Ross ulbricht over an image of the silk road and Trump | Illustration: Lex Villena

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

Why Donald Trump Made a Deal To Free Ross Ulbricht