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Fortune
Ben Weiss

The last week of FTX, according to the private messages of Sam Bankman-Fried, Caroline Ellison, Gary Wang, and Nishad Singh

A court sketch of Sam Bankman-Fried from Oct. 16, 2023. (Credit: Jane Rosenberg—Reuters)

Breathe. We’ve finally reached a pause in Sam-Bankman-Fried-palooza, as the trial of the former CEO of the now-bankrupt crypto exchange FTX is on recess until Thursday.

Prosecutors for the Southern District of New York started off small, calling a French cocoa bean trader to the stand to testify that he lost approximately $100,000 after FTX suddenly collapsed in November. But right after, the Justice Department brought out the big guns, including the three FTX insiders who flipped on Bankman-Fried soon after employees fled the Bahamas in November.

The testimony from Gary Wang, Caroline Ellison, and Nishad Singh has been electric. Equally eye-opening are messages between the three FTX lieutenants and their boss, Bankman-Fried, including the almost-all-lowercase messages they all shared in the final days before FTX collapsed.

This is the story of a crypto empire’s final week, as told by sad faces, hearted messages, and Bankman-Fried’s infamous “yup”s.

"Sad face"

A screenshot of a text exchange between Bankman-Fried and his lieutenants. Courtesy of the Southern District of New York

Four days after CoinDesk published an article leaking the balance sheet of Alameda Research, the crypto hedge fund founded and controlled by Bankman-Fried, FTX began seeing an increase in customer withdrawals.

"lots of withdrawals on ftx are queueing up," Singh, the former head of engineering at FTX, texted in all lowercase to Ellison, the former CEO of Alameda, and Bankman-Fried, on Sunday, Nov. 6.

"thx," responded Ellison before Singh followed up, saying that withdrawals were "continuing so far at about 120m/hr," meaning customers were withdrawing $120 million per hour.

"You wrote back with a sad face," prosecutor Danielle Sassoon said to Ellison while she was on the witness stand almost a year later. "Why did you write a sad face?"

"I mean, I was terrified," said Ellison.

"What did the defendant respond?" asked Sassoon.

"He responded 'oof,'" she said.

"Just having a really hard time"

A screenshot of a text exchange between Bankman-Fried and Nishad Singh. Courtesy of the Southern District of New York

On the same day Singh reported the accelerating customer withdrawals to Bankman-Fried and Ellison, Singh reached out separately to the former FTX CEO.

"one thing that'd seriously help me is if i didn't have debts," he wrote, referencing the hundreds of millions of dollars in loans he had taken out from FTX for venture investments, political donations, and personal expenses.

He told Bankman-Fried that, as FTX's demise looked more and more likely, he wanted to backdate a trade to pay off some of the hundreds of millions of loans. "sorry, i know this is not an important thing to focus on and not the point, i'm just having a really hard time, and I think this may help me get back, idk," he wrote.

"(will think about this)" responded Bankman-Fried, before telling him that a backdated trade was "probably fine."

When Singh was subsequently on the witness stand at his former boss's trial, prosecutor Nicolas Roos asked him why he wanted to get out of his loans. "I was really afraid of what it would look like," he testified, "that I would look really corrupt, that I would, you know—the interpretation to them would—would be—would be really negative."

"Did you go through with this transaction?" asked Roos.

Singh responded that he ultimately didn't. Why? "It felt wrong," he said.

"Increasing dread of this day"

A screenshot of a text exchange between Bankman-Fried and Nishad Singh. Courtesy of the Southern District of New York

On or about Nov. 7, one day after the text messages between the FTX insiders that detailed the increasing withdrawals, Ellison reached out to Bankman-Fried, her one-time, on-again, off-again boyfriend.

"this is the best mood I've been in in like year tbh," she wrote to him.

"wow," responded Bankman-Fried. "uh, congrats? because shit's exciting?"

"I think I just had an increasing dread of this day that was weighing on me for a long time, and that it's actually happening it just feels great to get it over with one way or another," she texted back.

When Ellison was on the stand, after the weight had finally been lifted off her shoulders and she pleaded guilty to crimes that could lead to a maximum of 110 years in prison, prosecutor Sassoon asked her why, at the time of her texts to Bankman-Fried, she was in such a good mood as FTX collapsed.

"To be clear, that was overall the worst week of my life," replied Ellison, as she broke down crying in the courtroom. "I felt a sense of relief that I didn't have to lie anymore, that I could start taking responsibility and being honest about what I had done."

Super fucked up/etc"

A screenshot of a text exchange between Bankman-Fried and Ellison. Courtesy of the Southern District of New York

On Nov. 8, after Ellison told Bankman-Fried about her sense of relief, Singh again privately reached out to the former crypto mogul.

"when i briefly called dan he was _very_ upset with us and blamed basically the three of us and said it was super fucked up/etc," he texted, referring to Daniel Friedberg, former chief regulatory officer of FTX. "ryne seems super on edge and likely to resign if we dont get this right," he added, in reference to Ryne Miller, former FTX general counsel.

"yup makes sense," Bankman-Fried texted back. "FWIW I don't hate the idea of them being pissed at me -- idk there are pros and cons, and probably mostly cons, but it might help them move on."

"this is wildly selfish of me, but they may need to know that it wasnt a ton of people orchestrating it," responded Singh, wanting to clarify the insiders' role in the fraud. "I think it makes them more likely to want to be here to help save the situation and the others at least."

Singh's message was subtle, but, on the witness stand almost year later, he said he wanted Bankman-Fried to exculpate him from fraud. "I wanted him to clarify that I wasn't orchestrating it and that I learned about it really late," he told Roos, a prosecutor. "I wanted Sam to clarify that he was orchestrating it."

'BH regulators'

A screenshot of a text exchange between Bankman-Fried and FTX insiders. Courtesy of the Southern District of New York

On Nov. 11, Bahamas-based FTX filed for bankruptcy, and the next day, the Securities Commission of the Bahamas ordered Bankman-Fried and Wang, the former FTX CTO, to appear at 2 p.m. at the Poinciana House, a government building that directly overlooks the ocean.

"Gary and I are with BH regulators," texted Bankman-Fried in what was called "small group chat," or a chat group on the messaging app Signal for FTX insiders, including Bankman-Fried's father, Joseph Bankman.

Five days later, on Nov. 17, Wang met with federal prosecutors, according to his testimony. On or around Nov. 20, Singh began meeting with the government. And on Dec. 8, after FBI agents raided her parent's house, where she had been staying, Ellison met with prosecutors, too.

All three have pleaded guilty, agreed to cooperate with the government, and took to the witness stand to testify against Bankman-Fried. With the prosecution's case all but finished, Bankman-Fried is the only one left who hasn't testified. His chance may come soon.

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