He Helped Create Silk Road — But Ross Ulbricht Should Be Freed

On March 27, 2024, Ross Ulbricht expressed a birthday wish from prison. “Today, I turn 40,” Ross had his family post on the Twitter account he uses to communicate with the outside world. “I pray I’ll get a second chance at freedom before this next decade ends.” He followed that up a couple of weeks later with a lament: “It’s been over 10 years since I’ve seen the night sky. This is one of the simple things I miss the most.”

Generally, Ross maintains a surprisingly positive attitude for someone who is facing the rest of his life in prison. He is always engaging, sharp, and intellectually curious in the many letters we have exchanged since 2015, when I first met Ross as he prepared for his federal criminal trial.

My interest in his case began in 2013 when I was working on DEEP WEB, a documentary about the Dark Net black market and forum, Silk Road, and the global hunt for its leader, known only as Dread Pirate Roberts, aka DPR. In October of that year, a young man named Ross Ulbricht was arrested in San Francisco on suspicion of being DPR. Ross was an unassuming 29-year-old physics grad, beloved by his friends and family and without anything resembling a prior history of wrongdoing, much less crime. From the beginning, the media portrayed Ross as a murderous drug kingpin presiding over a vast global cartel, and for the community on Silk Road, that simply didn’t add up. For starters, Silk Road was a relatively small site, and if Ross was DPR, this description of a ‘murderous drug kingpin’ didn’t track with the DPR that everyone knew from the forums — a modest, relatable peer with whom they shared their lives.

I was one of those community members, having joined the site early on to research the rise of Bitcoin. I immediately discovered that while inarguably a criminal operation, there was much more to Silk Road than its portrayal in the media. It was certainly a market for drugs, amongst other mundane and perfectly legal things, but contrary to erroneous news reports, it did not sell hitmen services, child porn, or guns. And while hyperbole made for eye-grabbing press reports, Silk Road was not a ‘vast global cartel’ but a sparsely populated platform on a small, impenetrable corner of the Internet. For many of its users, Silk Road was a vibrant and diverse community of people from around the world. They were not only there for drugs but for the freedom of an encrypted and anonymous space to convene and discuss everything from politics to literature and art, philosophy and drugs, drug recovery, and the onerous drug war. DPR was only one of the prominent voices in the active Silk Road forums.

The FBI shut down Silk Road at the same time as Ross’s arrest and thus began an investigation and trial that I hoped would answer many questions: Was Ross DPR? Was DPR responsible for all the activities behind the scenes at Silk Road? Did DPR order hits on several enemies that, while never resulting in actual murders, would indicate a much darker side to DPR than the community understood? What was the role of the corrupt law enforcement agents deep inside Silk Road and profiting from drug sales?

Many of us eagerly anticipated a measured and thorough investigation, but a media circus ensued. The government and press no better understood the Internet in those days than today. Added to that disconnect was the irresistible clickbait of a young, attractive, middle-class white kid from a good family, allegedly presiding over a “global drug empire.” A small cottage industry grew around Ross and Silk Road, spawning countless magazine articles, books, and movie deals. A flurry of stories painted the picture of a young man that no one knew and had to be constructed, including a salacious piece in this publication. Despite some excellent reporting from a handful of reporters in the tech press, a skewed and often wildly inaccurate narrative formed around Silk Road and Ross that followed him all the way to his brief trial.

I attended Ross’s trial and was dismayed to see the level of confusion from the judge to the jury, struggling to comprehend the complex and alien landscape of the Dark Net, Bitcoin, and the workings of Silk Road. There were some clear-cut discoveries: Ross was the creator of the site and the moniker Dread Pirate Roberts, even if others were involved in running operations and making decisions. And whatever the facts were, behind encrypted keyboards and anonymous chats involving murders for hire that never resulted in anyone’s death, things had taken a dark turn on the site.

Ross did not deny his involvement in Silk Road, though he continues to contest the allegation that he was the sole person in charge. At his sentencing on May 29, 2015, Ross made an impassioned statement of remorse to the judge, accepting responsibility for his part in the harm caused by Silk Road. He was then sentenced to double life imprisonment plus 40 years without the possibility of parole, a veritable death sentence usually reserved for cartel leaders and serial killers and more severe than what was requested by the prosecution. At the sentencing, every one of us in the crowded court and overflow room was stunned. Ross Ulbricht has been behind bars since October 2013.

I first met Ross while he was incarcerated in a high-security detention center in Manhattan awaiting trial, and after he was transferred to federal prison, we formed a closer relationship. The Ross I know is highly educated, insightful, remorseful, humane, and self-aware. He has been a model prisoner for these intervening years, teaching math and yoga and helping fellow prisoners get off drugs and prepare for release. It’s my firm opinion, and the opinion of many prison system and criminal-law experts, that his sentence is disproportionate to his charges and that he deserves clemency. This case indeed reflects just one of the millions of unjust sentences in the long and failed war on drugs, but that’s no excuse to ignore this case or any other that deserves to be heard and corrected. Our justice and carceral systems are long overdue for reform, and we can and should be arguing for clemency in all cases of unjust sentencing.

No matter what one thinks of Ross, Silk Road, or the crimes that may have been committed, 10 years in prison is more than sufficient and customary punishment for those offenses or sins. Ross Ulbricht should be free.