Dan Loeb Reveals DOJ Threat to Trump Over Ross Ulbricht’s Turnaround in Final Hours of First Term
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 that he would “come after him” if he overturned the sentence of Ross Ulbricht, the creator of the Bitcoin-powered Silk Road market. After the reported threat, Trump rescinded the commutation, forcing Ulbricht to serve an additional four years in prison before receiving full parole in January 2025 during Trump’s second term.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 compassionate efforts. “On the last day of Trump’s 45th term, we were sure he was going to get out,” Loeb said. “And the Justice Department, for whatever reason, said, ‘If you commute his sentence, we’ll follow it,’ to the president. So, as I understand it, he revoked the commutation.”
The account is the first public report of such a threat from the DOJ in the closing days of Trump’s first presidency. It has not been independently confirmed by other sources so far, and no DOJ official has been named as issuing the warning. The claim is based on Loeb’s recollection, which may have been relayed through a chain of representations that included crypto figures such as Riva Tez, Charlie Kirk, and White House adviser David Warrington.
DOJ leadership in January 2021
Jeffrey A. Rosen served as Acting Attorney General following the departure of William Barr in late December 2020. Richard Donoghue was Acting Deputy Attorney General. The Office of the Clerk of Pardons, the DOJ unit that reviews clemency applications and issues recommendations, operated under his supervision. Presidents, including Trump, often bypass OPA’s standard procedures for politically sensitive cases.
The alleged threat appears to go beyond the DOJ’s usual advisory opinions on issues such as sentencing, victim impact, or enforcement priorities. Ulbricht was serving two life sentences and 40 years following his 2015 conviction for charges including running a criminal enterprise, online drug distribution, money laundering and racketeering. Contrary to popular belief and fabrications widely circulated by the mainstream media, Ulbricht was not prosecuted for any crimes related to murder-for-hire.
Silk Road, which relied heavily on Bitcoin for transactions, represented the first major experiment in using an alternative currency to the dollar, making the case and its history a staple in the Bitcoin community.
A warning filed as a potential retaliation against the President himself would create dramatic tension between the executive branch and the Justice Department over clemency authority. Such a pushback is likely due to institutional concerns about being seen as soft on major drug-trafficking and money-laundering cases tied to the early Bitcoin economy.
The Four-Year Delay and the Political Outcome
The DOJ’s reported intervention in the final days of Trump’s first term cost Ulbricht four more years in prison. As Loeb recounts, Charlie Kirk later led a humanitarian effort. “This was his only request to the president,” Loeb said, referring to Kirk. Kirk’s advocacy helped turn Ulbricht’s release into Trump’s first promise to libertarians and the crypto community during the 2024 campaign. Trump delivered on that promise with a full and unconditional pardon at the start of his second term.
Ironically, the delay strengthened the “Free Ross” movement. What began as a sympathetic act in a case viewed by many in Bitcoin circles as a sign of government exploitation turned into a powerful political force. The campaign highlighted the issues of disproportionate sentencing, self-preservation, privacy tools, and resistance to the unpopular and ineffective war on drugs, themes central to Bitcoin’s ethos of financial sovereignty and especially important to the libertarian voting scene. This momentum and Trump’s promise to pardon Ulbricht is widely expected to win Trump the liberal and crypto vote in 2024.
Extensive Bitcoin Content
Loeb has positioned his involvement in Ulbricht’s case as part of broader criminal justice reform, linking it to his philanthropic efforts through education and concerns about opportunity and income inequality. He identified three categories of forgiveness: those who were wrongly convicted, those who suffered moral abuse, and those who were sentenced disproportionately. Ulbricht, who admitted wrongdoing on the Silk Road while denying murder-for-hire allegations, fits the latter category in Loeb’s investigation.
The episode highlights the ongoing tension between law enforcement, the creation of Bitcoin, and the liberal culture that makes up a large portion of US society. Silk Road, one of the first Bitcoin markets, remains a reference point in discussions about decentralization, privacy, and deregulation. Similar cases continue to garner attention in the Bitcoin community, including Bitcoin activist Ian Freeman, the developers of the privacy tool Samurai Wallet, and Roman Storm of Tornado Cash—all of whom face charges that many consider to be attacks on Libertarian leaders, trade freedom, self-restraint and financial privacy tools.
