Skip to main content
film review

Amir Taaki and Alex Winter on the set of Deep Web, a documentary focusing on Ross William Ulbricht’s arrest and trial.

Hidden away as part of the unindexed area of the Internet known as the "deep Web," the Silk Road website was an online underground bazaar, connecting buyers and sellers for all kinds of things, including illegal drugs such as heroin, cocaine and LSD. Everything was anonymous and theoretically untraceable, via the Tor network, paid for in the digital currency, bitcoin.

Somehow, the FBI managed to crack it, purportedly from a log-in vulnerability that led to an IP address. In October, 2013, they arrested 29-year-old Ross William Ulbricht while he was logging into the administrator's site of Silk Road at a San Francisco public library.

Ulbricht's arrest and trial are the primary subject of the new documentary by actor-turned-filmmaker Alex Winter (he made the Napster doc, Downloaded). Although it's a fascinating subject, the director doesn't bring much rigour or insight to the complexity of the case. Keanu Reeves, Winter's former co-star from the two Bill & Ted movies, provides some Matrix resonance to the narration.

The FBI said that Ulbricht, a former science and engineering grad student, was Silk Road's mastermind, operating under the title Dread Pirate Roberts (a name taken from the novel and film The Princess Bride). He was charged with money laundering, computer hacking and drug trafficking and attempting to procure murders, though the murder charges were later dropped.

The trial, held in Brooklyn, N.Y., in January and February of this year, attracted Internet-freedom protesters and was avidly followed by bloggers. Ulbricht's defenders claimed the handsome, intelligent, former Eagle Scout (he resembles Robert Pattinson) was an idealist and a martyr who saw the creation of an almost unregulated Internet market as an act of freedom, unshackling humanity from the tyranny of taxation and government control.

Ulbricht's anarchist-libertarian philosophy was consistent with the postings of the site administrator, Dread Pirate Roberts, but his defence insisted Ulbricht was not, in fact, running the site. They insisted that an incriminating log found on Ulbricht's laptop had been planted there by a rival, the "real," but unknown, Dread Pirate Roberts.

Winter, relying on an interview with Andy Greenberg, who covered the story for Wired, comes down on the side of Ulbricht as a hero with only a few reservations. At best, the film is an introduction to a disturbing streak of self-righteous, libertarian Internet ideology.

Among the subjects interviewed is Cody Wilson, the former Texas law student who attempted to disseminate guns through 3-D printers, on the theory that better access to guns equals more democracy.

Other subjects, including Silk Road vendors who are interviewed with faces and voices disguised, make the case that online drug dealing is a form of harm reduction. It's a position endorsed by one former cop, who speculates fewer people would get shot if drug users bought online.

Certainly, the FBI case has a rotten smell: There's the mystery about how the agency obtained Ulbricht's identity and the subsequent charges against two of the officers for stealing hundreds of thousands of dollars during the investigation. But Winter's doc can't rest there. He flies off in several directions, taking swipes at the folly of the war on drugs and the privatization of the prison industry.

None of this succeeds in elevating Ulbricht to the same moral level as such Internet whistle-blowers as Edward Snowden or Julian Assange. Deep Web simply sidesteps issues of Ulbricht's culpability, expressed in letters to the court from parents and siblings of people who died from drugs allegedly purchased on Silk Road. The worst blind spot is the film's reluctance to see through the superficial paradox of Ulbricht's behaviour: Is it so hard to understand that a smart, well-meaning zealot can rationalize activities that are dangerous, criminal and wrong?