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Manhattan Fold ’Em

Maguire took his home game seriously. He even had a cash-counting machine. The buy-in started deceptively small, at $5,000. “In the first hour, half the table reloaded three or four times,” one regular remembers. “By the end of the night, some guys are in for $50,000 or $75,000, sometimes $100,000. That was what was magical about the game. It’s not like guys couldn’t afford it, but the $5,000 buy-in gave them the security they needed to get started.” Around 2004, Maguire felt less comfortable hosting. “Tobey is a vegan, and he’s a little eccentric in some ways,” a friend says, “but you get a bunch of guys, we’re playing in his kitchen, chewing tobacco, ordering pepperoni and sausage pizzas, and he just couldn’t stand it. One night he was like, ‘How can we keep this game going without having all these scumbags come to my house?’ ”

Maguire and a friend approached Feinstein at the Viper Room. “Yeah, it’s going to be great,” Feinstein told people about his game. “And I’m going to have a hot piece of ass serving drinks.”

Feinstein told Bloom she was in charge of making everyone happy. But Feinstein had no direct involvement in the game. That left Bloom to do everything from fixing cocktails to helping the players settle accounts at the end of the night. Before long, she was hiring massage girls and managing the player list. No one else wanted the headache of rounding up players and texting everyone the final lineup, so Bloom handled all the contacts Maguire and the others gave her and started building a list of her own. The only thing that players had to do was wait for a text from Molly saying who was coming.

The Viper Room basement smelled like a bathroom and didn’t look much better. But it was both private and quiet, a safe distance from the main entrance and loud music. Players could come at seven and close the place down with no one even knowing they were there. The game wasn’t raked—although technically the Viper Room games would have needed a license to be completely legal, the absence of a rake made it less of a target for law enforcement. Bloom and the card dealer worked for tips, and it didn’t take Bloom long to realize that more money on the table meant bigger tips for her.

As the mandatory blinds went up, so did the pots. After a while, the buy-in went up, too. New players with fat wallets were more than happy to lose money for the chance to play with Maguire and his friends. DiCaprio isn’t a natural gambler; he played what poker players call a tight game, taking few risks. But just having him there from time to time made the game even hotter. As the game became an open secret, security became so tight that one night even Maguire’s then-girlfriend, Jennifer Meyer, couldn’t get in to deliver his vegan meal. The circle widened to include Rick Salomon, Paris Hilton’s sex-tape co-star, and Joe Francis, the Girls Gone Wild auteur (such a bad player he tried to ask a question in the middle of one hand). Bloom had made herself indispensable. One day, when she and Feinstein squabbled over something minor, the regulars of the poker game rallied around Bloom and followed her as she took the game to a player’s house, then to suites in the Four Seasons, Beverly Hills Hotel, and the Peninsula.

Within a few years, the buy-in had exploded to $100,000. New players came in with bigger bankrolls and serious poker chops: Real-estate mogul Bob Safai, impostor–perfume founder Larry Hahn, Affleck, Damon (just once, losing $40,000), and Phil Ivey. Bloom made it her job to keep the big fish happy and in the game. She recruited the prettiest girls she could find to offer neck rubs and keep drinks flowing. “Molly was able to play into people’s egos and desires,” a close friend says. “She knew how to make them want more. She made sure her players were pampered, and she was also very professional about it. She created an environment that appealed to the five senses, and who wouldn’t want that compared to a smelly basement?” On any given night, the winner was taking home $300,000. Armed guards with bulletproof vests sometimes stood by the door. There was still no rake, but Bloom was reportedly making as much as $400,000 a year in tips. “Ultimately, there were two people that never lost in that game—the dealer and Molly,” says one regular.

In 2007, Bloom started her own business, registering Molly Bloom Inc. as an event and catering company, and had her workers file the appropriate forms. She was paying taxes on her own income, and because she was the conduit who managed all the game’s money and cashed all the checks, she also paid taxes on every debt she didn’t collect. “In fact, she was terrible as a poker manager,” one source close to her suggests, “because she got stiffed for hundreds of thousands of dollars. But she was great at taking a terrible business model and turning it into something a lot of people wanted.”