The trial of Ross William Ulbricht, alleged proprietor of the defunct anonymous online narcotics bazaar known as Silk Road, began this week, and already it’s getting exciting. In the first day of testimony, Ulbricht’s lawyer admitted that his client had, indeed, founded Silk Road but denied that Ulbricht was the shadowy site administrator known as “Dread Pirate Roberts.” Ulbricht had abandoned the site early in its existence, his lawyer claimed, only to be lured back, disingenuously, by the people to whom he had handed it over. “They had been alerted that they were under investigation, and time was short for them,” Ulbricht’s lawyer claimed. “Ross was the perfect fall guy.”
As criminal defenses go, “I was set up by a shadowy Internet crime cartel” is more entertaining than most, and it’ll be interesting to see how the trial plays out. But Ulbricht’s ultimate culpability is far from the most interesting thing about this case. In a Wired piece republished on Slate, Andy Greenberg offers a good overview of some of the broader political and philosophical issues raised by Ulbricht’s case, like the limits of online anonymity and the implications of radical Internet libertarianism in a burgeoning surveillance state. But for a lot of people, the Ulbricht case raises other, less lofty questions: What is the future of using the Internet to buy drugs? Does it make sense to buy your narcotics off of platforms managed by dilettante nerds who are bad at crime? Or are you actually better off using traditional analog methods, and getting them from your brother’s sketchy friend Brian who lives down by the freight yards?
During its two-and-a-half-year lifespan, Silk Road was hailed as a paradigm shift in illegal markets: a decentralized, anonymized secure online marketplace that promised to make the drug trade safer and less violent. In the criminal complaint against Ulbricht, the federal government called Silk Road “the most sophisticated and extensive criminal marketplace on the Internet today.” And yet, if the government’s allegations are to be believed, Ulbricht himself—a former Penn State grad student who had once operated a used book business in Austin, Texas—was no criminal mastermind. Knowing what we apparently know now about Ulbricht’s inexperience and failures at operational security, it’s surprising that Silk Road lasted as long as it did.
In the early days of Silk Road, Ulbricht allegedly advertised the site on an online forum using a username that was tied to his real-world identity. Similarly, he allegedly used another easily traced username to post a programming question to the website Stack Overflow. According to the Justice Department, Ulbricht unknowingly let an undercover agent into his inner circle. He apparently got conned out of $150,000 by grifters in an elaborate fake murder-for-hire scheme. When Homeland Security agents came to his apartment in San Francisco to question him about several fake IDs bearing his likeness that had been seized by postal inspectors, Ulbricht allegedly told them that, “hypothetically,” such things could be purchased on a website called “Silk Road.”
Ulbricht was also allegedly very open about the ideological motivations of Silk Road. In August 2013, Forbes ran a long interview with Dread Pirate Roberts in which he espoused the libertarian ethos of Silk Road and its broader societal implications. “Sector by sector the state is being cut out of the equation and power is being returned to the individual,” Dread Pirate Roberts said. “I don’t think anyone can comprehend the magnitude of the revolution we are in.”
This corresponded to Ulbricht’s real-life beliefs. Before Silk Road went live, for instance, he wrote on his LinkedIn profile that he was “creating an economic simulation to give people a first-hand experience of what it would be like to live in a world without the systemic use of force” exerted by governments; evidently this “economic simulation” was Silk Road. On his Google Plus page, Ulbricht had posted videos originating from the Mises Institute, a libertarian think tank. On Silk Road, Dread Pirate Roberts also expressed interest in the Mises Institute.
A lot of Silk Road users held similar beliefs and saw the site as a grand libertarian social experiment. In December 2014, researcher Tim Bingham told Reason that when Silk Road went down “we lost more than just a site that sold drugs. We lost a community of people that believed in something.” I take Bingham’s point, but it’s also worth noting that, first and foremost, Silk Road was a site on which drugs were sold, illegally, across state and international lines. I’m going to risk seeming callow and suggest that if you’re looking for a community of believers, go to church. If you’re looking to buy drugs, go to a professional.
While buying drugs from a real, live human can be scary, it also has its advantages. For one thing, if you buy drugs on the street, your dealer doesn’t have your home address. You’re also not putting a “wallet” of funds in the hands of the drug market that you’ll lose if the drug market shuts down, as happened to Silk Road users when the U.S. government seized the site in October 2013. And, counter-intuitively, the threat of real-world violence actually works to make the entire transaction safer: All parties to the transaction realize that they risk being injured or killed if they deviate from operational security procedures.
Speaking for myself, if I’m going out to buy drugs, I don’t particularly care about the ideological motives of the people facilitating my transaction. I want stability and operational security. And it’s hard to count on top-notch op-sec from first-time criminals who are figuring the business out as they go—from ideologues whose every revolutionary proclamation is helping the government connect the dots between their online and real-world identities.
The one big advantage online drug markets have over real-world transactions—anonymity—is lost if at every step you’re using your online identity to make political points that can be used by investigators to deduce your real-world identity. The best criminals and covert operatives maintain strict separation between their personal and professional lives. Ulbricht’s alleged failure to do so indicates not just an inexperience with crime, but an inability to accept that he was, in fact, a criminal. (And, yes, Ulbricht does stand accused of attempting to arrange the murders of six people who compromised site security. None of the murders actually happened. A talented criminal would have made sure that they did.)
The anonymity of markets like Silk Road can be a shield, but it can also make it harder for darknet market proprietors to share information and learn from the mistakes of their predecessors. About a month after the first Silk Road went down in October 2013, a successor site called Silk Road 2.0 rose in its place. In November 2014, an international law enforcement operation dubbed “Operation Onymous” brought down dozens of darknet markets, including Silk Road 2.0 and its alleged operator, Blake Benthall, a 26-year-old computer programmer with libertarian inclinations. Like Ulbricht, Benthall had a clean criminal record. Like Ulbricht, Benthall allegedly made a bunch of dumb mistakes; the server that hosted Silk Road 2.0 was registered to email@example.com. Like Ulbricht, Benthall was also allegedly very forthcoming about the revolutionary nature of his website.
If these markets are going to be sustainable, their founders need to think of them primarily as illicit businesses, not as experiments in individual liberty. There were several darknet markets unaffected by Operation Onymous, including Agora and Evolution, the latter of which not only sells drugs but also facilitates the sale of weapons and stolen credit-card numbers—something that Silk Road wouldn’t do. The people behind these sites appear to be primarily interested in profit and less interested in spreading some sort of message. When Greenberg reached out to the people behind Evolution with an interview request, he was politely but firmly brushed off. This is a good thing. As one darknet user told Greenberg in September 2014, “The libertarian ideals behind Silk Road were about giving everyone free choice. Now it’s gone past drugs to fraud. It’s about making money.” Online drug buyers everywhere should be glad.