The Real-Life Molly’s Game: Inside Hollywood’s Underground Poker Scene

Molly’s Game is a tantalizing 2017 film about Hollywood’s illegal underground poker scene. The film was based on a true story, Molly Bloom’s great poker empire that reached many of Hollywood’s elite and came crashing down as a result of an FBI investigation. The illegal poker games were designed to attract A-list Hollywood actors and celebrities, and were held in private homes and hotels around Beverly Hills. With high stakes games and contests that could easily reach millions of dollars.

It speaks to the popularity of poker, and gambling, even among the richest celebrities in America. Dubbed the Poker Princess, Molly Bloom created what was arguably the greatest illegal poker scheme of recent times.

Who Was Molly Bloom

The Poker Princess grew up in Colorado, in quite an accomplished family. Her father was a psychologist and professor at Colorado State University, and he mother was a ski instructor with a clothing line. She took an interest in competitive skiing in her youth and became a member of the US Ski Team. She finished third in a regional competition in 1999, but suffered a back injury while attempting to qualify for the Olympics. Bloom would later give up her skiing career and go to university, where she studied Political Science.

She then moved to Los Angeles and worked at The Viper Room nightclub as a bartender. A club that was marred in controversy because of its association with celebrities and drug usage, The Viper Room was already a well known establishment. Tobey Maguire approached one of the owners, Darin Feinstein in 2004 about hosting high stakes poker games in the basement. Feinstein hired Molly Bloom to cater to the players and run the games, which is where her empire really took off.

Building the Underground Poker Empire

The film dramatizes Molly Bloom’s relationship with the owners and her role in the poker games. In 2007, Bloom started her business, named Molly Bloom Inc, that served as an event and catering company. Originally, she had little knowledge of poker and gambling, but after years of exposure to high stakes games and endless rounds of poker, Molly Bloom gained the know-how and experience needed to run her games. Breaking away from the Viper Room, Bloom had the contacts and expertise to independently run her games.

She moved her operations to private homes in Beverly Hills, as well as hotels. Naturally, Bloom attracted plenty of publicity and unwanted attention for her part in organizing these games, and in 2009 she moved to New York. She continued to organize the games until 2013.

Exposure and Downfall of the Empire

In 2013, Molly Bloom’s game was finally up. She was arrested alongside 33 others for being a part of a $100 million money laundering and illegal sports gambling operation. Molly didn’t have the necessary permissions or gaming licenses to host poker tournaments, and she had taken a percentage of the pot – also known as a poker rake. This basically changed the games from being “friendly social gambling” to organized gambling and real money poker cash games. When the FBI raided her home and froze her accounts, they found her network was a lot larger than initially thought.

Molly’s client base expanded to hedge fund managers, East Coast financiers, and other high profile figures who were being investigated for financial crimes. She was even linked with the Russian mob, and associated with a Ponzi scheme. She faced a maximum of 10 years in prison, which was reduced to just 1 year on probation and 200 hours of community service. Also, she had to forfeit $125,000. And with that, her poker empire came crashing down.

Famous People Who Played Molly’s Game

Tobey Maguire was the first high profile celeb who came by Molly Bloom’s way, but in the space of a few short years, she built a large repertoire of contacts. Bloom apparently didn’t just host high stakes poker games and act as a personal host for them. She also got to know a lot of these A-listers personally. Even claiming to have some form of social relationship with them.

Actors such as Leonardo DiCaprio, Matt Damon, Ben Affleck (who is a well-known card counter and gambler), the Olsen twins, and Macaulay Culkin were known to play Molly’s Game. The investigation exposed many sports people, celebrities, actors and wealthy individuals, including professional poker players Phil Ivey and Rick Salomon.

Molly Bloom didn’t take all the blame, as many of the top celebs involved also took on some of the heat. Tobey Maguire was sued, among with other actors who had taken part in the games. A lot of the details about the investigation, and who was actually involved are quite hazy. There are lots of high profile figures who still deny their association and refuse to be involved. Though Tobey Maguire, who won between $30 to $40 million, was the focus of the criminal investigation. As the other high profile celebs hadn’t won enough to merit prosecution. After 2013, Tobey Maguire reduced his output in Hollywood and took on fewer acting roles.

Why Did Molly’s Game Get as Big as it Did

The exact details of Molly’s operation remain the subject of great interest, and conjecture. We don’t know how much money exchanged hands, which celebs won and lost, or who played who. But the fact that it happened, and so many of Hollywood’s elite got in the action is just a testament to the glamour and allure of playing poker. The game has attracted people from all walks of life. From the wealthiest individuals to characters like Archie Karas, who rose to the top and then plummeted straight back down.

Poker is a game that combines skill and chance, with a lot of players misunderstanding the balance between the two. It is seen more as a game of wits, and the player who wins is seen as the more talented or strategically inclined over their opponents. But that is not really how poker works. Luck and chance dictate the game, by the draw of a card. Sure, an experienced player can bluff and draw on their knowledge of the game to anticipate what will happen. And then they can make the most of a good hand, or avoid losing heavily if the flop, turn and river don’t fall in their favor.

Though, as luck can have it, a player can beat an opponent with a better hand if they time their bluffs, and scare their peer into believing they will lose. It is a test of psychology, nerves, and trying to read how others play the game. And all the while, trying to make your own moves and actions unpredictable, so that they don’t latch onto you.

The Appeal of Poker Beyond Making Money

So in that way, poker is not just about winning money. It can also be seen as a measure of intellect and cunning. If a player wins, they aren’t just taking the pot. They can feel a rush of dopamine as they relish the win. The element of control in poker makes the win all the more valuable.

Similarly, the feeling of loss is also amplified. Gambler’s remorse in poker is quite complex. A losing player may feel regret for their actions. Especially if they were enticed into raising the pot, or folded against a player who had a worse hand. Though regret and remorse can quickly turn into dopamine. The player may be enticed to try again and win it back in the next round. They may believe they have sussed out their opponent. And can then turn the tables in the next game.

It can build fallacies such as overconfidence or gambler’s conceit. We give more weight to the actual players and their capabilities. And it can be especially dangerous with wealthy people who aren’t experienced at the game. They can end up pumping in huge sums of money, convinced that they can outplay their opponent, and then get a poor draw and end up losing their money.

Play Poker Responsibly and Legally

As a rule of thumb, you should only enter poker cash games that cost around 5% or less of your poker bankroll. If you have $200, then a $10 buy in is ideal, as you can fund plenty of rounds. It helps you get past short term variance and get an idea of who you are playing against. And then you can raise the stakes if you feel like you have the edge.

When playing poker, make sure you only do so at legally recognised venues or gaming sites. The 2011 FBI crackdown of PokerStars, Full Tilt Poker and Absolute Poker is another example of a big shakedown in the world of poker. The Federal Court determined that these sites were working illegally in the US, and thus shut them down. It resulted in thousands of players either losing their money, or getting frozen out of their accounts. And while some players received the money eventually, some players never saw their bankroll returned.

Thus, when looking for online poker rooms, be sure to always check for gambling licensure. Choose a gambling site that is regulated in your country or state. And if there is none, then you should check to see if there are any overseas or international poker sites that have good reputations. Only pick licensed sites, which have the approval of the MGA, UKGC, Curacao Government, Kahnawake, or other leading gambling regulators. These licensed sites provide responsible gambling tools, which you are encouraged to use to ensure you don’t overspend.