How New Doc “Deep Web” Shines A Light On The Dark Net

Director Alex Winter believes the man behind Silk Road is being treated unfairly–and we must reconsider what it means to be cyber citizens.

How New Doc “Deep Web” Shines A Light On The Dark Net
Ross Ulbricht in Jail, Still from the documentary Deep Web [Photos: courtesy of Deep Web, Lyn Ulbricht]

Earlier this year, Ross William Ulbricht was sentenced to life in prison without the possibility of parole for his involvement with the dark net drug market Silk Road. Ulbricht was slammed with all seven of the charges brought against him, including computer hacking, drug trafficking, money laundering, and even what’s known as the “kingpin” charge, which is more commonly doled out to cartel leaders and mafia members. Serious crimes? Yes. Worth life in prison? Director Alex Winter doesn’t think so.


In his documentary Deep Web, Winter gains exclusive access to Ulbricht’s family and key operators of Silk Road for an engaging breakdown of one of the most seminal cyber cases in recent history. Winter wades into the murky allegations of Ulbricht’s murder-for-hire plots, the mystery of Silk Road ambassador(s) “Dread Pirate Roberts,” and the raging debate over online anonymity and the cryptocurrency Bitcoin to extract a narrative that breathes humanity into the nether regions of the web and challenges how the media covers and the government prosecutes cyber crimes.

Anonymity in a Crowd

Winter rose to fame as an actor in the ’80s and ’90s, most notably starring alongside Keanu Reeves as Bill S. Preston in Bill & Ted’s Excellent Adventure. It was this period of newfound stardom that compelled Winter to seek solace in the burgeoning realm of the web.

“At that time, the anonymity was really fascinating,” Winter recalls. “I was just beginning to come to prominence as an actor, and I really cherished my privacy and there was this amazing community where you could be anonymous and talk about intriguing subjects and meet other people–it was just an extraordinary community.”

Alex Winter

That feeling of community was the impetus for Winter’s 2013 doc Downloaded, chronicling the meteoric rise and crushing fall of Napster. It wasn’t necessarily the business or music angle that interested Winter, it was the fact that a group of kids managed to connect millions of people across the world within one service.


Deep Web is really a continuation of that same conversation,” Winter says. “Whatever you think of Ross Ulbricht or whatever you think of the legality or whatever you think of drugs, again, the significance that can’t be overlooked was it was the first time anyone had created an anonymous global community that worked: It was big, it was effective.”

Dismantling Myths

Although Winter is careful to highlight the communal spirit of Silk Road, its libertarian-leaning politics, and Ulbricht’s claim that it made drug transactions safer, he’s not trying to squeeze a devil-shaped cutout through an angel-shaped hole in Deep Web.

“Changes are coming so fast and so intensely that it’s creating a lot of fear and misinformation,” Winter says. “Silk Road fell in three of the most contentious areas we face today, which are cyber, the drug war, and the idea of the financial markets in some way being impacted by unregulated currency. But at the end of the day, it was a fairly pokey dark net community, and to watch it being treated this way–people built up the myth and they attacked the myth.”

Part of the myth Winter has been trying to debunk with both Deep Web and Downloaded is that of the hoodie-wearing, lone-wolf hacker–an image that continues to circulate in shows like Mr. Robot.

“They’re always these social miscreants in a hoodie who have no friends, who can’t function, who are totally solitary, who are completely Machiavellian or who have very warped, psychopathic views, and that is just not the case,” Winter says. “There is something very foul about the way we’re responding to these technological changes and how we’re demonizing this generation that’s mostly a brilliant generation.”


A Call For Change

What sets Deep Web apart for Winter as a filmmaker was the challenge of documenting a story as it was unfolding. His previous doc, Downloaded, was a retrospective of Napster 14 years after its run in the news cycle. With Deep Web, however, Winter was forced to gamble on the outcome of Ulbricht’s case, which, as it turned out, wasn’t such a high-risk bet.

“I’ve seen what happened to Barrett Brown, a journalist sentenced to five years in prison for his connection in the hack of private intelligence firm Stratfor. I’ve seen what happened to Aaron Swartz, a programmer who committed suicide while under a federal investigation for data theft at MIT. I’ve seen what happened to Jeremy Hammond, an activist sentenced to 10 years in prison for hacking Stratfor–I know the way we prosecute cyber,” Winter says. “The duality of that is while we were able to finish the movie, it was a shockingly depressing end, so it was certainly bittersweet. I would have rather seen justice be meted out with a bit more efficacy.”

Whether or not Judge Katherine Forrest wanted to make an example out of Ulbricht or use him as a scapegoat for the U.S.’s failing “war on drugs,” as many people have theorized, Ulbricht can’t escape the severity of his crimes. “Make no mistake: Ulbricht was a drug dealer and criminal profiteer who exploited people’s addictions and contributed to the deaths of at least six young people,” Preet Bharara, the U.S. attorney for the Southern District of New York, said in a statement after Ulbricht’s hearing. “Ulbricht went from hiding his cybercrime identity to becoming the face of cybercrime, and, as today’s sentence proves, no one is above the law.”

Still, Ulbricht’s sentencing certainly wasn’t a death knell for other architects of the dark net–there has been a subsequent string of anonymous online drug markets since Silk Road’s takedown, including Silk Road 2.0 (run by former Silk Road administrators), Agora, and Evolution–but it certainly was a dramatic shot across the bow. The tendency to brush everyone associated with hacktivism or the dark net with a broad stroke is what concerns Winter and sets the tone for Deep Web—that the “brilliant generation” he mentioned is perceived as more of a threat than an asset to what he feels is the current point of contention pertaining to cyber: personal privacy online.

PGP encryption software and networks like Tor aren’t just for “basement-dwelling hackers,” Winter says–they’re invaluable tools anyone can use to keep their data safe or have any privacy online. What he fears, though, are stories like the Silk Road saga tainting how the average citizen views said tools.


“The problem with the way these people are being demonized is it’s very hard for the average citizen to say, I want to go over to that side of the fence where that ‘creep’ lives,” Winter says. “We need better privacy tools. We need better encryption. We need to be able to go dark. This notion of, if you have nothing to hide, you have nothing to fear, is so destructive.”

Deep Web is now available on iTunes and BitTorrent.

About the author

KC covers entertainment and pop culture for Fast Company. Previously, KC was part of the Emmy Award-winning team at "Good Morning America," where he was the social media producer.