Molly’s Game: The True Story behind the Movie about Underground Gambling and Molly Bloom

Gambling of Molly's Game Poster 25 Apr

Molly’s Game: The True Story behind the Movie about Underground Gambling and Molly Bloom

When you lead a hectic and compelling life that includes rubbing shoulders with the elite of Hollywood and sports, you ought to know that you might end up seeing your story unfold on a movie screen. Add a poker game to the mix, and you’ll have an extraordinary tale that’s bound to receive accolades. This is precisely what happened to Molly Bloom whose autobiographical book inspired the talented Aaron Sorkin. His directorial debut includes the likes of Jessica Chastain, Kevin Costner, and Idris Elba.

So, is Molly’s Game a true story? According to him, Sorkin tried to involve Bloom as much as possible during his writing process. That’s why he relied on her memoir for the most part. But the question is — how accurate is this movie about underground gambling and Bloom’s life? Especially because we all know that directors like to spice things up by putting in colorful details that may or may have not occurred. All for the purpose of attracting a broader audience. Let’s see how genuine this film really is.

Bloom was a Professional Skier

In the opening scene of the film, we hear Molly who’s reminiscing about a fall she endured during qualifications for the Olympics. This tumble left her with a debilitating back injury that put a stop to any aspirations she had about becoming a professional skier. Yet, this didn’t happen in real life. Yes, she was a bona fide skier who wanted to show her prowess at the Olympics. But it was a spinal fusion surgery that caused her a lot of back pain. At one point, she decided that she couldn’t endure this anymore. Molly turned her back to this career which might have been decisive in her becoming a poker princess later in life.

Her Exposure to High Stakes Poker Games

Before she surrounded herself with Hollywood royalty, Bloom went through a number of jobs. When she moved to Los Angeles, she was even a cocktail waitress, but it was when she met Darin Feinstein that her life took a different turn. He was the owner of The Viper Room and Bloom became his assistant. And it didn’t take him long to involve her in his underground gambling business. The movie got it right when it depicted Feinstein as a horrible and unscrupulous employer.

Casino Game Underground

What’s more, the scene in which Bloom brings him a bag of bagels only to have him reject it is real. He called them “poor people bagels” much to her horror. Although being difficult, he was the person who introduced her to all the big names in the city. According to one interview, Bloom wanted to appease all the players who participated in his poker game. She even tried to find which music and food they liked. By her own admission, she would dress to the nines to try and impress everyone. And impress them she did — so much so that jealous Feinstein fired her. After this, she opted to start her own game and used all the contacts she had acquired while working for him.

Is The Cobra Lounge Real?

According to Molly’s memoir, it isn’t — the real action transpired in The Viper Room. And it’s still operating in all of its capacity on the Sunset Strip in West Hollywood. At one point, Johnny Depp owned it for about 11 years (from 1993 to 2004). Popular culture fanatics are probably familiar with it as the place where the actor River Phoenix died following a drug overdose back in 1993. And it was a favorite haunt of many A-list celebrities. So it’s only natural that it served as the go-to place for underground poker.

Molly’s First Night at The Cobra Lounge

No wonder that Bloom was so captivated by this world of poker from her first night. Namely, she was exposed to exorbitant sums of money and had a chance to count $100,000 in cash! She caught the attention of many players who were extremely generous. As the movie correctly shows, she earned $3,000 in tips that first night while a poker game was unfolding. This encouraged her to start focusing on poker and try to learn as much as she could. And she spent many evenings on the Internet conducting thorough research on all things poker.

How Did She Start Her Business?

Like you can see in the movie, Molly was on top of her game — charming everyone and getting into the world of underground poker one step at the time. Her bubbly personality helped her build up useful contacts that proved to be a valuable thing. To be specific, Feinstein wasn’t all too happy about the attention she was receiving. Apart from this, her independence irritated him. This was why he fired her on the spot. Unbeknownst to him, Molly was keen on continuing what she’d started. And she utilized all of his contacts and started to vie for them. She was successful in luring some of them from The Viper Room to her own place.

What the movie doesn’t show is that Bloom registered an events and catering company to cover for her underground gambling business. In 2008 she started inviting high-rollers into private homes and various hotels, as seen in the film. During this period, players would wager as much as $4 million.

What Was the Buy-in During Her Games?

When you have Wall Street titans, Hollywood royalty, and sports stars at the private house you rented so that they could play some poker games, you know that the stakes would be high. Bloom, drawing from her experience in The Viper Room, was well aware of this. As she needed to provide wages for her staff and generate some profit herself, she started including a buy-in. At first, players were required to pay $10,000 which didn’t seem like a substantial amount to them. However, the amount increased over time. So, is this part of Molly’s Game a true story?Casino Game with Molly and Charlie Jaffey

During an appearance on Ellen, Bloom admitted that it was and that, over time, she charged a $250,000 buy-in. In the movie, you can see people losing their money like it’s nothing. Bloom was amazed both by this and the extent to which they found this game compelling. One player even lost $100 million in one evening alone. According to Molly, he paid this amount the very next day which left everyone shocked.

The Who’s Who of Molly’s Game

Due to obvious reasons, Sorkin wisely decided not to name the celebrities who were regular players in this underground poker game and squandered away a lot of money. Yet, Bloom chose to identify some of them in her memoir. And trust us, the names would leave you baffled, especially if you hadn’t been following the news before watching the movie. In other words, a number of A-listers were exposed in the media without Bloom’s help. Even though the actual list is far more extensive, Molly concluded that it would be best to protect some of them from exposure.

We’ll mention four of them who were alleged participants in Molly’s game:

1. Tobey Maguire

Michael Cera brilliantly depicts Player X who also appears in the book. He can be seen manipulating other players and exhibiting unacceptable behavior. Many believe that Player X is actually Tobey Maguire — the famous actor and passionate poker player. Aaron even hinted that it was him in the film. Namely, there’s one line about how Player X is known for portraying a superhero (Spider-Man, anyone?). Bloom found it difficult to deal with his mood swings during the weekly games.

At one point, Player X bluffed which prompted another player to believe that he would win. Then Player X exposed his hand only for the poor fellow to realize that he had tricked him. Allegedly, Tobey offered to cover his loss if the player would give him 50% of his winnings. When Bloom found about this, she called him angrily, but he remained unaffected. Following this, Bloom lost control of the game much to the delight of Player X. Molly wrote that she found about this from Tobey himself.

In addition, this wasn’t the biggest of his transgressions. At one point, he asked Molly to bark like a seal if she wanted to get $1,000 from him. Of course, she refused and Tobey was fuming. The episode ended when he stormed off. Admittedly, this goes well with Player X’s personality who, by Molly’s account, was the worst tipper and a sore loser.

2. Leonardo DiCaprio

This name doesn’t come as a surprise if you’re aware of how close Leonardo DiCaprio and Maguire are. But even Molly said that Leo wasn’t a frequent guest at her weekly game. It would seem that Tobey would bring him only so that he could attract billionaires and play against them. Basically, Leo wouldn’t pay the entry fee — Tobey would cover for both of them and parade Leo around the room.

3. Ben Affleck

Another familiar name is that of Ben Affleck. Although we can’t see this in the film, some say that Matt Damon would tag along to play which proves that Molly’s game included the Hollywood royalty. As for Affleck, it’s sort of a known fact that he’s a passionate gambler. Most recently, he made headlines when it was discovered that a Las Vegas casino banned him from playing Blackjack because of a cheating scandal. From her part, Molly described him as being quite an astute player because of his buy-in choice.

4. Alex Rodriguez

In her book, Bloom wrote that the famous Yankee player would also frequent the game in New York. Although notably, she didn’t really explicitly say that he was there to play. Yet, she confessed that she wanted him to come because of his appearance. He would make even the business titans look at him in awe. They would idolize him which, in a way, expanded the circle of players. In the past, there were rumors about his love of gambling, but his team strived to squash them all down.

Her Run-in with a Mobster

Gambler Molly BloomMolly’s encounter with a mobster ended in him putting a gun to her head. Prior to this event, Bloom had worried about her security and hired a driver. Little did she know that he would introduce her to his friends who were mobsters. Hearing about her fear, they suggested that they would keep her safe if she gave them a part of her profits which she refused. After several weeks, a man arrived at her house and then pointed a gun to her head. He threatened to harm her family. Then he took off with her jewelry and money.

She didn’t leave her apartment for a week so that no one would see her bruises. After this, the mobsters called her once again and wanted to meet with her so that they could discuss the deal. She accepted out of deep fear. But before the meeting took place, she saw that the FBI had arrested a vast number of people due to their connections to a mob.

Is Idris Elba Playing a Real Person?

Sadly, no. In this movie about underground gambling, he plays a fictional character. Obviously, she had to hire lawyers at one point, but none of them was Charlie Jaffey. Sorkin didn’t want to contact Jim Walden, who was Bloom’s lawyer. According to him, he wanted to create a new character who would be right for the story. Thus, he didn’t want to worry about him being historically accurate.

How It All Ended

You might wonder how Molly got busted by the Feds. Well, she was loaning money to her players believing that they would be able to pay her off. And she ended up getting cheated a lot. She would write big checks and not receive anything in return. Therefore, she decided to take a percentage of the pot. By her own admission, she broke the law.

Additionally, as per the movie, her downfall occurred when Bradley Ruderman planned a Ponzi scheme. During one game, he squandered $5 million away which belonged to his investors. This attracted the attention of the FBI who started revealing the whole thing. They began following Bloom and listening to her conversations so that they could create a case against her. Is this part of Molly’s Game a true story? Well, Bloom says that it is and that it accurately shows her undoing.

Her Punishment

During a hearing in 2014, she pleaded guilty as a result of which a number of charges against her were dismissed. The judge was mild towards her and she received 200 hours of community service. Apart from this, she had to pay a $200,000 fine and was sentenced to one year of probation. Bloom, played by Chastain, also receives this sentence in the movie.

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