Silk Road

In 2011, Jared Der-Yeghiayan, a special agent with Homeland Security Investigations in Chicago, began collecting intercepted packages from the Chicago airport that contained various drugs. After a few months of collecting hundreds of packages, he visited one of the recipients and found that the drugs were ordered from an online shop on the dark web, called Silk Road. He told Jared that anyone could access the site from the dark web, connect with a dealer, and have the drugs shipped right to their home.

The site was named Silk Road after the historical trade route network that connect Europe to East Asia, initially known for trading silk and other goods.

Throughout 2011, Silk Road was being investigated independently by Homeland Security offices, the Federal Bureau of Investigation, the Drug Enforcement Administration, and single officers of other government organizations; everyone was racing to be the first to find the person in charge, that went by the alias Dread Pirate Roberts. The name Dread Pirate Roberts came from the film and novel The Princess Bride, in which the title is passed down from one criminal to the next to keep their identities anonymous, yet their name known and feared by others. The public became aware of the site after Adrian Chen posted an online article about the site, titled “The Underground Website Where You Can Buy Any Drug Imaginable;” Chen even spoke to the creator through the site to gain more information. Senators and political figures held press conferences demanding that the site be shut down, which only brought more traffic to the site worldwide.

By 2013, Silk Road claimed to be making sales of up to $1.3 million every week. The owner of the site, and the individual buyers and sellers, were anonymous because 1) they were on the dark web, where their transactions were encrypted and IP addresses couldn’t be traced, and 2) the transactions were made using untraceable Bitcoins, which was fairly new at the time the website went live in 2011. Similar to an eBay purchase, Silk Road would take 3-12% from each transaction made, which would make the creator an unknown millionaire by this time.

The FBI had agents working undercover in the site as buyers, some even took control of seller accounts to get closer to the creator. DPR would respond to all inquiries, even from the media, but nobody could get personal information from him. The FBI and DEA arrested one of DPR’s top employees, “chronic pain,” an alias for Curtis Green, to question him about the site, even forcing him to partake in an elaborate scheme to fake his own torture and death; their plan was to get DPR to trust another user on the site, “nob” who was an undercover DEA agent posing as a dealer and hitman on the site. DPR began ordering hits from nob to eliminate untrustworthy sellers or scammers, which he felt it was necessary to protect his community.

The investigation carried on for two years when Gary Alford, a young special agent with the Internal Revenue Service, was also assigned to the case to attempt to trace the transactions from the site. In his investigating, he Googled Silk Road to see what had been posted about the site before 2011, when the first article hit mainstream media. He found a few blog sites where a user named “altoid” was boasting about a new site that sold different strains of mushrooms. Alford read through every post that altoid made online and found a post where he asked for programming help for a new site and listed an email featuring the name Ross Ulbricht. This breakthrough initially went unnoticed because it was inconclusive, but Alford investigated Ulbricht’s further.

At this time, the FBI’s cybercrime unit was able to locate the server used to house Silk Road. It was encrypted and routed to Iceland, but they were able to trace the administrator’s log in site to an internet café in San Francisco, Bello Café. FBI agents and Gary Alford from the IRS compared notes of possible suspects. Ross Ulbricht became the prime suspect, as he was living in San Francisco at the time and had links to various usernames that were found throughout the investigation.
Jared Der-Yegiayan, the first agent to find evidence of Sillk Road, joined the FBI team to help catch Ulbricht while working on the site. The agents were able to locate Ulbricht’s apartment and observe him as he walked to the Glen Park Library down the street. There were agents stationed at every corner, in the coffee shop he frequented, and in the library. They waited for him to settle in the library and open his computer before staging a distraction. Two agents sat behind Ulbricht and staged a fight to distract him while a third agent quickly grabbed his computer as he turned around. They successfully collected the laptop while it was open in the administrative section of the site, which only DPR had access to, and was able to do so before Ulbricht could force a shut down or encrypt his computer.

Ross Ulbricht was born in Austin, Texas and earned a bachelor’s degree in physics from the University of Texas, and a master’s degree in engineering from Pennsylvania State University. He held libertarian views and openly questioned government authority. Ulbricht’s goal in creating Silk Road was to “sell drugs in a secure and predictable way, we will eliminate the violence of obtaining drugs by traditional methods.” He also felt that individuals should be able to consume drugs without government intervention. In an online forum he also stated, “what we are doing is more important than my insignificant life… it’s about how human beings organize and relate to one another.”

Ulbricht was 29 when he was arrested and faced charges for drug trafficking and murder for hire for Green and four other individuals, though no bodies were ever found. Ultimately, he was tried as the “kingpin” of a criminal enterprise, conspiracy to commit money laundering, computer hacking, and traffic narcotics. The jury took only three and a half hours to deliberate and he was sentenced to life in prison.

If you’re interested in learning more, A&E has a documentary on this story, called Silk Road: Drugs, Death and the Dark Web. Deep Web is another documentary, narrated by Keanu Reeves, that focuses on the arrest and trial of Ross Ulbricht. CaseFile has a three-part podcast series about the case from the perspective of the site’s creator. There is also a novel by Nick Bilton, titled American Kingpin.