The Silk Road Defendant Didn't Stand a Chance. Would He on Appeal?

Why did Ross Ulbricht's lawyers make such a weak case? 'Perhaps to try and accumulate appeal points,' the judge wrote.

Ross William Ulbricht

Source: NY Daily News

The Silk Road trial came to an abrupt and almost anti-climactic end Wednesday when Ross Ulbricht was convicted on all seven counts he faced for running the online black market. It took the jury less than four hours to reach a verdict.

Ulbricht's defense was also noticeably quick, consisting of less than two full days of testimony, even though his lawyers initially indicated their case would take one or two weeks to present. For its part, the prosecution spent over two weeks piling up evidence that Ulbricht was the mastermind behind the site.

He now faces the possibility of life in prison and is scheduled to be sentenced in May. Joshua Dratel, Ulbricht's lead attorney, says he will appeal. "We believe there were significant errors at trial, including the limiting of defense cross-examination, the preclusion of defense experts, and the exclusion of certain defense evidence in the form of documents and other exhibits," he says.  "The extraordinarily short time the jury spent deliberating for a trial of this length and density demonstrates that these elements had a devastating effect at trial." 

Prosecutors had plenty to work with. Jared Der-Yeghiayan, a Department of Homeland Security Agent, testified about how he had infiltrated Silk Road, getting a job working for the Dread Pirate Roberts, the pseudonymous leader of the operation. The agent eventually set Ulbricht up to be caught in a public library, logged on to his laptop as the Dread Pirate. The two men were chatting online at the very moment Ulbricht was arrested.

A college friend of Ulbricht’s testified that Ulbricht told him he had made the website, a notorious online bazaar used mostly to buy and sell drugs but also to traffic in fake IDs, tools for computer hacking, and other contraband. The prosecutors were able to link Bitcoins that Ulbricht possessed to Silk Road accounts. The laptop he was using at the time of his arrest contained a diary full of damning confessions. 

The defense’s strategy to counter all of this was to admit two basic facts: Ulbricht had founded the site in 2011, and he had been running it in late 2013. But in between, Dratel argued, Ulbricht fled the site and was lured back to it only when the real Dread Pirate Roberts realized the jig was up. Dratel said in his opening statement that he planned to show how things that seemed obvious were actually false.

His plans were repeatedly undermined by the judge’s decision to side with the prosecutor on key points.

Even before the case started, in mid-January, Dratel lost his first major battle. He tried to get the bulk of the evidence thrown out, saying the Federal Bureau of Investigation hadn’t shown that its probe was legal. Many computer experts suspected the FBI wasn’t telling the whole truth when it described how it found the Silk Road’s servers. For outside observers of the case, this was perhaps the most important issue, given its significance for how law enforcement officials conduct digital surveillance in the future. 

But Judge Katherine Forrest said Ulbricht couldn’t claim any privacy rights related to the servers, which were located in Iceland, without admitting he had access to them. He wouldn’t do so, and Forrest barred the defense from discussing any concerns about illegal search and seizure. Before the trial, the Electronic Frontier Foundation's Hanni Fakhoury said that the use of this evidence was potential grounds for appeal. 

The defense was also precluded from capitalizing on one of the most dramatic moments of the trial: the revelation that investigators at one time suspected that the Dread Pirate Roberts was actually Mark Karpeles, the disgraced founder of Mt. Gox, once the world’s largest Bitcoin exchange. If you're looking for gossip from the digital underworld, it doesn’t get much better than this. Prosecutors objected to much of the discussion about Karpeles, though, and Forrest sided with them on almost all points. The juiciest stuff was stricken from the record.

Dratel complained that the revelations came from documents that the prosecution itself had introduced. and claimed that suddenly removing this entire line of argument from his repertoire in the middle of a trial was unfair. His case, he said, was eviscerated. Forrest was unmoved. 

The reason the defense’s case seemed abridged was that the prosecution also objected to Dratel’s plan to use two expert witnesses: Andreas Antonopoulos, a Bitcoin expert, and Steven Bellovin, a computer science professor at Columbia University focused on network security. Forrest sided with the prosecutors, saying Dratel hadn’t given them enough information about the nature of the testimony or enough time to prepare for cross-examination. In a scathing opinion, she admonished the defense for not playing by the rules, saying there were consequences for doing so. 

“Why did the defense choose to proceed as it has?” she wrote. “This court cannot know. Perhaps a tactical choice not to show the defense’s hand; perhaps to try and accumulate appeal points; perhaps something else.” 

A second trial might turn out different if Ulbricht’s lawyers are allowed to pursue the arguments they had planned on and call the witnesses they wanted to. Maybe not, given the weight of the evidence presented against him. 

But the lawyers who ran Ulbricht’s case and the judge who oversaw it seem to agree: The jury didn’t hear the best defense that could have been mounted.