Ray William Johnson: True Story Podcast - Remember Her? She Got Rich - The Molly Bloom Story

Episode Date: January 26, 2026

Molly Bloom was a former competitive mogul skier whose Olympic dreams ended after a severe injury, pushing her into the world of high-stakes underground poker in Los Angeles, where she eventually ran some of the most exclusive illegal games in Hollywood, attracting A-list actors, professional athletes, and powerful businessmen. As the operation grew, Bloom became deeply entangled with Russian mob figures who helped bankroll and protect the games, dramatically raising the stakes and the risks.

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underground poker games for celebrities like Leonardo DiCaprio and she goes to prison for it and then they end up making a movie about her. Now the woman's name is Molly and Molly is only 19 years old when this story starts and she's living in Colorado and Molly she's got something good going for her. She really really excels at mobile skiing. In fact, she's one of the best in the U.S. ranked third in the whole country and she's on the U.S. ski team. But one day, in 1998, she runs into a big problem. She's attempting to qualify for the upcoming Winter Olympic Games, when suddenly, kapow, she gets injured.

And this is devastating for her. I mean, skiing is her whole life. She spent years training for the Olympics. She was really hoping to make a name for herself. Now what's she going to do? Well, ultimately, she decides to change course and go to law school. However, before that, she plans to take a year off and move to Los Angeles. I guess just to have some good times before she has to go back to school and be all serious about studying again.

So in 2001, she moves to Los Angeles, and she gets a job as a cocktail waitress. And all of that is going fine. But then one night, she meets this dude, Darren. And Darren, he works in real estate. He also co-owns this sort of famous nightclub called, the Viper Room. You might have heard of it. And Darren, he appears to really like Molly. I mean, she seems like a go-getter. So he asks her if she wants to come work for him as his executive assistant. And Molly, she's like, all right. And she goes and she works for him for a while. But here's

where it gets interesting. In 2004, this famous actor enters the story, Toby McGuire. And so Toby apparently knows Darren and one night he approaches him and he gives him the idea to host a high stakes underground poker game in the basement of the Viper Room and if he does he could get like A-list celebrities

to come and play and Darren is like yeah sure of course anything you need buddy but he's not about to oversee a poker game himself so he turns to his assistant Molly and he puts her in charge of it here's the thing about that though Molly she

doesn't know anything about poker, much less running a whole game. So she goes home and she starts Googling stuff about how to play and like what kind of music do poker players like. And she figures it out and she sets the whole game up. And people show up to the game like important people, like billionaires and Wall Street investors and A-list celebrities like Leonardo DiCaprio and Ben Affleck and Matt Damon, and of course, Toby McGuire. And, you know, they all play, and I assume everyone has a good time. And at the end of the first night, Molly has made $3,000 in tips, just from, like, being nice and making sure everyone is comfortable.

And this is great money for her. So it's at this point that she realizes this whole underground poker thing might be something big for her. Like, it might be an opportunity to get connected to all these big shot people and really make a name for herself. So she gets to work, and she starts studying poker obsessively. She learns the rules and the strategies and the language, and she gets really good at all this.

She also starts doing more than just being nice. Not only is she now fixing cocktails and helping players settle their accounts, but she also starts managing the player list and hiring massage girls. You know what I'm saying? So now she's in charge of all of this. And in order to get to the game, all these big players have to go through her. And this goes on for years. And the games get bigger and bigger.

And the buy-ins for the games get higher and higher. Which is great for Molly because, you know, it means bigger tips. So all this is going really well for her. Until 2007, when something unexpected happens. One night, she and her boss, Darren, they get into an argument at work. And Darren, he straight up fires her. Now, that sucks for her, but that's not going to be the end of Molly. That's just not who she is.

She is a hustler. And since she's been the face of these underground poker games and everyone has been going through her, she decides to start her own game. And in 2008, she begins hosting her own underground poker games out of nice hotels around Los Angeles. And by this point, Molly is making a ton of money. About $4 million a year, just from tips. And that's great and all, and, you know, she's happy, but apparently it's not all fun. Like she has to deal with a lot of sh**y people.

Sometimes the people playing don't pay the money they lost, and she has to deal with them. Plus, some of these rich guys are just straight up rude to her. Not only that, but at some point, old Toby McGuire, who still plays her games all the time, he allegedly starts being a dick to her too. Like one night he just begins to treat her like shit and he offers her a thousand dollar chip to bark like a seal that wants a fish. And of course Molly refuses.

Like she's not about to bark like a seal for a tip and be humiliated. And then allegedly Toby gets all offended and pissed off and he storms out of the game. And eventually he's so pissed off that he convinces the other players to move locations to another rich guy's house away from Molly, which ultimately ruins her whole operation.

However, like I said, Molly is a hustler. She's not going to let guys like Toby stand in her way. So in 2009, she moves from Los Angeles over to New York City. And there, she just reboots her whole operation. She sets up new high-stakes poker games at nice hotels around the city, and she starts bringing in new clobes. clientele and she continues to make millions of dollars off of all of this. This is going really well for her. And she feels like she could do this job forever. Until, until,

until Molly decides to not only set up the games and host them, but to become the house, meaning she's fronting some of the money and taking a percentage of the winning pot. And up until this point, she was only making money off of the tips. But now, she's sort of acting like the casino. Once she introduces this aspect to the games she's running, this officially makes her whole operation illegal. Not only that, but she unknowingly isn't vetting the players that she lets into her games well enough.

And she ends up accidentally letting some guys play who have ties to the Russian mob. And on top of that, I guess the Italian mob hears about her operation and how much money she's making and now they want in on her business as well and they want her to pay them like a protection fee or something. And Molly's like, no, I'm not going to do all that. But then one night in 2010, they decide to make her pay. So she's at her apartment and someone knocks on the door. And so she goes and answers it and boom, it's some mafia goon pointing a gun at her. And then pow, pow, he starts beating her. After he beats her, he takes everything from her safe, cash, jewelry, everything. Then he threatens her and her family. Now, lucky for her, the feds coincidentally end up arresting a bunch of mob members

for reasons completely unrelated to Molly. And once these mob guys go to prison, they can no longer harass her. So she continues her illegal underground poker business. But then, in 2011, the FBI gets word of the game she's running and they bust in and they raid one of them and they also end up freezing all of her assets. And so now she knows it's about time to quit the illegal gambling business. But unfortunately for her, it's too late. In 2013, bam, she gets arrested. And I don't have a mugshot, but here's what she looks like in real life. And so ultimately, Molly takes a plea deal and she only gets sentenced to just one year of probation after all that, and 200 hours of community service.