'Deep Web' Director Alex Winter on Silk Road Boss's Harsh Sentence: 'A Stunner'

Earlier this afternoon, Ross Ulbricht—the mastermind behind the deep web market Silk Road—was sentenced to life in prison. After the verdict, we caught up with Alex Winter—director of Deep Web: The Untold Story of Bitcoin and The Silk Road, a documentary film airing Sunday May 31st at 8 PM on EPIX—for an interview. Winter was in the courtroom this afternoon and has been following the case intently.

MOTHERBOARD: First off, what was it like to be in the courtroom today and what was your reaction to the sentencing?
Alex Winter: I'm still processing it. It was a lot to take in. Ross getting life in prison without the possibility of parole was a stunner for everyone in the room. There was an audible gasp from the entire gallery where I sat when the sentencing was read. We also heard Ross make a statement today. I've never met the guy, I've never heard him talk. [Even having made the film], I know very little about him. He seemed to start by making a prepared statement and then rolled into an emotional summation of his feelings, of what he had done wrong, his remorse, and his motives for why he did what he did. It was a very emotional, heartfelt, tear-filled statement. It was not cold, clinical, nor was it perfectly put together.

Towards the end, he really wanted to make a statement in response to the prosecution's claim that Silk Road was not a political engine… and that it was only about greed and criminality. Ross took exception to that. And he wanted it known that his motives for Silk Road were vehemently born from a desire to use technology to help people. You could call him a liar, or say he was insincere, or that it was convenient for him to say that. You could even say it's the most naive and absurd thing you've ever heard. But that's what he said, and it was really powerful to hear those words.

Where do you stand on these ideals for Silk Road, and if it was indeed born out of these political motives and ideals?
As frustrating as it may be to hear: I don't know. All I can tell you is that having been around anonymous communities for the past 30 years, and I really plunged into them in the 1980s, I know this world really well. I know the people and their motives really well. I watched this world grow from the newsgroup era of hundreds of people, to Napster, to Silk Road with over a million people in a particular group. I don't exonerate what these people have done, but I've been studying them. As a filmmaker, all I wanted to do was present what I absolutely knew based on my research and then raise questions about what I did not know.

So to answer your question: I do believe Silk Road was created for mostly political reasons. All the people I've spoken to, and these are the chief architects, the moderators, the vendors, the operational security people of Silk Road, all of these people are political animals. Most of them came from the hacktivist movements. They are technologically sophisticated, they are politically active and they are extremely anti-drug war. They're not necessarily libertarian, in fact many of them hate libertarians. Now, Ross was obviously of that ideal, but Silk Road wasn't a predominantly libertarian environment, but it was pro-privacy and anonymity. These people were fairly young, in their 20s and pretty idealistic and radical.

The harm reduction argument, that Silk Road provided a better alternative to selling drugs on the streets. How does that hold up in your opinion?
It's an extremely thorny subject matter. The judge obviously had harsh words to say about the harm reduction claim. And to be honest with you, arguing that Silk Road provided harm reduction is an extremely radical position to take. I can tell you, from the people I've spoken to in the community, the political philosophy was not just saying this was going to reduce harm and violence on the street level. Their position was that using technology, and Tor and Bitcoin to drive drug sales, it would create such an unstoppable brushfire of these types of market places that it would make enforcing the drug war next to impossible to the point that it would force reform. That's an incredibly radical idea. It's way more radical than someone just saying "maybe there was some good to Silk Road."

Personally, I do think the drug war has gone on for four decades and is a disaster. It's just one of the horrible blights in American history. We'll look back on the drug war as an onerous moment in our history. But that doesn't mean I'm advocating some of these extremely radical stances.

And in the documentary, you make clear that you have some gripes with how the investigation was handled and what we know about it.
I say it loud and clear in the film and I stand by it: we don't know how they found the Silk Road servers. We do not know. That does not mean that they did anything illegal, it just means that we've not been allowed to have a satisfactory conversation about how the servers were found in a hidden service.

It complicates things further when this investigation is the first of its kind.
Completely. I'm dumbfounded when otherwise intelligent tech journalists come to the defense of the government on this one. It's a simple question and nobody's been given a satisfactory answer. Let's have a conversation. We live not only in a post-Snowden era, but we live in a post-Sony hack era. We live in an era where people's Social Security numbers and birth certificates are being stolen.

How has Ulbricht's arrest and the fall of Silk Road impacted the deep web?
It has not deterred anything. The black markets are proliferating at a rapid pace… the parallel[s] between Napster and Silk Road are uncanny. You shut down Napster, then you have a hundred copy cats, then a few years later you have Bittorrent. Once it's decentralized, it's game over.

I think we're in the same place now, where we have literally hundreds of copycats of Silk Road since it went down. And something that was originally born out of this idealistic, trust-based motive is gone. A lot of these new sites could care less about trust. "I'll take your money and bail." They don't care about harm reduction. They're mercenaries. We have a lot of these now, and most of them don't carry the same ideals as Silk Road.

So the new sites are just taking the capitalist qualities of Silk Road and stripping everything else away.
Which is what always happens. That is like the natural water down a stream. It's like watching a car accident in slow motion. There's no deterrent.

You've followed, investigated and researched this case closely. What is the biggest unanswered question for you?
I have so many questions. Where the hell was the rest of the money? If as claimed that there was $18 million of bitcoin found on Ross's laptop, then where is the other $70 million unaccounted for in fees from Silk Road?

There's Ross's journal. Why did he write in that journal? And why, in 2013, when the heat was rising all around him, he started hammering away on his diary like a LiveJournal acolyte. It doesn't get brought up much, but Ross made almost no journal entries prior to 2013. So why, when the heat was on, did he start singing like a canary to his laptop. I would love to sit across from him and ask him if it was really his journal and why did he write in it.

Another question is how much administrative rights did those two agents have. We know they had a lot of control over Silk Road. Did they have administrative rights to the Dread Pirate Roberts account, as some people in tech world believe they did. If so, that's a huge can of worms. Are the chat logs which have been read in court in the last year during the trial really Ross's? Or is it [federal agent] Mark Force using the DPR account. I have so many questions I don't even know where to start.

And we'll probably never know.

All these questions will remain unanswered.

Finally, to the people who haven't been following this story, or know about Bitcoin, Silk Road, Ross Ulbricht and the deep web, why should they care?

There are several core issues that impact everybody. As Ross said today in court, whether you believe it or not, one of his primary motivators for creating Silk Road was to use technology to create more privacy and anonymity for the average citizen. In the digital age, our privacy can no longer be ignored. It's an important issue. You can no longer throw out the ridiculous axiom that "if I have nothing to hide, I have nothing to fear." The Silk Road case strikes at the heart of the technology movement to create more privacy and anonymity tools for everyone.

Second, we have to consider what needs to be reformed in our constitution and legal system with regards to search and seizure in the digital age, to put in proper safeguards for American citizens to protect them from unwarranted search and seizure of their private data. Third, it strikes at the heart of the drug war, which I mentioned earlier.

I didn't make a film of whether Ross is innocent or guilty. I didn't make The Jinx or CitizenFour. Ross is an unknown. What I want people to take away from this, especially the average Joe, is that this world is very complicated and we can no longer hide the fact that we're living in the digital age. We can't just put our heads in the sand and go none of this stuff matters to me. That's the takeaway I want people to have.