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On Friday the 29th of May, Ross Ulbricht was sentenced to life in prison. His crime was masterminding the online drug marketplace known as the Silk Road. To quote his mother, the sentence seemed “draconian,” causing observers to wonder just how it was possible for someone who had not been charged, let alone convicted, of anything resembling a capital offense to be sentenced to life without the possibility of parole.

Deep Web, the latest documentary from actor and film maker Alex Winter, presents the story of the Silk Road’s rise to fame and of Ulbricht’s subsequent trial.  But the film is more than just a primer on the Ulbricht case; Deep Web aims to be an accessible but substantive public introduction to those dark networks that exist within the vast unindexed data that make up the mass of the Internet. It is also an exploration of the theoretical and social consequences posed by the current legal structures that govern what many still consider an ungovernable space.

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A look at who uses the Dark Net and why.

Context for illegal marketplaces like Silk Road is given through interviews with law enforcement agents, as well as cryptographers and hackers who see themselves as counter cultural soldiers, not criminals trying to turn a buck through the illegal activities that anonymity on the deep web can enable. The film positions the Internet generally and the deep web specifically as a source of democratic power: a place where journalists, free speech activists, and indeed government agencies, can meet, speak and operate under the cover of darkness. The deep web, we are told, is largely used for good.

Like Winter’s previous film, the Napster documentary Downloaded, Deep Web foregrounds how the communities that grow around subversive anonymous and peer to peer networks have the capacity to advance a philosophical discourse that can eventually make its way to the mainstream. The Silk Road is presented as an anti-statist drug marketplace whose primary goal was to undermine violence of America’s endless war on drugs.

Tracing the origins of the dark web to the cypherpunks of the nineties, the film positions the Silk Road as one development in a long line of countercultural happenings, along with Wikileaks  and the coming 3D printer revolution as pioneered by agitators like Cody Wilson—Prometheans bringing the black fire of cryptography to the people.

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“Deep Web” traces the origin of Dark Nets to pioneering cryptographers.

In its second half, the film shifts its focus away from the political philosophical promise of anarchistic web communities to the direct confrontation with American law enforcement and the judicial system. The picture it paints is a disturbing one. Anyone who followed the story in the news will be familiar with the way murder for hire accusation was presented and withdrawn before the trial, but the extent to which Ross Ulbricht’s chances of receiving a fair trial was subverted is truly shocking. Beyond the evident railroading of one man, the film presents the complications that emerge when the fourth amendment is interpreted in a digital age. It is quite possible that the ways search and seizure played out in Ulbricht’s case have set some dangerous precedents.

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Ulbricht with his family before his arrest.

Ulbrict himself is presented as someone quite apart from the drug lord kingpin that he was portrayed as by Judge Katherine Forrest when he received his sentence. A math whiz who left the sciences to become an entrepreneur—establishing a short lived book selling marketplace that donated a percentage of its profits to charity—Ulbricht denies having been the Silk Road’s actual founder, or even the sole administrator who communicated on SR’s forums as the ever-replaceable “Dread Pirate Roberts.”

From the time it emerged in 2011, to its first intermittent “shutting down,” the Silk Road had seen over a billion dollars’ worth of transactions.  The network’s popularity had exploded after a story about it appeared on Gawker, yet Ulbricht, if he really was the sole person communicating as Dread Pirate Roberts, could only be coerced into speaking to the media by the fact that a rival marketplace was doing everything it could to become the premiere choice for deep web drug buyers and sellers.  Ross, it seems, had loftier goals in mind than vainglorious self-promotion, or, at the very least, he was putting his libertarian ideals to use alongside the mercantile activities he oversaw. It’s hard not to take this idealistic aspect of the man seriously when in his private letters he writes:

Now, my goals have shifted. I want to use economic theory as a means to abolish the use of coercion and aggression amongst mankind. To that end I am creating an economic simulation to give people a firsthand experience of what it would be like to live in a world without the systemic use of force.

Deep web is available through Epix and is set for release on Itunes and VOD on September first.


Jose Alvarado

Jose is a fan of all things horror and sci-fi related. He's played Sonic The Hedgehog 2 more than any other game in existence, but has never managed to collect all the chaos emeralds