The 2013 SF Sting That Captured Ross Ulbricht, Silk Road Operator Pardoned by Trump

While President Trump’s pardons for Jan. 6 rioters were the most public of his first day, he also granted clemency the next day to a man who operated an international dark web marketplace, partly from his home in the Bay Area.

Ross Ulbricht was living in San Francisco when he was discovered as the creator of Silk Road, an online black market used to facilitate the trade of more than $200 million worth of illegal drugs and goods with bitcoin in the early 2010s. The complex sting operation that got him arrested happened in an unlikely spot: the science fiction section of the city’s Glen Park library.

Until this week, Ulbricht had been serving two life sentences, plus 40 years, in a high-security prison in Colorado after failed appeals. For years, libertarians and cryptocurrency enthusiasts had championed his release, adopting the rallying cry “Free Ross” online and at conferences. Trump said Tuesday on his social media platform Truth Social that he told Ulbricht’s mother he had pardoned her son “in honor of her and the Libertarian Movement, which supported me so strongly.”

“The scum that worked to convict him were some of the same lunatics who were involved in the modern-day weaponization of government against me,” he wrote.

Ulbricht’s arrest came in October 2013, when Department of Homeland Security agent Jared Der-Yeghiayan sat outside Cafe Bello on Diamond Street and used a secure chat app to ask his “boss” — screen name Dread Pirate Roberts — to check on a flagged message sent by a Silk Road user, according to a transcript of his testimony during Ulbricht’s 2015 trial.

After a two-year investigation, Der-Yeghiayan had infiltrated the site and was working as a support staff member under the screen name Cirrus.

He had first discovered Silk Road working at O’Hare Airport in Chicago, investigating mail seized for illegal drugs, he told the jury. In June 2011, he started noticing packages with just one or two ecstasy pills in them.

They had commercial envelopes, printed sticker labels and were addressed to multiple different addresses across the U.S. — all of which he said was unusual for parcels containing such small quantities of drugs. Month over month, the airport’s drug seizures were increasing, and so were similar packages. In October, a colleague told him about a new underground website, Silk Road.

“I found it was a market that was similar to an online market that was similar to, like, Amazon, for instance, that had items for sale that were mostly illegal in nature that I could see,” Der-Yeghiayan recalled during his testimony. “Drugs and various other things.”

Der-Yeghiayan said he started going on the marketplace, which could only be accessed through the dark web and disguised users’ identities and locations. He placed over 50 orders from different sellers throughout the investigation, he said, and received them in envelopes matching the strange ones at O’Hare.

His time browsing Silk Road also led him to a separate website, he testified: a forum that Silk Road’s operator, Dread Pirate Roberts, used to post updates and that buyers and sellers also used to chat and review purchases.

In July 2013, Der-Yeghiayan bought the screen name of a support staff member who had been working for Dread Pirate Roberts. He said he went by Cirrus and became a moderator with greater access to Silk Road’s marketplace and forum, as well as a private staff chat with its shadowy operator. He would work 10-hour days cleaning up forum discussions and looking over flagged messages sent on the marketplace.

In his testimony, Der-Yeghiayan said a team of investigators connected Ulbricht as the possible user behind Dread Pirate Roberts around the same time after finding posts he made about Silk Road — under another fake name — on separate online forums.

However, the team still needed to link him to Dread Pirate Roberts directly and gain access to his laptop, which they suspected was being used to run the hundred-million-dollar site.

So Der-Yeghiayan and his team traveled to San Francisco, he said, and camped out outside a cafe they discovered Ulbricht often worked at, just a few blocks from the brown multi-family home where he was living.

Around 3 p.m. on Oct. 1, they saw Ulbricht leave his house and walk in and out of Cafe Bello, looking for a seat, before giving up and crossing the street to the Glen Park library.

A few minutes after Ulbricht walked up the stairs to the library’s main floor, Der-Yeghiayan spotted Dread Pirate Roberts becoming active on the Silk Road staff messaging site.

“As soon as I saw him come online, I then initiated a chat with him, trying to ask him to go into a specific place on the Silk Road — into the admin panel to log in to check something,” Der-Yeghiayan said.

Once Der-Yeghiayan knew Ulbricht had logged onto the Silk Road marketplace, he said other agents moved in, pulled his laptop out of reach and handcuffed him.

Der-Yeghiayan went into the library, where another agent took photos of the computer with his Blackberry.

“I saw on the computer screen the same chat that I had with Dread Pirate Roberts minutes earlier,” he said.

Later, the team found sheets of yellow note paper in Ulbricht’s garbage can that appeared to be related to Silk Road, and clicking back through the browser he had pulled up to help Der-Yeghiayan, they were taken to a web address that referred to him as Silk Road’s “mastermind.”

Silk Road was shut down the next morning, and Ulbricht was ultimately convicted of distributing narcotics through the Internet, conspiracy to commit money laundering, conspiracy to traffic fraudulent identity documents and other charges. A seller on Silk Road has claimed that he arranged five murders-for-hire for Ulbricht, but the Department of Justice said in 2023 that it did not have evidence that those murders took place.