In December 2023, Angela McArdle, the chairwoman of the Libertarian Party, flew to Mar-a-Lago to meet with Donald J. Trump.
Mr. Trump wanted to learn how to win over libertarian voters, a constituency he believed could help him win the presidency again, Ms. McArdle in an interview. He had an answer: Free Ross Ulbricht, a Bitcoin pioneer who was sentenced to life in prison in 2015 for creating Silk Road, the world’s largest online drug market. Mr. Ulbricht was seen as a libertarian hero for building an illegal market outside the reach of government.
“I like to set people free,” said Mr. Trump, according to Ms. McArdle. Five months later, he hosted him at the national convention of the Libertarian Party, where he announced on stage that, if elected to the presidency, he would release Mr. Ulbricht.
On Tuesday, the day after his inauguration, Mr. Trump kept his promise. He called the mother of Mr. Ulbricht, Lyn Ulbricht, to tell her personally that he had fully pardoned her son, who is now 40. In a post on Truth Social, Mr. Trump said the decision was “in honor of her and the Liberty Movement, which has supported me so strongly.”
The grace of Mr. Ulbricht was not an obvious agenda item for Mr. Trump. Unlike the nearly 1,600 people who were pardoned or transferred this week for their involvement in the Jan. 6 uprising, Mr. Ulbricht had little direct contact with the president. But the move was long in the making, after more than a decade of activism by supporters of Mr. Ulbricht – including cryptocurrency investors, libertarian politicians and especially Ms. Ulbricht, who has been a vocal advocate for her son’s release.
Many of them enjoyed an unusual level of access to Mr. Trump. As it became clear last year that Mr. Trump would be the Republican nominee, they waged a behind-the-scenes lobbying campaign to secure a pardon — including a pledge to raise money for his campaign — in what has become a case study in how a special interest group can mobilize to influence the president.
Ms. McArdle said he contacted Mr. Trump from Richard Grenell, one of his longtime advisers and a former acting director of the National Intelligence Service, who suggested she treat talks with Trump like a business negotiation.
“Rick was like, ‘He’s a deal-maker, Angela,'” she said. “Don’t be afraid to ask for something.”
Mr. Grenell, Mrs. Ulbricht and the Trump administration did not respond to requests for comment.
The grace of Mr. Ulbricht shows “that if you have a concentrated base of people around Trump, you have a very good chance of a pardon,” said Dan Richman, a former federal prosecutor who teaches at Columbia Law School. “There are problems with the pardon system that works that way.”
Mr. Ulbricht started 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 only access through a special browser. Silk Road facilitated more than 1.5 million transactions, generating more than $200 million in revenue from the sale of heroin, methamphetamine, cocaine and other drugs, authorities said. Users traded anonymously with Bitcoin, then a new cryptocurrency, and could post Amazon-style product reviews.
In 2013, the FBI arrested Mr. Ulbricht in a San Francisco library and accused him of running Silk Road. In court, prosecutors presented evidence that Mr. Ulbricht had also called for the murders of people he saw as threats to the business, although he was never tried on murder-for-hire charges and there was no evidence that any murders took place.
At least six deaths were attributed to drugs bought on Silk Road, prosecutors told the court. A federal judge in the Southern District of New York, where the case was heard, called Mr. Ulbricht “king of a global digital drug-trafficking operation” whose actions were “horribly destructive to our social fabric.” In 2015, he was sentenced to life in prison for drug distribution, money laundering and other charges and was eventually transferred to a federal prison in Arizona.
The punishment struck some jurists as harsh. He also drew protests from libertarians who opposed tough drug penalties and cryptocurrency enthusiasts who saw Mr. Ulbricht as a pioneer.
Silk Road “got a million people on board Bitcoin,” said David Bailey, the chief executive of the news outlet Bitcoin Magazine, which campaigned for Mr. Ulbricht. “It represents many of the ideological views of our community.”
From prison, Mr. Ulbricht strengthened 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 technology.
“I guess I’m the estranged father in prison who can’t be there to help raise his child,” he wrote in the letter, which was later published by Bitcoin Magazine.
On social media accounts maintained by his family, Mr. Ulbricht also shared artwork, updates on prison gardening and thoughts on new technologies. The accounts posted links to online petitions calling for clemency, tagged Mr. Trump and members of the Trump family.
Behind the scenes, Ms. Ulbricht worked to popularize the “Free Ross” slogan, which became a rallying cry at crypto conferences. He also connected with Republican politicians and far-right influencers, hoping to reach Mr. Trump.
After losing the 2020 election, Mr. Trump considered releasing Mr. Ulbricht and at least one lobbyist were paid $22,500 to help secure his release, according to financial filings. But Mr. Trump left office without taking action.
“The greater the hope, the greater the disappointment and our hopes were high for a commutation of the sentence,” the family of Mr. Ulbricht on social media in January 2021.
The new Republican election campaign offered a new opportunity.
In 2023, Ms. Ulbricht renewed her push to connect with prominent Republicans, including Vivek Ramaswamy, who was running for president, two people close to her said. Mr. Ramaswamy, who did not respond to a request for comment, pledged to free Mr. Ulbricht if elected and spoke openly about the meeting with his mother.
Then, at the end of 2023, Mr. Grenell contacted Ms. McArdle, who requested on behalf of Mr. Trump tips on courting the libertarian vote, he said. Soon he was on a plane to Florida to meet Mr. Trump.
At the meeting, Mrs. McArdle told Mr. Trump that Mr. Ulbricht has been the victim of prosecutorial overreach and a biased criminal justice system, echoing allegations the former president made after he left office.
“It’s the same courts in New York that are giving you a hard time,” he said, she told him.
Last year, Mr. Trump and his staff also met with Mr. Bailey and other representatives of Bitcoin Magazine, who pushed for the release of Mr. Ulbricht. Tracy Hoyos-López, who worked for the magazine, has said publicly that the introduction was arranged by Paul Manafort, the campaign chairman of Mr. Trump in 2016. (Ms Hoyos-López is the daughter of Hector Hoyos, a friend and former business associate of Mr Manafort.)
On social media, Mr. Bailey announced that he planned to raise a “$100 million war fund for the Trump campaign.” He also went to Mar-a-Lago in June, he said in an interview, where he introduced Mr. Trump a letter from Lynn Ulbricht.
Until then, Mr. Trump had already vowed to free Mr. Ulbricht at the Libertarian Party convention. He doubled down on that pledge in July at a Nashville conference hosted by Bitcoin magazine, saying he would commute Mr. Ulbricht — allowing him to walk free, but without erasing the conviction. At that time, Mr. Trump also met privately with Ms. Ulbricht, said Ms. McArdle, who was informed of the meeting.
Ms. McArdle has come under fire from other libertarians for her dealings with Mr. Trump. However, he was still in touch with the new government last week and asked Mr. Trump to give Mr. Ulbricht full pardon, not just conversion. “Promises made, promises kept,” a Trump staffer emailed her, according to a copy of the message seen by The New York Times.
On Tuesday night, Ms. McArdle, Mr. Bailey and Ms. Hoyos-López gathered in a live stream on X to await updates. Mr. Bailey told listeners that Mrs. Ulbricht was in Arizona, preparing for her son’s release.
A few hours after the pardon, an X account controlled by the family of Mr. Ulbricht posted a photo of himself leaving the prison with a small plant and a sack of items.
“FREEDOM!!!!” the post said.
Kenneth P. Vogel contributed to the report. Susan C. Beachy contributed to the research.
