Silk Road mastermind: drug kingpin or libertarian ideologue gone astray?

[Update: Ross Ulbricht was sentenced to life in prison without possibility of parole.]

On Friday, US District Judge Katherine Forrest will sentence Ross Ulbricht, the operator of the “deep web” drug bazaar the Silk Road. Mr. Ulbricht, who was found guilty in February of narcotics, hacking, and conspiracy in connection with Silk Road’s operation, faces 20 years to life in prison. The sentence hearing will be held Friday in New York.

In a 16-page letter requesting that Ulbricht be given “a lengthy sentence, one substantially above the mandatory minimum”, prosecutors asked the judge to send a message with Ulbricht’s sentencing, claiming that it would deter others from following in his footsteps, Wired reported.

But while some say that Ross Ulbricht was a hardened criminal intent on lording over an illegal drug market that sold over $1 billion of nefarious merchandise, others who observed the operation closely say that Ulbricht’s Silk Road was a community based on libertarian ideologies and a commitment to reduce the violence inherent in the drug trade. Money, they say, was a secondary motive, a means to measure success.

“People think of the Silk Road as a place where drug addicts and drug dealers commune just to do business. And it certainly was that. But there was also a real ideological, political community, and a really tight knit one,” says Andy Greenberg, the only journalist to chat online with the Dread Pirate Roberts, the pseudonym for the Silk Road operator, and a regular observer of the underground marketplace.

“They saw what they were doing as a kind of like, the beginning of a revolution, and freeing people from government control over what they bought and sold, not just a way to score drugs. They really believed they were changing the world.”

Nevertheless, critics are quick to point out that philosophical convictions do not justify the harm the Silk Road did by allowing dangerous, illegal substances such as cocaine and heroin to be easily obtained. And prosecutors refuted the idea that illegal drugs could be included in the category “victimless contraband,” which the Silk Road administrators claimed to permit.

"Ulbricht bears responsibility for the overdoses, addictions, and other foreseeable repercussions of the illegal drugs sold on Silk Road," wrote US Attorney Preet Bharara in a letter to the judge before sentencing. "It does not matter that he did not personally handle those drugs; neither would a traditional kingpin."

In a documentary film "Deep Web," directed by Alex Winter, several former administrators of the Silk Road, speaking on condition of anonymity, describe the intellectual community that existed on the Silk Road’s forums, side by side with the drug market.

According to those familiar with the site, philosophical treaties were posted regularly on Silk Road’s forums, and discussions about Austrian economics and free-market philosophy were held regularly. Some of the intellectuals whose theories dominated the conversations were Ludwig von Mises and Murray Rothbard, a libertarian political theorist and an economist of the Austrian school of economics.

“There were many threads that had great political and philosophical discussions. Sure there were illegal things going on, but this was a real community of like-minded people,” said one of the anonymous vendors speaking in the documentary.

There was also a Dread Pirate Roberts book club.

“He mentions in one long message this book called 'Alongside Night,' and it’s an interesting fictional libertarian book about a future where the U.S. government is trying to control everyone and there is this underground black market that represents the rebel movement,” says Mr. Greenberg.

“He said that was the book that kind of crystallized his idea about the Silk Road.”

And unlike other online illegal marketplaces, the Silk Road’s libertarian philosophy limited what was sold on the site, observers say. The Dread Pirate Roberts mandated that it was impermissible to sell anything that was meant to harm innocent people. For example, child pornography, the services of hit men, anything stolen, counterfeit money, and coupons that were meant to defraud people, were all among the items banned. The sale of private documents, such as receipts and university diplomas, also was strictly prohibited. Other sites on the deep web didn't have such restrictions.

According to Daily Dot journalist Aaron Sankin, these restrictions were enforced in accordance with a tenet of libertarian thought.

“In a sense, private documents like receipts or diplomas are written evidence of legal contracts. The importance of contracts between consenting individuals is a crucial tenet of libertarian thought and an issue the Mises Institute [a proponent of Austrian economics] has examined in detail on multiple occasions,” explained Mr. Sankin.

“In a libertarian-minded, small-government state, it’s the prevalence of these types of contracts that keep a civilized society from slipping into anarchy.”

However, critics dismissed the philosophical side of Silk Road.

During a press conference in June 2011, the year Silk Road was launched, Sen. Charles Schumer, (D) of New York, characterized it as “more brazen than anything else by light years.”

“It’s a certifiable, one-stop shop for illegal drugs that represents the most brazen attempt to peddle drugs online that we have ever seen,” Senator Schumer said.

More than 13,000 items were offered on the site, including an abundance of illegal drugs. Roughly $1.2 billion in sales were realized through the site.  

And not everyone on the Silk Road was a libertarian ideologue. Undoubtedly, criminals used the site to line their pockets.

“When he would post these political manifestos, people would chime in and say ‘we love you’ and ‘we agree, we’re so excited to be part of this movement’…They did seem to be on board with this political thing. But there were a lot of people who weren’t that vocal who were behind the scenes doing a lot of business,” says Greenberg.

“Eventually it was clear that the Silk Road was such a gigantic thing, it’s hard to imagine that all of those people were doing it for a political cause. Eventually it became a massive business.”

Although he continued to live a modest lifestyle, according to reports, Ulbricht personally amassed millions of dollars from bitcoin transactions linked to the Silk Road.

During his trial, his beliefs were barred from being brought up as part of the defense’s case, Motherboard reported.

Instead, the defense argued that Ulbricht had started the site to reduce the risks faced by users who would otherwise purchase drugs off the street.

In rebuttal, a defense filing revealed that the prosecutors intended to introduce evidence of six overdose deaths attributable to drugs bought from vendors on the Silk Road, The New York Times reported.

During the trial, a drug dealer testified to having sold more than 2,400 orders of heroin through the Silk Road. His testimony left some observers wondering whether the site had made it easier for people to purchase drugs who otherwise wouldn’t have.

Ulbricht’s intentions are unlikely to sway Judge Forrest, observers say. Instead, Ulbricht and 97 of his friends and family members have written to the judge, saying that he learned his lesson and asking her to impose the most lenient sentence possible.

In his letter, Ulbricht, expressed remorse for his actions and asked for "a small light at the end of the tunnel," a reason to stay healthy and redeem himself outside of prison.

"Even now I understand what a terrible mistake I made," he wrote.

"I've had my youth, and I know you must take away my middle years, but please leave me my old age."