Molly Bloom is the first convicted felon I’ve interviewed and she reminds me of that fact almost immediately, concluding: “I had created a pretty giant mess for myself.”
The mess in question is the subject chosen by Aaron Sorkin for his directorial debut, Molly’s Game. His is the latest rendition of Bloom’s story, which has been told many times – in courts, in depositions, in the tabloids and in her own memoir – the story of how a small-town girl from Colorado ended up organising and running the most exclusive high-stakes poker games in LA and New York before she became addicted to drugs, entangled in the Italian mob, the Russian mafia and, eventually, was arrested by the FBI, who seized her assets.
The film stars Jessica Chastain as Bloom, stubbornly sticking to her guns as she enters a plea deal, but refuses to give up the names and secrets of the men who had trusted her, because she did not want to destroy other people’s lives and families.
When the real Molly Bloom talks about the fictional Molly Bloom, she refers to her on-screen counterpart as “her”.
“I like that [scriptwriter Aaron Sorkin] wrote a flawed character,” she says. “What I like about Aaron is I think he tells the truth. I like that he didn’t shy away from the drugs or the bad choices or even some of the inner dialogue of ‘I’m peddling a vice here’. And that we’re still allowed to like her.”
It’s not surprising that Bloom chooses to separate her real self from the film version. Not many living people see their actions and decisions replayed in glorious Hollywood technicolour. Watching her life story being told in a glossy, Oscar-buzz-worthy movie must be a disconcerting experience.
What is surprising is that the Hollywood version is not actually that far from the truth. In fact, the real-life story arguably had more star power – in Sorkin’s film, the poker players include an unnamed A-list actor referred to as “Player X” and played by Michael Cera. In real life, Bloom was dealing cards to Tobey Maguire, Leonardo DiCaprio and Ben Affleck.
I infiltrated and ultimately put myself in a position where I was running and operating a boys’ club
But Sorkin doesn’t use their names; this isn’t a film about the men playing high stakes – it’s about the woman who got them in the room. In Bloom’s own words: “I infiltrated and ultimately put myself in a position where I was running and operating a boys’ club.”
In the film – just as in real life – Bloom is often the only woman in the room and, despite appearing in total control, she is so often undermined by men around her, from the boss who expects her to work for free to the poker player who spitefully steals her game from under her nose to the mob henchman who beats her up in her own apartment and threatens her with a gun in her mouth.
So, after running the boys’ club, is she a feminist?
“Yes. One hundred per cent. Always. And as feminists, we should do it differently. I do think we have a great responsibility and a great opportunity to do power differently. To lead with compassion.”
And on the note of doing things differently, Bloom is excited that Molly’s Game completely eschews a love story for its central character, a (still) unusual decision in cinema: “I know it wasn’t strategic on [Aaron Sorkin’s] part, but I find, personally, that there’s this movie that is two hours and 25 minutes and very entertaining, but not a single second is dedicated to describing her or defining her by her romantic entanglement, groundbreaking. I love that choice.”
She is even planning on turning her skills to the cause of women’s empowerment. She wants to work on co-working spaces that introduce female entrepreneurs to one another and perhaps start a new social network.
The film has allowed Bloom to see herself in a different light: “The past seven years have been so mired in dealing with the indictment, dealing with the debt, dealing with all my bad decisions. So, seeing that movie kind of reminded me of some of my better ones.” When I ask what she is proud of, if anything, she smiles and tilts her head: “Just navigating the disaster with integrity.”
It clearly means a lot to Bloom that she is being portrayed by Chastain in the movie, with an uncanniness that has spooked her real friends and family. But it is Chastain’s off-screen persona that excited Bloom. The actress has been outspoken on the film’s press tour about Weinstein and the culture of inequality and abuse in the film industry. She is known as a principled actress and has been praised by Dylan Farrow for stating she will never work with Woody Allen.
This tenacity is exactly why Bloom was so delighted to have Chastain depict her: “I love her as an actress, but I also love that she’s so morally courageous, that she fights for justice, that she uses her platform the way she does, that she’s a real person.”
And, despite her many facades – the tabloid “poker princess”, the Hollywood darling, the convicted felon – Bloom is a real person, too. And she’s mainly concerned with keeping herself grounded: “I have lunch with my grandmother, who has memory issues, four times a week and she’s completely in the present moment. She doesn’t give a shit if there’s a movie coming out about me.”
Ultimately, the Hollywood attention only excites her so much – after all, she has already survived through brighter lights and bigger bucks.