The Non-Drug User's Guide to the Silk Road Trial

Ross Ulbricht goes on trial on Tuesday for allegedly running a billion-dollar online drug bazaar, and the result could affect a lot more than the drug trade
Photographer: Getty Images

The federal case against the man accused of running Silk Road, once the preeminent online black market, promises testimony about millions of dollars in drugs, phony hit men, and references to the Princess Bride. But the trial, which starts on Tuesday, will be closely watched for reasons that go beyond sordid details. By making its case against Silk Road and its alleged proprietor, prosecutors will be offering a rare glimpse into how the justice system deals with the darkest corners of the Internet. 

Silk Road was designed to be anonymous. Users had to use Tor, a tool that obscures the identity of Web users. All transactions were carried out in Bitcoin, a cybercurrency favored by those trying to cover their tracks. During its heyday, from early 2011 until 2013, sellers used the site to sell hundreds of kilograms of narcotics and other illicit goods worth hundreds of millions of dollars, according to federal prosecutors. At the center of the operation and taking a cut from every transaction, prosecutors argue, was Ross Ulbricht, the man charged with criminal conspiracy, drug trafficking, computer hacking, and money laundering. 

The party ended in October 2013 after federal agents apprehended the 29-year-old Ulbricht and identified him as the "Dread Pirate Roberts," the nom de Internet used by the person operating Silk Road. At the time of his arrest, Ulbricht was logged into Silk Road from his laptop and sitting in the science fiction section of a library in San Francisco. Prosecutors argue that Ulbricht's involvement went beyond drug running and computer hacking to arranging a number of assassinations of people who threatened his business. One of those murders-for-hire was staged by a federal agent, and prosecutors don’t think the other killings ever took place. While Ulbricht has been indicted for paying $80,000 for a hit in Maryland, he isn’t facing any charges for violent crimes. 

Ulbricht's imprisonment for the last 15 months has hardly ended illicit online commerce. People have found their drugs through such marketplaces as Evolution, Agora, and Silk Road 2.0. Sites like these are also subject to raids by law enforcement—hundreds of domains were shut down in a single operation in November—with new ones constantly taking their place. This weekend, a new market called Silk Road Reloaded set up shop, using an alternative to Tor as a way to guarantee users’ anonymity. The industry will be watching the Silk Road case closely.

Ulbricht has drawn more support than your average alleged online drug dealer. His lawyer, Joshua Dratel, has represented a number of high-profile terrorism suspects, and Roger Ver, a libertarian entrepreneur, has donated $165,000 to his defense. Libertarian activists and the Electronic Frontier Foundation have expressed concern about the way the government has handled the case. Lyn Ulbricht, Ross’s mother, wants to turn the trial of her son into a referendum on government surveillance. “The defendant and the allegations in this case are secondary,” she told in November. "I know they’re controversial, much of it cannot be defended in terms of, you know, people’s morality or whatever. What’s really important here, and dangerous here, is how the government is operating.”  

There’s a widespread feeling that the Federal Bureau of Investigation is obscuring how it conducted its investigation. In a court filing, the agency said it noticed a weakness in the Silk Road’s website that was inadvertently leaking the IP address of its server. Security analyst Nik Cubrilovic attempted to replicate the problem and couldn’t do so. Cubrilovic thinks the FBI hacked the site to get that information and is giving an intentionally vague explanation to avoid admitting it. “The FBI have good reason to not mention any bugs or forcing the server to do anything, and to pretend that they simply picked up the IP addresses from the wire, since such actions would raise concerns about how lawful their actions in uncovering the IP addresses were,” he wrote in a blog post. 

Dratel already tried to argue that the FBI’s methods against his client violate the constitutional ban on illegal search and seizure, but Judge Katherine Forrest didn’t agree, so Ulbricht’s defense won't be able to raise such questions during trial. Still, information about the FBI’s investigation could come out in the courtroom and change the equation. If Ulbricht is found guilty, the use of this evidence could be the subject of an appeal, says Electronic Frontier Foundation's Hanni Fakhoury. Some observers worry that allowing the evidence to stand could have wide implications for what limits law enforcement will face when it comes to hacking. 

Dratel also fought to bar prosecutors from bringing up certain evidence in court. While Judge Forrest decided against the defense in most instances, she did block prosecutors from citing the availability on Silk Road of such bomb-making books as Homemade C-4: A Recipe for Survival. Prosecutors will be allowed to say they found a copy of The Construction & Operation of Clandestine Drug Laboratories on Ulbricht’s computer.

Others have focused on the idea that Ulbricht could be found guilty of drug trafficking by running a website that other people were using to sell and buy drugs. Generally, websites haven’t been held accountable for the actions of their users. Fakhoury says that Silk Road isn’t a great test case for this issue, given that it was explicitly encouraging drug sales. But he notes that other cases, such as one in which FedEx has been indicted for allegedly helping foster illicit pharmaceutical sales, are closer to the blurred lines and could set a dangerous precedent. “What will be interesting is to see how the government treats more borderline sites,” Fakhoury says.

The purest libertarian argument, put forward by Ver, is that online drug bazaars in and of themselves aren’t such a bad idea. "Many people are making the argument that the platform should not be held responsible for what the users do,” he said in an e-mail. "I agree with this reasoning, but for me the stronger motivating factor is that I think each individual owns their own body and has the absolute right to put whatever they want into it.” 

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