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As Silk Road’s Ross Ulbricht Gets a Life Sentence, Alex Winter Says ‘Nobody Expected It’

As Silk Road's Ross Ulbricht Gets a Life Sentence, Alex Winter Says 'Nobody Expected It'

In March, Alex Winter’s documentaryDeep Web” premiered at the South by Southwest Film Festival as its story was developing: The film’s subject, Ross Ulbricht, the 31-year-old founder of underground e-commerce network Silk Road, had been convicted on seven charges associated with the marketplace, a billion-dollar operation that relied on the digital currency bitcoin. Though Ulbricht, a college-educated libertarian, hardly fit the traditional criminal profile, the government alleged he was primarily responsible for Silk Road’s involvement in online drug trafficking. On Friday, Ulbricht’s story entered another dark chapter, as the judge overseeing his case sentenced him to life in prison. 
Winter, an actor perhaps best known for playing Bill in the “Bill and Ted” movies opposite Keanu Reeves — who narrates “Deep Web” — is no stranger to the challenges facing technologically-empowered communities in the 21st century. His 2012 documentary “Downloaded” explored the history of file-sharing, from the early days of Napster through the present, when several unknown variables remain — as Ulbricht’s fate proves. While Winter has no plans for a sequel, he was in the room for yesterday’s sentencing, shortly before jumping on the phone with Indiewire to discuss the verdict. “Deep Web” premieres on Epix this Sunday at 8pm eastern. 

What was the mood like in the courtroom today?

It was suffocating — emotionally draining. It’s not a partisan feeling. I was sitting with journalists and people who made very harsh opinions against Ross and those who were in between. It went on for a very long time. We heard Ross speak in court for the first time. Nobody expected him to get life. I think worst case they were assuming would be something above the 20-year minimum. But in terms of prison sentences, this is very different — maximum security without the possibility of parole. My takeaway is that it’s just tragic, no matter what he did. We ended up with this debate about privacy, anonymity and this radical, anti-war, anti-drug movement versus the government. You really heard both sides argue their cases. You didn’t hear that during the trial. The judge spent a long time explaining why we had to make an example of Ross to the fullest extent of the law. 

How do you relate to the movie, which you finished months ago, now that Ross has been sentenced?

I basically saw it playing out this way from the beginning — in general, I mean. I assumed the government would win this case. The movie I made speaks to the story as I see it. It doesn’t condone this radical behavior; it looks at it with compassion, not empathy. This radical movement grew up on the internet over 30 years. Silk Road was one particular offshoot, not the leading one, but the movie represents a snapshot of that crazy moment in time. I don’t have the answers about what will happen next. I don’t think anyone does right now. 
Do you think he’s guilty?

It’s an irresponsible question to answer in the definitive. He was faced with a lot of these murder-for-hire charges. There’s evidence that points to culpability, but he was never formally charged. So it’s weird to see him put away for life when he wasn’t charged. I understand that’s not illegal, but there’s a lot I don’t know about what went on behind the scenes there. Yes, there’s guilt. I’ve never felt Ross was innocent of all these charges. He was caught red-handed, logged into the administrative section of the website. He’s admitted to it. It goes beyond that. What’s he guilty of? Does the punishment fit the crime? 

You weren’t able to interview him for the film. Will you speak to him now?

I might, but I have to ask myself what the purpose of it would be. I’m not making “Paradise Lost.” I’m not making a trilogy here. I’m done. I don’t want to cross the line of what I wanted to do as a filmmaker. I like that it’s about an unanswerable question. I made this as a filmmaker for narrative purposes. I’m not a journalist. It would make me feel parasitic to make more movies. I remain in contact with the family because I care about them. 
But there is a kind of makeshift trilogy here about the challenges of the internet age, with your previous movie “Downloaded” and “Citizenfour”…

I definitely have another tech movie or two in my back pocket. I do want to tell at least one more story about it. I think “Deep Web” is simpatico with those other movies. I don’t think you can call Ross an activist hero like Edward Snowden. That would be presumptuous. But it is a similar political radicalism that provoked Snowden to take action. I would argue that such radicalism was there even in the early days of Napster. Right now, technology is a thorny subject because it is unpalatable to people. but it can be liberating to many on the political landscape. And there are great stories to be told there. I like that you don’t know if you can love or hate Ross. Those paradoxes are really interesting to me. 
His story is being developed by more than one Hollywood studio. How do you feel about those projects? 

I’ve spoken to most of the people working on those narratives. Fortunately, they’re all really smart. But I wouldn’t want to be their shoes for all the tea in China. [laughs] I don’t know how you make a coherent narrative with these unknowns without having to make stuff up under ethically questionable circumstances — not that it hasn’t happened before.

Moving beyond this project, what motivates you as a filmmaker?

I want to tell stories that make invigorating shows and movies. I just sold a one hour pilot to Hulu that involves contentious civil rights issues. That’s what I’m working on at the moment. These are the stories that interest me. I like telling real world issues in an artistic fashion. I grew up loving Costa Gavras and Frederick Wiseman movies. I’m not saying I’m like them, but I’m very motivated by them. I think this process has aesthetic value, not just topical value. 
Given those motives, are you frustrated when people see you on the street and only recognize you from “Bill and Ted”?
It doesn’t bother me. Really. It’s been my day-to-day life for 30 years. I started getting recognized on the street when I was young because of my Broadway career. You learn to process that. I was mentored by people like Yul Brynner, who wore a lot of hats. They told me that you can do multiple things in this industry. It’s okay. So I don’t mind. In a way, while it’s not humbling, it allows me to distance myself from this work. It’s a collaborative effort to make a movie. For any artist, it does get past them. I’m not the best arbiter of my own work. 

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