Molly Bloom reveals how she built one of the most exclusive, high-stakes underground poker games in the world - an insider's story of excess and danger, glamour and greed. In the late 2000s, Molly Bloom, a twenty something petite brunette from Loveland Colorado, ran the highest stakes, most exclusive poker game Hollywood had ever seen - she was its mistress, its lion tamer, its agent, and its oxygen. Everyone wanted in, few were invited to play. Hundreds of millions of dollars were won and lost at her table. Molly's game became the game for those in the know - celebrities, business moguls, and millionaires. Molly staged her games in palatial suites with beautiful views and exquisite amenities. She flew privately, dined at exclusive restaurants, hobnobbed with the heads of Hollywood studios, was courted by handsome leading men, and was privy to the world's most delicious gossip, until it all came crashing down around her. Molly's Game is a behind the scenes look at Molly's game, the life she created, the life she lost, and what she learned in the process.
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You were workin' as a waitress in a cocktail bar..
Molly Bloom moved to Los Angeles from Colorado, seeking fame and glory. Working as a waitress in a cocktail bar, she stumbled into a job as personal assistant to an abrasive guy named "Reardon" with nebulous business dealings and connections to all sorts of rich and famous people. This leads to Molly running poker games attended by Hollywood A-listers and billionaires. At first working for tips alone (which could total tens of thousands of dollars a night in games where celebrities are dumping half a million dollars on the table), Molly climbs her way up until she is running the games herself, with an exclusive invitee list in LA and New York. This ultimately proves to be her undoing - when she is merely collecting tips, her job is in a legal gray area, but basically she's safe (she actually retains a lawyer, makes sure to pay taxes on her earnings, and so on). But as she became more ambitious, and greedier, once she's actually organizing the games and collecting a "rake" (the house's share of any money bet), she has become the operator of an illegal gambling enterprise. And that's how the book ends, with Bloom given the full FBI home-invasion treatment and then awaiting trial.
I found this book very interesting as a rags-to-riches-to-convicted-felon story of a former cocktail waitress, but Molly's Game is not really very much about poker. (Molly herself was never really a player, and I think her knowledge of the game never extended beyond what she needed to run it.) Instead, it's really a glimpse at celebrity culture and the world of the 1%-ers at play, and also a story about Molly herself, whom I found to be an interesting and somewhat sympathetic character, yet rather lacking in self-awareness for all that she writes a tell-all about herself.
One of the interesting things about her memoir is that she freely names names - big names. A few people she keeps obscured (like her original boss, the mysterious "Reardon"), but she talks openly about games involving Ben Affleck, Leonardo DiCaprio, Tobey Maguire, A-rod, and numerous Hollywood executives and billionaires who also came to her games. Surprisingly enough, there really isn't a lot of "dirt" on any of them, since all she has to say is that they liked to play poker and play at being alpha males, as you'd expect.
Except Tobey Maguire, who really comes off as a jerk in this book. According to Bloom, Tobey actually organized the games (using Bloom as his intermediary) for his own profit. His not-so-secret scheme was basically to go "whale fishing," luring very rich, very bad players to his game with his buddies like Leonardo DiCaprio, whose buy-ins he was actually paying for. It worked very well for Maguire, who has actually won poker championships, but as Bloom tells it, Maguire was cheap, a bad tipper, a sore loser, and eventually he squeezed Bloom out of the game because he resented the relatively small amount she was making for her work to keep it running. She tells about one night when he tried to make her "bark like a seal" for her tip after a game, and when she refuses, this seems to be the point where he starts moving to get rid of her.
All of that is interesting if you like celebrity gossip and poker stories, but I was also interested in Bloom's own development. She's never exactly bad, but it's clear that she went swimming with sharks, knowing what she was doing, and wanting to be involved in that world of money and glamour, but thinking she could somehow avoid becoming either a shark or shark-bait herself. The breakdown in her personal relationships, as she loses one rich boyfriend after another to her career ambitions, does not make her reconsider her life choices.
Eventually, having been essentially run out of Los Angeles (by Tobey Maguire, if her account of his behind the scenes machinations is correct), Bloom succeeds in starting up in New York City, running games for super-rich Wall Street types on a level above even what she was running in LA. Suddenly she is collecting a rake from games with $250K buy-ins, and making millions.
This is the point where she runs into organized crime. What struck me was her naivete - did she really think she could be running games like this in New York City and not attract the attention of the big boys? Apparently she did. Even when a couple of goons corner her and explain to her that she's just acquired some partners and how things are going to be, she thinks she can just say no thanks.
This works about as well as you'd expect, though she is saved from her own stupidity by a fortuitous major FBI operation that rounds up all the guys who were about to continue her education the following week. She flees back to Colorado, but in the aftermath of the FBI operation, her name gets dropped and eventually the FBI comes after her too.
My impression of Bloom, reading her own memoir, is that she was hungry for money and glory, but neither ruthless enough for that world nor scrupled enough to maintain boundaries. So it was no surprise that everything came crashing down. Still, it's clear she wasn't a hardened criminal, and the super-rich, entitled men she was organizing games for would certainly never face any consequences.
I'll be interested to see if Bloom is actually able to parlay this into any sort of meaningful future. According to her post-publication interviews, her current angle is trying to get it turned into a movie or TV deal... naturally.