Modern field guide to security and privacy

'Deep Web' director talks Ross Ulbricht, the Silk Road's 'Rorschach figure'

Alex Winter's documentary 'Deep Web,' which examines the Silk Road black market and its convicted mastermind, premieres Sunday night on the EPIX network.

Deep Web LLC
Bitcoin pioneer Amit Taaki (left) and Alex Winter (right) on the set of "Deep Web"

Based on his best known movie role, Alex Winter isn't the person you'd expect to film a documentary on the complex and murky world of the Silk Road black market.

Mr. Winter, after all, played Bill in “Bill & Ted’s Excellent Adventure.” But “Deep Web,” which makes its debut on the EPIX network Sunday at 8 p.m., is actually his second documentary on the intersection between idealistic Web communities and illegal actions. His first, “Downloaded,” chronicled Napster.

Between 2011 and 2013, Silk Road was a hidden website accessible only via the anonymous Tor browser, run by the pseudonymous "Dread Pirate Roberts," later identified by the FBI as Ross Ulbricht. Winter chronicles the site and Mr. Ulbricht's eventual trial as seen through the eyes of vendors and supporters, friends and family, ideologues, and the police.

Ulbricht, now convicted of drug and conspiracy charges, and accused (but never tried) of hiring hitmen to murder people who threatened Silk Road, is scheduled to be sentenced on Friday. 

We spoke with Winter about his excellent adventure making “Deep Web.” Edited excerpts follow.

Passcode: One of the most interesting aspects of your film is how certain most of the people you interview are about how well they understand who Ross Ulbricht was and what Silk Road meant, and how none of those impressions line up at all. It makes it a frustrating subject. Do you feel like you have a handle on Ulbricht's guilt or even who he really was? 

Winter: I don't know. I honestly don't believe anybody knows. I told Lyn [Ulbricht's mother], "I'm not making a piece of advocacy. I appreciate you working with me. But at no point am I just going to come right out and say, 'This guy's innocent. He's being railroaded.' " I do not personally have concrete evidence in one direction or another.

So, what I felt was the correct thing to do, ethically and as a storyteller, was to present a snapshot of this extremely strange moment in time. These are the real people who were there. Most of these people were involved in privacy and Internet anonymity long before Ross Ulbricht ever got there. This is what they think. This is what the government thinks. This is what the libertarians think. This what the crypto-anarchists think. This is what all the core players in this world think.

It's a film that's not intended to be frustrating, but it's not shying away from the fact that this case itself is frustrating on a number of levels.

Passcode: It matches up with a lot of the confusion around the "Free Ross" movement online. People idealize him or hate him based on impressions of him that are often incompatible with each other. 

Winter: One of the problems Ross has is he has sort of become this Rorschach figure. Everybody is grafting their ideas of Ross onto Ross. The libertarians have put forward this idea that the Dread Pirate Roberts was this libertarian, peace-warrior who wanted to reduce violence and couldn't possibly have been behind attempting murder. In the film, Cody Wilson [director of the libertarian gun organization Defense Distributed, which published blueprints for 3D printable guns] says, "That's possible. But what the libertarians don't want to face is the possibility that he's actually the thing that I would prefer." Cody is crypto-anarchist. Cody's like, "That with what we know about DPR, it's possible that he became a full-blown revolutionary." That puts him on a different level than the one the libertarians want. And that they can't stomach that potentiality. To Cody, that would make him even more heroic.

And then the government, and I'd say most of the mainstream media, say that he's this misguided, weird loner kid who may have started with libertarian philosophies but along the way became this corrupted drug overlord, like Walter White [in "Breaking Bad"]. Meanwhile, Ross still claims he didn’t do it.

I sat in the courtroom with him. I've talked to all of his closest friends at length, his family. I've talked to people who have known him since he was 6 years old and were still really close friends with him when he got arrested. The Ross that I came to know was this super bright kid who put himself through college and grad school on two full scholarships back-to-back, whose friends he'd had his entire life. He wasn't a loner. He had the same very close-knit group of friends since he was very young. And they all really loved him, and wanted talk to me about him.

Passcode: Something I think will surprise a lot of people is how much more than a drug marketplace Silk Road was to its users and vendors. It was a community complete with book clubs, discussions of Austrian economic theory, and lasting personal relationships. What ultimately was Silk Road?

Winter: Honestly, you really hit upon the reasons why I wanted to make this film. It's the heart of it. I'm 49 years old. I got really interested in online communities in the late 80s. It really struck me that there was something happening there that was going to grow and have an enormous impact on human interaction.

And then, when Napster happened in 1999, I was a huge proponent of Napster. And the thing I loved about Napster, and the thing that I was so excited to be part of for the brief time that it was online, was these global communities that I had to bend myself into pretzel knots to get on in the late 80s, were suddenly now easily accessible to anybody. We went from having communities with, at the very most, 200 people on it to 100 million overnight. So, to me, Napster was all about global community. In my mind, it was not about piracy at all.

The Silk Road is really similar. It is all about community. The darknet is all about community. It isn’t this William Gibson and Philip K. Dick isolation. But its Achilles' heel was what was good about it. It could become a community because it had a central server – a decentralized system couldn’t have been shut down. There was a very clear vision followed by the core architects of that system, so you felt like you knew these guys and you could trust them. They wouldn't allow things they thought would hurt people on the Silk Road. They wouldn't allow child pornography our counterfeit money, or hitmen on the Silk Road. They had these ethics. It felt like it was a vibrant collegiate, scholarly, academic, young, idealistic-minded community. That's how it felt.

Passcode: A lot of the defense of Ulbricht is predicated on his being guilty, but the market ultimately being a good thing – taking drug dealing off of the streets, promoting the sale of safer drugs. And that's in addition to the libertarian ethics a free market drug trade embodies. Was Silk Road good? 

Winter: That is a big question. It's not black or white. Silk Road was the work of very young, very smart, very idealistic minds – people who were not in it for the money. They really were intent on changing the world. That doesn't mean they're awesome. It's just a fact. And the fact is that Silk Road succeeded. It did change the world. There are, already, a proliferation of online free markets that are now becoming decentralized and much harder to shut down. We're in the infancy of this age.

Is that good? Did it reduce crime and make the drug trade safer? Of course it did. It's removed a lot of the harm and violence from buying from dealers in back allies. Is it some kind of blanket panacea for the drug world? Of course not. Is it completely removed from the darker aspects of drug interaction from that trade? Of course not. But did it have an effect on certain aspects of the drug world? Yes. It did. And will the other markets? Yes, they will, too.

Passcode: It's impossible to let you go without asking about casting your "Bill and Ted" costar, Keanu Reeves, as the narrator.

Winter: Keanu is one of my very closest friends. He's like my brother. We see each other all the time. We're always immersed in each others' work. I saw a lot of cuts of his doc ["Side by Side"]. He saw all the cuts of "Downloaded." He was one of the backroom consulting producers on this from before I even started shooting. His voice has a great presence and, because of movies like "The Matrix," he has a voice that people associate with these issues.

And it didn't occur to me to have him voice the movie until almost right before the debut. It was literally, two days before we went to the festival.

I don't love voice over in docs, personally. I really had hoped to not have voice-over in this. Narratively, what I had hoped to do was present two different sides trying to understand what happened. There would be Ross’s parents on one side, and Andy Greenberg, the Wired reporter, on the other – one with a very personal stake, and the other with a historical, technological stake. But without voiceover, there wouldn’t be any simplification of the ins and outs of how the deep Web works or the basics of Bitcoin. Somebody's got to guide people through that or they get lost.

Literally, as we were finishing, we looked at each other, and we were like, "Oh, God. The Bill and Ted community's going to freak out."


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