'Deep Web' Director Alex Winter on How His Silk Road Doc is a "Narrative About Unknowables"

Alex Winter with 'Deep Web' narrator, and his 'Bill & Ted' co-star Keanu Reeves.

Ross Ulbricht, the convicted creator and operator of online illegal drug market Silk Road, isn't a "known entity" in the film, Winter says, adding, "He's like a Rorschach test. Because so little is known about him, everybody has applied their beliefs onto him."

On Friday, the convicted creator and operator of online illegal drug market Silk Road, Ross Ulbricht, was sentenced to life in prison. Two days later, Deep Web a documentary about Ulbricht's case, the emergence of the Silk Road and privacy and anonymity online made its world television premiere on Epix.

Deep Web premiered at SXSW and played at several other film festivals this spring, but in its wake, Ulbricht's story continues to unfold. Writer-director-producer Alex Winter says that over the next year, people will find out even more about Ulbricht, but Winter says he's fine with his documentary telling the start of an ongoing story.

"The thing is it's a narrative, and it's a narrative about unknowables, to my benefit. That's thematically what I was driving at, that we don't know concretely exactly what happened," Winter explains. "We can make determinations. There have been convictions…It's not like we don't know anything, but there's a lot we don't know and its hard for us to wrap our heads around. So I know that I wanted to in a basic timeline — essentially start the movie with Ross' arrest and end it with his sentencing. That was always the guideline I gave myself. But just like [my] Napster [documentary, Downloaded], [Deep Web is] a story about the beginning of something. It's not about the end of something. The Silk Road is the very beginning of the story about the Darknet. In a way, it's literally an introduction before you get to chapter one of this private encryption battle that we're entering. So I knew it wasn't going to end. I knew there was way more to even Ross' story that people had gotten to hear and that even more is going to come out over the next year. I wasn't worried about that because to me, the three-act narrative in my head was sort of incumbent upon ending at the sentencing, knowing that it leaves us with this question of 'now what?' "

Winter says he'll continue to follow developments involving Ulbricht, whose legal team plans to appeal his conviction, but he has no current plans for another project about the man who went by the alias Dread Pirate Roberts.

Still, he explains that he's long followed the emergence of online communities and that it was this interest in the social, moral and ethical implications of those groups that led him to both Downloaded and Deep Web.

"As I was finishing Downloaded, I was watching the rise of Bitcoin and the Silk Road," Winter tells The Hollywood Reporter. "And like Napster, the Silk Road was a watershed moment in technology where ... a very big and almost never before seen anonymous community appeared. The Silk Road, like Napster, had brought more people together than ever before, but this time it was in this hidden corner of the Internet so now you have this massive community that was all fictitious user names, using a crypto currency that was capable of being anonymized [Bitcoin]. And, of course, they were using it to buy and sell drugs. That immediately struck me as interesting, and then when Ross was arrested in 2013, I sort of found my human way in. And it seemed like a really good focus of the story and a good way to tell the story of the implications of privacy and anonymity and the war on drugs in the technological space through the Silk Road and Ross' story."

Even though Deep Web is centered around Ulbricht, Winter says he still doesn't feel like his subject is a "known entity," like some of the other people featured in the film, including Ulbricht's mother and Wired's Andy Greenberg, who was the first reporter to interview Dread Pirate Roberts.

"The people that are the emotional center of this movie are not Ross, they're these people trying to figure out what Ross is," Winter says. The film presents competing narratives of who Ulbricht is, and when asked how he can reconcile these, Winter says he can't because he doesn't know exactly who Ross is. 

"It's possible Ross is all of those things. It's possible he's three of them. Maybe he is just one of them," Winter says of the different characterizations of him. "I honestly couldn't tell you. I honestly don't know who could tell you for sure."

"He's like a Rorschach test. Because so little is known about him, everybody has applied their beliefs onto him," Winter continues. "That's frankly, probably, at heart what my movie is most about: In the technological age, how difficult it is to know what's going on behind keyboard, the human implication to just start pasting your preconceptions onto the idea of what that person is."

Winter goes on to say he doesn't "really" have an opinion on the charges against Ulbricht and that his views are frequently changing.

"My opinion, it fluctuates constantly because sometimes I get more information [and it] tilts this way, and then I find out more information and it's like, 'Maybe it's gonna tilt that way.' " Most of the people that are deep inside the Silk Road story from a journalistic standpoint feel the way I do, where it's very twisty-turny and every week there's a new revelation," he says.

As those new revelations occur, perhaps one of the other two projects in the works about the Silk Road can address those developments. A&E IndieFilms and BBC Storyville announced in November that they had partnered with Vice Media's film division and U.K. production company Raw to make The Dread Pirate Roberts, about the rise and fall of Silk Road and Ulbricht. A movie based on Joshuah Bearman's lengthy Silk Road story for Wired is also in the works at Fox.

When asked why there's so much interest in the Silk Road and Ulbricht from Hollywood, Winter thinks its mostly because the case can be seen as a "salacious, Breaking Bad online."

"My guess is that most of the projects that we see about this story are going to focus on vice and that's probably why there's such interest, because it's drugs and guns and murder on the Internet," he says.

Still, he says, "My interest in it primarily comes from the implications of online communities and privacy and anonymity."

Deep Web premieres at 8 p.m. Sunday night on Epix.

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