He Helped Create Silk Road — But Ross Ulbricht Should Be Freed
Alex Winter
Cultural Commentary
The physics grad was sentenced to two life terms plus 40 years, but there’s no reason he should die in prison

On March 27, 2024, Ross Ulbricht expressed a birthday wish from prison. “Today, I turn 40,” Ulbricht 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, Ulbricht 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 Ulbricht 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 darknet black market and forum Silk Road, and the global hunt for its leader, known only as Dread Pirate Roberts, a.k.a. DPR. In October of that year, a young man named Ross Ulbricht was arrested in San Francisco on suspicion of being DPR. Ulbricht 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 Ulbricht 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 Ulbricht 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, among 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 War on Drugs. DPR was only one of the prominent voices in the active Silk Road forums. Editor’s picks Every Awful Thing Trump Has Promised to Do in a Second Term The 250 Greatest Guitarists of All Time The 500 Greatest Albums of All Time The 50 Worst Decisions in Movie History

The FBI shut down Silk Road at the same time as Ulbricht’s arrest, and thus began an investigation and trial that I hoped would answer many questions: Was Ulbricht DPR? Was DPR responsible for all of 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 who were 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 Ulbricht 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 Ulbricht that followed him all the way to his brief trial.

I attended Ulbricht’s trial and was dismayed to see the level of confusion — from judge to jury — struggling to comprehend the complex and alien landscape of the darknet, Bitcoin, and the workings of Silk Road. There were some clear-cut discoveries: Ulbricht was the creator of the site and was behind 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.

Ulbricht 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 were stunned. Ross Ulbricht has been behind bars since October 2013.

I first met Ulbricht 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 Ulbricht 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 Ulbricht, 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.
The physics grad was sentenced to two life terms plus 40 years, but there’s no reason he should die in prison
On March 27, 2024, Ross Ulbricht expressed a birthday wish from prison. “Today, I turn 40,” Ulbricht 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, Ulbricht 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 Ulbricht 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 darknet black market and forum Silk Road, and the global hunt for its leader, known only as Dread Pirate Roberts, a.k.a. DPR. In October of that year, a young man named Ross Ulbricht was arrested in San Francisco on suspicion of being DPR. Ulbricht 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 Ulbricht 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 Ulbricht 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, among 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 War on Drugs. DPR was only one of the prominent voices in the active Silk Road forums. Editor’s picks Every Awful Thing Trump Has Promised to Do in a Second Term The 250 Greatest Guitarists of All Time The 500 Greatest Albums of All Time The 50 Worst Decisions in Movie History The FBI shut down Silk Road at the same time as Ulbricht’s arrest, and thus began an investigation and trial that I hoped would answer many questions: Was Ulbricht DPR? Was DPR responsible for all of 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 who were 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 Ulbricht 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 Ulbricht that followed him all the way to his brief trial. I attended Ulbricht’s trial and was dismayed to see the level of confusion — from judge to jury — struggling to comprehend the complex and alien landscape of the darknet, Bitcoin, and the workings of Silk Road. There were some clear-cut discoveries: Ulbricht was the creator of the site and was behind 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. Ulbricht 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 were stunned. Ross Ulbricht has been behind bars since October 2013. I first met Ulbricht 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 Ulbricht 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 Ulbricht, 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.