Ross Ulbricht and Silk Road: the trial everyone should watch.

Why the Silk Road Trial Matters

Why the Silk Road Trial Matters

The citizen’s guide to the future.
Jan. 13 2015 10:13 AM

Why the Silk Road Trial Matters

Ross Ulbrich will be getting his day in court and everyone will be watching.

Silk Road trial.
An evidence list accidentally published by the court shows the prosecution’s plan to use screenshots from Ross Ulbricht’s seized computer to link him to the Silk Road.

Photo illustration by Slate. Photos by Thinkstock

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Ross Ulbricht is finally getting his day in court—15 months after plainclothes FBI agents grabbed him in the science-fiction section of a San Francisco library and accused him of running the billion-dollar online drug bazaar known as the Silk Road. It’s a day that anyone who cares about crime, punishment, and privacy in the shadows of the Internet will be watching.

If Ulbricht doesn’t take a last-minute plea deal and his trial begins as scheduled in a New York courtroom Tuesday, it will be the most significant case of its kind—in many ways the only case of its kind—to play out in front of a jury. The Silk Road anonymous drug market he’s accused of creating was an unprecedented experiment in online anarchy and black market commerce. And Ulbricht’s insistence until now on taking his case to trial means its fundamental issues will be argued in public.

Ulbricht, 29, faces charges that include running a narcotics, hacking, and money laundering conspiracy, as well as a “kingpin” charge usually reserved for mafia dons and drug lords. The case against him is likely strong; prosecutors already have shown in pre-trial hearings that they caught Ulbricht with his laptop seemingly logged into a Silk Road page called “Mastermind,” showing a detailed accounting of the site’s activities and finances. They’ve also revealed that they found a logbook on his hard drive and a journal that allegedly detailed his day-to-day activities running the site. (Stringer Bell was right, by the way: Don’t take notes on your criminal conspiracy.)


But Ulbricht’s defense team, led by renowned terrorism-case defense attorney Joshua Dratel and financed in part by donations from bitcoin mogul Roger Ver, won’t make it easy for prosecutors. We may see a lively, dramatic and precedent-setting trial. Here are a few reasons to follow it closely.

A Test of Anonymity and Surveillance Online

The Silk Road pioneered a new kind of online marketplace, one that’s open to the public but whose administrators, buyers, and sellers are anonymous, thanks to tools like the software Tor and bitcoin. The prosecution’s case will need to cut through that anonymity to prove Ulbricht is indeed the masked mastermind of Silk Road known as the Dread Pirate Roberts. For the industry of copycat sites that followed the Silk Road, including popular black markets like Evolution and Agora, that makes this trial a case study in the vulnerabilities law enforcement uses to attack the Dark Web’s hidden contraband bazaars and identify the people who run them.

An evidence list accidentally published by the court and spotted by the Daily Dot shows the prosecution’s plan to use screenshots from Ulbricht’s seized computer to link him to the Silk Road and the Dread Pirate Roberts identity. The defense plans to contest the authenticity of that evidence. In pre-trial motions the defense has cited United States vs. Vayner, in which the court ruled last year that some social media screenshots are inadmissible evidence because they too easily can be faked. “To the extent that the prosecution uses screenshots against Ulbricht, the argument will be that you can’t prove that screenshot is what you say it is,” says Electronic Frontier Foundation attorney Hanni Fakhoury. “[Defense attorney] Dratel’s doing his job, which is to raise as many challenges as he can.”


In an order Wednesday, Judge Katherine Forrest ruled against a defense motion to dismiss a trove of digital evidence it contested under the Vayner precedent. But she said Ulbricht’s lawyers could challenge the authenticity of each piece of evidence as it’s introduced. That could provide a series of tests of exactly what kind of materials represent, in the eyes of the court, a provable connection between an individual and his secret online persona.

One of the most controversial questions in the Silk Road case has been exactly how the FBI found the server that hosted the website. The prosecution all but admitted in pre-trial arguments that the FBI hacked into the site—without a warrant—to reveal its IP address and thus its location. Judge Forrest rejected the defense’s Fourth Amendment argument that a warrantless hack is an illegal search and ought to taint subsequent evidence stemming from the FBI’s investigation. But at trial, the defense could question FBI investigators about how they located the Silk Road, and could also repeat that Fourth Amendment argument in an appeal.

Radical Libertarianism on Trial

The Dread Pirate Roberts didn’t see himself as a mere cybercriminal. When I interviewed him in the summer of 2013, he described the Silk Road as, “at its core … a way to get around regulation from the state. If they say we can’t buy and sell certain things, we’ll do it anyway and suffer no abuse from them.” The anonymous, bitcoin-enabled commerce the Silk Road pioneered, he argued, was the beginning of a new era of anarchic markets with no regulatory control:

Sector by sector the state is being cut out of the equation and power is being returned to the individual. I don’t think anyone can comprehend the magnitude of the revolution we are in. I think it will be looked back on as an epoch in the evolution of mankind.

That revolutionary ethos has made the Silk Road and Ulbricht a cause célèbre for certain libertarians and anarcho-capitalists. “If Ross is convicted, the Internet will become a place of fear, and we will be at the whim of state power,” says Julia Tourianksi, an anarchist activist, in a video rallying supporters for a courthouse protest on the morning his trial begins. “The state is testing the waters. If we don’t give them a storm, we consent to our silencing.”

Ulbricht has expressed plenty of radical libertarian rhetoric in his public life. But his defense likely won’t bring up politics, says the EFF’s Hanni Fakhoury, even if he’s convicted and trying to minimize his sentence. “Talking about your motivation for why you commit a crime is not that important legally, unless it negates your criminal intent,” he says. “The judge will be looking for whether Ulbricht shows contrition. … [Politics] is probably a bad strategy.”

That won’t stop supporters from seeing every moment in the trial as another turn in the battle for Internet freedom. Win or lose, Ulbricht has become a martyr for the cause.

A Cryptoanarchist Courtroom Drama


The timeline of events the prosecution will lay out in Ulbricht’s case will be—political and privacy issues aside—one hell of a story. Ulbricht is accused of paying for the murders of six people, including a blackmailer and a potential informant. (Those murders-for-hire aren’t charged in the case. In fact, none of those alleged hits ever seems to have taken place. But a ruling Wednesday from Judge Forrest declares the murders fair game for the prosecution at trial as part of proving Ulbricht’s “conspiracy” charge.)

Glimpses in pre-trial hearings of the journal and logbook Ulbricht allegedly kept tell a story worthy of Breaking Bad: The records describe Ulbricht’s three-year journey from allegedly growing the first psychedelic mushrooms sold on the Silk Road, to the expansion of that digital creation into a booming online drug market and anarchist community, and eventually to the violence Ulbricht is accused of using to defend it. It’s a tale of rebellious ambition, revolutionary ideals, and potentially dark, Faustian bargains.

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