Silk Road Journal Found on Ulbricht's Laptop: 'Everyone Knows Too Much'

On Wednesday, prosecutors in the Silk Road trial began to lay out the wealth of evidence found on the laptop taken from accused kingpin Ross Ulbricht when he was arrested in a San Francisco library in October 2013.

The evidence presented by prosecutor Timothy Howard was the most comprehensive and damning thus far, including more than a thousand pages of chats between the site's pseudonymous operator Dread Pirate Roberts and Silk Road administrators. Also entered into evidence was a journal that dates back to at least 2010 describing the creation and operation of the site.

FBI computer scientist Thomas Kiernan, the second witness in the trial, testified about the day Ulbricht was arrested and the evidence gathered from his laptop.

"We waited for an opportunity to arrest the defendant with his laptop open to avoid encryption," Kiernan said, showing photos he took of Ulbricht's seized Samsung laptop screen on the day of his arrest. The photos showed Ulbricht was logged into a "mastermind" administrator panel as the Dread Pirate Roberts, also known as DPR.

Howard then began to ask Kiernan about the flood of evidence seized from the computer, including spreadsheets detailing Silk Road assets, scanned images of legal identification of various administrators of the site, the PGP public and private keys associated with DPR, a backup of the Silk Road website saved as .php files, weekly activity reports, and more.

One folder on the laptop also included an application for a form of paid citizenship for the Caribbean island of Dominica, filled out with Ulbricht's personal information, including his address, email, phone number and relatives' names.

The journal and chats found on the laptop paint a picture of a both naive and brazen budding black market mastermind.

"This whole thing has been on a wing and a prayer," he wrote at one point. "Besides basic PHP and HTML, I've learned everything on the fly."

Early in Kiernan's testimony, he read from Ulbricht's alleged journal a description of the site's origins.

"I began working on a project that had been on my mind for over a year," an entry from 2010 said. "The idea was to create a website where people could buy anything anonymously with no trail."

The entry then described how, after announcing Silk Road on some Bitcoin forums and elsewhere online, more and more people began to sign up. Ulbricht allegedly rented a cabin in Texas to grow the first products sold on the site: 10 pounds of psychedelic mushrooms.

"My first order, I'll never forget it," he said. "I was so excited I didn't know what to do with myself."

After the "infamous Gawker article," he said, referencing a 2011 article about Silk Road, the site became more and more popular.

"Silk Road will become a phenomenon," Ulbricht allegedly wrote in the journal. "People will ask me about it not knowing I was the creator."

He described the struggle of keeping the site secret while working another job and maintaining a relationship with his girlfriend. At one point, Ulbricht allegedly wrote, he partially confessed his secret to someone named Jessica.

"I felt compelled to reveal myself to her. She knows I work with Bitcoin, which is terrible," he wrote. "Everyone knows too much, dammit."

In 2011, Ulbricht allegedly wrote that he planned to expand Silk Road into "a brand people can trust and rally behind." A journal entry outlined plans for "Silk Road chat, Silk Road Exchange, Silk Road Credit Union, Silk Road Market, everything."

The journals and chats outlined an ongoing struggle of trying to do good while running an underground drug venture. In one 2012 chat, DPR debated with another adminstrator over whether the sale of cyanide on Silk Road should be restricted. Ultimately, he decided to allow it saying, "We want to air on the side of not restricting things. It is a black market, right? :)"

In another chat, a Silk Road employee expressed worry about a large money prize being given to a vendor with a known heroin addiction.

"He has been trying to quit, but Silk Road made it kinda tough," the admin said. "Fuck, what are we doing?" DPR replied. "Should have thought more carefully about dropping $4k on an addict. Maybe our next prize will be three months in rehab."

Records found on the laptop showed DPR paid employees anywhere between $900-$2,500 a week to help operate the site. One employee asked how to convert the payment discretely, to which DPR replied "I would avoid Mt. Gox if possible."

In one eerily ironic exchange, the Dread Pirate Roberts sought to assuage the worries of the user "scout," who was in the running to become an administrator but had doubts about getting found out.

"The way I look at is risk/reward," DPR wrote in the chat. "Put yourself in the shoes of a prosecutor trying to build a case against you, what evidence would they have? Sure, someone could stand behind you without you realizing it. But when you look at the chance of us getting caught, it's pretty small."

In his opening statements, Joshua Dratel, Ulbricht's lawyer, said he will be able to explain everything that was found on that laptop. If the evidence found on Ulbricht's computer does, as the defense argues, belong to Ulbricht, it appears that he acted as his own worst enemy, laying out all of the evidence against himself in handily labeled files and folders and documenting every step in his journal.

"I imagine someday, I will have a story written about my life, and it would be good to have a detailed account of it," Ulbricht allegedly wrote.

The public PGP key for DPR was saved as "DPR_key," the private key was saved in a separate folder named "keys," in a file named "silkroad.asc." The site logo, a green camel, was saved as "logo_highres." As promised, the prosecution showed a screenshot of the registration information from SilkRoadMarket.org, the name "Richard Page," next to a folder found on Ulbricht's computer called "aliaces" that listed the same name and information.

Kiernan's testimony will likely continue for another couple of hours on Thursday, according to prosecutors, after which the defense will have its chance to rebut the evidence in its cross-examination.