Inside the World of High Stakes Poker with 'Poker Madam' Molly Bloom

High-stakes card game landed one powerful woman in deep trouble.
2:48 | 06/22/14

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Transcript for Inside the World of High Stakes Poker with 'Poker Madam' Molly Bloom
We take you inside the world of high-stakes poker. And some names you'll recognize. What happens when that poker game becomes a crime for one ?son ABC's Amy robach with the interview tonight. Reporter: In the heart of Hollywood, hidden beneath the notorious viper room, a poker table and secret world. Of Molly bloom. This is where it all began? Yes. Reporter: She was the Hollywood madam of poker running a weekly underground high-stakes game for a table of celebrities. This was a $100,000 chip, actors like Matt Damon. I'll call it two grand. He was lovely. Modest. Down to Earth, a nice, smart guy. And he started with a pretty significant pack. Reporter: And Toby Mcguire. He won a lot. Yeah. How much money would be in that pot? Six figures over the years. Millions. Reporter: But if spiderman was a poker shark Molly says the look of Wall Street was left predator more bait. He would walk in with his headphones on and seem a bit detached. Why? Toby would put Leo in the game in order to attract bigger players. Reporter: None of the celebrities she mentioned will confirm attending her games, but she says their gambling met big bucks for her. Her income, topping $4 million in 2009. And because she made her money off tops alone, it was all perfectly legal. Until she moved across the country to host a game for new York billionaires and green got the best of her. Crossing the line into crime. Reporter: Did it feel wrong? Yeah, it did. Absolutely. But you didn't quit? I did not. Reporter: Finally the FBI caught up with her charged with a felony last month and got off with only probation. Is there any wisdom you have gleaned from observing the game of poker? And what you went through? Know when to fold. When things start to feel like you're on the wrong path, pay attention to those. That's when you fold them? Yes. As Kenny Rogers said, no when to fold them. A perfectly legal poker game takes an illegal turn. Thaermt you are allowed to accept tip from the game. But once you decide to take a rake and that is a percentage of the pot of the winnings, that is when you break the law. Who knew Leonardo Dicaprio had headphones. How do you play with head phones? We were told he was there as a magnet. He brought in and drew in all of the high rollers. Amy robach, we'll see you tomorrow morning on "Gma." Molly's game comes out on Tuesday. When we come back on a Sunday evening, how one man got

This transcript has been automatically generated and may not be 100% accurate.

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