Deep Web

After reminiscing on the nostalgic era of Napster in his last documentary Downloaded, Alex Winter is back with another tech doc, this time on the online drug marketplace Silk Road. Narrated by Winter’s old Bill & Ted co-star Keanu Reeves, Deep Web briefly examines a range of topics involving the un-indexed areas of the internet called the deep web, where Silk Road lived and thrived from 2011 to 2013. The title is a bit misleading though since most of the documentary details the prosecution of Silk Road founder Ross Ulbricht and pleads for his defense, barely discussing other topics on the deep web.

Deep Web spends the first five minutes brining non-techie viewers up to speed on the dark net, the cryptocurrency Bitcoin, and the anonymous web browsing tool Tor. While this crash course is actually quite informational (even for the more tech savvy), it’s an onslaught of information as the documentary presents facts on-screen in rapid-fire succession. But for those who couldn’t take down notes fast enough, the important details are that Silk Road was an underground marketplace that make it easy for users to buy illegal drugs. The concept is kind of like eBay, only that it mainly involved drugs and handled transactions anonymously to remain untraceable. In a little over two years, the site amassed nearly 960,000 users with an estimated $1.2 billion in sales.

Naturally, the moment the government caught wind of this hidden empire it became extremely interested. Gawker was credited as one of the first mainstream outlets to expose the site to the general public. Soon, everyone wanted to know who was behind the operation, some mysterious figure under the username Dread Pirate Roberts (referencing The Princess Bride). This included Wired Magazine journalist Andy Greenberg, who joined Silk Road early on and managed to land an interview with the notoriously elusive DPR. While he didn’t uncover the true identity of the mastermind, Greenberg discovered that DPR was a strong-minded libertarian who believed in free-commerce, idealistic principles, and promoting safe drug use. Which was something he respected on some level, even if he didn’t agree with everything the man allegedly did. Greenberg remained a prominent figure in the documentary, providing valuable insights from his research and adding intelligent perspective on the case.

Eventually the authorities pin everything on Ross Ulbricht, a man who they believe created and ran the online drug trafficking site. Along with that is the accusation that Ulbricht attempted several murder-for-hires to off those who may have leaked information on the site. Of course, his family and close friends proclaim his innocence. Once Ulbricht was apprehended, the documentary shifts into conspiracy mode, putting the legality of the FBI tactics in tracking him into question, and whether he was the only administrator using that moniker.

The problem with Deep Web isn’t that it becomes overly subjective (which it does), it’s the ineffective way the film gets it’s point across. The best example is the attempt to downplay some of the negative media attention on Silk Road. Showing a brief clip from a local news story about a six-year-old kid addicted to drugs purchased from Silk Road—a legitimate concern—is followed by an interview with a high-profile seller on the site who prides himself on refusing to sell heroin to customers who “aren’t mature enough.” Not only is this a weak argument for Silk Road’s stance on promoting safe practices, but it’s an unfair assumption that all sellers are that responsible, because clearly they are not. But the documentary downplays the harm that could come from such easy access to drugs, hardly even posing the question.

This leads to the biggest downfall of Winter’s documentaries. He doesn’t ask the hard ethical questions about his controversial subjects. It would’ve been interesting to learn Greenberg’s thoughts on the concept of selling drugs online, if the good outweighs the bad? Or better yet, if Ulbricht’s family would still support him if he was in fact the founder of the site. Also, there were a lot of angles explored, perhaps too many. Is the film about the legitimacy of Silk Road, the nature of the deep web, the war on drugs, for-profit incarceration, online privacy, constitutional rights, or Ross Ulbricht? Winter touches on all of these topics, but never forms a unified narrative out of them.

Deep Web delivers a one-sided expostulation for the war on drugs, the importance of encrypting data from an ever-intruding government, and the fall of the largest online platform for selling illegal drugs. But the documentary lacks direction as Winter attempts to juggle too much at once. It doesn’t stack up to other recent tech docs such as The Internet’s Own Boy and Citizenfour, which were successful at humanizing their anti-heroes while demonstrating their significance to protecting our digital rights. Unfortunately for Winter, he started this documentary before Ulbricht’s trial where he admitted to being the founder of Silk Road. Maybe Ulbricht didn’t end up being the protagonist he hoped? One of the many questions left unanswered.

Deep Web premiered on EPIX.