Molly's Game: The Real Story Behind the Hollywood Poker Nights — article cover

Molly's Game: The Real Story Behind the Hollywood Poker Nights

Donna Pratt·
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In the late autumn of 2007, at a poker room set up in a suite at the Viper Room on Sunset, a young woman named Molly Bloom was running what was, at that particular moment, the highest-stakes private poker game in Los Angeles. She was twenty-nine. She had skied competitively, read Dostoyevsky in the green rooms of Whistler, and ended up in California by a series of tangents too delicate for a feature film's timeline. Here are a few of the things, in no particular order, that did not quite make the edit.

1. The First Room Was Not The Commerce Casino

A fact the film tidies. Bloom's introduction to private poker was not in a glossy Beverly Hills penthouse but in a small game run by a Los Angeles real estate figure named Darin Feinstein, held at the Viper Room in its post-Phoenix incarnation. Feinstein was, at the time, involved in the club's management, and the game attracted the kind of player who considered himself too interesting for a casino and not quite interesting enough for a cardroom in Reno. The first version of Molly ran the game as a cocktail waitress and de facto organiser. The salary, if one could call it that, was two thousand dollars a night in cash plus whatever the players elected to tip her at the end of the evening. Tips in the Viper Room era, for reasons she would later explain at length in her book, occasionally reached five figures.

2. The Player Called Player X Was Tobey Maguire

In the film, an actor named Player X, played with wolfish joy by Michael Cera, is the most sinister of the regulars. Maguire has been named in the source material and in extensive contemporaneous reporting; he did not sue the book, which those who follow libel law will note is a meaningful non-action. The characterisations of his behaviour at the table, in particular the small and unflattering story about a tipping slight involving a stack of chips, appear in Bloom's memoir with sufficient specificity that even a charitable reader has room to draw conclusions. The actor declined comment at the time the book appeared and has, to the credit of a man who prefers to keep his dinner reservations, declined comment since.

3. The Game Moved East

After a falling-out with Feinstein that Bloom describes, in the book, with the cool precision of a woman who has already written the sentence in her head twice before typing it, she relocated the game to New York in 2010 or thereabouts. The New York game was played out of hotel suites at the Plaza and the Four Seasons and, on certain occasions when the hotels were inconvenient, the personal residences of various of the players. The stakes escalated. Pot sizes in the hundreds of thousands of dollars appear in the book and have been, to a reasonable extent, corroborated by other participants who later spoke on background.

The New York period introduced a different cast: financial professionals, a handful of European nationals whose visible income exceeded their visible employment, and at least one player whose connection to an organised crime family would, some years later, produce the federal indictment that ended the enterprise. The tonal register of the New York game, as Bloom tells it, was noticeably harder than the California one.

4. The Rake Question

In the film, a plot point is made of whether Bloom ever took a cut of the pot, which is the legal distinction between running a legitimate private game (which is broadly lawful in most jurisdictions) and operating an illegal gambling establishment (which is not). In the California years, she did not. The money came from tips. In the New York years, according to her own testimony and the plea she eventually entered, she did begin taking a small rake, reportedly five percent of the largest pots, which was the administrative decision that moved the enterprise across a line she had previously worked hard to stay on the correct side of. This is the single most consequential fact of her legal exposure and is given, in the film, roughly the same weight as the scene in which Jessica Chastain buys a particularly expensive winter coat.

5. The Indictment Was Not About Her

The federal sweep in April of 2013 that produced Bloom's indictment was, in its larger sense, an organised-crime investigation aimed at a Russian-American criminal network whose members had, among other things, been using her New York game as one of several venues for what prosecutors would later allege was a money-laundering and gambling-linked enterprise. Bloom was indicted alongside thirty-three other defendants in a single filing. Her involvement, as charged, was operational rather than central. She pleaded guilty in 2014 to a single count of conspiracy to operate an illegal gambling business, paid a fine, and received a sentence that included probation and community service but no custodial time, an outcome that reflected, among other things, her cooperation with the investigators on matters not directly involving her own conduct.

6. The Book Advance

Molly's Game, the memoir, was sold to HarperCollins in what industry sources reported at the time as a mid-six-figure advance. The book was written quickly, under an arrangement with a ghostwriter whose name does not appear on the cover, and was published in 2014 to a reception that was more respectful than one might expect. The film rights were acquired by a production company, eventually ended up with Aaron Sorkin, who made his directorial debut with the adaptation, and released in late 2017. The film received two Academy Award nominations. Bloom, by the time of the premiere, had relocated to the South and was working in consulting, or so she has said at the times when she has been asked.

7. The Players, Collectively

The cast of the Cobra Room years, which is the name Bloom's own accounts have sometimes used for the California game, included a mixture of poker players you might have heard of and a larger number you certainly had not. Houston Curtis, a television producer, was an early fixture. Alex Rodriguez, Ben Affleck, Leonardo DiCaprio, and Matt Damon have all been named as occasional participants in various stages of the game's history; which of them played at which stakes in which period is a matter on which the sources do not perfectly agree, and a person who wished to construct an authoritative roster would need a dedicated afternoon with a cross-indexed highlighter. The common thread is that the game was, in Bloom's careful construction of it, a place where the table conversation was as much of the draw as the cards.

8. The Lessons Bloom Takes From It

Bloom has, in her post-indictment appearances, consistently made two points. The first is that the California game, for all its excesses, was a cleaner enterprise than the New York game that followed. The second is that she did not see the line move until she was already on the wrong side of it. The line, in her telling, was the decision to take a rake, which she made at a moment of financial exposure she had not fully accounted for and which seemed, at the time, the obvious next step in a business that was producing the kind of pot sizes that made a five percent rake feel absurdly modest. What the federal charge document made clear, some months later, was that the rake was not the only line. Certain of her business relationships, extended in good faith to players whose backgrounds she had chosen not to examine too closely, had already involved her in a set of problems that the rake merely made formal.

There is a moral somewhere in this. It involves, I think, the distinction between the parties that tell you who they are and the parties that require you to figure it out. One has a cover charge. The other has a consequence. Bloom, to her credit, has chosen in the years since to be the sort of hostess who tells you the former. It is, by most measures, the better of the two.

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