​Attorneys for Silk Road mastermind ask for retrial

Supporters of Ross Ulbricht, the alleged creator and operator of the Silk Road underground market, stand in front of a Manhattan federal court house on the first day of jury selection for his trial on January 13, 2015 in New York City. (AFP Photo / Spencer Platt)
Lawyers for the California man convicted of operating the Silk Road website say their client deserves a retrial because the United States government obtained evidence using unlawful surveillance, then waited months to present it to the defense.

The motion, filed on Friday in the Southern District of New York, takes aim at how prosecutors produced and presented evidence used against Ross Ulbricht of San Francisco before a jury last month found him guilty of seven charges related to his involvement with the online marketplace, including counts of narcotics and money laundering conspiracies.

Ulbricht, 30, has not been sentenced yet, but faces the possibility of life behind bars when a ruling is handed down later this year for his part in operating the underground bazaar accessible on the so-called 'dark web' through the anonymous Tor network. In the meantime, though, his defense team now insists that the court reconsiders an earlier motion to suppress certain evidence – namely that gathered by a Silk Road server in Iceland targeted by law enforcement surveillance – because Ulbricht’s attorneys say it was obtained illegally.

In all, the latest filing contains a three-point argument for a retrial in the case against Ulbricht: Because the government “failed to provide exculpatory material and information in a timely manner,” his attorneys say, Ulbricht was denied his Fifth Amendment right to due process and a fair trial. Additionally, they argue that the material that was eventually provided to the defense, albeit delayed, raised new questions about the surveillance done on the Silk Road server that was not adequately addressed during trial. Thirdly, Ulbricht’s lawyers say the court needs to take into consideration the testimony of a noted bitcoin expert that was never delivered during the initial trial.

According to Ulbricht’s attorneys, the defense’s case was hindered largely on account of the prosecution’s failure to deliver evidence on time. Thousands of pages pertaining to the government’s case were provided to the defense only days before trial, Ulbricht’s attorneys wrote, and dozens of new exhibits were entered during the last week of proceedings.

Included within the evidence disclosed to Ulbricht’s counsel before trial, the motion reveals, were 5,000 pages worth of documents pertaining to the government’s first witness, Homeland Security Investigations Special Agent Jared Der-Yeghiayan. The trove of details, Ulbricht’s attorney say, was “produced less than two weeks prior to trial – and, in some instances, 30 months after the information was memorialized,” and was among the dozens of documents provided to the defense ahead of trial. Approximately 230 new exhibits were added by the government after the deadline for submissions in December, Ulbricht’s team says, and dozens more were modified or removed without warning before the trial got off the ground in mid-January.

Had the defense been given ample time to examine the evidence, Ulbricht’s attorneys argue, then they may have been able to more successfully wager to fight to suppress evidence gathered through surveillance of the Silk Road server.

“In particular, text messages between SA Der-Yeghiahan and a confidential informant,” the defense argues, “…demonstrate unequivocally that the government was conducting warrantless Tor network surveillance on a Tor exit node that would have enabled the government to capture information about the source and content of the data passing through the Tor exit node.”

In one of those conversations, the confidential informant allegedly told the federal agent that he was “100 percent running, logging and recording” information from the Tor node as it left the supposedly anonymous network.

“In the context of Mr. Ulbricht’s suppression motion, this surveillance raises some novel Fourth Amendment issues, and also provides further evidence that the government discovered the Internet Protocol (hereinafter “IP”) address for the Iceland server ending in ‘.49’ through warrantless Tor network surveillance,” Ulbricht’s team says.

Additionally, Ulbricht’s attorneys say that further texts between Der-Yeghiayan and the informant detail plans for the government to launch a distributed denial-of-service attack, or DDoS, against Silk Road, “with the express purpose of ‘listening’ to the Silk Road servers.”

“While it is not clear from the context of the text messages whether the government ever performed the DDOS attack discussed, it is known, from evidence in the record, that DDOS attacks on the Silk Road servers did occur, including one during the Spring of 2013, when the government was actively seeking to find the Silk Road servers, and during which period the government claimed to determine the IP address of the Iceland server by other means.”

Coupled with the inability of an acclaimed bitcoin expert to testify at Ulbricht’s trial as planned, lead attorney Joshua Dratel wrote that the case against his client could have turned out quite differently, and hopes the court will agree to a retrial. Attempts to accomplish as much aren’t necessarily new, however, with Wired’s Andy Greenberg acknowledging that Dratel called for a mistrial no fewer than five times over the course of this year’s month-long trial.

Prosecutors have until April to respond to the defense’s motions, and US District Judge Katherine Forrest is expected to sentence Ulbricht on May 15, lest she agrees to order a retrial.