The “Best Sports Sports Betting Scenes in Television and Movies” series returns with a look at Aaron Sorkin’s Oscar-nominated celebrity poker film, Molly’s Game.
“Success is the ability to go from failure to failure without losing your enthusiasm.”
This quote, uttered by Winston Churchill, is sound advice when applied to most facets of life. It is resiliency in plain terms, the act of picking yourself up and dusting yourself off after a disappointing result and giving it another go, undaunted.
This mindset is especially valuable in baseball, where even elite hitters like Alex Rodriguez fail two-thirds of the time. But when applied to poker, sports betting, and other forms of gambling, a delicate balance rests between successfully playing the long game and chasing one’s losses into a black hole of financial despair and/or addiction.
The Aaron Sorkin-directed film Molly’s Game, based on the memoir of the same name by real-life “poker princess” Molly Bloom, ends with Churchill’s quote, striking a hopeful note. But earlier in the film, Harlan Eustice (portrayed by Bill Camp) gets bluffed into folding by a far lesser player and proceeds to go on a sleepless, winless, two-day-long poker bender that causes him to skip out on his wife’s birthday party and puts him $1.5 million in hock to Bloom (Jessica Chastain, perfectly cast).
Bloom is not the sort of host who will resort to violent ends to collect a sizable debt, but such tactics are rendered moot when Eustice swiftly pays her back by virtue of a loan from Player X (Michael Cera, boyish as ever). A thinly veiled version of the actor Tobey Maguire, who tormented Bloom in real life as a regular at her exceedingly high-stakes game, Player X is no slouch at the table, bluffing a fish with a much stronger hand out of a $47,000 pot and punctuating his victory with an arrogant “F**k you!”
Big names, big (mi)stakes
A-Rod, Maguire, Leonardo DiCaprio, Ben Affleck, Pete Sampras, and the Olsen twins were among the celebs reported to have participated in Bloom’s game, which started in Los Angeles before heading east to New York. For most of the game’s lifespan, Bloom operated on the straight and narrow, which meant taking no payment beyond tips, properly accounting for employees, and filing tax returns associated with her multimillion-dollar annual income.
Eventually, however, her exposure to would-be welshers was sufficiently astronomical that she began taking a rake, which, as Bloom notes in the film, is the moment where she fell afoul of the law. Her judgment increasingly clouded by drug addiction, she gives the occasional Russian mob associate a seat at her table, which leads to her 2013 arrest for, among other crimes, racketeering, money laundering, and facilitating an illegal sports gambling operation.
Sports, it turns out, are part of the Bloom family’s DNA. Her brother, Jeremy, played professionally for the Philadelphia Eagles, and Molly was an Olympic-caliber moguls skier whose career on the slopes was cut short due to a freak injury while trying to qualify for the Trials. Her mom was a professional fly-fisher, and while Bloom’s overbearing, philandering dad wasn’t an accomplished athlete, he’s portrayed in Molly’s Game by the greatest sports movie actor of all-time, Kevin Costner.
An objectively stupid bet pays off
In the film, a broke Bloom retains the services of top-flight attorney Charlie Jaffey (Idris Elba), promising to pay his $250,000 fee from money she still has out on the street. After making a convincing argument that the case’s prosecutors have overreached during a closed-door meeting with them, Jaffey secures an exceptional plea bargain in which Bloom would serve no jail time and recoup her $4 million in seized income (plus interest) in exchange for the information on her hard drives.
But those hard drives contain some incredibly damaging dirt on some incredibly rich and famous people. And despite the fact that these individuals have all but abandoned her since her arrest, Bloom goes against her attorney’s advice and refuses to take the deal — opting to simply plead guilty and let the chips fall where they may in court, a potential 10-year prison sentence waiting in the wings.
On its face, Bloom’s no-strings-attached guilty plea is the biggest — and stupidest — risk in a film full of them. But it’s a bet she ultimately wins, one rife with the sort of zero-sum certitude required of a truly elite athlete — or gambler.