Three months before the cryptocurrency market imploded last year, Caroline Ellison, the 27-year-old head of crypto hedge fund Alameda Research, was plagued by self-doubt.

“I’ve been feeling quite unhappy and overwhelmed by my work,” Ms Ellison wrote in a Google document in February 2022. She added: “At the end of the day I can’t wait to go home and turn off my phone and have a drink and get away from it all .”

Mrs. Ellison had a lot on her mind. She didn’t think she was well-suited to run Alameda or a particularly decisive leader, she wrote in another Google document. She also went through a breakup with Sam Bankman-Fried, the billionaire entrepreneur who founded Alameda and later FTX, one of the largest cryptocurrency exchanges in the world. They became friends and Ms. Ellison worried about “doing things weird” and “causing drama.”

“It doesn’t really feel like there’s an end in sight,” she wrote in the February 2022 document.

Now Ms. Ellison is set to be a star witness at Mr. Bankman-Fried’s criminal trial, which is scheduled for October 2.

Mr. Bankman-Fried, 31, is accused of misusing billions of dollars taken from client accounts and faces eight counts of fraud and violations of election law. His spectacular fall, which sent FTX and Alameda into bankruptcy, transformed Ms. Ellison from a powerful – yet relatively private – figure into a target of tabloid speculation. In December, she pleaded guilty to fraud charges and agreed to cooperate with the federal prosecutors investigating her former boyfriend.

His case is rushing to a courtroom showdown in Manhattan. Two other top FTX executives, Nishad Singh and Gary Wang, also pleaded guilty and agreed to cooperate. In June, after weeks of legal wrangling over the charges against Mr. Bankman-Fried, the judge in the case set a fast-track schedule for the run-up to the trial, asking prosecutors to come up with witnesses and produce other final materials. . Prosecutors are expected to begin preparing at least some witnesses in August, two people with knowledge of the matter said.

As Mr. Bankman-Fried’s one-time girlfriend and one of his earliest employees, Ms. Ellison had a unique insight into the FTX founder. She also recorded many of her thoughts in writing, making observations about her personal and professional life in a handwritten diary and in Google Docs that circulated among lawyers involved in the case, according to documents reviewed by The New York Times and four people familiar with the matter. the research

The documents, which have not been previously reported, offer new insights into Mrs. Ellison’s psychology during the final months of FTX. Mrs. Ellison, now 28, was a a prolific writer whose Tumblr posts about Harry Potter and Jane Austen have been widely dissected. But the Google documents are more personal and raw, with some directly addressed to Mr. Bankman-Fried, illustrating the complexity of their relationship and her ambivalence about Alameda.

In one Google document addressed to Mr. Bankman-Fried in April 2022, Ms. Ellison wrote that an earlier breakup with him “significantly diminished my excitement about Alameda.” Life at the hedge fund, she added, “felt too related to you in a way that was painful.”

A representative for Ms. Ellison’s legal team and a lawyer for Mr. Bankman-Fried declined to comment. A spokesman for the US attorney’s office for the Southern District of New York in Manhattan, the unit prosecuting the case, also declined to comment.

Ms. Ellison, a Stanford graduate, met Mr. Bankman-Fried at Jane Street, the quantitative trading firm where he worked after college. They shared a commitment to effective altruism, the charitable movement that gained followers in the tech and financial industries.

After Mr. Bankman-Fried left Jane Street to start Alameda in 2017, he recruited Ms. Ellison as a dealer. In 2021, he promoted her to co-chief executive, along with another early hire, Sam Trabucco.

Mr. Bankman-Fried and Ms. Ellison also began a shaky romantic relationship, with multiple breakups and reconciliations. At times, Ms. Ellison worried that Mr. Bankman-Fried thought she was not good enough. When he was around, she wrote in the February 2022 Google document, she had “an instinct to shrink and become smaller and quieter and defer to others.”

After one breakup, Ms. Ellison ceased communication with Mr. Bankman-Fried. “I felt pretty hurt/rejected,” she wrote in the April 2022 Google document. “Not giving you the contact you wanted felt like the only way I could regain a sense of power.”

By last year, Mr. Bankman-Fried had become one of the world’s most prominent crypto-entrepreneurs, his face plastered on billboards and magazine covers. His fame seemed to make life at FTX and Alameda difficult for Ms. Ellison.

Staying meant “having to be around you all the time, hearing people talk about how great you are all the time,” she wrote in the April 2022 document.

Mrs. Ellison was compensated much less generously than other top executives at FTX and Alameda, although it is unclear whether she was aware of this. According to court filings, the exchange’s founders and other key employees received $3.2 billion in payments and loans. Of that total, $6 million went to Ms. Ellison, compared with $587 million for Mr. Singh, FTX’s chief engineering officer, and $246 million for Mr. Wang, one of the founders. Mr. Bankman-Fried received $2.2 billion.

In May 2022, the crypto market crashed, sending coin prices soaring and plunging several prominent companies into bankruptcy. During the crisis, regulators alleged that Mr. Bankman-Fried, Mr. Wang, Mr. Singh and Ms. Ellison filled a hole in Alameda’s accounts using billions in customer funds deposited with FTX.

Even before then, Mrs. Ellison doubted her own abilities. In the April 2022 document, she made a list of areas where she struggled, including “leadership” and “decisiveness.”

“Running Alameda doesn’t seem like something that I’m that comparatively advantageous or well suited to do,” she wrote.

By last fall, Mr. Bankman-Fried had lost faith in Alameda. He considered closing the company, according to court records, and invested more than $400 million in another business venture, Modulo Capital, which was led by a different former Jane Street trader he also dated.

Ms. Ellison expressed jealousy and resentment toward Modulo in some of her writings, as well as a sense that she was being squeezed out, two people who have seen the documents said.

Mr. Bankman-Fried’s business empire collapsed in November after a run on deposits exposed an $8 billion deficit.

“I’ve just had a growing fear of this day weighing on me,” Ms. Ellison wrote to him in a message that month, which was extracted in court records. “Now that it’s actually happening, it’s great to finish it.”

In December, Mr. Bankman-Fried was arrested in the Bahamas, where FTX was based, and taken to jail not far from the luxury penthouse he and Ms. Ellison shared with eight other roommates, including Mr. Wang and Mr. Singh. Mr. Bankman-Fried is now under house arrest at his parents’ home in Palo Alto, California.

People who know Ms. Ellison say they have been struck by her earnestness and her willingness to admit her own shortcomings. In court in December, she said she was “really sorry” for fraud. “I knew it was wrong,” she said.

Ms Ellison is expected to repeat that claim at Mr Bankman-Fried’s trial, which is expected to last four or five weeks. Much of the trial will revolve around messages that Mr. Bankman-Fried and the three associates exchanged on the Signal messaging app, said two people briefed on the matter.

As a woman in the male-dominated crypto industry, Ms. Ellison may appear more sympathetic to the jury than the other co-workers, lawyers familiar with the case said. In interviews last yearMr. Bankman-Fried shifted some of the blame for the collapse to Alameda, saying he had little involvement in the day-to-day management of the hedge fund.

Moira Penza, a former federal prosecutor, said top government aides had placed blame on the witness and that the “power differential” between Ms. Ellison and Mr. Bankman-Fried could make her a persuasive voice.

“This does not seem to me to be an effective strategy to get the defendant to blame,” Ms. Penza said. “Especially with someone who was once a romantic partner.”

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