MANHATTAN (CN) - No more than two days after trial began, an undercover agent testifying against alleged Silk Road founder Ross Ulbricht completed one of the government's central tasks by tying him to the website's elusive leader: the Dread Pirate Roberts.
Named after a character in "The Princess Bride," a William Goldman book adapted into a beloved 1987 movie, the Dread Pirate Roberts led an anonymous online marketplace that takes its name from the fabled road connecting Asia to the Middle East.
While prosecutors describe the website as a criminal underworld, its advocates defend it as a mechanism to free their economic lives of government and corporate interference.
The loftier depiction of the website took a hit on Wednesday when Department of Homeland Security agent Jared DerYeghiayan showed jurors a message from the Dread Pirate Roberts, also known by his initials DPR, describing himself as leading an "international narcotics organization."
On Thursday morning, DerYeghiayan gave a blow-by-blow account of Ulbricht's arrest on Oct. 1, 2013, inside San Francisco's Glen Park library.
Moments before his FBI colleague Tom Kiernan effected the arrest, DerYeghiayan said that he drew Ulbricht onto the "dread" account though a ruse he pulled at a nearby Cafe Bello just down the street from the library.
A "few moments" after Kiernan entered the library, DerYeghiayan said that he signed onto a staff chat through the account of a former administrator named "Cirrus." DerYeghiayan had posed as "Cirrus" for months before the arrest and even collected a Bitcoin salary of roughly $1,000 per week.
In the initial moments of their chat, "dread" asked "cirrus" whether the latter still sold and exchanged Bitcoins online, and "cirrus" said that he stopped because of "reporting requirements," a transcript of that chat shows.
"Damn regulators, eh?" dread quipped.
After some more small talk, cirrus told dread to look at a flagged message on Silk Road, which was spam by a competitor "atlantis."
Kiernan, the FBI agent, took pictures of this chat on Ulbricht's screen in the library, as well as the flagged "atlantis" message, evidence showed on Thursday.
When clicking backing on Ulbricht's Tor browser, DerYeghiayan said that he found an administrative screen of Silk Road with "mastermind" on the URL. DerYeghiayan did not previously know that the page existed, he said.
After Ulbricht's arrest, "Dread" never responded to "Cirrus," he added.
Agents uncovered another connection after obtaining a search warrant for Ulbricht's house, where they found handwritten messages on two crumpled, yellow leafs of paper. Neither of the papers had the words "Silk Road" on them, but both contained language identical to that which appeared in Dread Pirate Robert's postings about the website's new buyer's rating system.
Under the new language, a four-star rating meant "Solid, would recommend," Dread Pirate Roberts announced on Aug. 11, 2013.
One of the crumpled papers in Ulbricht's home described a four-star rating the same way, the agent testified.
Ulbricht's attorney Joshua Dratel began his cross-examination shortly before afternoon recess, and immediately tried to cast doubt upon the connection between his client and the storied online moniker.
During opening arguments, Dratel unveiled the defense position that Ulbricht was a "fall guy" for the "real" DPR, who took over the website and gave it a darker turn.
His first questions related to a so-called PGP key, short for "Pretty Good Privacy," an encryption method meant to verify that the identity of a person who sent a message.
Dratel asked DerYeghiayan whether the PGP key associated with Dread Pirate Roberts could be shared, sent or stolen. Each time the witness replied yes.
DerYeghiayan also agreed that the fictional Dread Pirate Roberts is not one person, but assumes many identities to assure what Dratel called the "continuity" of his legacy.
In fact, DerYeghiayan agreed that he told his superiors in August 2013 that he believed that the Dread Pirate Roberts account had changed owners in April, and that it was often frustrating to keep track of the online identities of his targets.
DerYeghiayan wrote an email in June 2013 likening this problem to the iconic Abbott & Costello skit.
"Sheesh, who's on first again?" he wrote.
Other cross-examination questions aimed to demystify and destigmatize the encryption technologies discussed in the case. Not all of them belong to any criminal underworld, Dratel noted, emphasizing their use among Chinese and Iranian dissidents.
Tor, which is short for The Onion Router, originated in U.S. Naval research before becoming a popular tool for military, journalists, law enforcement and average citizens, he noted.
Shortly before court took a lunch recess, Dratel also said that his client's arrest caused an astronomical spike in the value of Bitcoins. The digital currency also associated with cryptography went from a little more than $100 per coin to $1,200.
"People who were holding Bitcoins at the time of Mr. Ulbricht's arrest could really make a killing, right?" Dratel asked.
DerYeghiayan agreed that people would hold onto their currency after that event.
Dratel also challenged the idea that the leaders of Silk Road, a "sophisticated" enterprise, would be so lax in matters of security as his client is accused of being.
"Are they the type of people who would leave handwritten notes in a wastebasket?" he asked.
"I don't know," DerYeghiayan replied.
Cross-examination continues this afternoon.
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