Why Trump Freed Ross Ulbricht, the Silk Road’s Dread Pirate Roberts


Last September, I spent an evening at a meetup near Atlanta titled “Bitcoin Enters the Mainstream Political Arena.” It was the first time that the group of mostly white, mostly male, mostly bearded thirty- and forty-year-olds, had convened to focus their attention on the politics of cryptocurrency—which had suddenly, rather shockingly, become front and center. Donald Trump, who called bitcoin “a scam” back in 2021, had recently headlined a bitcoin conference and released ads saying things like “You know, they call me the crypto President.” Near the door of the Atlanta event, held on the patio of an airplane hangar, sat a stack of Bitcoin Magazines with Robert F. Kennedy, Jr.,’s face on the cover. Joey, a theatre director in attendance, explained Kennedy’s role in recent events: “When Kennedy came along—and he’s for bitcoin—Trump said, ‘Oh, shit, I’m gonna start losing people over bitcoin.’ So he shifted.” Joey shrugged. “We’ll take it.”

The crypto crowd, long the butt of jokes, was thrilled by its sudden shift in status—even if some doubted the authenticity or durability of Trump’s support. They were finally being taken seriously by one party, at least. T-shirts displayed their enthusiasm using insider lingo and jokes that, to the uninitiated, took a bit of explaining: “SINGLE, TAKEN, HODLING,” Joey’s shirt read. There were boxes beside each word; “HODLING” was checked. (“HODL” is an acronym for “hold on for dear life,” which refers to crypto’s crazy-making volatility.) Get it? I made the rounds, as the group of three dozen caught up, drank beer, and ate barbecue. I asked why most seemed enthusiastic about Trump. There was his increasing closeness to crypto-enthusiasts like Kennedy; his stated willingness to embrace crypto-friendly policy; and also, notably, his promise to release a now forty-year-old man from prison: Ross Ulbricht.

Ulbricht was pardoned last week, at the close of the second day of Trump’s Presidency, a day after Trump’s pardon of roughly fifteen hundred people involved in the January 6th insurrection. The delay had caused some of Ulbricht’s acolytes to worry. “People were posting in our chat, like, ‘O.K., there’s an hour and a half left of Day One . . . ’ ” Rich Clarke, the bitcoin meetup group’s organizer, who works in real estate, told me. “And a lot of my friends on Facebook were posting things like ‘Hope It Happens.’ ” He went on, “I think it was a shrewd move to pardon Ross sort of all on his own, after Trump did the mass pardons. It kind of gives the gesture more gravitas.”

In 2011, Ulbricht, an Eagle Scout from Austin, Texas, founded Silk Road, an online black market that existed until his arrest, in 2013, for crimes related to drug trafficking, money laundering, and computer hacking. According to authorities, more than a million transactions took place on Silk Road, out of the government’s regulatory reach, generating more than two hundred million dollars in revenue. Drugs like methamphetamine, cocaine, and heroin made up a huge portion of the site’s sales, from which Ulbricht apparently took millions in commissions. Silk Road “lowered the barriers to drug dealing by enabling drug dealers to reach customers online they could have never met on the street,” a federal prosecutor said in a closing argument. (Prosecutors also presented evidence that Ulbricht was involved in a murders-for-hire plot, but the government admitted that there was no evidence that the alleged targets had been harmed, and charges were not pursued.) In 2015, Ulbricht, who went by the dark-Web sobriquet Dread Pirate Roberts—a reference to a shifting character in “The Princess Bride”—received two life sentences without the possibility of parole.

What made Ulbricht a crypto hero, ultimately, was that Silk Road had offered one of the first clear use cases for bitcoin: all transactions on the dark-Web site were made with the then nascent cryptocurrency, which, thanks to pseudonymous addresses at the disposal of buyer and seller, provided a significant degree of cover. Of course, this use case was, perhaps, not the ideal one for a new currency wishing to be seen as legitimate. “For better or for worse, the Silk Road did have a huge impact on bitcoin in its early days, in its public perception, in its adoption,” Clarke told me. “And Ross has, in the past, apologized because he’s not certain—nor am I—whether Silk Road was a net positive for bitcoin.”

But freeing Ulbricht remained a big issue for libertarians like Clarke, who, given their laissez-faire philosophy, embraced pro-crypto policy before most Republicans or Democrats. At the Libertarian Party’s national convention last year, Trump went onstage and announced that he’d free Ulbricht if elected. This had impressed folks at the meetup, many of whom described themselves to me as libertarian. I ended up having one of my lengthiest conversations with a young man named Michael Tidwell, who wore a “FREE ROSS” T-shirt. (Everyone there referred to Ulbricht by his first name, as if he were Prince or Madonna or LeBron.) Tidwell told me that he’d never voted in a Presidential election before, unless you counted writing in “Rare Pepe”—a crypto meme character—in 2016. “Biden and Harris could free him and they’re not,” he told me. “At least Trump is saying he’d do it.”

On January 21st, Trump did it. He announced Ulbricht’s pardon
on Truth Social. It was everything that Ulbricht’s supporters wanted, save, perhaps, for Trump’s misspelling of Ross’s last name (which was subsequently corrected). “I just called the mother of Ross William Ulbright to let her know that in honor of her and the Libertarian Movement, which supported me so strongly, it was my pleasure to have just signed a full and unconditional pardon of her son, Ross,” Trump wrote. “The scum that worked to convict him were some of the same lunatics who were involved in the modern day weaponization of government against me.”

After Ulbricht’s release, I called up a few members of the Bitcoin Atlanta Meetup group, which hosted Ulbricht’s mother back in 2017. “Some punishment was deserved,” Clarke told me. “But not that. The magnitude of the sentence was what really set him apart. This was redemption for an otherwise cruel and unusual punishment.” Others in the group felt the same way. Clarke posted a forward-looking message on Facebook, which he repeated to me, “I’m so happy that Ross is now a free man after over a decade in prison. It’s my hope that Ross can use his experiences and whatever influence he has, owing to his high profile, for good in his new life as a free man.” He guessed that Ulbricht would be “active” in criminal-justice reform. (Ulbricht has not yet given any interviews, but he posted a video to his X account, on Thursday night, viewed more than ten million times, in which he said, among other things, “Let it be known that Donald Trump is a man of his word.” Ulbricht, sounding emotional, went on, “This is an important moment for everybody everywhere who loves freedom and who cares about second chances.”) Later, Clarke sent me his favorite humorous response to the pardon, a meme he’d seen on Facebook: “Heartbreaking: Trump condems man to 20 years of libertarian podcast apperances.”

One of the meetup group’s only outspokenly anti-Trump members was just as thrilled. “Ross’s pardon is unambiguously good news,” the man, who asked not to be identified, told me. “I personally believe the book was thrown at him for his strong anti-authoritarian, libertarian blog posts to make an example of him. His sentence was truly cruel and unusual punishment.”

I also spoke to one of the group’s other frequent attendees, formerly employed in I.T., named Mel Dodd. He told me that the libertarians and crypto-enthusiasts he knew were “overjoyed” by the pardon of Ulbricht, the recent resignation of the Securities and Exchange Commission chairman and noted crypto-critic Gary Gensler, and Trump’s prohibition of establishing a U.S. Central Bank Digital Currency, which would pose a threat to cryptocurrencies like bitcoin. (They were also, obviously, thrilled that bitcoin has surged in value by around fifty per cent since Trump’s election, and now traded at more than a hundred thousand dollars.) “There is less of a ‘will he keep his promises’ skepticism now, but still a lot remains,” Dodd said. Most notably: whether Trump will create a “national stockpile” of bitcoin, as he also signalled he would do prior to his election. “Will they really do it—and really do it right—or will they screw it up the way politicians usually do? There’s a general skepticism of anything Trump or any politician does. But if they do something good, we’ll stand up and cheer.” On Thursday, Trump issued an executive order titled “Strengthening American Leadership in Digital Financial Technology,” which, among other things, outlined the creation of a “working group” to consider crypto policy, including the creation of the “national digital asset stockpile.” Its first recommendations would be expected in six months’ time.

Trump didn’t wait that long to launch his own $TRUMP coin, which he débuted a few days before his Inauguration. The coin features an image of Trump from the moment of the assassination attempt on him, last July. “Its valuation went up to twenty billion or something like that,” Clarke told me. “And yet his team or whoever is running this thing still controls most of it.” An affiliate of the Trump Organization reportedly owns eighty per cent of the supply of the coin, whose valuation peaked around fifteen billion dollars and now sits at about half that, following the introduction of a $MELANIA coin. (Trump’s teen-age son, Barron, meanwhile, has been named the “DeFi visionary” in a vaguely defined Trump crypto platform called World Liberty Financial.) “It’s kind of a classic pattern of something that usually doesn’t end well,” Clarke said.

Dodd advised reserving judgment. “The Trump coin will stand or fall on whether it’s accepted or not, like every other thing introduced to the American free market,” he said. “There’s a lot of cringe products that come out of the American market all the time. But you can win on a cringe product. The money that the Hawk Tuah girl made on her meme coin is just as good as any other money.”

Ross Ulbricht may be a millionaire again already. According to Conor Grogan, a director at Coinbase, one of the largest crypto-trading platforms, some of Ulbricht’s crypto fortune may have evaded seizure following his arrest and conviction. “I found ~430 BTC across dozens of wallets associated with Ross Ulbricht that were not confiscated by the USGovt and have been untouched for 13+ years,” Grogan posted to X a day after Ulbricht’s pardon. “Back then these were probably dust wallets, now, collectively, they are worth about $47M. Welcome back Ross.” ♦

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