Can Donald Trump Really Free Ross Ulbricht?

Overview

Ross Ulbricht, the mastermind behind an infamous online marketplace that facilitated the sale of illegal drugs called Silk Road, has been a polarizing figure in discussions about criminal justice & internet freedom. Serving two life sentences plus 40 years without the possibility of parole, Ulbricht's harsh sentence has been a flashpoint for debate. Now, with Donald Trump’s recent pledge to commute Ulbricht's sentence if re-elected, many are asking: Can Trump really free Ross Ulbricht?

A Brief Backstory

Launched in 2011, Silk Road quickly became the go-to platform for anonymous transactions involving illegal drugs, fake IDs and even hacking services—all paid for with Bitcoin. The site's founder, Ross Ulbricht, operated under the pseudonym "Dread Pirate Roberts," a nod to the fictional character from The Princess Bride. In 2013, the FBI arrested Ulbricht in a San Francisco public library, seizing his laptop and effectively shutting down Silk Road. After a highly publicized trial, Ulbricht was convicted in 2015 on multiple charges, including money laundering, computer hacking and conspiracy to traffic narcotics.

Trump's Unlikely Interest

At first glance, Donald Trump might seem an unlikely champion for Ulbricht’s cause. Throughout his political career, Trump has been a vocal advocate for harsh penalties on drug dealers, even proposing the death penalty for major offenders. However, Trump’s criminal justice record also includes some surprising acts of leniency, such as his commutation of Alice Marie Johnson’s life sentence for a nonviolent drug offense, which was widely praised.

Still, in a move that many didn't anticipate, Trump explicitly promised at the Libertarian National Convention to commute Ulbricht's sentence on his first day in office if re-elected in 2024. The presidential candidate acknowledged that Ulbricht has already served over a decade behind bars and indicated that he believes this time has been sufficient punishment for his crimes.

Speaking on this, Ross took to Twitter to thank Trump for his support, expressing his optimism about finally getting a second chance.

Why It Could Actually Happen

If Trump does get elected, he would have the absolute authority to pardon Ross on his very first day in office, and no one could legally challenge that decision. But why would he do it? Well, for one, Trump’s promise to free Ulbricht could be seen as a strategic move to court the libertarian and tech-savvy voters who view Ulbricht as a martyr for internet freedom and Bitcoin.

Some might also say it’s an indirect way to woo the crypto community, especially since he has recently dubbed himself the “crypto president”. His latest NFT release also seems to be part of a campaign effort to reach out to the diverse crypto market, which you can read more about here.

Moreover, Trump has shown a willingness to make bold, controversial decisions that go against the grain of conventional politics. His previous commutations, coupled with his support for the First Step Act—a bipartisan criminal justice reform law—underscores his confidence in securing Ulbright's release once in office.

Politically, this move could also be seen as an attempt to distance himself from the “tough on crime” rhetoric that dominated his first presidential campaign, appealing instead to voters who favor a more measured approach to justice reform. Given Trump's history of making decisions that resonate with his base and capture public attention, the commutation of Ulbricht’s sentence could very well become a reality​.

Potential Roadblocks Ahead

Of course, it’s not all smooth sailing. The decision to commute Ulbricht’s sentence would undoubtedly be met with major opposition. Many still view Ulbricht as a dangerous criminal who misused technology to cause significant harm. On top of that, Trump's current legal battles and his polarizing political persona might complicate or delay any such commutation efforts.

Final Thoughts

While the prospect of Ross Ulbricht walking free may have seemed impossible just a few years ago, Trump’s recent promise has injected new hope into the movement advocating for Ulbricht’s release. Whether this is a genuine commitment or a strategic political maneuver, it’s clear that the possibility is now on the table. Given Trump’s history of controversial and unexpected decisions, it’s not out of the realm of possibility that Ross Ulbricht could be a free man if Trump returns to the White House.

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