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The origin story of Ross Ulbricht is no different to any story in Silicon Valley. It’s that of a young, smart, well-educated man, who grew up in an upper-middle-class suburb and had an idea that would change the world. Other men like him started services like Uber to disrupt the taxi business, Airbnb to disrupt hotels, or Yelp to disrupt the restaurant industry. Ulbricht chose to disrupt the drug market—illegal drugs. Ulbricht’s start-up, which he called the Silk Road, matched drug buyers and drug dealers, who shipped the product right to your door as if it was a box of tissues or a new book, and like Amazon, he took a small commission. Unlike Travis Kalanick of Uber, or Brian Chesky of Airbnb, Ulbricht, who went by “the Dread Pirate Roberts” (a reference to The Princess Bride) as a secret sobriquet, was eventually caught in a public library in San Francisco and sentenced to spend the rest of his life in jail.
On Tuesday, the Daily Beast reported that Donald Trump was exploring pardoning Ulbricht, writing that Trump “has at times privately expressed some sympathy for Ulbricht’s situation and has been considering his name, among others, for his next round of commutations and pardons.” According to a government official who was involved in the case against Ulbricht, the reports are indeed true, and Trump is indeed mulling a pardon. There are several reasons why this could be. Ulbricht’s mother, Lyn, has been on an understandable and persistent campaign to see her son freed from jail, and has traveled across America, meeting with politicians and supporters, trying to nullify his conviction. And, for some, Ulbricht has long been a cause celebre, lumped in with Julian Assange and Edward Snowden as people who, from behind a computer, crossed legal boundaries but with altruistic goals in mind. Supporters of Assange point out that he was simply trying to show atrocities being committed by the government; Snowden was driven by a desire to expose the fact that NSA was spying on its own citizens, and Ulbricht was trying to help people from being hurt in drug deals gone awry. The three men are often supported by the libertarian superfront of left- and right-wing rejectionists who Venn diagrams of differing political viewpoints with one single overlapping belief: that anything libertarian is not illegal. For Trump, that’s a good way to rally his base and gain sympathizers on the left.
After writing the book American Kingpin on Ulbricht and the Silk Road, I’ve often been asked if the punishment fits the crime—if Ulbricht should be pardoned or see his sentence commuted, given that he was punished with two life sentences plus 40 years for starting and running the Silk Road. At his trial, which I sat through for almost a month, the evidence against him was insurmountable. A juror I spoke to after the trial told me that she and her peers unanimously found Ulbricht guilty within the first few minutes of deliberations, but waited in the jury room to finish lunch, hoping to make it seem as though they had mulled his fate for longer, as they felt for his family. There wasn’t a shadow of a doubt that he was the creator and operator of the Silk Road, and that the site had caused irreparable harm to others.
During the trial, we had all watched as the prosecutors presented mountains of evidence showing that Ulbricht had approved the sale of almost every drug imaginable—even to minors. That he had allowed the sale of cyanide and guns. That he had created incentives and promotions to enable more people to sell more drugs on the Silk Road, and that he had believed he would never, ever be caught. And, perhaps hardest of all for the jury to watch, that at least six people had died from drugs they had purchased on the Silk Road, including a teenager in Australia, who had had an adverse reaction to a hallucinogen and had jumped out of a hotel window.
Given how high-profile the case was, the courtroom was often filled with more people than there were seats. On the right of the room, two dozen journalists packed in together—a mishmash of local news beat reporters, some tech journalists for big news outlets, and a few sympathetic bloggers from more esoteric crypto sites. On the left of the room sat Ulbricht’s family, including his mother and father, Lyn and Kirk Ulbricht, and his sister, as well as supporters and friends. What we all shared in common, from the prosecutors to the journalists to the defendant’s family to even the judge was that we were almost all white. Day in and day out, I would take the elevator up to the courtroom, and listen to the prosecution and the defense battle it out, arguing over the arcane details of the case, with one trying to argue that the Dread Pirate Roberts was Ross Ulbricht, and the other trying to argue that he was framed. I got into the habit of rarely leaving the courtroom at lunch, and just sitting there in the empty space for an hour and thinking about the case.
A couple of weeks into the trial, I stepped off the elevator and saw an African American woman in her early 20s, with a little baby in her arms, waiting in the hallway outside the courtroom. The baby was crying and fussing, and the woman was trying her best to hush the child with a bottle of milk. It was clear that the mother was overwhelmed by the enormity of where she was standing. As I walked into the courtroom that day, the Black woman stayed outside, and I thought nothing of it. But at lunchtime, when court was dismissed for an hour, and everyone else was gone, I watched the woman with the crying baby enter the courtroom and take a seat, alone, without anyone else around her. A little time went by, and the judge returned from her chambers, as a Black man in his early 20s was led into the courtroom, handcuffed and in a beige prison-issued jumpsuit, and he was told by two prison U.S. Marshals to take a seat. The exact seat that Ross Ulbricht had been in just 45 minutes earlier.
I remember the details of that moment as someone does when they witness a car crash: Certain things are as clear as day, others hazy. What stands out with such clarity, even years later as I think about it now, is the way the prisoner turned, offered a hopeful and regrettable smile to the woman with the baby, and how she smiled back and blew him an equally hopeful kiss. I remember watching U.S. District Judge Katherine Forrest, the same judge who had been residing over Ulbricht’s trial, as she entered the courtroom again, and reviewed the paperwork of this prisoner. And I remember how eerily empty the courtroom felt. The kind of empty when you can hear someone’s feet shuffle, or papers being turned.