If alleged Silk Road mastermind Ross Ulbricht had awoken on October 1, 2013 and decided to toss his laptop into the San Francisco Bay, he might still be a free man today.
But Ulbricht didn't, and prosecutors in his New York trial seized on the contents of the computer Wednesday, painstakingly wading through screenshot after screenshot of highly incriminating chat logs, journal entries, and expense reports found on it. The material, which even included a citizenship application for the island nation of Dominica, spanned years and appeared to explicitly tie Ulbricht to the dark net marketplace.
Ulbricht was arrested on the afternoon of October 1 while sitting at his laptop in the science fiction section of a San Francisco public library. FBI computer scientist Thomas Kiernan testified Wednesday that a male-female FBI team pretended to have a domestic spat behind Ulbricht, causing their target to rise from his seat. At the time, Ulbricht was chatting online with an undercover Homeland Security investigator who was secretly working for the site's administrator. Before arresting Ulbricht, the agents quickly grabbed his computer, leaving it open and unencrypted, and exposing what prosecutors allege was Ulbricht's secret life as Silk Road's head honcho, the Dread Pirate Roberts.
Among the thousands of pages of chat logs on the computer was one between a user called "sSh" and "myself" — a label auto-assigned in logs by the Pidgin chat client to a person prosecutors allege was Ulbricht.
"May I ask to whom I am speaking?" asked sSH. "A formality, of course."
"dpr, and you are?" the local user replied, using an abbreviation for the Dread Pirate Roberts.
In January 2013, Ulbricht was allegedly chatting with a user called "scout." The woman behind scout would later create the "cirrus" account that Homeland Security Agent Jared Der-Yeghiayan commandeered to infiltrate Silk Road. At the time, she was concerned about the possible legal repercussions of her involvement with the site. Ulbricht allegedly attempted to allay her fears.
"The way I got over it is by looking at the risk/reward," they said. "Put yourself in the shoes of a prosecutor… there's nothing on your laptop for them to use."
Yet Ulbricht's laptop apparently contained meticulous records, and even what appeared to be a backup copy of the entire Silk Road site.
In a journal entry from February 2012, Ulbricht allegedly wrote about conceiving Silk Road. "The idea was to create a website where people could buy anything anonymously, with no trail whatsoever that could lead back to them," the entry read.
"Little by little, people signed up," the author wrote. "Then it happened. My first order. I'll never forget. The next couple of months I sold about 10lbs of shrooms through my site."
In 2010, Ulbricht allegedly grew psychedelic mushrooms in a cabin in Bastrop, Texas — illicit merchandise that later became the first drugs advertised on the site soon after it launched in early 2011. That experience was outlined in an entry read aloud by prosecutor Timothy Howard.
By the time Silk Road was shut down the day after Ulbricht's arrest, investigators say the site, which utilized the anonymizing Tor network, had handled some $1.2 billion in bitcoin transactions, the vast majority of which were drug sales.
Other journal entries found on the computer show the author speaking highly of a user called "Variety Jones," describing the person as a "mentor" who helped resolve coding hiccups and security lapses.
Elsewhere, the diarist recounted recruiting and hiring Silk Road's first staff members. A text file titled "interview_questions," aimed at possible recruits asked, "How do you intend to launder your earnings?"
Ulbricht's defense attorney Joshua Dratel has conceded that Ulbricht started Silk Road, but argues his client gave up soon after on the "economic experiment," handing over the reins to others who later framed him. The horde of data culled from Ulbricht's laptop appears to directly contradict that version of events. In addition to the chat logs and journal entries, expense reports and records of his net worth run without significant interruption from 2011 to the fall of 2013. One journal entry is dated the morning of his arrest.
Agent Kiernan, who kept Ulbricht's computer open and active for several hours after the bust to avoid having it revert to a locked status, said a private PGP encryption key found on the Samsung laptop synced with a matching public key posted on the Silk Road by the Dread Pirate Roberts. The private key was stored in an aptly named "keys" folder.
Nicolas Christin, an assistant research professor at Carnegie Mellon University who focuses on the dark net, said that, though the evidence was damning, the PGP key — a data encryption tool that provides cryptographic privacy and authentication — might be the least of Ulbricht's worries.
"The key could have been shared by several people," Christin told VICE News. "In particular, it could have been passed on from one owner to its successor."
The possibility that multiple users — and multiple people using the Dread Pirate Roberts handle — were in control of Silk Road at various times is central to the defense.
"I am curious to see how they will try to explain the diary away," added Christin. "In theory, files could have been planted on the laptop by somebody else, but demonstrating this convincingly to the jury is going to be tough."
Some of the chat logs took on a tragicomic air in light of the possible life sentence Ulbricht faces for charges that include conspiracy, narcotics trafficking, and money laundering.
In one, a Silk Road staff member calls attention to the situation of a recovering heroin addict who had won a vacation as part of a Silk Road marijuana-themed "420" giveaway. The employee, called "flush," said he thought the trip might cause the user, who he had been personally counseling, to relapse.
"I should have thought more carefully about dropping 4k on an addict," Ulbricht allegedly responded. "Maybe our next prize will be 3 months in rehab."
Another Silk Road staffer worried about a user listing cyanide on the site. Ulbricht allegedly responded that "we want to air on the side of not restricting things," and decided to allow it.
Also included the laptop's labyrinth of folders were scanned images of identifying documents belonging to Silk Road staffers, something Ulbricht is said to have required before hiring them. Prosecutors showed the license of a man named Andrew Michael Jones — also known as Silk Road employee "Inigo" — who was busted for drug trafficking and will testify against Ulbricht.
The laptop revelations came a day after presiding Judge Katherine Forrest threw out key portions of testimony that described federal investigations into former Bitcoin kingpin and Mt. Gox owner Mark Karpeles. Last week, defense attorney Dratel positioned Karpeles as the person who set up Ulbricht and left him "holding the bag."
Dratel objected to the introduction of nearly every screenshot Wednesday, but Forrest overruled him each time.
Kiernan, who will continue on the stand Thursday, has yet to be asked by prosecutors about journal entries said to show Ulbricht attempting to order assassinations.
It's unclear how the defense will attempt to rebut Wednesday's evidence. It's rare for a prosecutor to be presented with a goldmine such as the journals and logs. In that respect, they may support Dratel's claim that Ulbricht was simply too careless to be the famously secretive Dread Pirate Roberts.
One journal entry, however, pointed to a different reason for the record keeping.
"I imagine that someday I may have a story written about my life," it said, "and it would be good to have a detailed account."
Follow Samuel Oakford on Twitter: @samueloakford