As the creator of Silk Road, a dark web market that used bitcoin to facilitate millions of dollars in sales of heroin, cocaine and other drugs, he had been sentenced to life in prison in 2015 without the possibility of parole.
One afternoon in May, Ross Ulbricht strode into a banquet hall at the Venetian Resort in Las Vegas, the venue for one of the world’s largest cryptocurrency conventions.
Dozens of crypto enthusiasts rose to applaud, cheering as he made his way to a table at the front. Dressed in a dark suit and red tie, Ulbricht sat next to several of his biggest supporters, who had paid $5,000 apiece to dine with him at a luncheon advertised as a “personal” welcome back celebration.
“I have been in an alien world for a long time,” Ulbricht, 41, said as the applause died down. “Now this world is alien to me.”
The walk was far different from the one Ulbricht had taken four months earlier, when he was released from a high-security prison in Tucson, Arizona, wearing a gray sweatsuit. As the creator of Silk Road, a dark web market that used bitcoin to facilitate millions of dollars in sales of heroin, cocaine and other drugs, he had been sentenced to life in prison in 2015 without the possibility of parole.
Ulbricht seemed destined to spend the rest of his life inside a cell. After he was arrested, he lost access to bitcoin that would now be worth billions and was ordered to pay nearly $200 million in penalties.
But then Donald Trump, the Republican presidential candidate, made a promise to the Libertarian Party, whose members were some of Ulbricht’s staunchest supporters. If they voted for him in the 2024 election, Trump told a party leader, he would commute Ulbricht’s sentence. A day after Trump’s inauguration in January, Ulbricht received a full pardon.
Ulbricht has embarked on a strange and unexpected afterlife. His comeback is the type of surreal spectacle that has defined the Trump era, where rap sheets are no barrier to reinvention. And he has come to embody the growing bond between Trump and the crypto world, a once-lawless industry that now wields astonishing influence in Washington.
Ulbricht seemed destined to spend the rest of his life inside a cell. After he was arrested, he lost access to bitcoin that would now be worth billions and was ordered to pay nearly $200 million in penalties.
But then Donald Trump, the Republican presidential candidate, made a promise to the Libertarian Party, whose members were some of Ulbricht’s staunchest supporters. If they voted for him in the 2024 election, Trump told a party leader, he would commute Ulbricht’s sentence. A day after Trump’s inauguration in January, Ulbricht received a full pardon.
Ulbricht has embarked on a strange and unexpected afterlife. His comeback is the type of surreal spectacle that has defined the Trump era, where rap sheets are no barrier to reinvention. And he has come to embody the growing bond between Trump and the crypto world, a once-lawless industry that now wields astonishing influence in Washington.
Ulbricht’s visit to Las Vegas was the first stop on a cross-country speaking tour that has, at times, resembled a political campaign.
Ulbricht has leaned on powerful allies in the crypto industry to help fund his new life, accepting digital currency donations worth about $31 million. He has visited the Grand Canyon and chronicled a camping trip and spa session on the Instagram account he shares with his wife, Caroline Ulbricht.
The comeback tour has appalled many of the people who put Ulbricht in prison, according to seven of those officials who spoke with The New York Times but declined to be identified for fear of upsetting his supporters. They called his release and subsequent ascent a perversion of justice.
Exactly what Ulbricht aims to achieve is unclear. (He declined to be interviewed.) On social media, he said he gave the speeches to “thank all of you who supported me at my lowest.”
But friends and associates said his speaking gigs were also motivated by a desire to reframe the narrative around Silk Road, which was linked to the drug-related deaths of at least six people. Ulbricht has been working on a memoir, according to emails and audio recordings obtained by the Times, and hired a lawyer to try to prevent the release of a documentary featuring detailed interviews he conducted while he was in prison.
Rodney Bridge, a resident of Perth, Australia, whose 16-year-old son took a hallucinogen bought from Silk Road and then jumped off a hotel balcony in 2013, called Ulbricht’s comeback tour “a disgrace.”
“He’s got $31 million someone’s given to him, and the guy’s wealthy as can be,” Bridge said. “Well, I’ve lost my son, and other people have lost their children and parents over this.”
Ulbricht had a strikingly ordinary life until 2013. He lived with roommates in picturesque neighborhoods in the Bay Area and spent most of his days hunched over his computer, like any other Silicon Valley professional.
Then in October that year, federal agents arrested him at a public library. They had finally put a face to the mysterious online figure known as the Dread Pirate Roberts, creator of Silk Road.
For more than two years, the Dread Pirate Roberts had befuddled the government with his expansive marketplace, which could be accessed only through a special anonymizing online software. Silk Road became the world’s best-known dark web purveyor of illicit drugs, where anyone could use bitcoin to order narcotics and rate them like any other product.
At a federal trial in New York City in 2015, prosecutors accused Ulbricht of making “it easier for drug dealers to get users hooked.” He maintained his innocence. While he created Silk Road, his lawyers argued, he didn’t run it day to day.
As his case made international headlines, Ulbricht became a cause celebre for libertarians and crypto enthusiasts, groups already inclined to distrust authority. They considered Silk Road a digital utopia, where bitcoin was the basis of a liberated online economy.
In February 2015, Ulbricht was convicted on charges including money laundering and distributing narcotics online. Judge Katherine Forrest called his actions “terribly destructive to our social fabric” and gave him two life sentences, a punishment that surprised even the prosecutors.
Almost immediately, Ulbricht’s supporters began campaigning for his release. Lyn Ulbricht, who raised her son in Austin, Texas, spoke at libertarian gatherings, casting the case as a miscarriage of justice.
She eventually exhausted the appeals process, leaving a presidential pardon as his only way out.
“Ross is condemned to die in prison, not for selling drugs himself but for creating a website where others did,” his mother wrote in a 2018 petition to Trump.
Trump’s first term ended without a pardon, crushing Lyn Ulbricht, whose personal life was falling apart as she dedicated herself to the cause. She divorced her husband and moved to Tucson near where Ross Ulbricht was imprisoned.
Her son’s life was changing, too. Shortly after Ulbricht was sentenced, he received a letter from a French tech worker in Los Angeles, Caroline Debrion. She told him that she had followed the trial and thought he could use support. They exchanged letters almost every day.
Debrion posted from her own Twitter account, and began working with Ulbricht’s mother to secure his release. Eventually her relationship with the inmate turned romantic. They married last year.
Against the wishes of Lyn Ulbricht, who had shielded her son from the media, Debrion helped persuade Ulbricht to participate in a Silk Road documentary, a last-ditch effort to sway public opinion. (Both women declined to be interviewed for this article.)
Over the next four years, filmmaker Blake Harris recorded more than 80 hours of prison phone calls with Ulbricht. Seemingly resigned to a life behind bars, Ulbricht spoke openly about running Silk Road, according to Harris, countering a core legal defense that he had stopped operating the site before it exploded in popularity.
A week and a half after Trump’s inauguration, Ulbricht emailed Harris from a new account. “I’m free :),” read the subject line.
But the real purpose of his note was business. Ulbricht informed Harris that he was interested in buying the documentary.
Through a lawyer, Ulbricht offered $1.77 million for the documentary. Harris said he knew any sale to his subject would be ethically suspect. Harris made his subject a counteroffer of about $10 million, two people familiar with the discussions said. Ulbricht walked away from the negotiations.
Ulbricht has reveled in postprison life. He has traveled across the United States, while remaining wary about crossing international borders because he could be arrested in another country, a person close to him said.
Ulbricht has also been embraced by the newly ascendant crypto industry.
Industry executives have shown support. The day after Ulbricht was pardoned, the crypto exchange Kraken, one of the largest in the country, donated $111,111 in bitcoin to a digital wallet that Ulbricht controls.
In June, the same wallet received an anonymous donation of 300 bitcoin, or about $31.4 million at the time. It’s unclear where the money came from. But online sleuths have pointed to evidence that the donor was someone involved in AlphaBay, a now-defunct drug marketplace that had emerged as one of Silk Road’s successors.
The same month, those funds moved to an account on Kraken, suggesting that Ulbricht may have cashed them out, according to analysts at the data firms Arkham and Nansen.
