The Celeb Stories behind Breakout Poker Movie ‘Molly’s Game’

23 July 2018, by Shihaam Isaacs

If you haven’t heard about it yet, Molly’s Game is a 2018 movie all about a real life, real-world underground celebrity poker ring, organised and orchestrated by a woman named Molly, who herself isn’t a poker player. This ‘based on a true story’ narrative is the directorial debut of Aaron Sorkin and, if that name sounds familiar to you, he’s the pen behind a string of big-name biopics including Moneyball, The Social Network and Steve Jobs.

Sticking to the now tried and trusted formula of the biopic, Sorkin wrote the screenplay based on the bestselling memoirs of Molly Bloom, an ex-Olympic level skier turned underground poker organiser.

Molly’s Game – The Plot

Molly’s Game starts off with Molly, played brilliantly by Jessica Chastain, on the ski slopes, participating in an event for the 2002 Winter Olympics. Things go wrong, and Molly ends up severely injuring herself, effectively ending her potential career as an Olympic skier. Her overbearing father, played by Kevin Costner, wants her to go to law school as the next best thing, but she decides that it would be better for her to take a year off.

To finance her gap year, Molly takes a job as a bottle-service waitress at an upmarket club where she meets Dean, a real estate developer. He offers her a job as his office manager, which she accepts but is soon roped into helping him run his underground (illegal) poker ring. Dean’s poker ring is no ordinary backroom deal; he attracts some serious celebrities, sports stars, investment bankers and other heavy hitters.

Molly is no poker player, but she makes her money from tips given to her by the players. Since these poker games often start with a minimum buy-in of $250,000 or more, Molly’s tips are enormous because she knows how to keep these heavy hitters happy. However, there is one player, called ‘Player X’ who Molly really wants to impress, since this player can attract even bigger fish to the game.

After learning that Molly is making more money in tips than anticipated, and is becoming very adept at managing the poker games independently, Dean decides to fire her. Unfortunately for Dean, it's a bit too late, and Molly continues organising and running bigger and bigger celebrity poker games on both coasts.

So, Who is Player X?

Read the book or watch the movie and you know that Molly’s Game is all about super A-list celebrities playing underground poker. We’re talking about big names here; Leonardo DiCaprio and Ben Affleck are just two that were named by Bloom in the book, while others identities have been kept confidential.

But the real drawcard here is ‘Player X’ a central figure in the book as well as the movie. Player X is a great player but also, not such a nice guy. While Michael Cera plays ‘Player X’ in the movie, readers of the book know that this amalgamated character is based on Toby Maguire. Bloom recounts a number of incidents where Maguire comes off as, not only a complete jerk but unscrupulous and manipulating, eventually orchestrating her demise as underground celeb poker organiser.