Here’s What to Expect from the Silk Road Trial

After spending the past year in a Brooklyn federal prison, Ross Ulbricht will finally head to a New York City court on Tuesday where prosecutors will try to prove he is the mastermind behind the anonymous billion-dollar online drug market Silk ​Road.

FBI agents arrested Ulbricht, now 30, in the science fiction section of a San Francisco public library in October 2013, charging him with creating and operating the illegal site under the pseudonym the Dread Pirate Roberts.

"Silk Road emerged as the most sophisticated and extensive criminal marketplace on the internet," the government said in court filings after Ulbricht's arrest. "The website was used by several thousand drug dealers and other unlawful vendors to distribute hundreds of kilograms of illegal drugs and other illicit goods and services to well over a hundred thousand buyers worldwide."

Ulbricht, a mild-mannered, libertarian-leaning Texan, is being tried on charges of narcotics trafficking, distribution of narcotics by means of the internet, narcotics trafficking conspiracy, continuing criminal enterprise, conspiracy to commit and aid and abet computer hacking, conspiracy to traffic in fraudulent identification documents, and money laundering conspiracy. He faces a maximum potential sentence of life in prison.

Ulbricht is also accused of soliciting the murder-for-hire of multiple people he believed had threatened Silk Road. Those charges won't be directly inclu​ded in the case but are allowed to be used as evidence for the conspiracy charge, according to Wired.

His lawyer, Joshua Dratel, has a history of defending tough cases, including those of a Guantanamo Bay inmate and an al Qaeda affiliate.

In order to get a conviction, the prosecution will have to prove that the Dread Pirate Roberts was running the Silk Road and that Ulbricht was the Dread Pirate Roberts. The government has compiled a wealth of evidence to do this, a list of which was inadvertently released by the court and published by th​e Daily Dot.

When Ulbricht was tackled and arrested in the library, his laptop remained open and connected to a Silk Road master page with an overview of his activity on the site, according to t​he FBI. The computer also allegedly contained a diary detailing the creation and maintenance of Silk Road, as well profits from the enterprise collected in the semi-anonymous internet currency Bitcoin.

The prosecution plans to use screenshots of this evidence in the case. Ulbricht's attorney tried to have that evidence ​dismissed under the precedent of United States vs. Vayner, a case that says screenshots are too easily faked to be used as evidence. Judge Katherine Forrest ruled ag​ainst the motion to dismiss this evidence, but said the defense can challenge the evidence on a case by case basis during the trial.

Ulbricht's defense is being funded in part by Bitcoin mogul Roger Ver, who says he is supporting Ulbricht in part because he opposes the war on drugs.

"I donated money to the case because I think that each individual owns their own body, and has the absolute right to put whatever they want into it," he told Motherboard. "The police, judges, and jail guards who lock people in cages for ingesting substances without the permission of strangers, are the ones committing evil and need to stop.

"If Ross Ulbricht is DPR and helped facilitate these voluntary interactions, he is a hero for helping provide the technology that allowed peaceful people to ignore the violent threats from strangers calling themselves politicians and law enforcement. If Ross is falsely accused, and was not DPR, then he deserves the best defense money can buy. Either way, he deserves the support of anyone who is opposed to the war on drugs."

The case will address many issues that have never before been argued in a US court, and many believe it will set precedents for privacy and the extent to which the government holds people responsible for content on their sites and servers.

One of the biggest issues in the case is whether the FBI found the website's server illegally through hacking, which the defense argued constituted an illegal search under the Fourth Amendment. However, Judge Forrest rejected that a​rgument on a technicality in October. She said Ulbricht did not substantially demonstrate the servers belonged to him, therefore he couldn't claim the hacking was a privacy violation. Admitting the servers belonged to Ulbricht seems like an admission of guilt by the defense, but Forrest said he still could have done so.

"Defendant could have established such a personal privacy interest by submitting a sworn statement that could not be offered against him at trial as evidence of his guilt (though it could be used to impeach him should he take the witness stand)," Judge F​orrest wrote. "Yet he has chosen not to do so."

Julia Tourianksi, an anarchist who will protest outside the trial with her activist group Brave the World, said there is a lot at stake.

"In the larger sense, this trial is testing the waters for how much the state can step on our freedoms, and how fast they can move towards closing the internet and making it a closed space where people are worry about liability and not able to have freedom of conversation and freedom of thought."

Tourianksi said she worries the prosecution will intentionally pick an older pool of jurors that does not have a grasp on some technical aspects of the case. Because of this, she said her group will hold signs outside the courthouse for the duration of the trial reading, "Life in prison for a website?" to remind the jurors of the consequences of their decision. (Update: In follow-up conversations, Tourianski made additional statements to Motherboard said that she misspoke and that the group planned general protests unrelated to jurors. She added that the group's signs will now read something to the effect of "Say no to violence, take the Silk Road.")

Her involvement in the Bitcoin community also motivated her support for Ulbricht, she said.

"Together with free speech, having a site where anonymous payments can be made with Bitcoin is a vital step towards financial and economic independence without being infringed on by the state," she said. "But the state is recklessly oppressing these rights, and we need to do something and show that we care."

However, Nicholas Weaver, a researcher at the International Computer Science Institute, said the larger precedents being discussed surrounding the case are overblown.

"I don't see this trial as being the big thing on internet freedom the defense has been making it out to be in public," he said. "Silk Road was not just a passive listing service, but an escrow service, a reputation service, and a dispute resolution service, and thus it was actively involved in every drug transaction."

However, Weaver does say the gravity of the charges brought against Ulbricht imply the FBI is making an example of him.

"[The case] shows if you want to run a Silk Road style operation, move to Sochi, because if the FBI can identify you, they will arrest you, they will throw you in jail and throw the book in on you," he said. "If you notice the charges, many of the drug charges specify quantities of drugs that carry very specific mandatory minimums––and that's deliberate. If Ulbricht is convicted, he's looking at a long time in jail."

The extent to which the case establishes precedents will play out as the trial gets underway this week. Dratel said it's "hard to tell" how long the proceedings will last, but he estimates they will take around four weeks.

Motherboard will be covering the trial as it unfolds, so check back here for updates.