Review: Alex Winter's "Deep Web" about Silk Road's Ross Ulbricht

Going in to see the movie Deep Web, which played yesterday and today at the Montclair Film Festival, I was most interested in the question "Who is Ross Ulbricht?" Is he the libertarian idealist who created Silk Road to let people do what the government doesn't want them to do? Or is he the scheming drug lord who put out contracts on associates who had betrayed him, as alleged by the government? Though the movie was fascinating, I left with my question unanswered.

This is no fault of the filmmaker, whose challenge was to make a documentary about someone he had little access to. Despite interviews with family, friends and business associates, Ross Ulbricht appears as a shadow in this movie. We see him in a few home movies, we see his LinkedIn profile, but we never really see or hear Ross Ulbricht talk about the subject at hand.

We hear more from Dread Pirate Roberts, a pseudonym that was at least partly Ross Ulbricht. We see many of his posts on Silk Road forums, with highlights to show the complexity of his motivations. DPR seems more interested in ideals than money, he wants to make the world a freer and safer place. But he's a businessman who values loyalty and doesn't tolerate people who don't make good on their promises.

The central voice of the film is that of Wired Senior Reporter Andy Greenberg, listed as "Consulting Producer" of Deep Web. Because much of the film surrounds Silk Road forum postings and the legal case against Ulbricht, it relies heavily on Greenberg to boil down and assess voluminous posts and complicated proceedings. Greenberg doesn't quite have the screen presence the film needs from him, but hey, that's not his job. But so we don't miss the point, there's always a poster of Edward Snowden behind Greenberg in his office.

The film has at least two narratives that make for a sometimes conflicted message. One narrative is the libertarian argument in favor of online drug markets, another is that the government has prosecuted Ulbricht unfairly, perhaps illegally.

The moral argument in favor of Silk Road is particularly resonant in this post-Ferguson post-Baltimore era, and I wish the film had followed this thread further. The gist of it is that real-life drug markets are violent scourges that ruin communities, and moving them online removes most of the violence associated with the illegal transactions. Silk Road succeeded by bringing accountability to these transactions; a transaction gone bad would result in a seller losing reputation instead of someone getting killed. In a sense, Silk Road functioned as a government beyond the reach of domestic law. By contrast, the War on Drugs results in police inflicting violence and punishment  on people and communities causing harm out of proportion to the benefit of extending the rule of law.

In the context of this war, it's small wonder Ulbricht doesn't get the benefit of the legal doubt. It's hard not to compare Deep Web with the film I saw last year at Montclair Film Festival, Brian Knappenberger's The Internet's Own Boy. Both films recount the story of a bright young man turned entrepreneur, who is driven by idealism to do something to which the legal system reacts with brutality. Both films prominently feature analysis by the eminently reasonable Cindy Cohn and the starker views of Chris Soghoian. Despite the emotional power of Knappenberger's film, Popehat's Ken White criticized it for its naive view of the legal system. White's cynical view is that we shouldn't be so outraged that Aaron Swartz was singled out for extreme prosecution, because that's what our legal system does to most people it turns its attention to today. This point would go double for Ross Ulbricht. The prosecution of Ulbricht was unfair, but that's exactly how most drug-related cases are prosecuted. "Drug kingpins" who complain about the feds hacking their computers can't expect much forbearance from judges who advance in the system by being "tough on crime", and rich white folks shouldn't expect to be treated differently.

Unfortunately for Winter, the most shocking revelation in the Ulbricht case came after most of the current film was shot, and is only mentioned briefly at the end - two of the agents investigating Silk Road were indicted for stealing over a million dollars worth of bitcoin from the site after they had infiltrated and taken control of the site. It's hard to imagine that this won't play a major role on appeal.

As far as I can tell, Deep Web get its facts right. It manages to avoid many of the silly characterizations of Bitcoin in the popular media (for example, bitcoin enables anonymity but it's not automatic). The only quibble I have is the title. "Dark Web" would have been more accurate, as well as more dramatic.

Over all, I found Deep Web an extremely engaging telling of an important story. But it ends in an unsatisfying place, with a shoe dropping. See don't miss it when it airs on May 31; you'll be able to enjoy what happens next.

Trivia note: Both Ross Ulbricht and I, in our past lives, published scientific articles on the incredibly obscure topic of adsorption-controlled molecular beam epitaxy of oxides. Yep.

• "Adsorption-controlled growth of EuO by molecular-beam epitaxy", Appl. Phys. Lett. 93, 102105 (2008); http://dx.doi.org/10.1063/1.2973180
• "Adsorption controlled molecular beam epitaxy of rubidium barium bismuth oxide", J. Vac. Sci. Technol. B 8, 332 (1990); http://dx.doi.org/10.1116/1.585064

Deep Web premieres on May 31 at 8PM EST on EPIX.

Here's the Trailer: