Although many will probably reject the idea of hearing about someone's politics in an interview (especially after the recent Presidential election), it feels necessary in this case that I confess I am not a Libertarian. With that in mind, the first half of Winter's film, which delves heavily into the notion of personal privacy as an absolute necessity, raises as many questions as it does answers. Deep Web contains a roster of interview subjects from both sides of the Silk Road debate, namely a number of former Silk Road vendors whose faces are obscured and voices are altered, and a number of law enforcement and government agents, including Chris Tarbell, the former FBI agent who arrested Ulbricht. Although this supports the idea that Winter is presenting an even-handed look at both sides of the debate, there is a sense that the movie leans in the direction of Silk Road's members and the idea that their community was created for good. Although the second half will make a legitimately compelling case for this defense, the first half presents little more than the word of "Dread Pirate Roberts", in the form of an interview given to Wired reporter Andy Greenberg, in which he states that nothing designed to harm people will ever be sold on Silk Road. Of course, the case can be made that some of the drugs sold on the site are harmful (even if the anonymous sellers outline their methods of determining who and who not to sell to), and the same technology that allows Silk Road to exist also ends up providing protection for, say, child pornographers -- an issue Greenberg only talks about for a few seconds. The film also features Cody Wilson, who comments that some of these people "want to entirely cripple the government's ability to enforce law" as footage of his 3D-printed gun appear on screen. Nearly every one of the subjects speaking in defense of these ideas are white men, whose desire for freedom from surveillance in illegal drug trade can seem narrow-minded and idealistic in the face of a world of other systemic injustices. It'd be fair to say that Winter's 90-minute film doesn't have time to engage a debate that arguably has no great answer and could fill several films all on its own, but there is the sense that the movie presents an idea with obvious moral complexities and mostly ignores them.
That said, the second half of the film presents a far more compelling case in favor of Silk Road, as the focus shifts to Ulbricht, the unlikely kingpin behind the entire Silk Road operation. In the second half, the movie shifts away from the perpetual battle between privacy and security and into the effects that Silk Road actually had on the drug war in the United States, namely the odds that it vastly reduced violent crime surrounding drugs. Without stepping into the debate as to whether or not drugs should be decriminalized (which the film does not address), Winter does offer up an interview with Neill Franklin, the director of Law Enforcement Against Prohibition, who outlines the string of corporations and entities, including law enforcement itself, that profit off of the drug war. There is also Washington Post reporter Christopher Ingraham, who notes that the site allows buyers to hold sellers accountable, not just for their product but how they allow their product to be sold.
The film also taps into another matter of privacy that feels easier to digest, which is the nature of the Fourth Amendment, and whether or not the FBI or NSA violated it in their arrest and prosecution of Ulbricht, as well as their manipulative legal tactics both introducing the dubious "hired hitman" charges into the case, and pushing out witnesses and evidence that would help exonerate Ulbricht of many of his supposed crimes. Although one can argue that Winter's approach to depicting Ulbricht skews toward the manipulative in the form of numerous photos and videos of him smiling and being goofy -- the positive version of Ulbricht's defense lawyer Joshua Dratel's comment that the murder charges were "poisioning the atmosphere" of his defense case -- he also has plenty of material with Ulbricht's parents, Kirk and Lyn, whose personal efforts to help clear their son's name help support the material.
In terms of the filmmaking, Winter applies graphics and photographs of articles and information at any opportunity, and frequently shoots in cramped close-up, which is sometimes awkward but certainly adds to the sense that the film has a deliberate style. Winter also enlists his old co-star Keanu Reeves as narrator. If there's any real flaw, it comes at the beginning: the film's cursory explanation of how the dark web of the title actually functions, from a practical point of view.
The Video and Audio
The other extra, found under the set up menu, is an audio commentary by director Alex Winter. Winter is a wealth of information, kicking off by explaining the backstory that led him to make the movie, before diving into some of the challenges of getting connected to people who are fiercely protective of their privacy. His comments also suggest that he believed his portrait (perhaps predictably, although perhaps not) is unbiased and does not aim to pick sides between the administrators of Silk Road and Ulbricht and the government and law enforcement people who also contributed to the film.