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Hot Docs Review: Alex Winter’s Silk Road Documentary ‘Deep Web’

Hot Docs Review: Alex Winter's Silk Road Documentary 'Deep Web'

Are you outraged when you see insurmountable evidence proving that your government peeks into everything you do online? Do you find the idea that “an observed life is not a free life” to be true, and the consequences of such a life morally repugnant on an essentially human level? If so, Alex Winter’s new documentary might just do the trick for you. “Deep Web” works in tandem with recent docs, “The Internet’s Own Boy: The Story of Aaron Swartz” and Laura PoitrasOscar-winner “CitizenFour,” to depict the US government as an evil omnipresence bent on squashing individualism in the digital age. Because, you see, in spite of its misleading title, “Deep Web” is really about the trial of Ross Ulbricht, the alleged creator and supervisor of Silk Road, which was, of course, the biggest black market that operated in the non-indexed depths of the Internet from early 2011 to the end of 2013. Had Winter steered his documentary closer to its title’s promise, it may have been a truly invigorating and consuming piece of work. As it is, however, it’s got a slow connection and limited bandwidth capacity, painstakingly detailing the mere frameworks of an individual without ever getting to the core of anything.

READ MORE: Alex Winter Discusses His 1993 Cult Hit ‘Freaked’

Depending on the viewer’s personal knowledge about darknet markets, the anonymity network TOR, the use of Bitcoins as digital currency, and the variety of other crypto-anarchic tools used by today’s hacktivists and cypherpunks, the expository opening sequences of “Deep Web” will feel either unnecessary, inadequate, or somewhere uncomfortably in the middle. For me, in case some readers are wondering, I came in with very rudimentary knowledge on the subject and was very much looking forward to learning more about Silk Road, the people who use it, what they use it for, and the religiously loyal community it created. I was expecting a documentary called “Deep Web” to actually delve into those depths. Alas, before one gets the chance to be fully immersed in the concept of darknet, or Silk Road as a non-violent haven for anonymous sellers and buyers, we get introduced to Andy Greenberg. He’s a journalist working for Wired magazine, determined to track down Silk Road’s MVP, the site’s main administrator who adopted the moniker Dread Pirate Roberts (“The Princess Bride” FTW!) When Greenberg convinces DPR to do an interview, “Deep Web” hits its peak, introducing a topic for debate that extends far beyond the contents of one documentary: this mysterious figure comes off as a deeply libertarian thinker, with strong principles and beliefs about the free market, and sees Silk Road as a community of likeminded individuals, not merely a black market for drug dealers. The questions of whether it should exist, how and why the government wants to control it, and various other socio-political and ethical questions are left for the viewers to discuss amongst themselves, while “Deep Web” turns a corner and starts following the arrest and trial of Ross Ulbricht, a.k.a. DPR. Or, is he?

The mystery surrounding Ulbricht revolves around whether he even is DPR, if he’s just part of a team of administrators who use that one account, or if others in fact – as his attorneys wanted to explain – framed him. We begin to get insight into Ulbricht’s family, we follow his mother as she tries to raise awareness and convince people that what the government is doing to Ross is fundamentally unconstitutional. Among the charges of computer hacking and money laundering, the most damaging was the one that alleged how Ulbricht hired hitmen through Silk Road to kill people. These murder-for-hire charges were ultimately dropped for lack of evidence of any murder actually occurring, but since it was part of the prosecution’s statement, the picture of Ross Ulbricht as a violent criminal had successfully been painted for the jury. “Deep Web” follows Ulbricht’s trial up until a month ago (it’s on-going), catching up with Greenberg from time to time, and getting insight from other crypto-anarchists like Cody Wilson (famous as the 3D-printing gun guy) and other hacktivists who share a strong faith in open-source software and an even stronger mistrust of authority.

The core issue with “Deep Web,” and something that ‘Internet’s Own Boy’ and “CitizenFour” didn’t have as much trouble with, is that its main subject is shrouded in so much ambiguity that it’s difficult to make him into a compelling protagonist. And there’s no question that Ulbricht is portrayed as a protagonist here, a victim even. The amount of time Winter dedicates to the Ulbricht family, his use of very deliberate title cards, and even his choice for the documentary’s prologue, all point to an undisputed subjective opinion. These are the good guys, and they’re fighting a authoritarian government with intentions to control your freedom. Like I mentioned in the beginning, if this is a principle close to your heart then the time you invest in “Deep Web” won’t be for naught. But others might side with Andy Greenberg, as I do, when we last see him, genuinely conflicted over the virtues of Silk Road and its founder. There’s very little in the way of balance, or exploring the more damaging consequences of having unregulated black markets on the Internet (great, Silk Road doesn’t allow for child pornography, weapons, or hitmen, but what of the other black market sites on darknet that are way less strict in this regard?) It’s an undoubtedly fascinating subject, but don’t be surprised if you walk away feeling like it’s yet to be explored to its fullest potential. [C]

“Deep Web” premieres May 31st on EPIX at 8 PM ET/PT.

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