On October 2, 2013, Ross Ulbricht was arrested at the Glen Park branch of the San Francisco Public Library, his laptop open and connected to the library wi-fi. The government claims he is the Dread Pirate Roberts, the infamous kingpin of the Silk Road, an online black market for drugs and other illicit goods. Ulbricht’s trial began today, after many delays over the last few months.
The prosecution said in their opening statement that he was “literally caught with his fingers at the keyboard, running the Silk Road.” And that was just the beginning: the laptop was not only logged into the Silk Road, it contained chat logs and other files, including a journal. Between these files, the information seized from the Silk Road server, and various drug dealers turned witness, Assistant U.S. Attorneys Serrin Turner and Timothy Howard seem confident they can prove beyond a reasonable doubt that Ross Ulbricht is the Dread Pirate Roberts.
But Ross Ulbricht’s lawyers tell a different story. Although they concede that Ross Ulbricht did create the Silk Road as “a kind of an experiment, an economic experiment,” they say he handed the reins of the site over to someone else—someone who, under the same pseudonym that Ross Ulbricht had used, the Dread Pirate Roberts, had then committed the crimes that Ulbricht is now being charged with. When the other DPR (or multiple other DPRs) found out that law enforcement was onto them, they tricked Ulbricht into getting involved with the Silk Road again. According to the defense, the real Dread Pirate Roberts is still out there, and the prosecution’s case is merely “a digital contrivance that left [Ulbricht] holding the bag when the real operators knew their time was up.”
Joshua Dratel, Ulbricht’s attorney. Illustration by Susie Cagle.
The defense’s theory of the case is a deft form of legal jiu-jitsu, taking the numerous technical faux pas of Ross Ulbricht and some of his inexplicable behaviors (documented extensively in the media), and using them to bolster the assertion that Ulbricht could not be the criminal mastermind described in the indictment. Their theory might square away with some of the odder details in the case. The Dread Pirate Roberts’s early operational security failures may make more sense if there are multiple DPRs of varying technical competence. In the heyday of the Silk Road, the Dread Pirate Roberts was notoriously secretive when dealing with his own lieutenants. Yet Ross Ulbricht used his own personal Gmail address when making forum accounts to promote the Silk Road in its early days. Note, also, that in an interview with Andy Greenberg in 2013, the Dread Pirate Roberts claimed to have inherited the site from a predecessor.
Regardless, initial reactions from some experts have been extremely skeptical. Nicholas Weaver, a researcher at the International Computer Science Institute (ICSI) points to the hoard of bitcoins seized from Ross Ulbricht (valued somewhere between 18 and 20 million dollars at the time of the seizure). It’s not just a suspicious amount of money: the Bitcoin blockchain is an open ledger that publicly records all transactions. “The defense attorney better hope Ulbricht really was a brilliant Bitcoin trader, because that defense is easy to shred otherwise,” says Weaver. “Bitcoin is insanely traceable. The Silk Road bitcoins are well known, not just the ones seized but the entire cloud of Bitcoins. Add in the known purchases from law enforcement, and it becomes downright trivial to create the ‘history cluster’ that is Silk Road.”
The defense states that Ulbricht was merely a speculator in Bitcoin, making his fortune off the huge fluctuation in the market that occurred from 2011 to 2013. (By the end of 2011, 1 BTC was about $2. In October 2013, when Ulbricht was arrested, 1 BTC was about $140).
So far the prosecution doesn’t have anything positive to say about cryptographic technologies like Bitcoin or Tor. Timothy Howard’s opening statement made much of how Bitcoin enables anonymous transactions. He also repeatedly called Tor “a dark and secret part of the Internet.” In response, the defense pointed out that bitcoins are traceable by design, and that Tor was created by the U.S. government “for legitimate means.”
For the defense, the matter of the Dread Pirate Roberts’s identity is essentially obscured by the Internet’s very nature. “The Internet is an unusual place,” Ulbricht’s attorney said in his opening statement. “People can create and fabricate profiles of themselves and others in ways we couldn’t imagine 20 years ago.” On the Internet, “not everything is at it seems… you don’t know what or who’s on the other side [of the screen]. You don’t know if they’re telling the truth or whether they are what they present themselves to be.”
As for the physical, offline Ross Ulbricht, his appearance in court today was the first time the public had glimpsed him since his bail hearing in November. When he first entered the courtroom, he seemed in good spirits although he looked sallow and pale. Tall, thin, and clean-cut, the 30-year-old appeared in a navy blue blazer, khaki pants, and tie. He resembled an overgrown prep school student. Once seated, Ulbricht turned to smile and wave at his parents, giving his mother a thumbs-up while silently mouthing reassurances. But when his mother left the room during jury selection some hours later, he looked to be on the verge of tears.
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