It’s not often a borrower bails out its lender, especially when it’s to the tune of hundreds of millions of dollars.

Alameda Research, the firm founded by crypto billionaire Sam Bankman-Fried that last month extended a $500 million line of credit to crypto broker Voyager Digital, itself owes the company $377 million, according to Voyager’s Chapter 11 bankruptcy filing.

It’s an unexpected revelation that’s come to light by way of a bankruptcy that has seemed like a foregone conclusion since Voyager disclosed that hedge fund Three Arrows Capital owes it more than $600 million.

A table on page 13 of the bankruptcy filing, which was submitted in a New York district court today, shows that Alameda Research owes Voyager $377 million at an interest rate of 1% to 5%. The outstanding balance includes a $75 million unsecured loan, according to a list of Voyager’s largest unsecured claims on page 119 of the filing.

list-of-voyager-digital-borrowers
List of Voyager Digital borrowers from its Chapter 11 bankruptcy filing. Source: Court document

Alameda Research did not immediately respond to a request for comment from Decrypt.

Alameda’s debt makes it Voyager’s second largest borrower after the insolvent Three Arrows Capital, which also goes by 3AC.

When the extent of 3AC’s trouble became clear, largely because of $200 million it lost in the Terra collapse in May, its lenders began to realize that huge 3AC loans on their books were about to go into default. 

Once 3AC was no longer able to make payments, Voyager issued a default notice last Monday. Then, on Wednesday last week, a British Virgin Islands court ordered 3AC to liquidate. That means 3AC must cease all operations and allow the court to oversee the selling of its assets to offset what it owes creditors, including Voyager Digital.

It’s worth pointing out that Sam Bankman-Fried, founder and CEO of cryptocurrency exchange FTX, has a vested interest in seeing Voyager made whole. At one point, Alameda and its venture arm, Alameda Ventures, were the single largest Voyager shareholders with 11.6% of all outstanding shares, according to a June 17 press release.

At the time, Voyager stock (VYGVF) was trading at just over $1.

A week later, on June 23, Alameda announced in a press release that it had surrendered, or returned in exchange for no money, 4.5 million of its shares. Those shares were worth $2.6 million at the time and VYGVF was trading at $0.56 per share.

Alameda’s share surrender brought its stake in the company to 9.49%—just below the 10% threshold that would have made it an “insider” in the eyes of the U.S. Securities and Exchange Commission. This is the same SEC rule that required Tesla CEO Elon Musk to disclose his stake in Twitter in April, ahead of making an acquisition offer.

On Wednesday afternoon, after the Toronto Stock Exchange suspended trading of Voyager Digital’s stock, it ended the day trading at $0.27.

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