U.S. Agent Wondered If Silk Road Had Multiple ‘Dread Pirates’

A U.S. agent who worked undercover on the Silk Road black-market website told jurors he considered the possibility, just weeks before the arrest of Ross William Ulbricht, that the identity of the site’s anonymous boss, “Dread Pirate Roberts,” might have changed during the investigation.

Prosecutors claim Ulbricht, 30, started the site and ran it until his arrest in October 2013. Jared Der-Yeghiayan, a Department of Homeland Security special agent, testified today in Ulbricht’s criminal trial that in August 2013 he wondered whether the real person behind the screen name had changed 16 months earlier.

“There was always a level of distrust about who you were talking to,” Der-Yeghiayan said under questioning by Ulbricht’s lawyer, Joshua Dratel.

Dratel was seeking to show that his client gave up control of the site within months of starting it and was then set up as a “fall guy” by the new operators.

Ulbricht faces as much as life in prison if convicted of conspiracy and Internet drug trafficking in the trial in Manhattan federal court, which started Tuesday and may last as long as six weeks.

Der-Yeghiayan testified that agents maintained at least a dozen accounts on the illicit website, taking over the online identities of cooperating witnesses including a woman who went by the name “Scout.” The agent said investigators often didn’t know who they were dealing with. In a June 2013 message, Der-Yeghiayan expressed frustration over the uncertain identities on Silk Road.

“Sheesh, who’s on first?” he asked.

Drug Trades

The government claims more than 1 million drug sales were done through Silk Road, with customers using bitcoins to buy drugs and other illegal goods. The site barred ads for child pornography, weapons of mass destruction, counterfeit currency, murder-for-hire and stolen credit cards, Der-Yeghiayan said.

In testimony today and yesterday, Der-Yeghiayan told jurors he worked as a Silk Road site administrator for several months as part of the government’s investigation, communicating online with Dread Pirate Roberts and coworkers known as Libertas, Samesamebutdifferent and Inigo, without knowing their real identities. Der-Yeghiayan said he used the name Cirrus, concealing the fact that he was a law-enforcement agent.

Ulbricht took his online identity from a character in the 1987 film “The Princess Bride,” according to prosecutors. In the film, “Dread Pirate Roberts” is a name taken by a series of men who pass the identity to chosen successors and retire.

Unique Key

Der-Yeghiayan testified that Silk Road’s Dread Pirate Roberts used a unique cryptographic key consisting of a long string of characters, to identify himself to users of the site. In his questioning, Dratel suggested the key could be passed from one person to another, like a car key or file key.

Silk Road was operated on the Tor network, which routes communications through a series of computers to allow users to be anonymous.

Prosecutors claim Ulbricht tried to arrange the murders of at least six people who threatened his multimillion-dollar business. No murders were actually carried out. Ulbricht is charged separately in federal court in Baltimore for one of the alleged plots.

The case is U.S. v. Ulbricht, 14-cr-00068, U.S. District Court, Southern District of New York (Manhattan). The murder-for-hire case is U.S. v. Ulbricht, 13-cr-00222, U.S. District Court, District of Maryland (Baltimore).

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