Why Donald Trump Made a Deal To Free Ross Ulbricht

Ross Ulbricht was arrested at 29. Now, he's 40. He faces a double life sentence plus 40 years with no possibility of parole for creating the Silk Road, a dark web drug marketplace that facilitated $1.2 billion in bitcoin-denominated transactions.

"I'll spend the next few decades in this cage. Then, sometime later this century, I'll grow old and die. I'll finally leave prison, but I'll be in a body bag," he told an interviewer at a 2021 virtual blockchain conference.

But a second chance might be coming for Ulbricht, from an unlikely savior.

"If you vote for me, on day one, I will commute the sentence of Ross Ulbricht," Donald Trump told a crowd of attendees at the 2024 Libertarian National Convention.

Trump made a deal with the Libertarian Party. And now, Ulbricht might not have to spend his middle and old age behind bars. He might not have to leave in a body bag if Trump makes good on his promise.

Will he?

In the coming months, career FBI officers and Department of Justice (DOJ) attorneys may dredge up lies about Ulbricht so that Trump will change his mind. They may appeal to some of his draconian instincts. They may try to pin on Ulbricht some of the disastrous outcomes of the drug war.

But Trump should ignore the saboteurs and keep his promise to free Ulbricht. Here's why:

Ulbricht's arrest on October 1, 2013, at the Glen Park Branch of the San Francisco Public Library was like a scene from an action movie. As he was downloading an interview with Vince Gilligan, the creator of Breaking Bad, he was simultaneously administering the Silk Road in another browser window.

Undercover FBI agents staged a physical fight behind him. When he turned his head to observe the commotion, another agent snatched his laptop before he could close the cover, which would have encrypted the contents of its hard drive.

The FBI keeps a picture of the computer on display as a trophy from the hunt.

But Ulbricht was no Walter White, the frustrated high school chemistry teacher who transforms into a violent drug kingpin in Gilligan's series, driven by his lust for power and retribution. Ulbricht was an Eagle Scout, who majored in materials science and engineering at the University of Texas at Dallas on a full scholarship. He was passionate about libertarian philosophy and Austrian economics, and read Ludwig von Mises and Murray Rothbard.

He wrote on LinkedIn that he wanted to use economic theory "as a means to abolish the use of coercion and aggression amongst mankind" and create "an economic simulation to give people a first-hand experience of what it would be like to live in a world without the systemic use of force."

"I was trying to do something good," said Ulbricht in a 2021 jailhouse interview. "I was trying to help us move forward."

And he did. Ulbricht created an underground e-commerce website called the Silk Road. He was its first vendor, selling homegrown psilocybin mushrooms. The Silk Road became the eBay of drugs, with trusted sellers earning higher ratings, and the message boards filled with tips for safer drug use. It established an ethical code of conduct: No fake degrees, no child porn, no stolen goods. "Our basic rules are to treat others as you would wish to be treated and don't do anything to hurt or scam someone else."

"I was trying to help us move toward a freer and more equitable world," said Ulbricht.

At the same time, the Obama administration's justice department was pressuring banks and credit card companies to stop servicing gun shops, adult websites, and payday lenders, even though what they were doing was completely legal.

The Silk Road demonstrated that, with bitcoin, you could buy things on the internet by circumventing payment rails that the government controlled. Online trade had become virtually unstoppable.

"Back then, bitcoin made me feel like anything was possible," Ulbricht says in his jailhouse interview.

Ulbricht became a hero to libertarians. But others say he got exactly what he deserved.

"Life in prison without parole. Anybody else? Any other wise guys want to do it? That's what you'll get," gloated Bill O'Reilly on Fox News at the time of the sentencing.

For his part, Ulbricht is remorseful and regretful, telling his interviewer from the jailhouse that "we all know the road to hell is paved with good intentions, and now here I am. I'm in hell."

Does he deserve this fate? As Ulbricht became paranoid that he'd be caught, did he stray from his high-minded ideals and "break bad" like Walter White? And does that mean Trump should think twice before freeing him?

Ulbricht's friends were shocked at his arrest. They described him as "sweet-natured," "loyal," and "guileless and nonaggressive." He comes across as poetic and sensitive in his artwork and an online interview with a friend posted before his arrest, where they each muse about their first love and plans for the future.

But many who oppose freeing Ulbricht say that he was also a contract killer, pointing to uncharged allegations that he tried to hire hit men to take out digital bandits during his tenure at the Silk Road.

But when you look closer, things get murky. Here's what we know:

When building their case, prosecutors drew on chat logs from a moment of crisis at the Silk Road. The site's top administrator, Curtis Green, had just been arrested. It looks like he might have stolen about $350,000 worth of bitcoin.

"Nob," a participant on the Silk Road, was chatting with the site's top administrator, who called himself the "Dread Pirate Roberts." He told Nob, "This will be the first time I have had to call on my muscle," and asked that Green be "beat up, then forced to send the bitcoins he stole back."

Later that day, the Dread Pirate Roberts messaged Nob again: Can you change the order to execute rather than torture?

Nob sent the Dread Pirate Roberts pictures of what looked like Curtis Green being tortured and killed.

It turns out that Nob was DEA agent Carl Force, one of two investigators on the case who went to prison for embezzling bitcoin during the investigation. He had staged Green's murder as part of a sting operation.

But Ulbricht's defenders say that the Dread Pirate Roberts who was chatting with the corrupt undercover agent who set up a fake hit wasn't actually Ross Ulbricht.

After all, the name was inspired by the film The Princess Bride to describe a character inhabited over and over by different individuals through many generations.

When the Dread Pirate Roberts granted an interview to Forbes two months before Ulbricht's arrest, he insisted that he was not the site's founder.

"I didn't start the Silk Road, my predecessor did," he told the Forbes journalist, who pressed to ask if he wrote the comments in the Silk Road forums. "The most I am willing to reveal is that I am not the first administrator of Silk Road," replied the Dread Pirate Roberts.

The jury never saw this interview. Green, the man targeted for the fake hit, has said there were "multiple" people with access to the account, including himself.

Green told Ulbricht's mother that he doesn't believe Ulbricht was the one who put out the hit and claims the undercover agent, Carl Force (aka Nob), also had access to the Dread Pirate Roberts' account.

There were other hits also ordered by the Dread Pirate Roberts that didn't lead to any actual known murders.

Federal prosecutors never charged Ulbricht with attempted murder, but the federal judge who sentenced him to two life sentences plus 40 years with no possibility of parole nonetheless referenced these episodes in her decision.

She also said that Ulbricht should serve as a public example for acting as though he "was better than the laws of this country."

Well, maybe he is. The drug war is the real villain in his story. It has cost $1 trillion while fueling decades of black market crime and violence—all as U.S. overdose deaths increased.

Black markets often become violent because there are no legal mechanisms for contract enforcement, and their participants become desperate to avoid being caught, which is what happened to the Silk Road.

It's ironic that Trump, the man who openly admires China and Singapore's death penalty for drug dealers, might be the one to free the founder of the world's first major dark web drug market.

But if there's one thing Trump likes, it's a good deal.

One of his most audacious deals of the 2024 campaign was with the Libertarian Party, which never wins but sometimes covers the spread in close presidential elections.

Trump showed up at their convention and proclaimed himself something of a Libertarian himself, to which he was met with a chorus of boos.

But behind the scenes, something else was going on. Trump had struck an agreement with the Libertarian Party leadership: Don't spoil this election for me, and I'll free your boy Ross.

Libertarian National Committee chair Angela McArdle told Reason that Trump's former Director of National Intelligence Richard Grenell set up a meeting between her and the president at Mar-a-Lago during the 2024 campaign.

"Rick [Grenell] is like, 'Well, President Trump is a deal-maker,'" says McArdle. "'You ask for the world. You ask for whatever you think you can get, and it'll probably land in the middle. He likes making deals.' I was anxious to ask too much and have Ross fall by the wayside. So I really hit it home like, 'We just want you to free Ross Ulbricht. Like, it's the most important thing.' And he said, 'I love freeing people. I'll do that.'"

After the party's nominating convention, McArdle vowed that the party would only back its own candidate—Chase Oliver—in noncompetitive states favoring the Democrats. Trump won by thin margins in several swing states while the Libertarian Party finished with its lowest vote share in 16 years.

"It was sort of this like a glorious miracle, the way things unfolded with Chase [Oliver]," says McArdle. "It couldn't have been better for making sure that Donald Trump was incentivized to stick to his promises and felt like secure in it and that he wasn't going to get screwed over in this deal."

So now it's time for Trump to keep his end of the bargain.

The Silk Road began as Ulbricht's idealistic attempt to make the black market just a little safer by creating a place where people could vet buyers, avoid risky in-person transactions, find untainted drugs, and share safety information.

That it ultimately seems to have fallen prey to some of the same violent forces as has every other black market in history only shows how hard it is to fix the problems prohibition causes—whether it's violence or increasingly dangerous synthetic drugs like fentanyl, which is driving the overdose epidemic and has only grown worse since Silk Road's shutdown.

Unless, and until, the government wises up and takes a different approach to drugs, our choices are places like the Silk Road and its many imitators since, or the cartels.

While Trump has vowed to "take down the cartels, just as we took down the ISIS caliphate," history has shown that's easier said than done. America tried "decapitating" the cartels in the early 2010s, and it led to an even bloodier situation in Mexico.

The last war on the cartels created a power vacuum enabling the rise of the notorious "El Chapo." Once he was arrested, others took his place, and the cartel transformed into a more decentralized and resilient "umbrella" structure. The new leadership increased the fentanyl flow, with seizures nearly doubling between 2021 and 2023.

As long as there is a strong demand for drugs in America, it seems that there will be willing suppliers. Drug prohibition has failed, and no amount of bluster about executing dealers or going to war in Mexico is likely to change that.

But even if you disagree and think Trump can somehow finally win the drug war, it still doesn't justify keeping Ulbricht locked up through his 40s.

He has served his time and expressed remorse.

"I'm sorry to the extent that my actions led to drug abuse and addiction," he said in his 2021 jailhouse interview.

He's been a model prisoner, pursuing his master's degree in psychology, teaching and serving as a conflict mediator on the inside, and collecting over 150 signatures of support for his release from fellow inmates.

On all counts, this certainly would be a far more defensible intervention than President Joe Biden's self-serving pardoning of his son Hunter for all potential crimes covering more than a decade.

Ulbricht, a first-time offender, has suffered enough. Donald Trump made a deal, and many of Ulbricht's supporters voted for him—or at least not against him—because of that deal.

It might not be pretty, but it's politics in 21st-century America. Trump got what he wanted. Now it's time to set Ulbricht free.

*CORRECTION: This post previously included incorrect information about a plea deal offer.

• Producer: John Osterhoudt
• Graphics: Lex Villena