Chapter 42: Molly Bloom on poker princess privileges and pushing past pomposity

Chapter 42: Molly Bloom on poker princess privileges and pushing past pomposity

March 18, 2026 · 55 min · Season 1 · Episode 42

About this episode

Molly Bloom shares her journey from a world-class skier to running exclusive underground poker games and the challenges she faced along the way.

Join me on the couch in Molly Bloom's hotel room at the Four Seasons in downtown Toronto. Molly began her career as a world-class skier, but while training as a pre-teen was diagnosed with severe scoliosis. Her doctor told her she could never ski again, but even as a pre-teen Molly had incredible strength of mind and she ended up back on the slopes only a year after her surgery. By age 21, she was ranked #3 in North America. She then took off to LA and began running one of the most exclusive, high-stakes, underground poker games in the world, featuring players like Alex Rodriguez, Tobey Maguire, Leonardo DiCaprio, Ben Affleck, and was raking in millions of dollars per year. Then what happened? The feds went after her! The mafia went after her! And there was a dramatic takedown. While awaiting sentencing, she wrote her life's story in her memoir, Molly's Game . That book became a bestseller and was turned into a movie written and directed by Aaron Sorkin, writer of The West Wing and The Social Network , starring Jessica Chastain (as Molly), Idris Elba, and Kevin Costner. Molly has been featured on Ellen , NPR , LA Times , VICE , and many more. But beneath the surface is a story…

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