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 behaviour.”

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 legalised, 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 court-room 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, public relations 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.

In his own remarks, Clark didn’t comment on that murder-for-hire conversation—which he at one point claimed had been fabricated by Ulbricht but later conceded was real. Instead, he focused on his benevolent intentions in running the Silk Road, which he argued had saved thousands of lives through its prevention of overdoses from adulterated drugs. At the same time, he acknowledged that at least six people named by prosecutors had in fact overdosed and died from Silk Road narcotics.

“If the Silk Road hadn’t existed, would those people be alive today? Probably yes,” Clark said. “Did we save thousands of lives? Yes, but we took some too.”

He compared his actions to the so-called “trolley problem” thought experiment in ethical philosophy, in which someone must choose which track a train will take when people are tied to both tracks. “It’s not Philosophy 101 for me,” he told the judge. “I pulled the switch.”

Clark and his defence attorney also spent much of their sentencing statements describing the abysmal conditions of his detention over the past several years in Thailand and then a New York jail. His attorney told the court he was traumatized by witnessing torture and sexual assault in a Thai jail, was denied basic health care, and arrived in the US weighing just 93 pounds.

At the Metropolitan Detention Centre in Brooklyn, Clark described corruption and neglect, which led to his falling from his bunk while experiencing vertigo in 2021, breaking his pelvis, and being left to suffer overnight despite his pleas for help.

Judge Stein acknowledged those years of suffering and mistreatment but concluded that he was “not persuaded they afford a substantial reduction” in Clark’s sentence.

Separately, Clark made strange new claims in his statement – without evidence – that he had spent $800,000 of Silk Road’s revenue to buy hacking tools that could be used to de-anonymize users of the dark web engaged in child sexual exploitation and had then provided those tools to the UK and US governments. One Bangkok-based hacker who Clark says sold him a hacking tool, who goes by the handle the Grugq, denied any such sale to Wired.

“I never sold such an exploit and certainly wouldn’t have sold it to him,” the Grugq writes. The judge didn’t appear to factor these unsubstantiated claims into Clark’s sentence, but suggested that he should provide his computer skills to the US government.

Clark’s strange story of hacking paedophiles should perhaps be taken with a grain of salt given his long history of apparent misdirection. Prior to his extradition from Thailand, he made claims of a corrupt FBI agent hunting him and secret information he could provide to the Thai government, ostensibly in exchange for his release – claims which were never borne out or mentioned by his defence prior to sentencing.

In his chats with Ulbricht prior to the Silk Road takedown, too, Clark had a tendency to grandiose ideas. At one point he suggested ways that he might rescue Ulbricht from prison should he ever be identified and arrested.

“One of the things I’d like us to look at investing in is a helicopter tour company … seriously, with the amount of $ (dollars) we’re generating, I could hire a small country to come get you.” he wrote. “And remember that one day when you were in the exercise yard, I’ll be the dude in the helicopter coming in low and fast, I promise.”

No such rescue operation ever appeared for Ulbricht. And no such salvation appears to be coming for Clark either.

“Everybody take a good look,” Clark said at one point during his sentencing statement, dramatically turning to the courtroom’s small audience. “This is probably the last time you see me before I get killed.”

• A Wired report