As Americans and the world grapple with how last week’s election will reshape the next four years and beyond, few have as much personally at stake from a new presidential administration as one 40-year-old man in a federal penitentiary in Tucson, Arizona. For Ross Ulbricht, creator of the legendary dark-web drug market known as Silk Road, who has been in prison since 2013, a Donald Trump presidency could mean the difference between freedom and a lifetime in a cell.

“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,” Ulbricht wrote on X one week after the election, through an account controlled by his wife. “After 11+ years in darkness, I can finally see the light of freedom at the end of the tunnel. Thank you so much, @realDonaldTrump. 🙏”

After the government identified him as the administrator behind Silk Road’s cryptoanarchic marketplace and arrested him in an FBI sting in late 2013, Ulbricht was convicted in 2015 on seven charges relating to money laundering, computer hacking, and the distribution of narcotics and was sentenced to life in prison without the chance of parole. Nearly nine years later, at the Libertarian National Convention this May, then-presidential candidate Trump promised to commute Ulbricht’s sentence “on day one” if reelected, letting him walk free. There were cheers from the audience—many waving “Free Ross” signs—for the former dark-web mastermind, who has become a cause célèbre in the cryptocurrency and libertarian worlds.

Now that Trump has emerged victorious, however, Ulbricht and his supporters must wait at least another agonizing nine weeks to find out whether the president-elect—who has a history of abandoning campaign promises and who once rejected calls to pardon Ulbricht at the end of his first term—will act on his pledge.

“Regardless of what one thinks of Silk Road, Ross’ actions, or the political aspects of Trump and the largely right-wing crypto community’s support for Ross, I firmly believe his sentence is unjust,” says Alex Winter, the actor and director who released a documentary about Ulbricht’s case in 2015. Winter says he has corresponded intermittently with Ulbricht over the years since then. “He’s already been in prison for over a decade, and he should be free.”

However, Winter has less faith than Ulbricht in Trump’s vow to grant him clemency. “I’m not someone who trusts Trump to be true to his word,” Winter says. “So it’s a bit anxiety-provoking to wait and see if he makes good on this promise.”

For two and a half years starting in 2011, the Silk Road pioneered the dark-web market model of using bitcoin to allow buyers and sellers to trade in hundreds of millions of dollars worth of highly illegal contraband—eventually including every type of narcotic imaginable as well as counterfeit documents and money laundering services—while hiding their identities through the anonymity software Tor. Ulbricht, using the pseudonym “Dread Pirate Roberts,” led the site as its highly vocal creator: He set the site’s rules based on his anarcho-capitalist principles, which involved allowing only “victimless” forms of crime, in theory. He posted manifestos to its user forum about how the Silk Road would change the world, and even hosted a book club on the site focused on libertarian philosophy.

As Dread Pirate Roberts, Ulbricht came to be seen by many on the Silk Road as a kind of revolutionary hero, one who was reducing violence in the drug trade by moving it into a well-run online system. At the same time, drugs purchased through Silk Road have been linked by the US government to at least six deaths by overdose. At Ulbricht’s trial, meanwhile, prosecutors laid out shocking evidence that he had paid to have no fewer than six people killed who had threatened him and the Silk Road—though one of those would-be killers he allegedly hired was an undercover DEA agent and another appears to have been a scammer.

No actual killings took place. Nor was Ulbricht charged with murder or attempted murder in his Manhattan trial. Yet the alleged violence and the deaths of Silk Road users by overdose contributed to the decision of the judge in the case to sentence him to life in prison, a sentence beyond even the 20-plus years that prosecutors had asked for.

After Ulbricht was taken into custody, his mother, Lyn Ulbricht, began to campaign for a reappraisal of his sentence and for early release. The campaign slogan “Free Ross” has since been splashed across T-shirts, mugs, and protest signs, and circulated widely as a social media hashtag. More than 600,000 people have signed a petition in support. Lyn Ulbricht did not respond to interview requests.

“If you consider yourself a cryptoanarchist or anarcho-capitalist, what Ross did was basically facilitating free trade,” says Jameson Lopp, an early bitcoiner and the founder of the cryptocurrency-focused security firm Casa. Like many libertarian Free Ross supporters, he argues that the Silk Road resulted in an overall reduction in violence and suggests that perhaps the sale of the drugs it offered should be legalized. “My belief is that you should be able to do whatever you want with your own body.”

Beyond that ideological basis, the Free Ross campaign has been built atop the premise that Ulbricht’s sentence is wildly disproportionate, given the nonviolent nature of the charges, the absence of any criminal track record, and the relative brevity of the sentences handed down to others involved in Silk Road. (Though Ulbricht’s second-in-command received a 20-year prison sentence, other collaborators have already completed their prison terms.) Ulbricht was responsible only for operating the marketplace through which narcotics and other contraband was sold, not for distributing it himself, his supporters argue.

Those who advocate for an early release also object to the murder-for-hire allegations—for which he never faced trial—influencing the sentence Ulbricht received. “They said he committed murder then dropped it from the trial. He was never convicted or even tried for it,” wrote cryptoanarchist developer and activist Amir Taaki in a statement posted to his X account. “So why even bring that up? To confuse people. To spread propaganda.”

Nonetheless, those murder-for-hire allegations—which Southern District of New York prosecutors didn’t bring as charges but did support at trial with chat logs and Bitcoin blockchain transaction records—played a key role in quashing the Free Ross campaign’s attempt to lobby for a pardon during Trump’s first term. The White House in 2020 considered freeing Ulbricht but ultimately rejected the idea because of the alleged role of violence in the case, according to one former government official involved in the process who spoke to WIRED on condition of anonymity.

Since then, though, the political landscape around cryptocurrency—and Ulbricht’s case—has shifted. The Free Ross campaign has received growing support among libertarian politicians, prison reform activists, and particularly members of the crypto industry, for whom Ulbricht is something of a martyr for his part in spreading the bitcoin gospel and demonstrating utility for the technology through Silk Road. “Trump has seen that there’s real money behind the crypto industry and that they’re willing to help him and his campaign,” says Lopp. “He’s a businessman, and he follows his incentives.”

Whatever the moral or political case for Ulbricht’s early release, the severe sentence imposed by the judge—and upheld on appeal—is consistent with the sentencing guidelines for the crimes of which he was convicted, former prosecutors say. “While there is no question that his sentence was extraordinarily long, extremely punitive sentences are quite common for defendants who presided over large-scale drug operations; for defendants whose drug trafficking is closely tied to the deaths of multiple customers, and for murder-for-hire schemes,” says Daniel Richman, professor of law at Columbia University and former US federal prosecutor. “Ulbricht’s sentence reflected the presence of all three of these factors in his case.”

At sentencing, the judge was also permitted to take under consideration the murder-for-hire allegations, despite them never having been charged at trial. “Until the Supreme Court rules otherwise, relevant but uncharged crimes of this sort can be and are regularly considered by judges,” says Richman.

Ulbricht has never fully acknowledged the harm inflicted by the Silk Road’s vast sales of drugs that included heroin and other opiates, and he still shows little remorse for his actions in his public posts to Twitter, argues Jared Der-Yeghiayan, a former Homeland Security Investigations agent who infiltrated the Silk Road undercover as part of the case against Ulbricht.

“The idea of him being released doesn’t bother me in the least,” says Der-Yeghiayan, who now works as the head of strategic intelligence at cryptocurrency tracing firm Chainalysis. “I do get bothered if there’s now a perception that he did nothing wrong, that doesn’t acknowledge the facts of the case.”

Given that Ulbricht has already spent 11 years in jail, though, the question remains whether that wrongdoing deserves a lifetime of imprisonment. While Ulbricht’s harsh sentence might be valid in a strictly technical sense, says Leeza Garber, a lecturer in law at The Wharton School at the University of Pennsylvania, in knotty cases like this, legal questions cannot be neatly isolated from ethical and political ones.

“Just because something is reasonable, that doesn’t mean that it’s right,” says Garber. “We have such complex and conflicting views on the war on drugs and use of prison in this country. Mix that with the idea that this crime occurred partly in cyberspace, and it becomes extremely messy. It’s hard to reckon with this confluence of issues.”

Some advocates for prison reform, a number of whom support Ulbricht’s petition for clemency, believe sentencing rules need to change. They think the emphasis should be on rehabilitation as opposed to retribution—and that parole should be reintroduced to the federal criminal system. They hope that Ulbricht’s release could act as a catalyst.

“Ross has served more than enough time. He has been a model prisoner. He’s a first-time, nonviolent offender. He poses zero safety risk to the community,” says Alice Johnson, CEO of the justice reform foundation Taking Action for Good, who spent two decades in prison herself for drug trafficking before her life sentence was commuted by Trump in 2018. “I believe that Ross’ case is going to pave the way for many others who have been unjustly given these draconian sentences to come home.”

A life sentence imposes on a person a specific psychological burden, says Johnson, that only hope, however forlorn, can help to assuage. “It will break most people, seeing others mark days off calendars. It’s knowing that you will escape incarceration only by death. There is no way Ross is not experiencing this,” she says. “Every day, you’re hoping and praying that something will change.”

When Trump promised to commute his sentence, Ulbricht was afforded hope anew. “Thank you. Thank you. Thank you,” he wrote in May in an X post, celebrating Trump’s pledge. “After 11 years in prison, it is hard to express how I feel at this moment.”

Johnson, a fervent Trump supporter, predicts that the president-elect will deliver on his pledge. “I don’t know if it will be on day one. But Ross can start—I’m almost afraid to say this—packing his bags,” she says.

Otherwise, Ulbricht has exhausted all remaining options available to him. “President Trump is his last hope for freedom,” says Johnson.

In a letter he wrote to the judge ahead of his sentencing, in 2015, Ulbricht acknowledged his “terrible mistake” and petitioned the judge for a chance to someday redeem himself as a free man. He now makes the same plea to Trump.

“I’ve had my youth, and I know you must take away my middle years,” wrote Ulbricht, in the letter to the judge. “But please leave me my old age.”