The FBI agents who arrested Ross Ulbricht in the science fiction section of a San Franciso public library in October of 2013 left nothing to chance. When plainclothes feds grabbed Ulbricht's laptop and put him in cuffs, the prosecution in Ulbricht’s case says he was chatting online with an undercover agent who had infiltrated the staff of Silk Road, the massive online drug market Ulbricht is accused of creating. Now that undercover agent has told his story for the first time. And he’s revealed that just before his fateful conversation with Silk Road’s kingpin, he had been watching Ulbricht from less than a block away.

On the second day of Ulbricht’s trial in a Manhattan courtroom, Department of Homeland Security agent Jared Deryeghiayan told the jury a detailed account of his final conversation with the Dread Pirate Roberts, Silk Road’s owner and Deryeghiayan’s boss for the three months the DHS agent spent as an undercover Silk Road staffer. As part of a coordinated law enforcement effort designed to prove that Ulbricht was the Dread Pirate Roberts and to seize his laptop before he could encrypt its hard drive, Deryeghiayan and a half dozen FBI agents surveilled Ulbricht as he left his apartment on October 1st, 2013, and walked to the Glen Park public library near his home. Then Deryeghiayan struck up a conversation with the Ulbricht over a dedicated chat system set up for Silk Road staffers, the better to catch Ulbricht red-handed in the act of managing the site.

"The plan for the arrest...was to get him into a position where we could have him in a public setting, and I could initiate a chat with him," Deryeghiayan said in response to questions from prosecutor Serrin Turner. "The purpose was that if indeed [the Dread Pirate Roberts] was Ross Ulbricht, we could get his computer in an open, unencrypted state."

Deryeghiayan, an agent based in Chicago, had actually infiltrated the Silk Road nearly two years earlier. He told the court that he had "taken over" and controlled the accounts of many buyers and sellers on the site, presumably users of the Silk Road who had been caught in illegal acts and cooperated with law enforcement to lessen their punishment. As an undercover buyer, he said he made more than fifty purchases of drugs on the site from more than 40 dealers in 10 countries.

Then in late July of 2013, Deryeghiayan says he took over the account of "Cirrus," a moderator on Silk Road's user forums (who had earlier gone by the name "scout") responsible for customer support and cleaning up spam and inappropriate comments in the forum. In that role, he often communicated by encrypted chat with the Dread Pirate Roberts—username: "dread"—via a special chat server called Staff Chat run on the anonymity network Tor. In exchange for ten to twelves hours a day of helping to administer and maintain the Silk Road and its community forums, Deryeghiayan says he was paid about $1,000 a week in bitcoins. (The coins, he says, were immediately converted to dollars and seized by the U.S. government.)

Deryeghiayan says he only learned the name Ross Ulbricht in September, from Internal Revenue Service agent Gary Alford, who had also been investigating the Silk Road. Ulbricht, he told the court "looked like a pretty good match."

A map showing the location of Bello Coffee, where the DHS's Deryeghiayan stalked Ulbricht, and the Glen Park library where he was arrested a few minutes later.

Later that month, Deryeghiayan flew to San Francisco, and on October 1st met up with the New York-based FBI team led by agent Christopher Tarbell. The FBI agents had watched Ulbricht as he worked the day before at a coffee shop near his home called Bello Coffee. So Deryeghiayan says he set up near the cafe with a laptop connected to the Internet via a mobile hotspot, and then went into the cafe to charge his laptop's battery. All the while, he was closely watching the "dread" name on Staff Chat, which remained online.

At 2:47pm, "dread" went offline, Deryeghiayan says, the cue that Ulbricht was leaving his house for his favorite public wifi connection. Deryeghiayan alerted the FBI agents and left the cafe to sit on a bench on the same block.

As Deryeghiayan and FBI agent Tom Kiernan watched from just a few feet away, Ulbricht walked up to the corner with a "small shoulder bag" containing his laptop. He waited for the light to turn green, then crossed and went into Bello Coffee. Thirty seconds later, he left the crowded cafe, seemingly to find a quieter spot, and headed for the Glen Park Public Library just one street north.

The FBI followed Ulbricht into the library, and Tarbell sent an email to the team, telling them to "make sure to pull the laptop first, then arrest," according to Deryeghiayan. He added that the team should "give time to the [undercover agent] to chat [with Ulbricht] before anyone initiates an arrest."

At 3:08pm, Ulbricht opened up his computer at a table in the library, and "dread" came online. With his laptop open and logged on to Staff Chat, Deryeghian walked over to library and up one of its stairwells to a discreet spot. Then he started a carefully planned conversation designed to make sure Ulbricht logged into a part of the Silk Road site designed for moderating comments flagged as spam. ("We were trying to get him online as DPR in the market as well as chatting," Deryeghian says.)

cirrus: hey

can you check out one of the flagged messages for me?

dread: you did bitcoin exchange before you worked for me, right?

cirrus: yes, but just for a little bit

dread: not any more then?

cirrus: no, I stopped because of reporting requirements

dread: damn regulators, eh?

ok, which post?

cirrus: lol, yep

there was the one with the atlantis1

At that moment, Deryeghian say the FBI grabbed Ulbricht's laptop and arrested him. "I sent a message to Tarbell that he should effect the arrest," says Deryeghian. "I was for waiting for a sign...As soon as he said 'oh, which post', I knew he was on the flagged message page." The Dread Pirate Roberts' last words referred to a competing Dark Web drug market known as Atlantis that had mysteriously shut down just a few days earlier.

Deryeghian's account will no doubt be used by the prosecution to demonstrate to the jury that the Dread Pirate Roberts is in fact Ross Ulbricht, the central question of the trial. But in its opening argument yesterday, Ulbricht's defense laid out a narrative in which the Dread Pirate Roberts inherited the site from Ulbricht just a few months after it was created, and then years later set up Ulbricht as the "perfect fall guy." It hasn't yet explained how the "real" Dread Pirate Roberts would have planted evidence on Ulbricht's laptop including a journal and logbook detailing his management of the Silk Road, nor why Ulbricht would logged into the Silk Road's admin page and communicating as "dread" until the moment of his arrest.

Deryeghian, however, is only the first witness in Ulbricht's trial, and has yet to even be cross-examined by the defense. Ulbricht's lawyers will no doubt have their own story about the day of his arrest. His lead attorney Joshua Dratel began on Tuesday by calling attention to the absurdity of Ulbricht using a public library's connection to manage a highly secretive drug empire.

“[The Dread Pirate Roberts] is someone who studiously avoided revealing his identity to anyone on the site…This same person goes to a public library and uses a public Wifi connection?” Dratel asked the jury. “That Ross is DPR is a contradiction so fundamental that it defies common sense.”

1Correction 1/15/2015 6:35pm: An earlier version of this post contained mistranscriptions of the chat between cirrus and the Dread Pirate Roberts, including attributing the final line to the wrong name.