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Ross Ulbricht Didn’t Create Silk Road’s Dread Pirate Roberts. This Guy Did

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More than 14 months after his arrest, Ross Ulbricht has been convicted of being the Dread Pirate Roberts, the masked figure who ran the Silk Road’s unprecedented online supermarket for drugs. But the man who first created that mask—and in many ways served as Silk Road’s mastermind just as much as Ulbricht—remains a mysterious figure, and one who by all appearances walked away unscathed from his involvement in the Silk Road’s billion-dollar drug operation.

As Ulbricht’s trial unfolded over the last month, one character appeared again and again in the chat logs prosecutors pulled from the laptop seized from Ulbricht at the time of his arrest: a man calling himself Variety Jones, and later, Cimon.

In the past year and a half U.S. law enforcement have arrested Ulbricht, three of his Silk Road staffers and even the administrator of a second Silk Road, but no law enforcement agency has publicly recorded capturing anyone using Jones’ pseudonyms. Yet based on Ulbricht’s chat logs and secret journal, Jones served as nothing less than Ulbricht’s “mentor,” advising the Dread Pirate Roberts closely on everything from managing the site’s dealers to hiding his money offshore to threatening enemies with real-world violence.

“[He] was the biggest and strongest willed character I had met through the site thus far,” Ulbricht wrote in a 2011 journal entry.

He has advised me on many technical aspect[s] of what we are doing, helped me speed up the site and squeeze more out of my current servers. He has helped me better interact with the community around Silk Road, delivering proclamations, handling troublesome characters, running a sale, changing my name, devising rules, and on and on. He also helped me get my head straight regarding legal protection, cover stories, devising a will, finding a successor, and so on. He’s been a real mentor.

To the average Silk Road user, Variety Jones was just a high-volume marijuana seed dealer, who took great pains to please his customers and ship his product the same day as their order. But behind the scenes, Jones may have had some sort of ownership, partnership or investment in the Silk Road. He’s not included in the list of salaried staffers found in Ulbricht’s accounting files. Yet over the anonymous and encrypted instant messaging system Torchat, he discussed with Ulbricht every inside detail of the market, from the site’s sales statistics to its org chart of employees.

When Ulbricht told Jones that he had revealed his Silk Road secret to both a programmer friend and to his ex-girlfriend, it was Jones who came up with Ulbricht’s Dread Pirate Roberts nickname. Ulbricht couldn’t even remember exactly what role the Dread Pirate Roberts had played in the film The Princess Bride. Jones explained that the Dread Pirate was a handle passed down from person to person, the perfect cover story for creating the illusion that Ulbricht had handed off ownership of the Silk Road if he were ever caught.

“You need to change your name from Admin, to Dread Pirate Roberts,” Jones wrote in an early 2012 chat with Ulbricht. He said that he had given the idea 12 hours of serious thought. “Start the legend now…Clear your old trail – to be honest, as tight as you play things, you are the weak link from those two [previous] contacts.”

Variety Jones’s relationship with Ulbricht had begun in late 2011, when he alerted Ulbricht to a hackable flaw in the site’s use of bitcoin and then started advising him on other technical upgrades. “He quickly proved to me that he had value by pointing out a major security hole in the site I was unaware of,” Ulbricht wrote in his journal. “We quickly began discussing every aspect of the site as well as future ideas. He convinced me of a server configuration paradigm that gave me the confidence to be the sole server administrator and not work with someone else at all.”

Jones remained Ulbricht’s closest confidant and problem solver for the next two years of the site’s existence. The chat logs between the two that prosecutors used as evidence in Ulbricht’s trial extended to more than a thousand pages. Ulbricht asked for Jones’ input in tasks as small as editing the text of warnings he sent to misbehaving sellers, or writing the advertisement for Silk Road’s annual 4/20 sale. Jones served as a penetration tester, searching out security vulnerabilities in Silk Road code written by its employees. And he even acted as a kind of PR consultant, warning Ulbricht not to speak with a Vice Magazine reporter who asked for an interview. “Nobody has ever regretted not doing an interview; lots of folks have regretted doing one,” Jones wrote.

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