DerYeghiayan had prepared well for the bust. By chatting with Ulbricht and having him log into the Silk Road administrative site, he had clearly shown that Ulbricht was acting as "Dread Pirate Roberts." The prosecution displayed for the jury screenshots of both of their chat screens side-by-side, showing they were the same conversation. And "Dread Pirate Roberts" never reappeared online once Ulbricht was jailed.
The law enforcement officers also found additional evidence back at Ulbricht's home, for which they had a warrant and searched once Ulbricht was in custody. There, they found crumpled pieces of paper in a trash can with terms such as "buyer wait," and "sales volume," which echoed the terminology "Dread Pirate Roberts" had then recently used in a discussion thread with fellow administrators, about revamping the site's customer and vendor rating system.
Through questioning of DerYeghiayan, the prosecution also made the case that Ulbricht had been "Dread Pirate Roberts" for the entirety of Silk Road, by examination of the forum messages posted by under that name, which had all been signed with the Pretty Good Privacy (PGP) encryption software.
Because the jury may not be technically inclined, DerYeghiayan explained in detail how messages that have a PGP signature can be verified as having come from the individual holding the private encryption key that signed the message. He said that forum messages from "Dread Pirate Roberts" going back to 2011 had all been signed with the same key, inferring that they had all come from the same individual.
While the Glen Park bust of Ulbricht had pretty clearly shown him to be logged on and working at that time as "Dread Pirate Roberts," further questioning from Ulbricht's attorney quickly showed the limits of how much could be concluded from the association.
One of the chief defenses Ulbricht's attorneys plan to use in this case will be to argue that while Ulbricht might have founded Silk Road, and did log on as Dread Pirate Roberts,he was not the only person using the account, and, in fact, had little to do with its sophisticated large-scale operations.
In cross-examination questioning with DerYeghiayan, Ulbricht's lawyer Joshua Dratel had pointed to where DerYeghiayan, in August 2013 internal correspondence, expressed concern that the "Dread Pirate Roberts" account might have changed hands at some point. It felt to DerYeghiayan, working undercover as Cirrus, like he was talking with a different "Dread Pirates Roberts" than he was earlier.
In fact, the entire investigative team at times felt that many of the Silk Road administrative accounts were operated by different people, and that managers of the site might have been logging in under multiple accounts, DerYeghiayan admitted under questioning. In one e-mail brought to the jury's attention by Dratel, DerYeghiayan even exclaimed in frustration in one e-mail "Who's on First?"
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