Illegal High-Roller Hollywood Poker Games of Molly Bloom

The 2017 gambling movie Molly’s Game featuring Jessica Chastain was an international hit, full of intrigue and dramatic scenes. However, the real-life events that the movie is based on seem even juicier. A-list celebrities like Leonardo Dicaprio, Ben Affleck, or even the Russian mafia all attended the high roller poker games hosted by Molly Bloom.

Molly Bloom is many things: author, Olympic skier, entrepreneur, executive assistant, but most importantly a poker tournament host. She operated an underground high-stakes gambling ring where people were known to lose over $100 million in a single night.

Rags To Riches

In the early years of her life, Molly Bloom grew up in the shadow of her highly reputable family of doctors and athletes. In order to live up to her family’s name, Molly pursued a career as a professional Olympic skydiver. After numerous injuries, she had to abandon that path and shifted her career to Los Angeles to attend law school.

Her start in Los Angeles was very bumpy, as Molly worked a minimum wage waitressing job barely making ends meet and living on her friend’s couch. However, the stars would align almost immediately after quitting her job. 

On her way out still in her working uniform, Molly would almost get run over and meet none other than Darick Feinstein. A billionaire and the owner of one of the largest Bitcoin mining operations, Feinstein hired her on spot after the incident.

She worked her way up and became the executive assistant of the mentioned billionaire, which is where her life would forever change. As an executive assistant, Molly personally ran and organized Feinstein’s highly exclusive poker games, which were frequented by the Hollywood rich and famous. 

Molly lived off the tips given by the wealthy elites, each night pocketing well over a few thousand dollars. Her work particularly caught the eye of the famous actor Tobey Maguire who would help her set out on her own and host independent poker tournaments.

Glory Days Of Molly’s Game

The word quickly spread about Molly’s exclusive underground gambling ring throughout Los Angeles and caught the eye of many other big sharks. The main draw of Molly’s club were the celebrities themselves. 

People were flocking and fighting over spots on one of the poker tables in order to be in the presence of famous actors and play alongside or against them. The games would often be hosted in some of the most upscale locations such as the famed Beverly Hills Hotel or Four Seasons with suites costing thousands of dollars per night. 

List Of Confirmed Celebrity Players That Attended Molly’s Poker Events

In her memoir, Bloom only mentions VIP players that had already been exposed by the media prior to the publication of the book. She has since stayed silent and hasn’t revealed any more information, regarding the players. However, the named VIPs in her book are: 

Tournaments were known to last for several days with enormous buy-ins of up to $250,000. Some high-profile players were even known to put expensive antique art pieces as collateral if they didn’t possess enough cash in person for the buy-in. 

At this point, Molly nicknamed the poker princess, making millions of dollars per year, and surprisingly it was all legal! Her business was registered as Molly Bloom Inc. and with the help of her lawyer, she ticked all the boxes.

Unfortunately for Molly, gamblers aren’t known to be the most honest of individuals. And as her underground empire grew, it caught the attention of the mafia and particularly Russian mobsters. 

The crime syndicates would extort her business for so-called protection money and threaten her life. On top of that, her own players would betray her by not paying their debts that they had racked up in Molly’s credit. This would ultimately bankrupt her and she would have to resort to commissioning a small percentage out of the prize pot. While commissioning is a normal practice in casinos, Molly didn’t possess a sufficient gambling license or qualifications and thus broke federal law.

The movie picks up and dissects the details of her court case and dealings with the Hollywood elite. In the movie, characters are portrayed under aliases but Molly has disclosed some of the names and identities in her book.

Among the aforementioned VIPs, Molly lists other notable names that took part in her underground poker games, which include: Rick Solomon, Alex Rodriguez, the Olsen Twins, Matt Damon, and many others.

Who Is Player X?

Besides the underground syndicates that literally put a gun in Molly’s mouth at one point, the movie has another antagonist. 

His real name was never officially revealed and in the movie, he’s only referred to as Player X. The mysterious poker player is described as a cunning individual and a “little green screen shit”. This led many fans to believe the mysterious player is none other than the original Spider-Man - Tobey Maguire. Mostly due to his negative portrayal in Molly Blooms’ memoir.

In the book, Molly alleges that Tobey Maguire was so rude that he once ordered her to bark like a seal for $1,000 among many other claims.

The author hasn’t confirmed or denied the fan speculation but the director of the movie Aaron Sorkin says that Player X isn’t a single person but in fact an amalgamation of multiple Hollywood stars who have mistreated Molly in some way or another.