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‘Free Ross’: Why Trump Wants Ross Ulbricht Released From Prison

Donald Trump pledged to free Silk Road founder Ross Ulbricht, should he win the 2024 US presidential election. Source: Truth Social/Bloomberg (Donald Trump/Source: Truth Social/Bloomberg)

(Bloomberg) -- Donald Trump has made a raft of promises to the crypto community should he win the US presidential election in November, including a pledge to commute the sentence of Ross Ulbricht, the founder of dark-web marketplace Silk Road. 

Who is Ross Ulbricht? 

Ulbricht, 40, was once better known by his online pseudonym “Dread Pirate Roberts” — a name taken from the film The Princess Bride. In 2011 he founded Silk Road, an online exchange that enabled users to anonymously buy and sell illegal goods and services with Bitcoin. During the two years it was in operation, more than $200 million worth of illicit activity flowed through the site, according to the Department of Justice. Ulbricht, who grew up in Austin, Texas and became an Eagle Scout, holds degrees in physics and materials science from the University of Texas and Pennsylvania State University, according to a website dedicated to the so-called Free Ross campaign. 

What was Ulbricht convicted of?

Ulbricht, who was imprisoned in 2013, is currently 12 years into serving a double-life sentence without the possibility of parole for drug trafficking crimes, as well as conspiracy to commit computer hacking and money laundering. While prosecutors alleged Ulbricht had tried to arrange five murders to protect his business, the government said it didn’t believe any were carried out. He’s incarcerated in a federal prison in Tucson, Arizona, having unsuccessfully appealed his sentence twice. At the time of his arrest, it was considered novel to prosecute someone for running a marketplace website, according to Preston Byrne, managing partner of Byrne & Storm. 

Why does Trump want him freed?

For Trump, it’s an easy chance to curry favor with the crypto industry. Crypto advocates, including some of Bitcoin’s original developers, have long championed a campaign to free Ulbricht. His case appeals to the sector because Silk Road was the first example of Bitcoin’s effectiveness as “a censorship-resistant transactional system at scale,” according to Byrne, who adds that Trump saying he’ll free Ulbricht sends the message that he’s taking input not only from industry titans but also “true believers.” Crypto traders also have raised constitutional concerns over his lengthy imprisonment for a non-violent crime.

“If you vote for me on day one I will commute the sentence of Ross Ulbricht,” Trump said in a speech in May at the Libertarian party convention. “He’s already served 11 years. We’re gonna get him home.” 

Among Trump’s other crypto pledges are the creation of a strategic Bitcoin reserve, as well as a promise to immediately fire Securities and Exchange Commission Chair Gary Gensler. The watchdog has led several enforcement actions against crypto companies under Gensler’s tenure, with his time in office set to end in 2026.

What else is known about Ulbricht?

Ulbricht maintains contact with the outside world through letters, blog posts and a managed X account. He remains a staunch advocate for Bitcoin, not least because of how the crypto community has rallied to his cause. To believers, Ulbricht embodies the original ethos behind Bitcoin — that it was intended as a digital payments ecosystem free from government oversight and rooted in cyberlibertarianism, a movement that views any attempt to interfere with technological development as antithetical to freedom. 

“Much more is being said about Bitcoin these days than when I was put in prison,” Ulbricht wrote in 2022, the text of which was published on his blog in April this year. “I thought I was putting Bitcoin to good use and giving people privacy and freedom. When illegal drugs were listed, I thought that was OK too, because I believed drugs should be legalized. Nevermind [sic] that they were outlawed and I was risking everything I held dear.”

©2024 Bloomberg L.P.