As people reflect on the life sentence handed down to the convicted mastermind behind Silk Road, many questions arise, including: Why would he risk setting up an unregulated online marketplace? Was the investigation leading to his arrest legal? And in this first-of-its-kind scenario, is his punishment fair?
These are the very issues a new documentary, directed by Alex Winter and having its premiere Sunday on Epix, seeks to explore.
Ross Ulbricht, 31, was sentenced to life in prison without parole after giving a final, tearful plea for leniency in a U.S. District Court in lower Manhattan on Friday. In February, he was found guilty on seven counts linked to his creating and operating Silk Road, including drug trafficking, engaging in a criminal enterprise and money laundering. When the authorities shut down Silk Road in 2013, it had hosted more than 1.5 million purchases and $1.2 billion worth of business over the course of nearly three years.
Deep Web, which takes its name from the online market’s hidden host, has been criticized for making the case for Ulbricht. Indeed, the film’s exploration of his guilt is superficial and there is an abundance of character witnesses singing his praises. But Winter suggests these concessions are necessary in order to draw the public into the complicated debates surrounding the case.
“It isn’t a piece of journalism,” Winter tells Newsweek when probed on the film’s possible biases. He says showing Ulbricht parents’ emotional pleas provides the average person with an entry point into the technologically complex case. The film explains “how his mom and dad had found themselves, from not being able to use their iPhone, to becoming experts in digital activism,” he says. 
Ulbricht’s alleged motivation for Silk Road was to create a market outside of the government’s purview. “I believed at the time that people should have the right to buy and sell whatever they wanted so long as they weren’t hurting anyone else,” he wrote in a heart-felt letter to the judge before sentencing. But the prosecution emphasized that people were hurt, highlighting the drug overdose deaths of some who bought narcotics from the site, as well as evidence suggesting Ulbricht ordered and paid for murders to protect his operation.
In Winter’s depiction, however, Silk Road wasn’t Ulbricht’s creation. Instead, it was the sum of like-minded people who were attracted by a similar product: drugs. “Silk Road wasn’t created and run by an individual. These technologies never are,” Winter says. “You had this sort of libertarian, crypto-anarchic faction that was very interested in creating a free market and...you also had people...[who] were very interested in combating the drug war...and then you had straight up criminality.”
Not only does Winter reject the idea that the final Silk Road product was Ulbricht’s doing, but his investigation linking Ulbricht to its creation is shallow. The film’s most direct implications of his guilt include him ordering fake IDs and having his laptop seized while logged in to Silk Road.
“The movie isn’t trying to make a case for or against Ross,” says Winter. Just as the parents’ passion can rope audiences into the bigger discussions, a clear demonstration of Ulbricht’s guilt could push them away. He says: “The point of the movie is to say that these are the issues surrounding this case—let’s unpack them.”
Though the concepts may seem unapproachable to the non-tech savvy, the saga of Silk Road’s rise and fall exposes a new frontier, one yet to be fully addressed by dedicated laws. In a time when it is almost impossible to participate in modern society without using a computer or leaving a digital trail, many are unknowingly perched, exposed, on this frontier.
One of the most contentious parts of the case, which the film mentions, is whether the FBI overreached when it gained access to Silk Road’s server in Iceland. The site used Tor, a type of software designed to hide the server’s physical location. But the way law enforcement describes it, agents essentially stumbled upon Silk Road’s IP address by playing with the site’s login page.
Experts interviewed in Deep Web say this makes little technical sense and a part of the story must be missing. One theory is that the FBI hacked into Silk Road, but if it did so without a warrant, that could constitute an illegal search—a violation of the Fourth Amendment.
“We should be having a public conversation about how search and seizures work in the digital age,” says Winter, something that has yet to happen on a grand scale. Last year, for instance, the Justice Department began leveraging a little-known committee to alter the way warrants are issued. The change would allow the bureau to obtain warrants to hack computers even if their locations or the identities of their owners were unknown.
Because judges are generally restricted to issuing warrants to the government for searches within their jurisdictions, some may consider this change to be a privacy overreach. The American Civil Liberties Union argues that such a rule change would assume that it’s acceptible for the FBI to hack remotely into computers using any means at its disposal—which could degrade cybersecurity and make the digital space less secure for everyone.
Just as one assumes privacy in one's own home, is there a place in the virtual space for people to act freely, unencumbered by the government’s watchful eye? Which tools and protocols are appropriate for probing into Americans’ online lives? And just because Ulbricht’s was a first-of-its-kind case, should he have been given “a lengthy sentence, one substantially above the mandatory minimum” of 20 years, as the prosecution requested?
Deep Web won’t provide any definitive answers to these questions, but if you look past its partiality, you’ll likely find even more pressing questions.