Poker queen Molly Bloom reveals Hollywood celebrities’ peccadillos

Ben Affleck and Tobey Maguire were regulars. 

Leonardo DiCaprio and Matt Damon joined the elite. 

Lesser celebrities pleaded to be allowed just to watch. 

Champagne and caviar flowed as drop-dead gorgeous models served gourmet cuisine, masseuses soothed weary shoulders and burly bodyguards watched over millions in cash. 

It was the world’s most glamorous high-stakes underground poker game, yet presiding over Hollywood’s aristocracy was the unlikely figure of a petite 26-year-old former cocktail waitress. 

Molly Bloom earned a staggering £3million a year just in tips from the high-rollers she hosted.   

She shopped on Rodeo Drive, holidayed in the Hamptons, flew in private jets and employed a retinue that included a chauffeur. 

Bloom’s rise in the male-dominated world of poker, her brush with the mafia and the FBI sting that finally brought her down are the real-life dramas that unfold in the acclaimed new movie Molly’s Game, which opens in the UK on New Year’s Day. 

Starring Jessica Chastain as brunette beauty Bloom opposite Brit star Idris Elba, Kevin Costner, Chris O’Dowd and Michael Cera, the film hides the true identity of the game’s all-star poker players. 

But Bloom has no such qualms, tipping her cards on celebrity peccadillos. 

“Tobey Maguire was the worst tipper, the best player and the absolute worst loser,” says Bloom of the Spider-Man actor. 

Ben Affleck was “polite, nice” and liked high stakes.  

“He didn’t stay all night like a lot of the guys. He always had a specific time when he would stand up at the table. 

“He would leave at a reasonable hour. 

“He never lost a great deal. 

He usually won.” 

At a table when many players bought starting stacks of £370,000, Affleck asked for only £37,000 in chips. 

“Ben’s buy-in choice told me that he was a smart player who liked to limit his downside,” says Bloom.  

At his first game Affleck was challenged by actor Rick Salomon, who earned millions as the co-star of Paris Hilton’s sex tape: “Hey, yo, did Jennifer Lopez’s a*** have cellulite on it or was it nice?” 

After a tense silence Affleck replied: “It was nice,” and pushed his chips into a huge pot as the players cracked up laughing. 

Matt Damon, who starred in 1998 poker movie Rounders, “was one of the nicest, most humble, down-to-earth guys I have ever met”, says Bloom. 

“There were no airs about him.” But DiCaprio had a “strange” poker style, she recalls. 

“It was almost as if he wasn’t trying to win or lose. 

“He folded most hands and listened to music on huge headphones.”  

Maguire brought DiCaprio to games in the hope of luring “whales” – multi-millionaires who wouldn’t mind losing fortunes to celebrities. 

“Most of the people who played had a serous obsession with the game,” says Bloom, 39. 

“These were people who were able to play cards for this many hours a week this regularly. 

“It was very compulsive. 

“Leo didn’t have that in him.” 

Maguire hated to lose and after throwing his chips across the table to a lawyer – invited because of his deep pockets – insisted that Bloom inform him of all new players in advance.  

Maguire also demanded a spread of vegan desserts. 

Though he helped promote Bloom’s game among his celebrity friends, at the end of long nights he would tip her just a few hundred dollars when other players gave thousands. 

But her club became the hottest ticket in town. 

“Every card player in Hollywood wanted to come to the games,” says Bloom. 

“Everyone’s friends and their friends wanted to come to watch.” 

The audiences were as diverse as the Olsen twins and rapper Nelly.  

The games began in 2004 in the back of the Viper Room, a club on Hollywood’s Sunset Strip, where Bloom worked as a cocktail waitress. 

She hails from a family of over-achievers: the daughter of a university professor she was an Olympic-class skier, with one brother an Olympian and another a Harvard-educated surgeon. 

Her poker games graduated to mansions and Beverly Hills hotel rooms by 2008 with a £190,000 buying just to get a seat at the game. 

There would be £1.5million on the table before a single hand was played. 

Bloom set up the venue, sent the invitations, hired dealers and beautiful waitresses, supplied the food and drink and kept Sinatra playing in the background. 

“The fact that every man was treated like James Bond only made the game a hot ticket,” she says.  

Bloom also vouched for the players’ debts and after each game she paid the winners and collected from losers, sometimes chasing them for days.

“I was bankrolling the games, vetting the players, extending the credit,” she explains. 

“My life was really stressful. 

“I didn’t have the traditional resource to collect on debts and I’m certainly not going to get violent about it. 

“Most game-runners behaved like gangsters when they got stiffed. 

“They sold the debts on the streets or hired muscle and manipulated people into paying, or worse.”  

But Bloom had something no other poker game had: the Hollywood A-list and players paid their debts just to be invited back. 

However Maguire felt that Bloom had grown too big for her Jimmy Choo boots and during one game humiliated her by ordering her to “bark like a seal who wants a fish” just to collect a relatively paltry £750 tip, she wrote in her memoir.

“What’s wrong?” he taunted. 

“You’re too rich now?” 

After years of success the A-list moved on and her Hollywood game crashed sending Bloom to New York where she hosted private poker games with even higher stakes for sports stars and Wall Street tycoons. 

Though her tips were huge – she earned £3million in 2009 without ever playing a hand of poker – her risks were astronomic.  

Soon the Russian mafia came calling, demanding a piece of her action in exchange for protection. 

When she refused Bloom was beaten up. 

Players increasingly failed to pay their debts and anxiety-ridden Bloom turned to drugs. 

The FBI, acting on a tip, raided one of Bloom’s games in 2011 and seized her assets. 

Grilled over her mafia connections she escaped with a warning. 

But two years later her luck ran out.  

Bloom was arrested for profiting from illegal poker games. 

Hosting a private poker game for tips is legal in America but Bloom crossed the line when she started taking a percentage of every hand played. 

She was hit with a £93,000 fine and a year’s probation, then wrote her 2014 memoir Molly’s Game, which inspired the movie. 

Bloom blames greed, ambition and naiveté for her downfall. 

“All those things,” she says. 

“But if she could choose, would she do it all again? 

“Yes, a thousand times yes.”