Nearly 10 years ago, the sprawling dark-web drug market known as the Silk Road was torn offline in a law enforcement operation coordinated by the FBI, whose agents arrested the black market's boss, Ross Ulbricht, in a San Francisco library. It would take two years for Ulbricht's second-in-command—an elusive figure known as Variety Jones—to be tracked down and arrested in Thailand. Today, a decade after the Silk Road's demise, Clark has been sentenced to join his former boss in federal prison.
In a Manhattan courtroom on Tuesday, Roger Thomas Clark—also known by his online handles including Variety Jones, Cimon, and Plural of Mongoose—was sentenced to 20 years behind bars for his role in building and running Silk Road. Clark, a 62-year-old Canadian national, will now likely spend much of the rest of his life incarcerated for helping to pioneer the anonymous, cryptocurrency-based model for online illegal sales of drugs and other contraband that still persists on the dark web today. The sentence is the maximum Clark faced in accordance with the plea agreement he made with prosecutors. 
Clark “misguidedly turned his belief that drugs should be legal into material assistance for a criminal enterprise,” Judge Sidney Stein said in his sentencing statement. “These beliefs crossed over into patently illegal behavior.”
Stein added that Clark was “clear-eyed and intentional” in his work as Ulbricht's “right-hand man” in the Silk Road's operations. “The sentence must reflect the vast criminal enterprise of which he was a leader,” Stein said.
In his own statement, Clark said that his work on the Silk Road had always been motivated by his political belief that drugs should be legalized, and the hundreds of millions of dollars' worth of dark-web drug sales he helped to facilitate were safer than drug deals that took place in the physical world. He argued in his sentencing statement that the site helped reduce violence in the drug trade, and that the Silk Road's ratings and reviews prevented the sale of adulterated drugs that would have caused greater harm.
“I just kept preaching to myself ‘harm reduction.’ That's how I got to sleep at night,” Clark told the judge, standing before a sparse audience in the courtroom looking thin and gaunt in baggy khaki clothes. “I'm proud and ashamed at the same time.”
Clark was, as prosecutors noted in their memo arguing for the two-decade sentence, more than a lieutenant on the Silk Road. He served as the site's security consultant, PR adviser, and even a kind of executive coach and friend to the site's boss, Ulbricht. Clark, who Ulbricht initially encountered as a marijuana seeds dealer on the market, was “the biggest and strongest-willed character I had met through the site thus far,” Ulbricht wrote in his journal.
“He has advised me on many technical aspect of what we are doing, helped me speed up the site and squeeze more out of my current servers," Ulbricht wrote. “He also 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.”
Clark was pivotal in key moments of the Silk Road’s history—including a particularly dark incident when he and Ulbricht resorted to violence, which loomed large in Clark’s sentencing. Clark played a crucial role in convincing Ulbricht that it was necessary to commission the murder of one of his employees who he believed had betrayed him and stolen bitcoins from the market. “At what point in time do we decide we’ve had enough of someone's shit and terminate them?” Clark wrote to Ulbricht at one point following the discovery of the theft, as recorded in chat logs that were recovered from Ulbricht's computer after his arrest. “We’re playing with big money with serious people, and that’s the world they live in.”
After Ulbricht agreed to have the staffer killed—in a bizarre turn, his death was instead faked by US federal agents investigating the Silk Road—Clark told Ulbricht that he had made the right move. "If you had balked, I would have seriously re-considered our relationship," he wrote. “We’re playing for keeps, this just drives it home. I’m perfectly comfortable with the decision, and I’ll sleep like a lamb tonight, and every night hereafter.”
Countering Clark's claims of interest in “harm reduction,” assistant US attorney Michael Neff pointed to those comments as evidence of Clark's “complete disregard for human life,” as he put it in Tuesday's sentencing hearing. For Clark, “the question of whether to end another man's life was simple and stress-free,” Neff told the judge in the prosecution's sentencing statement.
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