Deep Web: Deep Into the Darknet

From beyond the friendly internet-based interfaces of Gmail & Facebook, the documentary Deep Web takes a dive into the occasionally murky waters within the “darknet.” This untraceable, hard to access part of the web is home to not only vast databases of private information, but also shadowy black markets hidden by cryptographers. Alex Winter’s new film investigates a highly publicized case against a key member of the “darknet” to examine the underlying issues that impact everyone’s lives.


Among the most famous of the underground, online marketplaces was Silk Road, an internet black market primarily facilitating the exchange of illegal drugs. As Silk Road’s profits soared, law enforcement scrambled to dismantle the infamous “ of illegal drugs.” Whom federal agents came up with was Ross Ulbricht, an at the time 29-year-old former engineer that was involved in running Silk Road through the alias of the “Dread Pirate Roberts.”

Ulbricht was initially met with charges that ranged from money laundering to murder-for-hire; however, as the case moved closer to trial many of the most scandalous charges were dropped. The cloud of encryptions and accounts with shared access make the details of Silk Road’s alleged nefarious activities difficult to parse through, and a shady government investigation only raises bigger questions.

Documentarian Alex Winter turned his attention to Silk Road following the slew of misinformation in the mainstream media following Ulbricht’s initial arrest. As a man deeply familiar with the history of anonymous online communities, as well a filmmaker whose most recent documentary Downloaded chronicled the story of file-sharing service Napster, Winter was well-prepared to navigate a convoluted story in the hopes of examining its core issues.


Photo by Ron Travisano / Montclair Film Festival

Following the Mother’s Day screening of Deep Web, director Alex Winter held a detailed Q&A with the Montclair Film Festival audience. Read some excerpts from his answers below:

This is such a fascinating story, how did you first find out about it?

I’ve been involved in anonymous online communities since before the web, during the BBS Usenet era of the ’80s into the early ’90s. In those days it was very cumbersome to get online. Those communities have a lot of people on them, they were communities about art, philosophy, books, whatever. Because I was fairly heavily involved in that community, it’s easy to discover everything. In those days there were drug markets there, too. There was encrypted email. All the things that are going on today were going on then on a smaller scale.

I’m interested in the sociopolitical motivations behind the expanding of movements online. That’s why I made a film about Napster before this, which from my experience had little to do with music in terms of its motivations. In fact it had nothing to do with music. It was all about creating the first user-friendly global community on the internet which is exactly what it did do. We went in 1999 from having a handful of people on the internet communicating at one time in community spaces to, with Napster, overnight over 100 million people. From my perspective, at that time, that was its watershed contribution to technology. I always felt the music and the piracy issues were going to fade into the background which I think they will over time as Napster is seen as the evolution of this type of movement.

When Ross Ulbricht was arrested in October I knew about Bitcoin, I knew about the Silk Road, I wasn’t paying a lot of attention to the Silk Road, but I knew that the darknet was getting bigger and was getting utilized more by public people. It was becoming the way the usenet communities used to be. It wasn’t just journalists, dissidents and government agents, it was also people who just wanted to communicate with each other with privacy and anonymity on the internet. So that was growing.

When Ross was arrested and I saw the media was responding to his arrest–it wasn’t about whether I thought he was innocent or guilty–but when I saw the way the story was being told it was the same strange misinformation, skewed, lack of clarity, lack of thoroughness, lack of nuance that had happened with Napster. So I immediately set out to make a movie about it.

We literally planted a flag in the sand that day. I had Andy Greenberg slowly compile all the key players of the Silk Road. I’ve reached out to most of the core vendors and buyers from the Silk Road. I got unprecedented access to most of them, about 25 of them. Some in jail, some going to jail, some at large. And then eventually I got to the owners which took almost a year.

There are certain major details that are touched on only briefly in the film, what was some of your reasoning for that?

There’s an enormous amount of detail here that didn’t make it into the movie that shouldn’t be in the movie, it’s just over people’s heads… I take a very strong stand as a filmmaker as to what I do and don’t show. I have really strong ethics about going up to a line. A lot of people went over the line and claimed that Ross was a murderer and all these things [when] he wasn’t even being charged with murder much less convicted. To this day we read news articles where he’s being called ‘murderer.’ I tend to stand very squarely in the heart of what I know to be true.

Why hasn’t the ACLU gotten more involved or lodged a formal complaint?

I think that they are very measured and they’re waiting for sentencing. They’re waiting to see what happens with an appeal. But I can tell you there’s an enormous about of scrutiny going on from both the ACLU and the EFF.

Considering the way [that Ross’] trial was conducted is the feeling that there’s a good basis for appeal or not?

There’s a lot of room for appeal. As some of you may or may not know appealing a federal case is very difficult. Reversing a decision in a federal decision, assuming you get to appeal, is very difficult. So there’s no doubt they have a very difficult road ahead of them. However, the indictments against the allegedly corrupt agents, and the depth to which that corruption goes, is being examined. It goes far beyond just stealing Bitcoin. From my perspective that’s as much as I can legally talk about but they had pretty much total control of the usernames and logins of the site to do all kinds of stuff. There’s a lot of examination going into their involvement. I think there’s an enormous amount that we don’t know.

My movie is at the end of the day a movie. It’s not a piece of journalism and it’s not an attempt to tell the whole story. It is, in fact, plainly the opposite. It’s trying to say, “Here’s a lot of very complex questions. Here’s the 29 or 30-year-old kid that is kind of a cypher.” Nobody really knew anything about him. There’s a lot in the media, the family members’ perspective, there’s little bits that we got here and there but it doesn’t add up to a human being. So there’s a lot that we don’t know, there’s a lot that’s very frustrating, and there’s a lot that will probably be coming out over the next year or two. It’s a conundrum for sure.

Where does your movie go from here?

I sold it before I made it so it was paid for by Epix the cable network. It’s going to be all over TV in about two and a half weeks. It’ll be coming out on Epix at the end of May and it’ll be advertised by then. Then they have a window for most of the summer to just run it on their network, and then it’ll be Netflix, likely in January. VOD everywhere. It will have a good release, a lot of people will get a chance to see the film.

Why do you think the government tried to pin this all on one person?

That sort of gets into sort of an editorializing question. Obviously everybody has an opinion and no one knows the answer, right? It was fairly evident from the beginning, from the moment [Senator Chuck] Schumer came out and publicly said, “This site is evil. The darknet is evil. Somebody is running it. We will find them. We will arrest them.” That activated all law enforcement on this rabid hunt for this guy.

There was huge competition among the three letter agencies. The FBI, the DHS, the EPA, the IRS. They’re all competing to catch this guy, they’re in a swift race to catch him.

Once Ross was discovered they felt they had this identifiable American. They didn’t need to extradite him because the people involved in Silk Road are scattered all over the world, right? It’s the internet. You have Silk Road buyers in Australia, Silk Road buyers in England. Mark Karpelès is French and he was in Tokyo at the time. Here you had this kid, they caught him, he’s in jail, he looks like he had a lot of involvement, he was logged into Silk Road when they caught him.

For those of us who were at the trial, I was there for some of it, it was a jarringly swift trial. Again, not to get hyperbolic and say that it was railroaded. The reality of it is the defense never really got the chance to say anything. It was over really fast, even for the most hardened, cynical journalists who were in the room with me… Most of the tech press – Wired, Forbes, all these guys – they all went off to a bar and got drunk for nine hours because they were so totally shellshocked by how fast the whole thing was.

They know, like I do, a lot about how Bitcoin works. A lot about how cryptography works and we didn’t get to hear any of it. There was no explanation about how these technologies work. There was no real defense of how many people were on the Silk Road besides Ross. It just didn’t happen so it’s very jarring. Not to pound the table and say that justice wasn’t served. It may not have been. It’s really not my place to say. It’s just there’s an enormous amount that never came out. So from my perspective, and my knowledge of how the Silk Road worked, it certainly was very convenient to hang it on a single individual and build up this mythos for this individual being a murderous kingpin, which is sort of what you’re hearing in the media about him.

He may have done a lot of really bad things, he may have done dumb things, some of which we will never know the extent to which he did. We may never know. I personally haven’t seen evidence of a murderous, drug kingpin. If he gets [a] life [sentence] in May that’s why he would get [it].

Was there ever a concern while making this film about your own safety?

My mom asked me that. She’s like, “Are you safe?” There really wasn’t [a concern]. I went through this on Napster, it’s really sad but true. This sounds a little cavalier and I don’t mean it to but I knew the government was going to win. I knew that where the case was going to go, however long it took to get there, I knew they were going to win their case. They don’t really care about me won’t [lose].

And the Silk Road people I was never worried. They’re easy, accessible… I’m not condoning what they did but the thing to understand about encryption and building systems like this is I wasn’t in Breaking Bad. In order to be part of the Silk Road at a high level these people are physicists, mathematicians, programmers. Very technically adept, very smart. I’m not going to agree with all their values and their principles, but it wasn’t like I was rubbing elbows with criminals. So I was never really worried on the Silk Road side. I was more worried that the prosecution or the FBI or somebody would see me as an irritant. Which, again, I wasn’t out pounding tables or crying that hard a foul. I think that it was really about trying to present the story.

Also, there were so many other reporters talking about frustrations of not knowing how did the feds find the server within a hidden corner of the internet that no one else is able to see. Technologically speaking that’s very difficult. [It] requires a process that’s never really been satisfactorily explained. How did they then acquire that server? Did they have a warrant? No one’s ever seen one. That’s a secondary question.

The third one is, in terms of that server being in Iceland, how do the laws work around… there’s been claims that this was legal, claims that it wasn’t legal. There’s a lot of frustration around those question and one’s been allowed to have a conversation about. I’ve talked to the FBI, talked to the DHS. I was really interested in hearing their side of the story. I think they understood that I really did want their side of the story. I didn’t get it but I was asking for it [laughs].

When you were trying to sell the documentary, were you met with any pressure as to what to include or not include?

No, frankly the reason that I went with Epix is because they didn’t do that. We did a Kickstarter campaign for not a lot of money, we built a big community around the movie, then we cut a trailer, then we went to networks with that trailer. We had offers from almost everybody but a lot of them demanded that we take a very skewed position, which I didn’t feel comfortable doing. I didn’t know much about the story at that time, it just felt off. They wanted a very salacious – they wanted Walter White on the internet, you know? It smelled funky to me from the get go. Eventually it came down to realizing that was not the story but even then it smelled fishy.

Epix was very interested in our perspective which was a slightly headier perspective. It’s more about issues. It’s more about global movements, the motives behind these movements, fourth amendment issues, privacy in the digital age. Those are what I think are the most significant aspects of the Silk Road case for how they impact other people. But [Epix] was really supportive of not being salacious, of not  saying things that we couldn’t back up 100%. They were really great to work with for that reason.

Photo by Ron Travisano / Montclair Film Festival

Photo by Ron Travisano / Montclair Film Festival

Written by MFF Blogger Zachary Shevich