The week of March 8, 2015

The looming question after the Silk Road trial

By Patrick Howell O'Neill

A pile of new hundred dollar bills makes quite an impression in a criminal trial.

The jury in the trial of Silk Road mastermind Ross Ulbricht sat rapt in attention, fixated on government evidence number 917A: a photo of $1,000 in crisp notes in an ad promising money-laundering services for the top drug dealers on  the infamous anonymous black market. Ulbricht, charged with drug trafficking and continuing a criminal enterprise, could only sit and watch the spectacle unfold.

The problem is that this piece of evidence misled the jury—and the government knew it.


Prosecutors spoke only briefly about 917A, instead letting the jury soak in the visual while they read back only the ad’s most salacious text.

“$10,000 delivered to your doorstep in the form of 100 $100 bills (or U.S. bills of your choosing),” prosecutor Timothy Howard read to the jury. “You will be mailed genuine U.S. currency that has not been altered or linked to criminal activity.”

The Silk Road trial was full of little moments of deception.

The catch here is subtle enough that a juror almost certainly wouldn’t have notice it.

The advertisement listed is dated Sept. 30, 2013. That’s just two days before Ross Ulbricht was arrested and FBI shut down Silk Road. The seller, nicknamed “rickrossgold,” has a small gray zero next to his name, meaning he’d never received any feedback for selling an item on Silk Road. No one from the black market’s tight-knit community had ever heard of him, and the biggest money launderers operating on Silk Road at the time never shipped this kind of cash.

The government allowed the jury to believe they were looking at Silk Road’s greatest money launderer. In fact, the exhibit is essentially a fake—just another brush stroke in the prosecutors’ damning portrait of Ulbricht.

The Silk Road trial was full of little moments of deception like this, some far more significant than what Howard pulled off with the $100 bills.

The defense lost nearly every legal battle they faced. After a four-week trial, Ulbricht was found guilty on seven felony charges and now faces life in prison.

In unknown and hostile legal terrain, Ulbricht never had much of a chance to put up the defense he wanted to in trial. It’s been called “the trial that wasn’t” by Forbes legal analyst Sarah Jeong.

Deep Web is a political statement very much in the style of Dread Pirate Roberts himself.

Deep Web, a new documentary that premieres at SXSW and then on the Epix channel in the spring, is intended in part to be the defense that Ulbricht never got a chance to put forward in court.

Directed by Alex Winter, who’s responsible for the excellent Downloaded documentary about the rise and fall of Napster, Deep Web thoroughly questions the government’s story in a way that is extremely intriguing and entertaining.

But while Deep Web centers on Silk Road, it’s really about radical Internet freedom. Amir Taaki, a famous British-Iranian hacker who laid the software foundations for a more robust successor to Silk Road, opens the film with a manifesto that sets the tone.

“The fascists, they have the resources,” he says. “We have imagination. We are making the tools to take back our sovereignty. When we make a giant fuck you to the system; it’s breaking the stranglehold on the tools used against us.”

Cue the cyberpunk soundtrack.

While sitting in the courtroom during the Silk Road trial, I met half a dozen major studio Hollywood types aiming to bring the blockbuster story to television and movie screens over the next few years. Winter beat them all by securing the cooperation of the Ulbricht family and coming out with his film months before anyone else.

When it comes to legal questions, Deep Web doesn’t have a lot of answers. Instead, it asks key questions that were legally muted during the criminal trial or often deemed irrelevant in the court of public opinion. In the absence of answers, these questions are what’s left in the arsenal.

Winter argues that Silk Road potentially reduced drug-related violence, pointing to scientific studies to make his case, and makes a compelling case against the war on drugs. Near the center of it all lies the legal question that may make a difference in court one day: How did the police find the Silk Road?

Deep Web, a new documentary that premieres at SXSW and then on the Epix channel in the spring, is intended in part to be the defense that Ulbricht never got a chance to put forward in court.

As far as the jury knows, Ulbricht’s site was found because a lucky federal agent happened upon his name after using Google and searching through archives to find a few bread crumbs—Ulbricht’s name associated with accounts that first advertised Silk Road.

In fact, contrary to what was presented at trial, the police found Silk Road at least eight months earlier, when the server hosting the anonymous website was located in Iceland and copied for an investigation involving federal agencies across the U.S.


But how it all really happened—what crack exactly led to the location of the server and then the breaking of the investigational dam—is known only by the police. All the answers federal agents have offered have been shot down by the information security community. Security consultant Nik Cubrilovic told Wired that the government’s story “just doesn’t make sense technically,” a sentiment repeated by many security professionals.

We’re left with more questions than answers: Why was a file on Ulbricht’s laptop modified after he was arrested? How did Dread Pirate Roberts, the alias used by the admin of Silk Road, find out about the federal investigations headed his way?

Deep Web’s access has limits. It features a brief interview with lead defense attorney Joshua Dratel, but there’s no doubt he’s playing it close to the chest, as he has since Ulbricht’s arrest. And as a legal strategy, it makes some sense. He’s currently building a case for appeal, so trying his case in a documentary would be premature.

Deep Web is a political statement very much in the style of Dread Pirate Roberts himself. Using masterfully articulate hackers like Amir Taaki and Cody Wilson, the man most famously behind the 3D-printed gun, Winter puts together a treatise that would seem right at home on the Silk Road forums.

“I don’t want to say he was a hero,” Wilson says to close out the film, “but he was willing to do what most libertarians aren’t.”

Photo via Deep Web