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As Ross Ulbricht Is Sentenced, 'Deep Web' Reveals Silk Road's Back Alleys

"The notion that 'if you have nothing to hide, you have nothing to fear' is a destructive axiom of Orwellian proportions," says the film's director.


Was Ross Ulbricht, the Eagle-Scout-turned-felon behind Silk Road, the eBay of illegal drugs and services, a libertarian hero or a new-age American gangster? That is the question behind “Deep Web” a new documentary about the 31-year-old sentenced to a life sentence behind bars.

In February, Ulbricht was convicted on all seven charges connected to his running of Silk Road, an underground marketplace that used bitcoin as currency and which had reportedly facilitated a billion dollars in sales over the two years of its existence. The charges included drug trafficking, computer hacking and money laundering.

To his supporters, Ulbricht is an idealistic schnook — a young man with libertarian ideals who truly believed an online underground drug market was safer than the one that existed on the streets. To authorities, he is Dread Pirate Roberts, the man behind Silk Road who allegedly ordered the murder of his enemies.

“Deep Web” examines the underlying issues in the case around online privacy and of illegal search and seizure in the digital age. It is hard to watch this film and not walk away paranoid over how the volumes of data generated by our texts, emails and Facebook updates could be used against us.

Produced by cable channel Epix, the documentary draws heavily from Wired reporter Andy Greenberg’s 2012 book, “This Machine Kills Secrets: How WikiLeakers, Cypherpunks, and Hacktivists Aim to Free the World’s Information,” and includes interviews with Ulbricht’s parents, players from the ACLU and the Electronic Frontier Foundation, and hackers who are passionate about Internet freedom.

The film was directed by Alex Winter, whom you might remember as Bill from the “Bill and Ted” movies, and narrated by his old pal Keanu Reeves, who’s not only Ted from those same movies, he’s also the literal poster boy for the intersection of the human mind and the virtual world.

I caught up with Winter as the documentary was making the film festival circuit (the world television premiere is at 8 pm ET/PT May 31 on Epix) on the eve of Ulbricht’s sentencing, and I asked him many questions — none of which concerned the epic shirtless sax player in Lost Boys.

The interview has been edited for brevity and clarity.

So, to start: The Deep Web is a tool, and the fact that criminals use that tool — in addition to law enforcement and corporations — is convenient for those who’d like unfettered access to the information kept in it. Is that correct?

The Deep Web is just all the un-indexed code online. Within the Deep Web is the Dark Net, which is an area of the Internet used for privacy and anonymity online. It’s used for many purposes — mostly for government agencies, journalists, dissidents, and also for criminal activity.

How did you come to be aware of this story, and what made you want to follow it so closely as it developed?

I’ve been interested in online communities since the late ’80s, in the BBS/Usenet era, when I first encountered them. Both this film and my previous film, “Downloaded” (which was about Napster), examine radical, evolutionary online communities, the motives for their creation and their ensuing implications.

How did you get access to those hackers in London? What was it like being in this underworld — with a camera?

I worked to get inside access to all the core players in this world. That was my narrative agenda, such as there was a single agenda: To tell this story first and foremost from the perspective of the people who built it, and then secondarily from the people shutting it down (government and law enforcement) and the people reacting to it (the media).

Who did you not talk to that you wish you could have? For instance, why didn’t we get to hear from the federal agents or lawyers who prosecuted Ulbricht?

The agents who worked directly on the case declined to speak to me. I later discovered they had already given their story rights to another entity. The prosecutors are unable to discuss an ongoing case. I would have liked to interview Senator Schumer, but he declined.

The film and its story hinge on the idea of illegal search and seizure — the Fourth Amendment. Tell me about how you told the story of illegal search and seizure in the digital age — no cops bursting through doors without a warrant, just … typing. Not dramatic! As a filmmaker, how do you create drama there?

I agree, it is difficult to dramatize stories in the cyber space in a narrative film. But not in a documentary. I felt I had plenty of archival material and access to the real players to keep it dramatic.

Why isn’t the Fourth Amendment defended as passionately as the Second Amendment?

I think the general public is not yet aware of the need for privacy and anonymity, and how much of that has been eroded. The notion that “if you have nothing to hide, you have nothing to fear” is a destructive axiom of Orwellian proportions. The Sony, Target and Anthem/Blue Cross hacks have shown many people that they do need privacy protection. It’s a game of catch-up.

At the same time it’s a real conundrum for law enforcement [agencies], who need to be able to do their jobs. Additionally, the laws around search and seizure in the digital age have yet to be properly amended. It’s an exciting time, and also a very messy one.

It seems like Ulbricht is a tough sell as a hero. At best, he facilitated illegal drug sales. What’s your answer to people who say, “Why should I care about a drug dealer who might even be an attempted murderer?”

The movie doesn’t say the trial was unfair, and it doesn’t paint Ross as a hero. And it is not an essay or a piece of journalism. The movie is about the unknown, the contradictions, the challenges of this story.

If peer-to-peer is popping up over and over again, and arrests are made every week, isn’t this just playing into the same drug war scenario — making money for the drug enforcement agencies by giving them something new to do?

There are many people who believe that well-run online drug services would be hugely beneficial for reducing crime and violence in the drug trade and for moving drugs out of the criminal space and into the mental health space.

What was it like seeing Ulbricht’s mother transform into an activist? Was it incongruous to see a tiny little middle-aged lady speaking to rooms of hulking coder guys?

It was extraordinary. Lyn epitomizes the average citizen today, who feels apprehensive and even disinterested in technology, and then wakes up to the reality that this is the world we live in and we have no choice but to engage with it.

I, personally, felt a strange unspoken tension as Greenberg walked through the Wired offices at 1 World Trade. The Patriot Act is supposed to rescue us from future terrorist attacks, and part of me clings to that idea. The libertarian no-government-intervention argument just sounds like anarchy. If someone is galvanized by the events put forth in “Deep Web,” what is the next step? Dismantle the government? Work from within? Accept the risks inherent with freedom? What is to be done?

The people who have been galvanized by the movie tend to feel some need to learn more about the issues at play and take a more active role in protecting their privacy in the digital space. The dark net is filled with a myriad of types; libertarians, anarchists, social activists, neo-cons and so on. Some of these people are good, some are bad, and they aren’t a united front. What does tend to connect them is a belief that personal privacy is a basic human right and needs to be protected in the digital age.

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