Diary entries of Caroline Ellison, ex-girlfriend of Sam Bankman-Fried, show doubt, dread

Caroline Ellison, a former executive at failed crypto hedge fund Alameda Research, privately doubted her ability to lead alongside ex-boyfriend Sam Bankman-Fried and dreaded the day their fraud would be exposed, according to diary entries published Thursday.

Ellison, now 28, has pleaded guilty in connection with massive crypto fraud at FTX that was exposed in November 2022. She plans to testify against Bankman-Fried, 31, at his upcoming trial in Manhattan Federal Court.

“I just had an increasing dread of this day that was weighing on me,” Ellison wrote to Bankman-Fried that month, according to the New York Times. “Now that it’s actually happening it just feels great to get it over with.”

Ellison and Bankman-Fried had an on-and-off romantic relationship while they built Alameda into a large cryptocurrency hedge fund and FTX into one of the largest crypto exchanges in the world.

But their frequent separations and re-couplings, combined with volatility in the market, left Ellison constantly doubting herself, according to diary entries published by the Times.

“Running Alameda doesn’t feel like something I’m that comparatively advantaged at or well suited to do,” she wrote in an April 2022 entry that also listed her weaknesses as including “decisiveness” and “leadership.”

As Bankman-Fried rose to fame in the crypto world, Ellison felt uncertain about her future at Alameda with their relationship on the rocks, according to the documents.

Working at the firm meant “having to be around you all the time, hearing people talk about how great you are all the time,” she wrote in an April 2022 letter to Bankman-Fried.

Ellison was also paid far less for her work than Bankman-Fried and other Alameda executives, according to bankruptcy court documents filed earlier this year. It’s unclear if Ellison was aware of the discrepancy before its public disclosure.

When key personnel were paid $3.2 billion, Bankman-Fried got $2.2 billion, while executives Nishad Singh and Gary Wang received $587 million and $246 million, respectively. Ellison was paid $6 million.

In December 2022, Ellison apologized in court for the fraud and told a judge she “knew it was wrong” when it happened.