Deep Web Review [Hot Docs 2015]

Adam A. Donaldson

Reviewed by:
On May 4, 2015
Last modified:May 5, 2015


Like his last feature Downloaded, Alex Winter impressively tackles the various issues surrounding the black market Silk Road, making the various technological, legal and cultural questions both easy to understand and compelling for the average audience members.

Deep Web Review [Hot Docs 2015]


I’m not sure if it’s the intention of Alex Winter to carve out a niche for himself as the chief explainer of the digital age, but it seems like that’s what he’s doing. In 2012, he released Downloaded, a look at how Napster and file sharing has changed the music business and the perception of copyright, but that’s just the tip of the iceberg of how computers and the internet have changed things. Winter’s latest, Deep Web, tackles notions of privacy, intelligence and law enforcement in the internet age through the story of the man who may or may not be the most prolific drug trafficker in history.

The title, Deep Web, refers to a wide swath of the internet that’s hidden underneath all the cat videos, remixes and other bric-a-brac that makes up the internet as we know it, or what the computer literate call “the surface web.” Onto the Deep Web came a service called the Silk Road, an eBay for all manner of goods and services including illegal drugs, but the main appeal is that access to the Silk Road is anonymous and nearly untraceable. The appeal for criminals is obvious, but the service was also appealing to those who merely want the security of accessing the internet without have to worry about outside monitoring, be they hackers or government.

There are a couple of directions that Deep Web could have gone in. It could have explored the esoteric world of hackers and the dark corners of cyberspace, or it could have been about the criminal implications of the Silk Road and how it was seeking to subvert the War on Drugs. It also could have been a whodunit about the mysterious person behind the site who uses the pseudonym Dread Pirate Roberts, named after the heroic character of The Princess Bride. Deep Web is a bit of all three, but instead of a whodunit, the film is framed more as a did-he-do-it. Was the man tried and convicted of being the supposedly fearsome DPR, Ross Ulbricht, actually DPR? Was he framed? Was he a victim of circumstance?

What’s interesting about Winter’s approach is that he’s not out to prove that DPR and Ulbricht are one and the same, nor is he invested in trying to disprove it. The director is fairly even-handed in considering the possibilities. Some signs say yes, Ulbricht is DPR, but there are other reasons to suggest that he’s not. Winter’s preoccupation with Ulbricht’s story is that he seems to have been railroaded by the system, guilty until proven innocent. All the while, the government’s case has holes in it, adding unprovable charges about murder-for-hire and withdrawing them last minute, as well it’s strongly suggested that some of the evidence against Ulbricht was obtained illegally.

Winter also treats the existence of the Silk Road, and programs like Tor that are used to access it, rather even-handedly too. His thesis is that these are tools, not necessarily used for computer-perpetuated evil, but also an asset for people like journalists who want to keep a source safe, or even just the average person that doesn’t want a list of their Google searches to become a file in some NSA server somewhere. The real threat here is disinformation, a government preying upon a deficit in computer knowledge amongst the general population to make it easier to throw the book at people that buck the system, like Dread Pirate Roberts. Whether he be Ulbricht or not.

One could argue that there’s a kind of anarchic savoir-faire in the way the Silk Road and its inheritors are portrayed in Deep Web. While one may be a proponent of a free and open internet, you don’t need to pat cyber drug dealers on the back for their restraint in not sending, say, pure heroine to a newbie addict. True, the idea of the Silk Road is not necessarily bad, but neither is a yard sale, and if there was someone selling bricks of cocaine and machine guns at a swap meet, wouldn’t that be concerning to you about the notion of yard sales? That may seem like a simplistic comparison because a yard sale can happen in your neighborhood. Well, so can a meth dealer making millions in bitcoin shipping internationally.

As kind of scary as those potential implications maybe, there’s an important theme shared between Deep Web and Downloaded; just as taking down Napster didn’t stop the spread of file sharing services, the end of the Silk Road opened up several similar services, up to and including a new improved Silk Road with a new improved Dread Pirate Roberts. If the proverbial genie can’t be put back into the bottle, then at least we can be better informed about the nature of the Deep Web and why it seems so scary. The drug stuff maybe be bad, but the grander truth that Winter wants to get at is that we’re all vulnerable, and the miseducation of a government that can basically say or do anything to prosecute is a much bigger problem than one twenty-something that may or may not have got rich when he saw a need and filled it.

Deep Web is particularly impressive for managing to keep a number of balls in the air like some kind of master juggling act, from the history of Silk Road, to the case against Ulbricht and the various terminology and nomenclature of the Deep Web. Winter calls up on his former partner in excellent adventuring, Keanu Reeves, to narrate the story, and really, there’s no better voice to put to all this heavy computer stuff than the voice of Neo. Reeves especially seemed to enjoy reading the DPR side of DM chats with a Wired journalist that interviewed him. Maybe the former master of The Matrix can relate.

Despite having an ending to the movie, Deep Web still doesn’t have an ending to the real life story. Ulbricht will be sentenced sometime later this month, and he’s looking at a lot of jail time if the judge gives him the maximum. Considering how she’s bent over backwards to accommodate the prosecution, there’s no reason to think that she won’t. There’s no doubt that it’s slanted, but Deep Web does make you wonder though if we aren’t seeing a miscarriage of justice unfold here. Eric Schmidt said that “The Internet is the first thing that humanity has built that humanity doesn’t understand,” and if that’s true, then we’re now legislating without understanding. Justice is said to be blind, and it seems that there are some folks that want to keep it that way.

***NOTE: Deep Web will be premiering on EPIX on May 31 at 8 pm. Check your local listings.

Deep Web Review [Hot Docs 2015]

Like his last feature Downloaded, Alex Winter impressively tackles the various issues surrounding the black market Silk Road, making the various technological, legal and cultural questions both easy to understand and compelling for the average audience members.