyway,’” Curtis told the Observer. “I think for Tobey, it was more the thrill of knowing he’d made a good deal.”

How it plays out in the book:

No poker player can beat that juice, but Houston said he agreed. He could have procured much better options. There were plenty of people who would have staked him for better terms … hell, he could have gotten money on the street for better terms. But I think he realized, like I had, that staying in Tobey’s good graces was essential to staying in the game. If what Houston told me was true, Tobey owned Houston now, and they must have both known it. He owned 100 percent of his downside and was only realizing 50 percent of his wins, and he was the only one at the table who was playing for his mortgage.

“I’m going to make ten million this year on poker!” Tobey once exclaimed, not knowing that I knew that Houston had told me about the alleged arrangement they had.

Obsessing Over Bloom’s Tips

How it plays out in the movie: Initially, Bloom didn’t take a rake—a percentage of the pot in hands—which made the questionable legality of running the poker games a little less questionable. Bloom made her money on the tips she got from players, which, as the games’ buy-ins increased, grew larger and larger.

In the film, Player X is bothered by Bloom earning more and more money from the tips, saying he wants to cap it—as he puts it, “Your money is my money.” Bloom is, obviously, insulted by this.

How it plays out in the book:

He had taken to criticizing me about everything under the sun, especially how much I was making in my role. As my influence had increased, and my tips, so had his harping.

I didn’t like this. Tobey was powerful and tactical. There was a tiny nagging voice in the back of my head that was telling me that Tobey being unhappy spelled trouble for me, but I tried to stay focused.

Kicking Bloom Out

How it plays out in the movie: After the heated exchange about her tips, Bloom receives a text from Player X that says the game will take place at another venue—rather than the hotel she had set up for everyone—and there was no need for her to show up. She then gets a call from the cackling celeb, who triumphantly tells her, “You are so fucked.”

How it plays out in the book:

“You’re fucked,” he said gleefully.

“What does that mean, exactly?” I asked, trying not to cry.

“Arthur wants to have the game at his house from now on.” He sounded a little gentler when he heard the emotion in my voice.

It was obvious that this excluded me.

“Every week?” I asked, assessing the damage.


“Thanks for the heads-up.” I attempted to sound casual, but the words caught in my throat and the tears were coming hard and fast.

“I’ll try to talk to him for you,” he said awkwardly.

“Thank you,” I sniffled, wanting to believe him.

“I’m sorry,” he said, as if he had just realized that I was a real person with real feelings.

Though Player X is a memorable character on the periphery of Molly’s Game, the film is very much centered on Bloom as she weaves her way through the poker scene in Los Angeles and New York, before it eventually catches the attention of the FBI. Chastain is magnetic—so focusing on her character was a solid choice—and as Sorkin told The Hollywood Reporter, he wanted to make Bloom’s riveting true story the center of his film, rather than the celebrities that inhabited the world she created. Those ancillary stories are great, though, especially if you love celebrity gossip. Knowing them makes the movie a little more fun, so here are the best ones—including Maguire’s most egregious moment in Molly’s Game.

Leonardo DiCaprio

A best friend of Maguire, Leo came to play poker when Molly’s games were just starting out. As Curtis told the Observer, he believes Maguire used his famous friend to get big fish to come to the table: “Tobey was basically paying their entry fee, and using Leo as a lure to get these billionaires like Alec Gores and Andy Beal to come to the games.”

How it plays out in the book:

Not only was he devastatingly handsome, he was incredibly talented. He had a strange style at the table, though; it was almost as if he wasn’t trying to win or lose. He folded most hands and listened to music on huge headphones.

Rick Salomon

Salomon is probably best known for the sex tape he made with then-girlfriend Paris Hilton in 2004, but he’s a big-time poker player in his own right: He won $2.8 million at the 2014 World Series of Poker's Big One for One Drop event. In Molly’s Game, both sides of his persona are on display.

How it plays out in the book:

Rick Salomon showed up next. Rick was hot. He was crass and dirty, but he was still hot in a caveman kind of way.

I pulled him aside to show him the board.

“Wow, they are swingin’, huh?” he said, looking down at me. “Wanna fuck?”

I looked back at him, praying my face wasn’t as red as it felt.

“No thanks,” I said, as casually as if he had asked me if I wanted a Tic Tac.

He laughed.

“Give me $200,000.”

Ben Affleck

When Maguire convinced Bloom to increase the buy-ins for the L.A. games, he promised to bring Affleck into the fold. Affleck is a notorious gambler—the guy was allegedly kicked out of the Hard Rock Cafe in Las Vegas in 2014 for counting cards at a blackjack table. He doesn’t show up much in Molly’s Game, but Bloom characterizes him as polite and charming, and not that interested in talking about Jennifer Lopez’s butt.

How it plays out in the book:

I greeted Ben at the door. He was tall and handsome, with a relaxed charisma that not all icons have in person … As Rick [Salomon] took a seat, I saw him focus on Ben. I saw the wheels turning. Oh God, I thought, don’t let him say anything embarrassing. Rick had no filter.

“Hey, yo, did that Jennifer Lopez’s ass have cellulite on it, or was it nice?”

The table went silent.

Ben looked at Rick.

“It was nice,” he said, and pushed into a huge pot.

Alex Rodriguez

When Bloom takes her games to New York, she uses A-Rod the way Maguire had used Leo: He was a big name that elevated the status of the operation. When A-Rod shows up to one of the games, it naturally causes a bit of a ruckus. But it’s funny: Rodriguez is never described as actually playing poker. You can almost picture him on the sidelines, in a turtleneck sweater, gleefully reacting to folded hands and rivers.

How it plays out in the book:

When A-Rod appeared, tall, handsome, and very polite, the heads jerked up from the table. Men, no matter what age, ilk, or net worth, idolize a professional athlete. As they recognized him, they turned into excitable little boys. And as A-Rod took in the glamorous, well-appointed poker game I was running, a game that happened to have millions of dollars in chips on the table, the posturing started … Alex Rodriguez was watching it all, and having a great time.

The Olsen Twins

The Olsen twins—yep, them—brought a billionaire Bloom was interested in into the game, so they were allowed to stick around.

How it plays out in the book

When the Olsen twins showed up with a billionaire I was trying to land for a game, they were in, no questions asked.

And Yes, More Shitty Tobey Maguire

Maguire’s relationship with Bloom grew increasingly toxic—at one point in the book, she admits she got nervous if the actor was a dealt a few bad hands because he’d take out his frustration on her (and the generous tips she was making). By the end of the book, it’s revealed that Maguire orchestrated Bloom’s ousting from the games.

How it plays out in the book:

He held a thousand-dollar chip in his hand. He flipped it over a couple times in his fingers.

“This is yours,” he said, holding it out to me.

“Thanks, Tobey,” I said, reaching my hand out.

He yanked the chip back at the last second.

“If …” he said. “If you do something to earn these thousand dollars.” His voice was loud enough that some of the guys looked up to see what was happening.

I laughed, trying not to show my nerves.

“What do I want you to do,” he said, as if he were pondering.

The whole table was watching us now.

“I know!” he said. “Get up on that desk and bark like a seal.”

I looked at him. His face was lit up like it was Christmas Eve.

“Bark like a seal who wants a fish,” he said.

I laughed again, stalling, hoping he would play the joke out by himself and leave.

“I’m not kidding. What’s wrong? You’re too rich now? You won’t bark for a thousand dollars? Wowwww … you must be really rich.”

My face was burning. The room was silent.

“C’mon,” he said, holding the chip above my head. “BARK.”

“No,” I said quietly.

“NO?” he asked.

“Tobey,” I said. “I’m not going to bark like a seal. Keep your chip.”

My face was on fire. I knew he would be angry, especially because he had now engaged the whole audience, and I wasn’t playing his game. I was embarrassed, but I was also angry.

Though the dialogue in Sorkin’s film is a bit preachy—it’s Aaron Sorkin—Molly’s Game is the perfect vehicle for his idiosyncrasies: Sorkin and poker are a match made in heaven. That it’s all based on Bloom’s real-life experiences makes this one of the most fascinating true stories in years, and a revealing window into a high-stakes poker world in which a single hand could be worth more than most people make in their lifetime.

The film is absolutely worth your time. But if you don’t see it, just remember: Tobey Maguire in real life is much more like Bad Peter Parker in Spider-Man 3 than Peter Parker in the original movie.