Grenell, Ulbricht and the Trump administration did not respond to requests for comment.
Ross Ulbricht’s pardon shows “that if you have a concentrated base of people around Trump, you have a very good chance at a pardon,” said Dan Richman, a former federal prosecutor who teaches at Columbia Law School. “There are problems with the pardon system working that way.”
Ulbricht launched Silk Road in 2011 and turned it into one of the most popular outposts of the so-called dark web, a hidden corner of the internet that people can access only through a special browser. Silk Road facilitated more than 1.5 million transactions, generating more than $US200 million in revenue from the sale of heroin, methamphetamine, cocaine and other drugs, authorities have said. Users transacted anonymously with bitcoin, then a nascent cryptocurrency, and could post Amazon-style product ratings.
Lyn and Kirk Ulbricht fought for the release of their son. Credit: NYT
In 2013, the FBI arrested Ulbricht at a San Francisco library and charged him with running Silk Road. In court, prosecutors presented evidence that Ulbricht had also solicited the murders of people he considered threats to the business, though he was never tried on murder-for-hire charges and there was no indication that any killings took place.
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At least six deaths were attributed to drugs bought on Silk Road, prosecutors said in court. A federal judge in the Southern District of New York, where the case was tried, called Ulbricht “the kingpin of a worldwide digital drug-trafficking enterprise” whose actions were “terribly destructive to our social fabric.” In 2015, Ulbricht received a life sentence for drug distribution, money laundering and other charges and was eventually moved to a federal prison in Arizona.
The punishment struck some legal experts as harsh. It also drew protests from libertarians who opposed severe drug penalties and crypto enthusiasts who viewed Ulbricht as a pioneer.
Silk Road “onboarded a million people to bitcoin,” said David Bailey, the CEO of the news publication Bitcoin Magazine, who campaigned for Ulbricht’s release. “He represents many of the ideological views of our community.”
From prison, Ulbricht played up his connection to bitcoin. In October 2018, he sent a letter to his mother celebrating the 10th anniversary of the cryptocurrency’s founding and likened himself to a “proud parent” of the technology.
“I guess I’m the estranged father in prison though, who can’t be there to help raise his kid,” he wrote in the letter, which was later published by Bitcoin Magazine.
On social media accounts maintained by his family, Ulbricht also shared artwork, updates on his prison gardening and thoughts on new technologies. The accounts posted links to online petitions asking for clemency, tagging Trump and Trump family members.
Trump embraced the crypto world during his campaign. Credit: NYT
Behind the scenes, Lyn Ulbricht worked to popularise the slogan “Free Ross,” which become a rallying cry at crypto conferences. She also networked with Republican politicians and far-right influencers, hoping to reach Trump’s inner circle.
After he lost the 2020 election, Trump considered freeing Ross Ulbricht, and at least one lobbyist was paid $US22,500 to help secure his release, according to financial forms. But Trump left office without taking action.
“The higher the hope, the greater the disappointment, and our hopes were sky high for a commutation of sentence,” Ulbricht’s family posted on social media in January 2021.
The new Republican presidential campaign offered a fresh opportunity.
In 2023, Lyn Ulbricht renewed her push to connect with influential Republicans, including Vivek Ramaswamy, who was running for president, two people close to her said. Ramaswamy, who did not respond to a request for comment, committed to freeing Ross Ulbricht if elected and spoke openly about meeting his mother.
Then in late 2023, McArdle was contacted by Grenell, who asked on behalf of Trump for advice on courting the libertarian vote, she said. Soon she was on a plane to Florida to meet Trump.
Last year, Trump and his staff also met with Bailey and other representatives of Bitcoin Magazine, who pushed for Ulbricht’s release. Tracy Hoyos-López, who worked for the magazine, has said publicly that the introduction was arranged by Paul Manafort, Trump’s campaign chair in 2016. (Hoyos-López is the daughter of Hector Hoyos, a friend and former business partner of Manafort.)
On social media, Bailey announced that he planned to raise a “$US100m war chest for the Trump campaign.” He also went to Mar-a-Lago in June, he said in an interview, where he presented Trump with a letter from Lyn Ulbricht.
By then, Trump had already vowed to free Ross Ulbricht at the Libertarian Party convention. He doubled down on that pledge in July at a conference in Nashville, Tennessee, organised by Bitcoin Magazine, saying he would commute Ulbricht’s sentence — allowing him to walk free, but without erasing the conviction. Around that time, Trump also met privately with Lyn Ulbricht, said McArdle, who was briefed on the meeting.
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McArdle has faced blowback from other libertarians for her dealings with Trump. But she was still in touch with the new administration last week and requested that Trump grant Ross Ulbricht a full pardon, not just a commutation. “Promises made, promises kept,” a Trump staffer emailed her, according to a copy of the message viewed by The New York Times.
On Tuesday night, McArdle, Bailey and Hoyos-López gathered in a livestream on the social platform X to wait for updates. Bailey told listeners that Lyn Ulbricht was in Arizona, preparing for her son’s release.
Within hours of the pardon, an account on X controlled by Ulbricht’s family posted a photograph of him leaving prison with a small plant and a sack of belongings.
“FREEDOM!!!!” the post said.
This article originally appeared in The New York Times.
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