Three months before the cryptocurrency market exploded last year, Caroline Ellison, the 27-year-old chief executive of crypto hedge fund Alameda Research, was plagued by self-doubt.
“I’m a little dissatisfied and overwhelmed with my work,” wrote Ms. Ellison in a Google document in February 2022. He 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.”
Ms. thinks a lot. Ellison. He didn’t think he was suited to running Alameda or particularly decisive as a leader, he wrote in another Google document. He also broke up with Sam Bankman-Fried, the billionaire entrepreneur who founded Alameda and then FTX, one of the world’s largest cryptocurrency exchanges. They dated on and off, and Ms. Ellison about “doing things that are weird” and “causing drama.”
“It doesn’t really feel like there’s an end in sight,” he wrote in the February 2022 document.
Now Ms. is ready. Ellison to be the star witness in the criminal trial of Mr. Bankman-Fried, scheduled for Oct. 2.
Mr. Bankman-Fried, 31, is accused of misappropriating billions of dollars taken from customer accounts and faces eight counts of fraud and election law violations. Her spectacular fall, which brought down FTX and Alameda, changed Ms. Ellison from a powerful — but relatively private — as a target of tabloid speculation. In December, he pleaded guilty to fraud charges and agreed to cooperate with federal prosecutors investigating his ex-girlfriend.
His case is quickly heading for 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 allegations against Mr. Bankman-Fried, the judge in the case set a fast schedule for the start of the trial, requiring prosecutors to draft a witness list and produce other closing materials. Prosecutors are expected to begin preparing at least some witnesses in August, two people with knowledge of the matter said.
As a former girlfriend of Mr. Bankman-Fried and one of his earliest employees, Ms. Ellison had a unique perspective on the founder of FTX. He also recorded many of his thoughts in writing, making observations about his personal and professional life in a handwritten diary and in Google documents that circulated among lawyers involved in the case, according to documents reviewed by The New York Times and four people familiar with the investigation.
The documents, which have not yet been reported, offer new insight into the psychology of Ms. Ellison in the final months of FTX. Ms. Ellison, now 28, is 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 addressed directly to Mr. Bankman-Fried, describing the complexity of their relationship and his ambivalence about Alameda.
In a Google document addressed to Mr. Bankman-Fried in April 2022, wrote Ms. Ellison that an earlier breakup with him “significantly dampened my excitement about Alameda.” Life at the hedge fund, he added, “felt too connected to you in a painful way.”
A representative for Ms.’s legal team declined to comment. Ellison and a lawyer for Mr. Bankman-Fried. 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. met Ellison, a Stanford graduate, Mr. Bankman-Fried at Jane Street, the quantitative trading firm where he worked after college. They share a commitment to effective altruism, the philanthropic movement that has gained followers in the tech and financial industries.
After Mr. Bankman-Fried left Jane Street to start Alameda in 2017, he hired Ms. Ellison as a merchant. In 2021, he promoted he to co-chief executive, along with another early hire, Sam Trabucco.
Mr. also started Bankman-Fried and Ms. Ellison’s unstable romantic relationships, with many breakups and reconciliations. Sometimes, Ms. worries. Ellison that Mr. Bankman-Fried that he is not good enough. When he was around, he wrote in a Google document in February 2022, he had “an instinct to shrink and be smaller and quieter and defer to others.”
After a split, Ms. Ellison’s communication with Mr. Bankman-Fried. “I felt a little hurt/rejected,” she wrote in a Google document in April 2022. “Not giving you the contact you wanted felt like the only way I could regain a sense of power.”
Last year, Mr. Bankman-Fried has become one of the world’s most recognizable crypto entrepreneurs, his face plastered on billboards and magazine covers. Her fame seems to have made life difficult in FTX and Alameda for Ms. Ellison.
Staying means “having to be around you all the time, hearing people talk about how great you are all the time,” he wrote in the April 2022 document.
Ms. Ellison was paid less generous than other top executives at FTX and Alameda, though it is unclear whether he knew 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 to $587 million for Mr. Singh, FTX’s head of engineering, 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 spiraling and plunging several prominent companies into bankruptcy. During the crisis, regulators insisted, Mr. Bankman-Fried, Mr. Wang, Mr. Singh and Ms. Ellison filled the hole in Alameda’s accounts with billions in customer funds deposited with FTX.
Even then, Ms. doubted. Ellison is his own skill. In the April 2022 document, he made a list of areas where he struggled, including “leadership” and “decision-making.”
“Running Alameda doesn’t feel like something I’m into somewhat useful or appropriate to do,” he wrote.
Last fall, Mr. lost confidence. Bankman-Fried in Alameda. He considered closing the firm, according to court records, and invested more than $400 million in another trading firm, Modulo Capital, led by another former Jane Street trader he also dated.
Ms. Ellison expressed jealousy and resentment toward Modulo in some of his writings, as well as feeling he was being squeezed, two people who have seen the documents said.
The business empire of Mr. Bankman-Fried collapsed in November after a run on deposits exposed an $8 billion deficit.
“I just had a rising dread today weighing me down,” Ms. wrote to him. Ellison in a message that month, taken from court records. “Now that it’s happening, it feels good to get it over with.”
In December, Mr. was arrested. Bankman-Fried in the Bahamas, where FTX is based, and taken to a prison not far from the luxury penthouse he shared with Ms. Ellison with eight other roommates, including Mr. Wang and Mr. Singh. Mr. Bankman-Fried is now under house arrest at her parents’ home in Palo Alto, Calif.
People who know Ms. Ellison said they were struck by his diligence and his willingness to admit his own shortcomings. In court in December, he said he was “really sorry” for the fraud. “I know that’s wrong,” he said.
Ms. is expected to repeat. Ellison that statement in the trial of Mr. Bankman-Fried, which is scheduled to last four or five weeks. Much of the test will revolve around messages exchanged between Mr. Bankman-Fried and three collaborators on the messaging app Signal, two people briefed on the matter said.
As a woman in the male-dominated crypto industry, Ms. Ellison may have appeared more sympathetic to the jury than the other cooperators, said lawyers familiar with the case. 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 the government’s best cooperators accepted the blame on the witness stand and that the “power differential” between Ms. Ellison and Mr. Bankman-Fried could make him a compelling voice.
“It doesn’t strike me as an effective strategy to blame the defendant,” Ms. Penza. “Especially with someone who used to be a romantic partner.”