Hedge fund manager Dan Loeb has publicly claimed that the Department of Justice threatened President Donald Trump in the final hours of Trump’s first term in January 2021, warning it would “go after” him if he commuted the sentence of Ross Ulbricht, creator of the Bitcoin-powered Silk Road marketplace. After the reported threat, Trump withdrew the commutation, forcing Ulbricht to serve four additional years in prison before receiving a full pardon in January 2025 during Trump’s second term.
Loeb, founder and CEO of Third Point LLC, made the revelation on the All-In Podcast while discussing his role in criminal justice reform and Ulbricht’s clemency efforts. “On the last day of Trump’s 45th term, we were certain that he was going to get out,” Loeb stated. “And the Justice Department, for whatever reason, said, ‘If you commute his sentence, we’re going to go after you,’ to the president. So he, as I understand, he withdrew the commutation.”
This account is the first public report of such a direct threat from the DOJ during the closing days of Trump’s first presidency. It has not been independently corroborated by other sources to date, and no specific DOJ official has been named as delivering the warning. The claim rests on Loeb’s recollection, likely conveyed through the advocacy chain that included crypto figures like Riva Tez, Charlie Kirk, and then-White House counsel David Warrington.
DOJ Leadership in January 2021
Jeffrey A. Rosen served as Acting Attorney General after William Barr’s departure in late December 2020. Richard Donoghue was Acting Deputy Attorney General. The Office of the Pardon Attorney, a DOJ unit that reviews clemency petitions and issues recommendations, operated under their oversight. Presidents, including Trump, frequently bypassed standard OPA processes for politically sensitive cases.
The alleged threat appears to have gone well beyond typical DOJ advisory input on issues such as sentence proportionality, victim impact, or enforcement priorities. Ulbricht had been serving a double life sentence plus 40 years following his 2015 conviction on charges including operating a continuing criminal enterprise, narcotics distribution via the internet, money laundering, and hacking. Contrary to popular belief and widely publicized insinuations by the mainstream media, Ulbricht was never prosecuted on any charges related to murder for hire.
Silk Road, which relied primarily on Bitcoin for transactions, represented one of the earliest large-scale experiments in the use of an alternative currency to the dollar, making the case and its history foundational to the Bitcoin community.
A warning framed as potential retaliation against the President himself would constitute an extraordinary escalation in tensions between the executive branch and the Department of Justice over clemency authority. Such pushback likely stemmed from institutional concerns about appearing soft on major drug trafficking and money laundering cases tied to the early Bitcoin economy.
Four-Year Delay and Political Impact
The reported DOJ intervention in the final days of Trump’s first term cost Ulbricht four more years behind bars. As Loeb recounted, Charlie Kirk later took the lead on the clemency effort. “This was his only ask of the president,” Loeb said, referring to Kirk. Kirk’s advocacy helped turn Ulbricht’s release into Trump’s primary promise to libertarians and the crypto community during the 2024 campaign. Trump delivered on that promise with a full and unconditional pardon early in his second term.
Ironically, the delay strengthened the “Free Ross” movement. What began as advocacy for clemency in a case viewed by many in Bitcoin circles as emblematic of government overreach evolved into a potent political force. The campaign highlighted issues of disproportionate sentencing, self-custody, privacy tools, and resistance to broadly unpopular and ineffective war on drugs, core themes in Bitcoin’s ethos of financial sovereignty and of high importance to the libertarian voting block. This momentum and Trump’s promise to pardon Ulbricht are widely considered to have earned Trump the libertarian and crypto vote in 2024.
Broader Context for Bitcoin
Loeb framed his involvement in Ulbricht’s case as part of broader criminal justice reform, linking it to his broader philanthropy efforts on education and concerns over opportunity and income inequality. He highlighted three categories for clemency: the wrongly convicted, the rehabilitated, and those with disproportionately harsh sentences. Ulbricht, who acknowledged wrongdoing on Silk Road while denying murder-for-hire allegations, fit the latter category in Loeb’s assessment.
The episode highlights ongoing tensions between law enforcement, Bitcoin innovation, and the libertarian culture that makes up a large part of the U.S. public. Silk Road, one of the earliest Bitcoin marketplaces, remains a reference point in debates over decentralization, privacy, and regulatory overreach. Similar cases continue to draw attention in the Bitcoin community, including Bitcoin activist Ian Freeman, the developers of the Samourai Wallet privacy tool, and Roman Storm of Tornado Cash—all facing charges viewed by many as attacks on Libertarian leaders, the freedom of commerce, self-custody and financial privacy tools.
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