Ross Ulbricht’s Trial According to Opposition of Post-Trial Motions

On April 3rd 2015, the U.S. Attorney’s Office for the Southern District of New York filed the opposition for Ross Ulbricht’s post-trial motions. Ulbricht requested a new trial by arguing the Government was late in disclosing “Brady material,” and also wished to suppress evidence from the Silk Road server. The opposition declared both contentions as meritless. These filings give great insight into pretrial information obtained on Ulbricht by the prosecution, as well as substantial trial occurrences for both the prosecution and defense.


Ross Ulbricht was arrested on October 2nd 2013 outside a San Francisco Public Library. He was alleged to be “Dread Pirate Roberts,” the owner and creator of the hidden Silk Road marketplace. The marketplace allowed users around the world to purchase illegal drugs, guns, and other wares or services with Bitcoin. Due to the bearing of such allegations, Ulbricht was dealt a septuple of charges on August 21st 2014 with narcotics trafficking, narcotics trafficking by means of the Internet, conspiring to commit narcotics trafficking, engaging in a continuing criminal enterprise, conspiring to commit or aid and abet computer hacking, conspiring to traffic in fraudulent identification documents, and conspiring to commit money laundering.


The Government first called Special Agent Jared Der-Yeghiayan of HSI (Homeland Security Investigations) to testify regarding his undercover activity working as “cirrus” on the Silk Road support staff. He claimed to be in frequent communication with “Dread Pirate Roberts” through Silk Road’s messaging as well as the private employee chat. Der-Yeghiayan was able to take advantage of this direct access by chatting with “DPR” as agents prepared to arrest Ross Ulbricht. Der-Yeghiayan was then able to view the open chat he had with Ulbricht as “cirrus” on the seized laptop. According to the U.S. Attorney’s Office for the Southern District of New York, “He had been caught red-handed.”

FBI Computer Scientist Thomas Kiernan testified on behalf of the Government for his witness of Ulbricht’s arrest and laptop contents. Kiernan found personal journals, thousands of pages of chat logs, Silk Road expense spreadsheets, a maintenance log file, Dread Pirate Roberts’ private key, and Bitcoin wallets with 144,000 bitcoins worth approximately $18 million at arrest time. The logs spanned the entirety of Silk Road’s operation, and the private key was used for PGP encryption in conjuction with Dread Pirate Roberts’ public key to sign and verify Silk Road site notices. There’s no way to forge a functional PGP private key to correspond to a public key.

The next substantial witness was Richard Bates, a former friend of Ulbricht who testified on behalf of the Government. Bates stated he was repeatedly asked for programming advice by Ulbricht throughout the initial development of Silk Road. Despite initially telling Bates that the site was “top secret,” Ulbricht eventually showed him the website. In November 2011, Ulbricht told Bates he sold the site to another entity, however seized chat logs show this to be a lie told to Bates and Ulbricht’s ex-girlfriend.

Special Agent Gary Alford of the IRS testified he identified Ulbricht as “Dread Pirate Roberts” from early clearnet (standard internet) forum posts for publicising Silk Road’s initial launch. After tracing the clearnet account to one of Ulbricht’s email addresses, “Dread Pirate Roberts’” chat logs about travel plans matched Ulbricht’s emails and facebook posts. This aided in confirming “Dread Pirate Roberts” and Ulbricht as the same person. Additionally, these ties were found throughout the span of Silk Road’s operation, additionally confirming Ulbricht was in managing Silk Road throughout it’s operation.

HSI Special Agent Dylan Critten next offered testimony regarding the U.S. Customs interception of nine fake driver’s licenses. The licenses were for six different states and three foreign countries, all depicting Ulbricht. Critten came to Ulbricht’s identity during a controlled delivery of the fake identification. During the delivery, Ulbricht explained to Critten that “hypothetically” anyone could purchase a fake id or “anything else” from “Silk Road.” Critten had never heard of Silk Road, nor was involved with the Silk Road investigation. Silk Road files later corroborated the purchaser of the identification in question asked for “highest quality ID…” allowing him to “pass airport security” and “get through being pulled over by a cop.” Pursuing a similar line, Ulbricht later attempted to obtain citizenship on a Caribbean island.

The Government’s final testimony came from Ilhwan Yum, a former FBI Special Agent. Yum claimed the blockchain shows almost 90% of all Ulbricht’s bitcoins came directly from wallets belonging to Silk Road over many months. In a Silk Road operations log file, Dread Pirate Roberts noted he “moved storage wallet to a local machine,” the local machine being Ulbricht’s personal laptop.

Ulbricht’s defense opened by admitting he created Silk Road, but “handed it off to others” who later framed him. This showed similarities with the lie told to Ulbricht’s former friend and ex-girlfriend. Next, during Special Agent Der-Yeghiayan’s cross-examination, the defense pursued questioning regarding Mark Karpeles and Anand Athavale, two early “Dread Pirate Roberts” leads. Neither lead yielded substantial evidence regarding either’s involvement, and the defense was unable to provide any new evidence while attempting to create reasonable doubt as to Ulbricht’s overall guilt. After “one damning piece of evidence after another,” the jury came to a guilty on all count verdict after three-and-a-half hours.


Ulbricht argues for a new trial due to late disclosure of “Brady material.” The material in question are details from the investigations of Mark Karpeles, Anand Athavale, and DEA Special Agent Carl Force. Ulbricht’s laptop showed he was the one to lease a server from Kalyhost, Karpeles’ hosting company. Anand Athavale was a lead due to similarities with “Dread Pirate Roberts” in language and libertarian economics on the  “DPR” reading list, but this is as far as the similarities went. For this material to be considered “Brady material,” it must be exculpatory, have been suppressed by the Government, and be material enough to produce a different verdict. According to the Government’s opposition, Ulbricht can’t establish any of these three elements.

Ulbricht also argues for the suppression of evidence from the Silk Road server. To suppress this evidence, Ulbricht would have needed to show privacy interest in the server in due time which he did not. Special Agent Der-Yeghiayan, who made the statements in question, was additionally not involved in this part of the investigation. The Government’s opposition believes this suppression to be meritless.