Let Caroline Ellison’s Testimony Be a Reminder That Dating Your Boss Is Messy

“He directed me to commit these crimes,” the former CEO of Alameda Research said of her ex, Sam Bankman-Fried, on the witness stand Tuesday.

Let Caroline Ellison’s Testimony Be a Reminder That Dating Your Boss Is Messy
Photo:Bloomberg/ ED JONES (Getty Images)

Last week, the much-awaited trial for crypto wunderkind Sam Bankman-Fried began in a New York City federal court. SBF was arrested and charged with eight counts of wire fraud, conspiracy to commit fraud, and conspiracy to commit money laundering in December 2022 after taking money from clients of his cryptocurrency business, FTX, and moving it to his hedge fund, Alameda Research. And he took a lot of money—like almost $10 billion.

The modern Icarus-ness of it all makes for a wildly compelling tale. I say this in a Saturday Night Live Stefon voice: “This story has everything!”—a dude with a mop top rocking cargo shorts and sleeping on a bean bag chair who flies too close to the sun; a downfall that implicates superstars like Tom Brady and Giselle Bundchen; a polycule in a Bahamian beachside penthouse with his coworkers; and private diaries being leaked to the New York Times.

On Tuesday, one of the members of said polycule, SBF’s ex-girlfriend and the former CEO of Alameda Research (told you, it’s messy!) Caroline Ellison, testified against SBF. In December, Ellison—a Harry Potter-loving and blogging 28-year-old gal with a disturbing interest in “human biodiversity” (aka a modern spin on eugenics)—pleaded guilty to committing seven counts of fraud and money laundering.

A screenshot of a February 2019 post from Caroline Ellison’s alleged Tumblr account. Screenshot:Caroline Ellison’s Tumblr (Fair Use)

The biggest revelation from her testimony was that SBF ordered her to move money from FTX to Alameda. “He directed me to commit these crimes,” she told the court. At one point, SBF wrote in a memo shared in court Tuesday that Ellison “is not a natural leader, and probably never will be.” I have very little sympathy for Ellison but I imagine getting to sit on a witness stand and incriminate your frumpy ex-boyfriend/narcissistic boss, who had no trouble throwing you under the bus, must feel very satisfying.

Ellison and SBF’s romantic relationship was also the focus of some of her testimony. “The whole time we were dating, he was also my boss at work, which created some awkward situations,” she said. I’m hard-pressed to think of situations involving SBF that aren’t awkward, but in general, this feels like the understatement of the year.

The tension between SBF and Ellison was no secret. I mean, anyone could look at the situation and be like RED FLAG! But we also knew about these bad power dynamics because SBF had access to, and provided the New York Times with, Ellison’s Google Docs—which she treated like a diary—and where she wrote at length about her relationship with the FTX founder. In one doc from April 2022, Ellison wrote that her on-again-off-again relationship with SBF “significantly decreased my excitement about Alameda” and, in a section directed at SBF, wrote that work “felt too associated with you in a way that was painful.”

“He said there was a 5% chance he might be president someday,” she also declared Tuesday on the witness stand. While that revelation certainly made me laugh, Ellison’s old Tumblr posts show that that sort of egomania is her idea of a ~cute boy~. “Here are what I think are some ~cute boy things~,” she wrote in a now-archived February 2019 post. “Controlling most major world governments” and “low risk aversion” were two of the qualities she listed. Between his ambitions for the former and his demonstration of the latter, it seems like she found her guy in SBF!

Of course, ultimately, a man with both of those qualities would probably make a terrible boss who blows past common sense and/or federal trade guidelines. That just adds pesky baggage to the romance! I think of the many takeaways from this trial, one of them ought to be that being in a rocky polycule with your man-child boss is more trouble than it’s worth.

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