The Silk Road Defense: This Guy Is No Black Market Mastermind

Ross Ulbricht's lawyer says he was an idealistic and naive kid who got caught up with professional criminals and used as a fall guy

Supporters of Ross Ulbricht, the alleged creator and operator of the Silk Road underground market, in front of a Manhattan federal courthouse on the first day of jury selection for his trial on Jan. 13.

Photographer: Spencer Platt/Getty Images

Yes, his lawyer acknowledged in federal court that Ross Ulbricht started the Silk Road website that would in its brief heyday become the Amazon of illegal drugs. But he wasn’t a kingpin who oversaw hundreds of millions of dollars' worth of black market transactions. No, his lawyer insisted, Ulbricht was an idealistic and naive kid who got caught up with professional criminals and used as a fall guy once the Silk Road empire was doomed. 

“Silk Road was Ross’s idea, and he created it,” defense attorney Joshua Dratel declared on Tuesday during his opening statement. But Ulbricht’s intention was more to create a libertarian marketplace than an expansive online drug bazaar. “It’s a kind of experiment, an economics experiment," Dratel said, "and after a few months it got too stressful." 

Ulbricht, 30, has always maintained his innocence but it hasn’t been clear how he would argue for it. After all, when he was arrested in a San Francisco public library in October 2013, he had his laptop open to the Silk Road administrator's page. On the computer were diaries outlining the conception of Silk Road and its operation, according to prosecutors, as well as $18 million in Bitcoin. The haplessness of Ulbricht's arrest only underscores his complete lack of the savvy needed to run an operation like Silk Road, his lawyer explained. The defense will argue that the character on trial in Manhattan—the Dread Pirate Roberts, nom de Internet of the Silk Road's mastermind—is still out there somewhere. 

The Silk Road trial has promised to be both an important look at online crime and anonymity, as well as a great tale. Those who packed the federal courthouse on Tuesday got a bit of both. Timothy Howard, one of the prosecutors in the case, started his opening statement by describing "a dark and secret part" of the Internet with salacious details: 1 million drug deals had been completed on Silk Road, worth over $200 million, before it was shut down. Prosecutors claim that Ulbricht came up with the idea for Silk Road in 2009, built the website, and then advertised it by mentioning it in various drug-related chat rooms. The first products on the site: hallucinogenic mushrooms that Ulbricht allegedly grew himself. Prosecutors also claim that Ulbricht eventually attempted to resort to violence to maintain his power. If the defendant didn't enjoy the trappings of wealth, the government argues, it was only because he planned to lay low before escaping to the Caribbean.

The prosecution’s first witness, a special agent with the Department of Homeland Security, began seizing envelopes containing small numbers of Ecstasy pills in the fall of 2011. While the agency occasionally captured contraband being shipped through the mail, these envelopes were different. Envelopes with a few pills were almost always isolated events; in this case, however, agents found batches of identically packaged shipments making it clear that a sizable commercial operation had begun. DHS confiscated 3,600 envelopes over the next two years and arrested a number of dealers involved with the site. Information from those arrests helped the feds set up an employee account at Silk Road, which in turn allowed the government to communicate directly with the Dread Pirate Roberts. 

None of the Silk Road Jurors Read News on the Internet

The first day of a trial expected to last for more than a month saw the first instance of what promises to be a numbing task of explaining to jurors the rather esoteric technology used in the case. Prosecutors launched into a basic explanation of Tor, a tool for anonymous Internet browsing needed to access Silk Road, at about 4:30 p.m. on Tuesday. Several jurors were visibly droopy-eyed at this point. 

One technical point elided in Howard's remarks was the means by which investigators uncovered the location of Silk Road's servers and Ulbricht himself. This was a controversial point in pretrial hearings, with Ulbricht’s legal team claiming that much of the evidence should be excluded unless the FBI could explain how it was obtained. Judge Katherine Forrest instead told jurors that they should assume all evidence was obtained legally.

Lawyers from both sides of the case and the judge agreed that jurors wouldn’t need any specific technical knowledge to figure this case out. But it was impossible not to notice that Ulbricht isn’t quite being tried by his peers. During the jury selection process, not a single candidate said he or she had heard of Silk Road or had any particular knowledge of cybersecurity. Only a single potential juror explicitly claimed to get her news from the Internet; she didn’t make the cut. The final jury is evenly split at six men and six women, and only two are anywhere near Ulbricht’s age.

The defendant showed up in court looking preppy and comfortable in a dark jacket and khakis. He was engaged with his legal team, participating in huddles about which jurors to challenge. He also turned around periodically to smile and nod at his family during slow moments in the trial. At one tedious point near the end of jury selection he swiveled in his chair and feigned a big yawn. 

Dratel started his opening statement with a fatherly gesture toward Ulbricht, standing up from his chair and grasping his client by both shoulders. He then proceeded to talk about Ulbricht as a child who had gone astray but shouldn’t be punished too harshly for mistakes he didn’t quite understand. In large part, however, Dratel agreed with the prosecution: The Dread Pirate Roberts was a clever and sophisticated online criminal who knew how to cover his tracks and use ruthless tactics. But Ulbricht clearly wasn’t that person, according to his lawyer. Why would a criminal mastermind run his empire from the science fiction section of the public library? If Ulbricht was so vital to the online drug trade, how did Silk Road’s successor websites emerge just weeks after his arrest? 

Ulbricht's defense will argue that he fled Silk Road after things got out of control, soon after its creation. But about a month before his arrest, Dratel claimed, the people running the site learned that law enforcement had identified them. To avoid punishment, they reached out to Ulbricht and persuaded him to take on an administrative role—leaving him holding the bag. 

Then there’s the matter of the $18 million in Bitcoin found on Ulbricht’s computer when he was arrested. Dratel claims this virtual fortune came not from taking a commission on hundreds of millions of dollars' worth of drug deals, but from placing what turned out to be a great bet on Bitcoin when it was practically worthless. Dratel promised to show that the amount of money that Dread Pirate Roberts should have made through the site would dwarf anything Ulbricht was found holding. 

Explaining how a multimillion-dollar fortune is a pittance is just one of the counterintuitive narrative threads that Dratel is going to have to make convincing to jurors. But that’s what should make the next month so interesting. “This case, to a large extent, is about the Internet and the digital world,” said Dratel, "where not everything is at it seems.” 

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