Freeing Ross Ulbricht Is the Easiest 'Day One' Promise for Trump To Keep

The founder of the dark web drug marketplace Silk Road has been behind bars since 2013. Will the president-elect keep the pledge he made at last year's Libertarian Party convention?

Lord knows it's probably not smart to hold politicians accountable to their campaign promises. But President-elect Donald Trump is no typical politician and at least one of his campaign promises was both uniquely specific and uncontroversial enough to expect—or demand, really—follow-through.

"If you vote for me, on day one, I will commute the sentence of Ross Ulbricht," proclaimed Trump last May while addressing the Libertarian National Convention. The request was on a list of 10 demands the Libertarian Party shared with Trump before he spoke. If Trump has failed to follow through on his other memorable promise from the convention—he said he would "put a Libertarian in my cabinet"—this one is still in play. It would right a small but potent wrong when it comes to the carceral state, the deep state, the drug war, and a host of related bastions of state overreach. By most accounts a model prisoner who has been behind bars for almost a dozen years, Ulbricht deserves his freedom.

As readers of this site—along with crypto people, drug policy mavens, and others interested in the intersection of tech and social freedoms—know, Ulbricht is the founder of Silk Road, the pioneering dark web site that allowed people to buy and sell illegal drugs, mostly using bitcoin (indeed, Silk Road was arguably the first real test of bitcoin being used as a payment system on a regular basis). In a 2015 federal trial in the Southern District of New York, he was convicted of money laundering, computer hacking, and narcotics trafficking and sentenced to life in prison by Judge Katherine B. Forrest, who excoriated the former Eagle Scout for daring to step outside of the law:

"The stated purpose [of the Silk Road] was to be beyond the law. In the world you created over time, democracy didn't exist. You were captain of the ship, the Dread Pirate Roberts," she told Ulbricht as she read the sentence, referring to his pseudonym as the Silk Road's leader. "Silk Road's birth and presence asserted that its…creator was better than the laws of this country. This is deeply troubling, terribly misguided, and very dangerous."

Ulbricht was in federal custody for over a year before his trial started. In the run-up to the proceedings, the feds frequently asserted that Ulbricht not only operated the Silk Road as a freewheeling illegal marketplace (bad enough!) but that he had engaged in various plans to kill or physically harm people who had stolen money from or threatened him. They prepared a separate indictment against him in Maryland that included "attempted witness murder" that was quickly dropped after his conviction. Then–U.S. Attorney for the District of Maryland Robert Hur (more recently known for last year's special counsel report documenting President Joe Biden's memory lapses) said, "We have dismissed the federal charges based on the same conduct pending against Mr. Ulbricht in Maryland, which allows us to direct our resources to other cases where justice has not yet been served."

As Reason's Brian Doherty wrote at the time, that's not right. A major difference between the two indictments revolved around conspiring to murder people and it's hard not to see the feds using the murder charge as a cudgel against Ulbricht as a defendant and as a potent tool in the press surrounding the case. Almost inevitably to this day, whenever I mention Ulbricht, people bring up the utterly unsubstantiated murder charges.

Technically, Ulbricht has been in prison since October 2013, when he was first captured. But there's a different way of counting the days, especially for someone who, as his official Free Ross website stresses, was convicted only of nonviolent offenses. Two federal agents, one working for the Drug Enforcement Administration and one for the Secret Service, whose job was to gather evidence in the murder-for-hire case, ended up committing crimes themselves, including extortion, money laundering, and obstruction of justice. Between the pair, they boosted about $1.5 million worth of bitcoin (as of 2015) and pleaded guilty. One was paroled in 2020 and the other in 2021. Combined, they served less time than Ulbricht has.

Will Trump actually commute Ulbricht's sentence? The most recent pronouncement I could I find is from Truth Social last October. It's an emphatic declaration by Trump: "I WILL SAVE ROSS ULBRICHT!"

Trump's commitment to criminal justice reform is an underappreciated part of his first-term legacy. He was a major reason the FIRST STEP Act, which reduced federal prison time, got passed. Yet he didn't commute Ulbricht's sentence when he left office and he has sent consistently mixed messages regarding criminal penalties for drug offenses (early on in his 2024 campaign, he called for death sentences for "everyone who sells drugs, gets caught selling drugs").

Ulbricht's X account has been upbeat since the election ("Immense gratitude to everyone who voted for President Trump on my behalf. I trust him to honor his pledge and give me a second chance," he posted in November) but is mum on his hopes come next week. The Free Ross site, which hosts a petition calling for his release and operates the Free Ross X account, exudes similar vibes while reposting calls for clemency from the likes of former Rep. Matt Gaetz (R–Fla.) and Kelley Paul, the wife of Sen. Rand Paul (R–Ky.)

Among the many anticipated mega-dramas that may happen on next week's "day one"—Trump has promised to start mass deportations, end electric car mandates, and settle the Russia-Ukraine war, among other things—it may be easy to look past his promise to Ulbricht. But it's an easy one to keep, and a good one.