(Bloomberg) -- Sam Bankman-Fried was confronted with six fateful moments that might ultimately decide his fate when jurors begin deliberations Thursday. 

Each time, the FTX co-founder was motivated by “greed and ambition” and chose to perpetuate a massive fraud, prosecutors said. They boiled down their case against Bankman-Fried by presenting jurors with the six examples during closing arguments Wednesday. Bankman-Fried’s decisions deepened the woes of his two companies, the crypto exchange and trading firm Alameda Research.  

“The defendant was presented with a choice — to come clean or double down. Every time he chose to double down,” prosecutor Nicolas Roos said in the federal courthouse in New York. 

In the defense’s closings remark, Bankman-Fried’s lawyer, Mark Cohen, argued that Bankman-Fried didn’t intend to defraud customers and was unfairly cast as a “villain” and “monster” by the government. The once respected crypto mogul is facing decades in prison if convicted.

Here are the six examples prosecutors highlighted:

1) Binance Buyback  

Bankman-Fried’s alleged misuse of customer funds could be traced back to 2021, well before the market turmoil began, when he made the decision to buy out Binance’s stake in FTX for about $2 billion, according to the prosecutor. An early investor in FTX, Binance bought the stake in 2019, but relationships between the two exchanges had become frosty. 

Caroline Ellison, the former chief executive officer of Alameda, testified that she raised concerns that they didn’t have the money for the deal and would have to “borrow” from FTX. Despite that, Bankman-Fried insisted on the deal because buying out Binance’s stake was important to him, she said. 

“The defendant hated the fact that his rival owned part of FTX,” Roos said. Prosecutors displayed an email from Bankman-Fried, which showed he personally directed the transaction. In his own testimony, Bankman-Fried was evasive about which entity bought back the stake from Binance because the truth was “inconvenient,” Roos said. 

2) $3 Billion Investments 

The second moment came in the fall of 2021, when Bankman-Fried asked Ellison to run a risk analysis on what would happen to Alameda if he spent $3 billion on investments, the prosecutor said. Ellison’s calculation showed that under extreme market stress, Alameda could risk going bankrupt, and spending $3 billion would be a bad idea. Still, Bankman-Fried pressed ahead. 

“He kept digging,” Roos said. “You don’t have to go to MIT to know that you have more debt than you have money, and you want to spend more money, and you’re going to be in more debt...The only available money is the FTX customer money.” 

3) Repay Lenders 

In June 2022, when the crypto market crashed and the industry went into crisis, Bankman-Fried had another choice, Roos said. Should Alameda, already deeply in debt, pay back its lenders, such as Genesis, who were pressing to call their loans? At that point, prosecutors said Bankman-Fried was aware that Alameda owed $10 billion to FTX customers and didn’t have enough money to repay Alameda’s lenders. Bankman-Fried was so worried that Alameda was insolvent that he canceled a trip to Washington DC.  

Still, “he decided to double down when Alameda was already in significant debt and repay lenders,” Roos said. Of the $6.5 billion used to repay lenders, $4.5 billion came from FTX customers, amounting to as much as half of customers’ holdings on the exchange, Roos said. 

4) Fake Balance Sheet

In June 2022, Bankman-Fried allegedly directed Ellison to come up with alternative balance sheets to present to lenders, in an attempt to hide Alameda’s use of FTX customer funds and loans made to executives, according to the prosecutor. Ellison testified that she came up with seven versions of balance sheet and presented them to Bankman-Fried, who chose Alt. 7, which concealed almost $10 billion in borrowing from FTX customer money and $4.5 billion in related-party loans. 

“So he had to make a choice...and he decided to lie again,” Roos said. 

5) Pre-Collapse Spending

In September 2022, two months before FTX’s collapse, Bankman-Fried knew that Alameda owed $14 billion to FTX customers, and yet went on to spend more, according to the prosecutor. While he considered shutting down Alameda, Bankman-Fried eventually decided against it, because it had spent so much of FTX customers’ funds that it would not be able to repay them, Gary Wang, the co-founder of FTX and Bankman-Fried’s old friend, testified earlier. 

“What did the defendant do? Again he doubled down,” Roos said. In the same month, Bankman-Fried invested $250 million in Modulo Capital, a crypto trading firm, and $45 million on SkyBridge Capital, the investment firm founded by Anthony Scaramucci, as well as making more political donations, Roos said. 

Read the memo on Alameda shutdown here:  

6) False Tweets and Confession 

Bankman-Fried continued his lies into FTX’s final week, Roos said, misleading some customers into keeping their funds on the exchange. While he privately acknowledged in a chat group that FTX was short $8 billion in customer funds, he still tweeted on Nov. 7 that “FTX is fine. Assets are fine.”  

“Every witness said this tweet was false and misleading,” Roos said. 

Bankman-Fried also made a confession to Nishad Singh, FTX’s head of engineering, in a message, Roos said. As FTX was falling apart, Singh wrote, “this is wildly selfish of me, but they may need to know that it wasn’t a ton of people orchestrating it,” referring to the fraud. Bankman-Fried replied, “fwiw I don’t think that’s super” selfish “I think that’s probably correct.”

--With assistance from Ava Benny-Morrison.

©2023 Bloomberg L.P.