'Molly's Game': How Aaron Sorkin Bet the Farm on Poker-Queen Biopic – and Won

There are two things you should know about Aaron Sorkin. 

One is that the man likes to talk. A lot. This will not surprise anyone who’s seen the 1992 screen version of his play A Few Good Men, starring Tom Cruise and Jack Nicholson. Or has watched a TV show he’s had a hand in developing, like the one about an all-sports cable channel (Sports Night) or the one about an all-news cable channel (The Newsroom) or the Emmy-winning one about an all-drama idealistic White House (The West Wing). Or remembers the sharp, rat-a-tat-tat dialogue in the screenplays he’s written or cowritten for The Social Network, Moneyball and Steve Jobs. You know that shot in every film about New York summers, where kids are splashing around a gushing fire hydrant? Sorkin is the verbal equivalent of that hydrant. At one point, his publicist has to shuffle him off to his next interview while he’s still finishing an answer, which the gentleman is determined to extrapolate on from every conceivable angle. So the 56-year-old writer keeps chatting as we speed-stroll down a hallway – at which point it occurs to everyone concerned that they are taking part in a real-life Aaron Sorkin walk-and-talk scene.

The second thing – the bit that is surprising, given the reason Sorkin is at the Toronto Film Festival, in September of 2017, talking to journalists in hotel passageways – is that the man hates poker. “My TV is permanently tuned to ESPN, so you
can’t help but trip over the World Series of Poker every so often,” he says. “And it is the Worst. Spectator. Sport. Ever. I’ve tried watching a few minutes of it – even
while I was writing this movie, which is when it would have been the most useful to me – and it’s the exact opposite of ‘You can’t take your
eyes off it.’ You can’t keep your eyes ON IT! Because I don’t want any of these guys in their
Member’s Only jackets and bad sunglasses and backwards baseball caps to go home
with any money. I’m not rooting for anybody. Is there a way the waitress can win instead?!”

The game, in other words, is not why Sorkin decided to write and – for the first time in his decades-long career, direct – Molly’s Game (which opens wide on January 5th), the story of former Olympian hopeful-turned-underground “Poker Queen”-turned-enemy of the state Molly Bloom. As played by Jessica Chastain, this woman isn’t much of a motormouth, at least at first. Her skill lies in silently listening and playing very, very close attention to the ins and outs of how her boss’s invite-only crème de la crème card game works. Soon, she’s running her own high-roller, celebrity-filled poker nights, first in Hollywood and then in Manhattan. The Russian Mob takes an interest. So do the Feds. And then, when it behooves Molly to speak in order to save her skin, she shuts up. 

So yes, he could give a flying fuck about how an ace-high hand fares in a Texas Hold ‘Em showdown. But refusing to compromise your principles when the chips are down – now that was something the man admired. And a strong moral center was what Bloom had in spades. “Listen, I love watching superheroes with capes as much as any 12-year-old,” Sorkin says. “But integrity, character, doing the right thing … that’s what I love writing about. I basically keep writing characters that are variation of my father. And Molly reminded me a lot of my father.”

The man takes a quick breath. “And also if Wile E. Coyote was crossed with Jessica Rabbit.” 

Sorkin had actually been contemplating several projects when a lawyer “who I knew socially” passed along his client’s book to the screenwriter – a tome blessed with the Sorkin-level verbose Molly’s Game: The True Story of the 26-Year-Old Woman Behind the Most Exclusive, High-Stakes Underground Poker Game in the World. Despite the fact that the dreaded word poker was listed prominently in the title, he agreed to give it a read and found the book “fun … but I had zero interest in adapting it. None. Not in the slightest. And then I met Molly, and everything changed.” 

Specifically, Sorkin says, it was the disconnect between the story that Bloom’s book told and the real version of her tale. “It wasn’t just that she had a sly sense of humor and was smarter than I was – one does not have to be too smart to pull off that feat,” he notes. “It was the why behind Molly deciding to leave so much out of the book. She didn’t feel she could let people down when she’d given them her word, which was something that meant a lot to her. What actually happened was a lot more complicated, nuanced and emotional than what was on the page. 

“Plus when I met her,” Sorkin adds, “she’d just been sentenced to 200 hours of community service, had been handed a massive fine and was paying several millions’ worth of taxes on the money the government had seized! Yet Molly just seemed very casual about it. After that first meeting, I felt like I knew her well enough to tell her, ‘I’ve never met someone so down on their luck and who seemed so confident.'” He left that face-to-face knew that he wanted to tell her story. What the writer didn’t know was that he’d also just unwittingly signed up to become a director as well.