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From Molly’s Game to Molly’s Comeback

Five years after she was indicted by the FBI for her illegal poker operation, Molly Bloom—the subject of Aaron Sorkin's new movie Molly's Game—talks to 5280 about her Colorado roots and her path forward.

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Before running the high-stakes poker enterprise that eventually led to her indictment by the FBI, Molly Bloom was a Colorado-based competitive mogul skier who had her sights set on the Olympics. After a bad fall prevented her from making the 2002 team, she left the sport and relocated to Los Angeles. There, she snagged a gig as a cocktail waitress for celebrity poker games. Eventually, she took over and started running the games herself, catering to celebrity clients like Leonardo DiCaprio, Tobey Maguire, and Ben Affleck, and making millions of dollars in the process.

And that’s where things went wrong. In 2013, Bloom was indicted by the FBI. Her assets were seized, and the IRS came after her for back taxes. She was eventually sentenced to one year of probation, fined $1,000, and received 200 hours of community service.

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In 2014, Bloom—known in the tabloids as the “poker princess”—published her memoir, Molly’s Game. Now, her story is hitting the big screen, with Aaron Sorkin’s adaption by the same name, which hits theaters January 5. Bloom spoke with 5280 about growing up as a competitive athlete, her reaction to the film, and what it’s like to return home to Colorado.

5280: Can you give us sense of what growing up in Colorado was like for you?

MB: Loveland is a really small town and an amazing place to grow up. We spent our summers on the lake and our winters skiing. We grew up detached from the massive socialization that I think exists today. I come from a very high-achieving family. You know about my brother Jeremy I’m sure [two-time Olympian and former NFL player, Jeremy Bloom], and my other brother, Jordan, who is a Harvard-educated surgeon. There was a lot of sibling rivalry. When we were young, skiing is really where that sibling rivalry manifested.

How has training as a competitive skier shaped your life?

When you train as a competitive skier, you know there is palpable danger from potentially falling. From an early age I became very comfortable with risk. As an adult, I realized that I was more comfortable with risk than most people. The negative to all of this is that you build the tenacity that you want to win at any cost, and the next thing you know you are being arrested by the FBI. When my life fell apart, albeit by my own hand, I really drew on that athlete mentality to get back up.

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In your book you talk about being obsessed with success. Do you think you still have that obsession?

Being successful will always be important to me, but these days I’m not depending on the applause or the adulation as much. I have a healthier approach to what success is. Part of my obsession with success is inherent, and the other part comes from being Jeremy and Jordan Bloom’s sister. I have these brothers who are these incredible human beings, but also true prodigies. When I went out into the world in my twenties, I think I was trying to compensate for that. When I was running the poker games, I was successful, but it was all for money. No amount of that ever brought me total fulfillment. I realized that success needs to be greater than myself. There has to be a purposeful element to what I am doing.

You have spoken about being the only woman operating this kind of high stakes poker enterprise. What were some of the most lavish things offered to you to win your favor?

In the beginning when I was a cocktail waitress, there were players that would say ‘oh you’re so cute, let me buy you a handbag,’ but that quickly ended when my role changed and I started running the games. I controlled the list for the game, so I controlled access. I also financed the game, so I would have to extend credit to the players. Everyone wanted to get into this game, but there were only a limited amount of seats. Poker pros always wanted to play, and I never let them in because they would have been bad for the game. People offered me $100k, 50 rolls on their wins, gold bars, etc. just to get a seat at the table. The pros knew that they could give me $100k but they could win $5 million at the table.

When you were with Ellen DeGeneres a few weeks back, you told her that going forward you want to help women. Do you feel like you have wisdom for women about resilience and picking yourself up when you fall down?

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The first thing that helped me was to tune out the world: avoid social media, avoid the Internet, avoid the tabloids. Don’t feed into what other people are saying about you because people like a good takedown. Do as little crowdsourcing as possible. Meditation also profoundly changed my life. I found books where I could basically do Eat, Pray, Love in my living room. Something that also helped me was being angry and fueling that anger into something positive. There is liberation in having a broken life or being in ruins, because no one is expecting anything from you. You can quietly rebuild without any expectation. You get to see your personal strengths in the moments when your life falls apart. Don’t quit before the magic happens. A comeback is really magical and well-earned.

Do you think Jessica Chastain’s portrayal of you in the movie is an accurate reflection of who you are?

I met with different producers and screenwriters in the beginning, and I realized that there was a very bad version of this story that could have been written, a sort of female Wolf of Wall Street. I think that Aaron Sorkin wrote an incredible part. Jessica executed it beautifully. What I liked about her performance is that you can see strength and vulnerability at the same time. There are dimensions of a person that are inevitably going to be missing in a movie, but Aaron incorporated so much humanity into the film.

The scene toward the end of the film where you and your dad, played by Kevin Costner, sit on a bench and have this therapy session really illustrates your complex relationship. How much of that scene is true?

My dad and I had a complicated relationship, and I own a lot of that. He wanted greatness for us—and greatness to him wasn’t getting federally indicted by the FBI. When I got arrested by the FBI, he was mad, understandably. And I was mad at him for being mad. We didn’t speak for quite some time. He reached out before the indictment and basically said ‘I’m your dad and whether you want me there or not I’m going to be there for you.’ He came out to Los Angeles, and we had this turning-point conversation. It wasn’t the Sorkin version of that conversation; neither one of us were that funny or that clever. We laid everything on the table and it became this healing moment that changed our relationship forever.

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What is your relationship with Colorado these days?

My dad used to tell me that you will never appreciate Colorado until you move away and come back. Those are really true words. I have been back in Colorado since February and I couldn’t be happier to be back here. I just walk around these days asking myself how could I have ever left this place; it is so incredible. After being in New York and Los Angeles and living this crazy life, it feels so good to be back home. It feels as if I have returned to my real self in a way.


This interview has been lightly edited for length and clarity.

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