Where does the end of the Silk Road leave us?

Thirty-one is a young age to be handed two life sentences without parole. That’s the first thought that might have crossed someone’s mind when the news of Ross Ulbricht’s sentence came out last month. The next would be that it’s an awfully long time for someone who didn’t commit mass murder or high treason. Ulbricht, a.k.a. the Dread Pirate Roberts, is the creator of the once active and highly lucrative clandestine marketplace, Silk Road. With a layout similar to e-bay’s and the guaranteed* user anonymity of a TOR network**, Silk Road was the embodiment of a digital wet dream for narcotraffickers and their clients, enabling a more risk-free trade environment with the unwitting help of the post.

Screenshot of Silk Road webpage

A screenshot from the Silk Road website

The story of how a 27 year-old Ulbricht built Silk Road in 2011 and grew it into a $1.2 billion empire by 2013, only to become the target of a 2 year FBI investigation that spelled his downfall, is a fascinating one. Equivalent in its ability to inspire awe and disbelief as the success of other twenty-something web 2.0 prodigies, like Facebook’s Mark Zuckerberg – if Zuckerburg had been crossed with the interest and methods of Al Capone. What sets this particular story apart is the ambiguity of its location on a moral map, with both Ulbricht and Silk Road on the one side, and law enforcement and the justice system on the other, positioning themselves within the areas of “fair”, “not exactly okay, but harmless”, “wrong”, and “morally reprehensible”.

The many IDs found in Ross Ulbricht's possession, as entered into evidence by the U.S. Southern District Court of New York

The many IDs found in Ross Ulbricht’s possession, as entered into evidence by the U.S. Southern District Court of New York

A self-taught programmer, Ulbricht launched Silk Road as a platform for his libertarian belief that true freedom comes with economic autonomy. A platform in which any vendor (with the know-how to access the deep web) would be able to sell his wares of drugs and other prescription medicine to any willing buyer (with the know-how to access the deep web) in an unregulated environment and in relative safety from the long arm of the law. In the “Untold Story of Silk Road”, Wired writes that for Ulbricht’s alter ego, the Dread Pirate Roberts (or DPR for short): “the site was a political polemic in practice. ‘Stop funding the state with your tax dollars,’ DPR wrote, ‘and direct your productive energies into the black market.’

It’s unclear how the more traditional drug trade could be seen as funding the state through taxes – if anything the industry as a whole has been a drain on government resources that are directed to finance law enforcement and lengthy prison sentences – but that goes to show the influence that DPR had over Silk Road’s fanbase: because direct their energies they did. Through 1,229,465 transactions to be exact, totalling 9,519,664 bitcoin*** or $1.2 billion**** from February 2011 to July 2013.

Before the power high overcame him and he started soliciting murder-for-hire services to silence those he perceived as liabilities, Ulbricht’s ideology was intended to be harmless – albeit opportunistic and naive. In a world where the illicitness of drugs and the validity of a worldwide war on drugs are largely contested by economics, health and policy experts, Silk Road offered an easier, more direct, and presumably less violent, means to obtain narcotics. And, though he preached an anti-state political rhetoric, Ulbricht’s ideology wasn’t on the extreme end of the stick. The site still imposed rules – among them, “no child porn, stolen goods or fake degrees,” – and a fundamental code of conduct, “‘to treat others as you would wish to be treated and don’t do anything to hurt or scam someone else.’” If his thinking hadn’t devolved, maybe Ulbricht would just have been tagged by history as a bootlegger of the 21st century drug prohibition: definitely someone opportunistic and on the wrong side of the law; but like the 1920’s speakeasy owner, providing a means to a substance his clients would get their hands on, one way or another, whether the government deemed it permissible or not.

But, if Ulbricht ever had the intention of opening a fruitful debate against the effectiveness of current drug policy, his experiment failed miserably. Instead, his dissociation from his previous ideals “to treat others as you would wish to be treated”, and a growing arrogance over his elusiveness, ensured that DPR and Silk Road were as far from being drug reform advocates as possible. Their downfall resulted in a glowing victory for law enforcement who – thirsting for some taste of success within a failing drug war – latched onto the case with talon-like grips and ensured this, at least, would be viewed as an example of the triumph of their perseverance and, therefore, as a deterrent to those contemplating filling the vacuum left by DPR’s arrest.

The evidence mounted against Ulbricht was colossal. The digital diary he kept with boasts of “running a goddamn multi-million-dollar criminal enterprise” doing nothing to help his plea of innocence and claims to being framed by the real Dread Pirate Roberts. When the guilty verdict came, a mere 3.5 hours after the jury convened, prosecutors “demanded that the judge set ‘a lengthy sentence, one substantially above the mandatory minimum’ for Ulbricht.” This is where the justice system failed and overstepped its authority. Because, while Ulbricht’s non-guilty plea was ill-judged given the mountain of evidence against him; while his defence’s choice to make “academic arguments to say leniency was appropriate since Silk Road had reduced the overall harm associated with drugs” was just short of being cocky; and while the defence’s inference that Ulbricht was entitled to some leniency in his sentence because he was a white, well-educated boy from a respectable family was certainly erroneous, Ulbricht’s punishment far surpassed his crimes.

Ross Ulbricht is no angel; but his real crimes can be broken down to:

  1. distributing, aiding and abetting the sale of narcotics,
  2. engaging in a criminal enterprise (and, presumably, the money laundering, use of fraudulent IDs, tax fraud etc. that is part of the day-to-day business), and
  3. procuring murder-for-hire 6 times.

On this last count – evidently the most serious charge – to Ulbricht’s ignorance, one murder was faked by the DEA (the Drug Enforcement Administration) and no actual murders relating to the other 5 requests were ever uncovered. What’s more the 7 counts on which Ulbricht was found to be guilty and handed a life sentence in May do not include procuring murder-for-hire, for which he will be charged in a separate pending trial in Maryland. The life sentence he is now appealing was squarely based on his involvement as a deep web drug entrepreneur, rendering his involvement in murder-for-hire plots almost irrelevant.

Silk Road and its inevitable successors – Agora and Evolution among them – surely do more to hinder than help drug policy reform. They do make it clear, however, that it’s high time we moved in that direction, and handing out life sentences is not the right way to go about it.


* Guaranteed to a degree. The FBI was able to identify Ulbricht after his IP addressed leaked.

** TOR (The Onion Router): an open-access software permitting anonymous communication.

*** Bitcoin: A decentralized digital currency created in 2009.

**** At the then exchange rate.

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