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Silk Road Trial Begins; Ulbricht Denies Being 'Dread Pirate Roberts'

By Mark Wilson, Esq. on January 14, 2015 | Last updated on March 21, 2019

The trial of Ross Ulbricht, the alleged founder of the underground website Silk Road, began in Manhattan on Tuesday.

We can eliminate the "alleged" in front of "founder" because Ulbricht, who had always denied involvement with Silk Road, conceded in court that he did found the website, which trafficked predominantly in illegal drugs. But Ulbricht claimed he abandoned it after a few months.

As You Wish

It sort of seemed like an open-and-shut case. Federal agents tracked Ulbricht to a public library in San Francisco, where he was arrested while his laptop was logged in to a Silk Road administration page.

Ulbricht is charged with running Silk Road under the pseudonym "Dread Pirate Roberts," after the character in "The Princess Bride." (The more oblique reference to the character is that Dread Pirate Roberts isn't always the same person; it's a title assumed by different people.) Prosecutors claimed that 95 percent of the activity on Silk Road involved illegal drugs.

In his opening statement, however, Ulbricht's attorney Joshua Dratel said that the real Dread Pirate Roberts was still out there, somewhere. As proof, Dratel noted that a new Silk Road popped up a few weeks after Ulbricht's arrest. Though acknowledging that Ulbricht founded the site, Dratel said he did so only as an economic experiment.

An Internet Rorschach Test

The Silk Road case means different things to different people. Fourth Amendment enthusiasts would love to know how the FBI found the server that hosted the website. The FBI claimed that it used a security hole in the CAPTCHA on the login page to figure out the server's IP address, which wouldn't require a warrant; Ulbricht's lawyers, on the other hand, insisted that didn't make sense. The FBI's response? Essentially, "We don't know exactly what we did because we don't keep records of our own activity."

For fans of online privacy, Silk Road raises the question of whether any online activity can be truly anonymous. Silk Road was accessible only through Tor, the anonymizing proxy service, and yet somehow the Feds figured out where the server was and who operated it. (Of course, it helps that Dread Pirate Roberts was blabbing a lot to a fellow administrator, who turned out to be an undercover agent. If no one on Tor knows that you're a dog, then neither does anyone know you're an FBI agent.)

And finally, for Internet rights organizations like the Electronic Frontier Foundation, the case could shift the line demarcating when website operators are liable for illegal activity. "There has to be some question about where does the line get drawn. And the line drawing is done by prosecutors who are making judgment calls about what site operators are criminally responsible for what is happening on their site," EFF attorney Hanni Fakhoury told NBC News.

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