Some of the richest and most powerful men in Hollywood and New York would show up to gamble millions of dollars in these secretive high-stakes poker games.
And the one pulling all the strings at the center of it was a woman named Molly Bloom.
Now, the unbelievable true story of how Bloom, a brilliant Olympic hopeful who was bound for Harvard Law School, ended up heading an illicit gambling operation, is the subject of a new movie, "Molly's Game," starring Jessica Chastain.
"Everything that went on in Molly's life you can't believe that it's a true story, you think that it’s something Hollywood made up," Chastain told "Nightline's" co-anchor Juju Chang. "Reality is stranger than fiction."
Aaron Sorkin, the creator of the award-winning political TV drama "The West Wing," wrote the movie's screenplay and makes his directorial debut turning Bloom’s memoir of the same title and real-life telling of her experience into a dramatic feature film.
Bloom's transformation into the so-called "poker princess" began after an accident derailed her skiing career, prompting her to put off law school and move to Los Angeles.
"I worked for a guy who ran the game and, you know, my role was to bring these guys drinks or to sort of cater to them," Bloom told "Nightline." "And then, you know, within a year I became the owner-operator of the game and eventually I became the bank."
The legal poker game became one of the most exclusive in Hollywood. Bloom told ABC News in a 2014 interview that she was dealing-in famous actors and directors including Leonardo DiCaprio, Tobey Maguire and Ben Affleck.
The players in the movie, "Molly's Game," are fictional composite characters, which was a creative decision made by Sorkin.
"Just to be clear, in peeling back the curtain I don't dish on anyone. I wouldn't want to under any circumstances," the director reiterated. "Molly had to navigate a world of very powerful men who oftentimes weren't that respectful of her. And any time one of these powerful men felt that Molly wasn't sufficiently in awe of their power ... they would end her, they would ruin her and she would have to start over again."
But Bloom said for the players at her table, the lure of the game wasn't the money.
"They were very wealthy," she said. "They didn't want things they could buy whatever things they wanted. They wanted experiences ... They wanted to feel risk again. They wanted to feel scarcity they wanted to feel that rush of I’m going all in and I could lose."
At the height of her success, Bloom says she was making up to $4 million a year, all legally, by making her game the ultimate boy's club.
"I got to be the fly on the wall and there were some components to that that were amazing because I got an education on business, the art world, finance," she said. "But then I also got the other side of that which is listening to the way men talk about women."
"There are nights where there was there was a lot of just sort of degradation or disrespect," Bloom continued. "And you know, it's hard to hear."
In the movie, Bloom's success presented a threat to the men she worked with. Twice she was penalized for being too good at her job. She also ran afoul with the mob, which was graphically depicted in the movie.
Eventually, Bloom was indicted for operating illegal poker after raking the pot for profit. She pleaded guilty and was sentenced to a year of probation.
"In the beginning, it felt like I was a tourist in this world, a voyeur and I was sort of profiting from it and figuring it out and, you know, taking these calculated risks going up against the billionaire boys club,” Bloom said. "And then it became about something else. It became about the money and the greed."
Those mistakes, and what Bloom learned from them, are part of what drew Sorkin and Chastain to her story.
"I love the characters and purpose that other people might find earnest or roll their eyes at. I like heroes who don't wear a cape and don't have superpowers," Sorkin said.
"What I loved about this story is the sense of getting back up after you fall down," Chastain added. "You know Molly has this quality of no matter how many times she fails, how many mistakes she makes and falls down she's constantly getting back up."
"Molly's Game," a film that depicts how Bloom navigated her male players' machismo, is being released in a cultural tidal wave of the #MeToo movement sweeping Hollywood and beyond. Chastain, a crusader for female empowerment and an outspoken advocate for pay equality, said the film comes at "an exciting time right now."
"You know, 2017 I think, this is a year that hopefully the history books will write about," she said. "The fact that women are coming together and saying okay we are not going to be silent about the injustices that we face anymore."
Chastain, who marched at the Women's March in Washington, D.C., last year, added that, "In a way it's a bit selfish if I can't, if I don't use my platform to amplify the voices of those who have suffered, of those who don't have a platform as big as mine, then I don't know how, how do you go on each day."
Her performance as Molly Bloom has already earned Chastain a Golden Globe nod for best actress, something she said "was a surprise."
"This year though especially it was a surprise," she said. "Especially ... with the idea of coming forward and speaking up and using my platform to support those who are far more brave than anyone than me even amplifying their voices. The idea that it’s OK, I'm not being made to disappear in this industry, I'm allowed to have a voice, I'm allowed to do what I can to create a healthy environment for all of us. And I can still work."