At the corner of happy and healthy. ? How far would you go not just to make millions but to be in thick with Hollywood's a-list, friendly with actors on an first name basis, Matt, Ben, Leo? One woman... See More
At the corner of happy and healthy. ? How far would you go not just to make millions but to be in thick with Hollywood's a-list, friendly with actors on an first name basis, Matt, Ben, Leo? One woman nearly paid with her life to be part of the high-stakes world, even when she was 3,000 miles away if Hollywood. Here is Amy robach tonight with where the chips have fallen. Reporter: In the heart of Hollywood, hidden beneath the notorious viper room, a narrow hallway leads into a musty room, a poker table, and the secret world of Molly bloom. So this is where it all began. Yes. Reporter: She was the voluptuous Hollywood madam of poker, and she says she lured billionaires and celebrities alike. Faces you know from the red carpet drawn to her green felt table every week for an underground high-stakes game of no-limit Texas hold 'em. This was a $100,000 chip. Reporter: According to Molly ten years ago she was running errands for a rich entrepreneur when she took her first step into a shadowy world. At 27, she was given the responsibility to host the games for her boss and his high-rolling poker buddies, including Leonardo Dicaprio. He sat right there with his headphones. Reporter: And Tobey Maguire. Tobey was sitting right there. Reporter: Tobey and Leonardo together in the film "The great gatsby" and together in cards. And how much money was played in that first game? People had probably, you know, six-figure losses, six-figure wins. Reporter: A former cocktail waitress from small-town Colorado, Molly was immediately intoxicated by the mixture of glamour, wealth, secrecy and most of all, the cash tips she received from the winners. That first night, how much money did you make in tips? Around $3,000. And what was your reaction? I got in my car, I locked my car and I just was like screaming. Reporter: And nobody took a cut from the pot so Molly's Hollywood game and her tips were perfectly legal. And then the money just kept getting better. It did. Reporter: For Molly, perfecting the game for the a-list players meant studying their poker personalties. All right. I'll call the two grand. I'll gamble. Reporter: Matt Damon, she says, was nothing like the poker addict who gambled everything in the film "Rounders." He was lovely, modest, down-to-earth, a nice, smart guy. And to further that point, he never came back. Reporter: She says Damon's pal, Ben Affleck, was a regular whose pechant for gambling has made the news. Security at the hard rock hotel and casino told Affleck quote, "You're too good" and politely escorted him away from the blackjack table. He had the gambling gene. No question. Reporter: Just like the mild-mannered peter parker could morph into spiderman, Molly says Tobey Maguire assumed an alter ego when he put on his poker face. He was bloodthirsty. I used to call Tobey "Hannibal lecter" because he could just talk someone off of a good hand. Really? Just the person would be looking at their hand and know that they have the nuts, which is the top hand, and he could talk them out of it. He won a lot. Yeah. How much money would be in that pot? Six figures almost all the time. And how much was he winning? Over the years? Millions. How did he handle a loss? Not well. Reporter: If spiderman was a poker shark, Molly says "The wolf of Wall Street" was less predator, more bait, often playing with chips bought by Tobey. Tobey would put Leo in the game in order to attract bigger players. So Leo really wasn't into playing the game. He was there as the magnet. Yeah. Reporter: Molly says she realized she could control the game, satisfy Tobey and the regulars, and slake her burgeoning thirst for cash if she began recruiting new players. In poker parlance, whales. What's a whale? They have a lot of money and limited skill. They need to lose sometimes? Most of the time, you know? Most of the time. I mean, to keep these guys happy. Right. Reporter: And if a whale wasn't drawn in by her a-list actors, Molly says she had an ace in the hole, Alex Rodriguez. And here's a shocker. He once denied ever playing in the game. A-rod was a novice player but there's something that happens to grown men. No matter how successful they are, when a professional athlete comes into the room and they're reduced to kind of like, you know -- Teenage girls? Yeah. Reporter: Having stars at her beck and call gave Molly a sense that she belonged in their world. It felt amazing. Really amazing. And I felt like I was really, really good at something. There was a definite rush to it. Reporter: And a mainline of cash injected weekly by the good will of her winning players. Tips of five to ten percent added up and she says by 2009, her reported income topped $4 million. But Molly had designs on something bigger. Shleft the celebrities behind and moved to New York and the promise of even higher stakes. She set up a table in the posh plaza hotel and took aim at the big apple's ready supply of poker-drunk Russian billionaires and hedge fund managers. She says her take spiked up to $150,000 in a single game. I was hosting a game in new York, and there was $5 to $7 million on the table. Reporter: Even Molly admits greed got the best of her and she was persuaded to take a cut of every pot, called a rake, which is illegal, and for the first time, crossed a line. You know gambling is a staple of organized crime. Yes. Did it feel wrong? Yeah, it did. Absolutely. But you didn't quit? I did not. I'm gonna make him an offer he can't refuse. Reporter: And just like in the movie "The godfather," Molly says when two mobsters made her an offer she couldn't refuse, that she pay them for operating on their turf, she refused. They sent somebody to my apartment and he put a gun in my mouth. He hit me in the face and kicked me in the ribs and then just said, you know, "I think you'll feel differently the next time, you know, we have this conversation." Who did you call? I didn't call anybody. And you were deep into this world now. I was deep. Almost one of my first thoughts after he left was, "How am I gonna fix my face before the next game?" You never thought about, "I got to get out of this world. I got to leave?" Wow. Reporter: If a violent attack by the mob wasn't enough to get her out of the game, something else was. 17 FBI agents raided one of my games and I wasn't at that game. And that was terrifying. And I logged into my bank accounts and they were all seized, all frozen. So that was a pretty clear indication that I was in trouble. And you didn't have any money. No money. Reporter: She fled home to Colorado. I lived in the mountains. I started to live a very simple life. My phone was crickets. Reporter: She would lie low for two years, writing a book, "Molly's game," about her journey through the world of celebrities, billionaires and poker without knowing the ending. Until the FBI finally caught up with her. And, you know, they put me in handcuffs and sat me down on my couch and put this piece of paper in front of me that says, "The United States of America versus Molly bloom." Reporter: And just last month, Molly bloom made one more gamble. In a federal courtroom, throwing herself at the mercy of a judge by pleading guilty to illegal gambling in hopes of staying out of jail. All-in with a solid hand, she won, getting off with a sentence of probation. Is there any wisdom you gleaned from observing the game of poker and what you went through? Know when to fold. Pay attention to the signs. They're there. When things start to feel like you're on the wrong path, pay attention to those. That's when you fold 'em. Yeah. Molly bloom's book goes on sale early next week.
This transcript has been automatically generated and may not be 100% accurate.