Dan Loeb, the billionaire hedge fund manager behind Third Point LLC, dropped a bombshell on the All-In Podcast: the Department of Justice told Donald Trump on his final day as president in January 2021 that if he commuted Ross Ulbricht’s sentence, the DOJ would come after him.

Trump, according to Loeb’s account, withdrew the planned commutation. The creator of the Silk Road dark web marketplace would have to wait four more years for relief.

The threat that changed everything

January 20, 2021, was Trump’s last day in his first term. Trump had apparently been considering clemency for Ulbricht, who was serving a double life sentence plus 40 years, handed down in 2015 for his role in building and operating Silk Road.

Then, according to Loeb, the DOJ delivered a blunt message: commute the sentence, and we come for you.

Four years later, a full pardon

After roughly four years of sustained advocacy, Trump granted Ulbricht a full and unconditional pardon on January 21, 2025, just one day into his second term. The pardon reportedly fulfilled a specific ask from conservative commentator Charlie Kirk, though the broader “Free Ross” campaign had been building momentum for years, drawing particularly strong support from libertarians and the Bitcoin community.

Silk Road processed sales exceeding $200 million, predominantly using Bitcoin for transactions. Prosecutors portrayed him as a drug kingpin who endangered lives. Supporters argued his double life sentence was grotesquely disproportionate. The case became a proxy war over digital privacy, government overreach, and the limits of federal sentencing.

What this means for the crypto landscape

Silk Road was essentially Bitcoin’s first killer app, for better or worse. The prosecution of Ulbricht set early precedents for how the government would treat cryptocurrency-related activity, and the severity of his sentence sent a message that federal authorities were willing to throw the book at crypto-adjacent defendants.

Loeb’s revelation adds a new dimension to an already politically charged story. The idea that the DOJ would threaten a president over a clemency decision raises serious questions about the independence of prosecutorial power and its potential weaponization.