Trump’s ‘Free Ross Day One’ Unfulfilled

The rallying cry of “Free Ross Day One” that energized Bitcoiners throughout Donald Trump’s campaign has met with disappointment as January 20th—Inauguration Day—came and went without action on the Silk Road founder’s imprisonment. The disappointment extends beyond Ulbricht’s supporters to the broader cryptocurrency community, which had also hoped for immediate action on Bitcoin policy.

Bitcoiners Wait For “Free Ross” Promises to Materialise

While Trump explicitly promised to commute Ross Ulbricht’s sentence “on Day One” during a May 2024 speech at the Libertarian National Convention, recent statements from Ulbricht’s family have pointed to a broader January timeline. The family shared via their @Free_Ross social media account that he would be released this month, though they didn’t specify an exact date. However, prominent supporters, including Bitcoin advocate Jack Mallers, have consistently echoed the “Day One” mantra, setting expectations for immediate action on January 20th that went unfulfilled.

The cryptocurrency community, which significantly overlaps with Ulbricht’s supporters and largely leans libertarian, faced their own disappointment as hopes for a promised Bitcoin Strategic Reserve executive order also failed to materialize on inauguration day.

A Mixed Reception from Bitcoiners

Trump’s original promises came during a contentious appearance before the Libertarian National Convention, where he actively courted the party’s voters with pledges of criminal justice reform and crypto-friendly policies. “And if you vote for me, on Day One, I will commute the sentence of Ross Ulbricht,” Trump declared to cheers from an audience waving “Free Ross” signs, though the overall reception to his speech remained mixed with sustained boos and jeers.

The pledge to free Ulbricht, who is serving a life sentence for his role in creating and operating the dark web marketplace Silk Road, was a calculated appeal to libertarian leaning Bitcoiners.

From Campaign Promise to Reality

Ulbricht, now 40, was convicted in 2015 of multiple charges including distributing narcotics, engaging in a continuing criminal enterprise, conspiring to commit computer hacking, and money laundering. The case has become a rallying point for Bitcoiners who view it as emblematic of government overreach and a key moment in Bitcoin history, while prosecutors maintained that Silk Road facilitated over millions in illegal transactions and was linked to multiple overdose deaths.

Neither Trump nor the U.S. Attorney for the Southern District of New York took any action on the case during the inauguration day, leaving supporters who took the “Day One” promise literally increasingly frustrated. While the month isn’t over—and the family’s January timeline could still be met—the passing of the January 20th inauguration without immediate action has dampened the optimism of Ulbricht’s most ardent supporters who had hoped to see him freed as Trump’s first act in office.

The unfulfilled Day One promises highlight the complex political calculations surrounding both Ulbricht’s case and cryptocurrency policy. Trump’s pledges earned him momentary acclaim from Bitcoiners and Libertarian convention attendees. Late on January 20th, Elon Musk, who has emerged as one of Trump’s key advisors, weighed in on the situation, writing on X (formerly Twitter): “Ross will be freed too.” While this statement offers a renewed hope for Ulbricht’s supporters, questions remain about the timing and whether Trump will follow through on his commitments to the cryptocurrency communities, and what the delay might mean for his broader campaign promises to these voting blocs.