One afternoon in May, Ross Ulbricht strode into a gold-bedecked 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 and shout his name, cheering as he made his way to a table at the front. Dressed in a dark suit and red tie, Mr. 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,” Mr. Ulbricht, 41, said as the applause died down. “Now this world is alien to me.”
The walk was far different from the one Mr. Ulbricht had taken four months earlier, when he was released into the parking lot of a high-security prison in Tucson, Ariz., 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.
Mr. 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 J. Trump, the Republican presidential candidate, made a promise to the Libertarian Party, whose members were some of Mr. Ulbricht’s staunchest supporters. If they voted for him in the 2024 election, Mr. Trump told a party leader, he would commute Mr. Ulbricht’s sentence. A day after Mr. Trump’s inauguration in January, Mr. Ulbricht received a full pardon.
Now Mr. 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 Mr. Trump and the crypto world, a once-lawless industry that now wields astonishing influence in Washington.
Mr. Ulbricht’s visit to Las Vegas was the first stop on a cross-country speaking tour that has, at times, resembled a political campaign. In June, he lectured about prison reform to retirees at a libertarian conference in Palm Springs, Calif., before traveling to the remote mountains of New Hampshire to address a crowd of “live free or die” types. The next month, he appeared at an event for young Republicans in Tampa, Fla., praising Mr. Trump and calling for the decriminalization of drugs.
Mr. 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. He has spent time surfing, swimming and meditating on the beach. He was a guest of honor at President Trump’s special address to Congress in March.
The comeback tour has appalled many of the people who put Mr. Ulbricht in prison, according to seven of those officials who spoke with The New York Times but declined to be named for fear of upsetting his supporters. They called his release and subsequent ascent a perversion of justice.
Exactly what Mr. 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. Mr. 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 Mr. Ulbricht’s comeback tour “a disgrace.”
“He’s got $31 million someone’s given to him, and the guy’s wealthy as can be,” Mr. Bridge said. “Well, I’ve lost my son, and other people have lost their children and parents over this.”
At the Venetian in May, Mr. Ulbricht was a celebrity. He and his fans dined on potato salad and branzino at a lunch that had been organized by the Bitcoin Conference. He signed magazines with his face on the cover and posed for photos with his mother, Lyn Ulbricht, a relentless advocate for his release, and his wife, who married him while he was imprisoned. A few hours later, he gave a 30-minute speech in front of hundreds of Bitcoin investors.
“You even got President Trump to see that Bitcoin is the future,” Mr. Ulbricht told them. “You said, ‘Ross is one of us.’”
His freedom has brought the prospect of financial rewards. At the Bitcoin Conference, Mr. Ulbricht raised about $1.3 million in an auction of his possessions, including canvases he painted behind bars, an old sleeping bag and his prison sweatsuit.
One item sold for 5.5 Bitcoin, or roughly $600,000, nearly half the total haul. It was an inmate identification card that designated Mr. Ulbricht as prisoner No. 18870-111.
Dread Pirate Roberts
Mr. 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, where he had been working on his laptop. They had finally put a face to the mysterious online figure known as the Dread Pirate Roberts, the 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 Manhattan in 2015, prosecutors accused Mr. 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.
But chat logs obtained by the authorities showed the Dread Pirate Roberts discussing payments of more than $700,000 to order the murders of six people he thought threatened Silk Road’s success. (No killings occurred and Mr. Ulbricht has denied ordering murders. He was charged with murder-for-hire by U.S. prosecutors in Maryland, but that case never went to trial.)
Silk Road had other real-world consequences, including the deaths of at least six people who bought drugs from the site. One was Mr. Bridge’s son, Preston; another was a Seattle-area man who had been found unresponsive after injecting heroin in front of his computer, which was still open to Silk Road.
As his case made international headlines, Mr. Ulbricht became a cause célèbre 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, Mr. Ulbricht was convicted on charges including money laundering and distributing narcotics online. His crimes carried a minimum sentence of 20 years. But 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.
‘Free Ross’
Almost immediately, Mr. 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 started a website and Twitter account, @Free_Ross.
She eventually exhausted the appeals process. In 2018, the Supreme Court chose not to review Mr. Ulbricht’s case, 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 President Trump.
She started building a network of supporters with ties to Mr. Trump, meeting with far-right activists. She courted powerful figures like Senator Rand Paul of Kentucky, a longtime libertarian, and Palmer Luckey, the tech entrepreneur and Trump supporter who signed a letter to the White House urging clemency.
But Mr. Trump’s first term ended without a pardon, crushing Ms. Ulbricht, whose personal life was falling apart as she dedicated herself to the cause. She divorced her husband, who did not engage in the same public advocacy to free their son, and moved to Tucson near where Mr. Ulbricht was imprisoned.
Her son’s life was changing, too. Shortly after Mr. 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.
Ms. Debrion posted from her own Twitter account, @ClemencyForRoss, and began working with Mr. Ulbricht’s mother to secure his release. Eventually her relationship with the inmate turned romantic. They married last year.
“I dated so many jerks in L.A., and Ross was just very real and just super kind,” she said in 2021, according to a recording of a conversation with an associate obtained by The Times. “Ross is very, very romantic.”
Their relationship caused friction in the family. Ms. Ulbricht and Ms. Debrion sometimes butted heads, two people familiar with the women said. Against the wishes of Ms. Ulbricht, who had shielded her son from the media, Ms. Debrion helped persuade Mr. 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, the filmmaker Blake Harris recorded more than 80 hours of prison phone calls with Mr. Ulbricht. Seemingly resigned to a life behind bars, Mr. Ulbricht spoke openly about running Silk Road, according to Mr. Harris, countering a core legal defense that he had stopped operating the site before it exploded in popularity.
At times, Mr. Ulbricht’s interviews “contradict the narrative that he has clung to all these years,” Mr. Harris said.
Last year, as Mr. Harris and his filmmaking partner Jonah Tulis were completing the documentary, they got word of a twist: Mr. Trump had publicly vowed to free Mr. Ulbricht.
The promise came from a political bargain. In late 2023, as Mr. Trump ramped up his presidential campaign, he met Angela McArdle, the Libertarian Party’s leader, who told him that he could win the Libertarian vote if he promised to release Mr. Ulbricht.
“I love freeing people,” Mr. Trump told her.
‘I’m free :)’
A week and a half after Mr. Trump’s inauguration, Mr. Ulbricht emailed Mr. Harris from a new account. “I’m free :),” read the subject line.
“Got back from the Grand Canyon last night,” he wrote. “Pretty much the opposite of being locked in a cell!”
But the real purpose of his note was business. Mr. Ulbricht informed Mr. Harris that he was interested in buying the documentary.
“One way to put how I’m feeling now is like, ‘Man, I said way too much,’” he explained in February, according to a recording of a call between Mr. Ulbricht and Mr. Harris obtained by The Times. “You know, I didn’t need to say all that.”
Mr. Harris assumed his subject was worried the documentary might tie him more closely to Silk Road. On a March call, Mr. Ulbricht told Mr. Harris that he was working on a memoir and wasn’t sure if his account would match the documentary.
“I would feel so much better, so much better with my story back in my own hands,” he said.
Through a lawyer, Mr. Ulbricht offered $1.77 million for the documentary. Mr. Harris said he knew any sale to his subject would be ethically suspect. He considered selling the rights to others, including Mr. Luckey. Instead, Mr. Harris made his subject a counteroffer of about $10 million, two people familiar with the discussions said. Mr. Ulbricht walked away from the negotiations.
“I’ve never dealt with a subject who was as obsessed with control as Ross,” said Mr. Harris, whose past works include a 2020 documentary about gaming consoles and a 2009 mockumentary about a rock, paper, scissors competition. He said he planned to release his film on Mr. Ulbricht and Silk Road.
Mr. Ulbricht has found other ways to tell Silk Road’s story.
In one speech, he said he had set out to create an e-commerce platform “like Amazon” that users happened to use to buy and sell drugs. At other events, he has presented himself as a voice for the incarcerated and a defender of libertarian values, often appearing alongside his mother, who has started an advocacy group called Mothers Against Cruel Sentencing.
Only once on the speaking tour has he sounded apologetic. In front of the young Republicans in Florida, Mr. Ulbricht compared himself to a Big Tobacco executive.
“I played a role in people losing their freedom to addiction,” he said. “That will weigh on my conscience for the rest of my life.”
Nevertheless, Mr. Ulbricht has reveled in post-prison 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.
Mr. Ulbricht has also been embraced by the newly ascendant crypto industry. At the Bitcoin luncheon in Las Vegas, Justin Sun, a billionaire crypto executive who has worked closely with Mr. Trump’s family, said he would gladly offer Mr. Ulbricht a job.
“We’re happy to do anything with Ross,” Mr. Sun told The Times.
Other crypto executives have also shown support. The day after Mr. Ulbricht was pardoned, the crypto exchange Kraken, one of the largest in the country, donated $111,111 in Bitcoin to a digital wallet that Mr. 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, analyzing the transaction on the public ledger known as the blockchain, 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 Mr. Ulbricht may have already cashed them out, according to analysts at the data firms Arkham and Nansen.
Mr. Ulbricht could have a shot at an even bigger payday. In recent months, some U.S. officials who prosecuted him have privately discussed an outlandish scenario: He could return to court to try to claw back some of the funds seized from Silk Road.
Over the years, law enforcement has recovered tens of thousands of Bitcoin that hackers had stolen from the site. While in prison, Mr. Ulbricht forfeited his right to that digital currency, some of which has sat untouched in government-controlled wallets.
The pardon could give him an opening to claim some of those coins or other crypto that the government recovers in the future, legal experts said. Even a long-shot lawsuit could provide leverage for a settlement.
The potential prize would be immense. When Mr. Ulbricht was arrested, one Bitcoin traded for $132. Now it trades at about $110,000.
That means the government’s Silk Road stash is worth at least $7.5 billion.
Alain Delaquérière and Susan C. Beachy contributed research.
Audio produced by Patricia Sulbarán.
Read by Ryan Mac
Ryan Mac covers corporate accountability across the global technology industry.
David Yaffe-Bellany writes about the crypto industry from New York. He can be reached at [email protected].
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