The Deep Web (2015) – By Marcus Hoy

Alex Winter’s new documentary, tells the story of the Silk Road from the point of view of customers, dealers, and law enforcement officers. It’s also a very personal look at the life of Ross Ulbricht, who in February 2015 was sentenced to life imprisonment for his role in the running of the online marketplace.

At its height, the Silk Road boasted an estimated 900,000 users and generated more than $1 billion in annual sales. A combination of the Tor virtual private network and the Bitcoin virtual currency made transactions virtually untraceable, both for customers or dealers. The Silk Road, we are told, forged “new kinds of relationships” between people, totally free of government interference. Vast quantities of drugs were shifted, as well as other legal goods. But it was the illegal trades that eventually led to the downfall of the Silk Road and Ulbricht himself.

While Winter was unable to obtain an interview with the incarcerated Ulbricht, he persuaded his family and friends to speak out. We learn that Ulbricht was outwardly a nice guy, a geek with strong libertarian views who believed that the criminalization of drugs infringed our basic human rights. The Silk Road, he believed, was an ideal method of removing all violence from drug transactions, as well as increasing choice and improving quality.

But just how much did Ulbricht have to do with the Silk Road’s operation? According to the FBI, he was Dread Pirate Roberts or DPR, the criminal mastermind behind the site’s conception and operation.  The alternative narrative pursued by Winter is that prior to his arrest, Ulbricht had handed over the site’s operations to other, unnamed operators who subsequently lured him back to take the fall. Dread Pirate Roberts was not a single person, Winter’s narrative goes, but a shared moniker used by an unknown number of the Silk Road’s shady operators.

The movie features lengthy interviews with Andy Greenberg, the journalist who covered the story for Wired and interviewed DPR by email before he was unmasked, as well as interviews with Ulbricht’s family and former school friends. We are left with a picture of a charming, gentle guy who was following a strong passion.

The most compelling part of the story is how Ulbricht came to be arrested and the gravity of the charges that were then filed. Posing as both dealers and customers, FBA agents had infiltrated the Silk Road forums, and Ulbricht was picked up in a public library in October 2013 before he had chance to encrypt his computer. According to his supporters,  the FBI likely used illegal search methods to uncover Ulbricht’s identity, though this is denied by law enforcement authorities.

The trial that followed made headlines around the world. Under the persona of DPR, Ulbricht was accused of being the mastermind of a global drugs operation set up for the personal gain of himself and others. DPR even ordered “hits” on rival forum members, the FBI claimed, though charges of attempted murder were subsequently shelved.

According to the defense, Ulbricht was just one of a number of administrators using the DPR nickname and much of what was attributed to DPR could not be attributed to Ulbricht. The question of whether the FBI’s penetration of the Silk Road’s Iceland-based server constituted an illegal search was never addressed at trial, nor was the fact that two federal agents allegedly stole and extorted funds from the Silk Road and manipulated data. The movie claims that the defense was allowed to bring virtually no mitigating evidence to what was ultimately a flawed trial. Currently, Ulbricht faces spending the rest of his life in jail, though an appeal has been filed.

While it works as a classic “miscarriage of justice” movie, “Deep Web” doesn’t ignore the negatives of the Silk Road – the fact that blueprints for 3D guns were made available, for example, or the story of the teenage drug addict desperately waiting for his order to arrive. It offers insight into how digital evidence is gathered and the practice of online drug dealing, which, it points out, is more widespread than ever. While the Silk Road has been shuttered, it seems, the online trade in narcotics is here to stay.

Writer and Director: Alex Winter
Runtime – 90 mins