The First Silk Road Documentary Is a Dud

May 28, 2015 | Peter Yeh

From a documentary with a title like Deep Web: The Untold Story of Bitcoin and Silk Road, one expects new details on how the Silk Road vendors and community operates, how bitcoin enables deep web markets, and a discussion that could bridge the gap for the average person between the anarchic cypherpunks and fear-mongering government officials. The development of the deep web is a truly fascinating evolution, and even more important in our post-Snowden era. Instead, however, the documentary blows past all of the evidence accumulated during the infamous Silk Road trial, glosses over any of these discussions, and dedicates a majority of the screen time to Ross Ulbricht’s parents, trying to cast his guilt in doubt.

Launched in 2011, Silk Road was an online deep web black market that ran on the Tor darknet as a hidden service. Run by an admin using the pseudonym, “Dread Pirate Roberts”, users could browse and shop anonymously using Tor, and pay with the pseudonymous virtual currency, bitcoin. Drugs were shipped to a user’s house via the postal service. In 2013, the site was taken down, and Ulbricht, man behind the “Dread Pirate Roberts” was arrested. In January of this year, a highly publicized trial started in New York, culminating in money laundering, computer hacking, and conspiracy to traffic narcotics charges against Ulbricht.

In a quick phone interview, director and writer Alex Winter denied any sort of bias or sympathy towards Ulbricht, but there are clear filmmaking choices that betray a subjective view. To its credit, the documentary gathered an impressive list of journalists, former law enforcement, and even former Silk Road vendors. However, their insights are wasted as the documentary is a disorganized mess that tries to cover too many topics for its 90-minute runtime.

Nearly all those interviewed denied Ulbricht’s guilt and kept trotting out the ridiculous assertion that it was the defense being completely derailed that cost Ulbricht the case, and not the huge pile of evidence mounted against him. Ulbricht’s guilt was so overwhelmingly proven because of an incredible bit of arrogance: He broke the first and most important rule of OPSEC (operational security) in the hopes of a future book written about him. He took notes on his criminal fucking conspiracy.

The crime diary, how it matched up with the real world surveillance, and the positive trace on the bitcoin public ledger of Ulbricht’s bitcoins to Silk Road — all of these pieces of evidence are glossed over to help assert that Ulbricht is innocent. The defence’s attempt to present an alternative narrative of former CEO of defunct bitcoin exchange MtGox Mark Karpeles using impossible wizard-hacking with BitTorrent to plant the crime diary on Ulbricht’s laptop goes unmentioned because, according to Winter, “I didn’t feel ethically comfortable with dragging his name through.”

What is covered by the documentary is the suspicious circumstances by which the FBI located the Silk Road server. That is worth discussing. However, the documentary omits (a running theme) a vital legal point that Ars Technica points out: standing. Standing means that if you have a personal interest in the property, you can have a say in court. Despite an attempt from the judge to actually help the defense, the defense never claimed the server as his, meaning his 4th Amendment challenge against unreasonable search and seizure was denied. There’s much more the documentary does wrong, but these are some of the more glaring things.

The documentary doesn’t outright claim that Ulbricht is innocent, but does its best to fill your mind with so much doubt, it might as well. There’s even a few seconds of just “Free Ross.org” on the screen with Ulbricht’s mother standing before an applauding audience.

If this documentary were called Dread Pirate Roberts: The Untold Story of Ross Ulbricht, then I could forgive it. But it’s not. It is called Deep Web: The Untold Story of Bitcoin and Silk Road, but instead of being about the Deep Web, bitcoin, or Silk Road, it’s home movie time with Ulbricht’s friends and family.


If you want to learn about the Dread Pirate Roberts (Ulbricht’s alter-ego) and Silk Road, read the Forbes interview he gave. If you want to learn about the trial, read Sarah Jeong’s coverage on Forbes. If you want to learn about bitcoin, read this FAQ. If you want to learn about the deep web, listen to this podcast. If you already believe that Ulbricht is a freedom fighter that’s been wrongfully convicted and nothing will convince you otherwise, watch this documentary. And if you want to try to understand why Winter approached the documentary the way he did, then read this interview below:

What motivated you to make this documentary?

I”m interested in stories in this space for a long time. How the shift into the digital age is affecting us, affecting human culture, and broader questions about our rights to privacy and the difficulties of we take moving forward and some of the things we need to change. I just came out of telling the Napster story all about music and telling the story of how we got here, the cypherpunks who created this technology.

You got very close to Ross Ulbricht and his family. Do you feel as if that made you biased?

No not at all…I had a lot of compassion for them, they didn’t give me any information because they had none. I would have had to spend a lot of time with Ross to get a bias. The people I had access to, while close to ross in his real everyday life, knew not much more than I did.

What I was interested in with the story was really examining the human beings at the center of the story what it’s like in the inside, what it’s like to be inside the story, what it’s like the evolutions they had as a people and what that journey was like for them and then other people who were big parts for people in the cypherpunk community.


Do you believe Ross Ulbricht was the Dread Pirate Roberts?

I don’t really know. I think this falls in the same camp as those people, I don’t really know. I believe there would be an appeal. To boil it down, the government has made a very compelling case that he was, and the defense never got to be presented. There’s a lot we don’t know.

The documentary didn’t mention the Mark Karpeles/Mt. Gox theory at all, despite that being a pivotal moment in the trial. Instead, it focused on the judge’s dismissal of an agent’s testimony that said there were other suspects, initially. Why was Karpeles omitted and the hearsay dismissal kept in?

There was a lot of big moments in the trial. The problem with the movie — I didn’t make the movie about the trial, we couldn’t get all the details in, and it would have been mind numbing boring. We couldn’t cover it all.

Most people don’t know who Mark Karpeles is. I didn’t feel ethically comfortable with dragging his name through. I mentioned the details of what aspects of the case were.

The defense argued that the Tor network surveillance was warrantless, yet Ulbricht’s defense team never declared a personal privacy interest on the server, so his 4th amendment rights didn’t apply. Do you believe that was a mistake by his defense team?

No, I don’t believe the terms under which they were given that option were actually functional. I think the bigger question, is having a conversation whether they were done so with a warrant. The kind of legal harangue, over whether something was done legally or not.

I’m not Ross’s lawyer. I think it was seized illegally. It isn’t whether or not they were claimed, but whether they were seized illegally. I don’t know much about law or Ross’s case on the inside. Having a conversation about search and seizure in the digital age is very important. I don’t think, from my perspective, Ross was ever offered an option that was genuinely sincere.


Do you agree with the assertion that the Silk Road and online drug dealing would lead to a safer world?

As common sense will tell you that it did. The bigger problem that people have is that they think in black and white terms. You’re branded as thinking in black and white terms, like you support Silk Road, it will reduce a certain amount of violence. It doesn’t mean it was good, it doesn’t mean it was a Shangri-la. It was a statistical fact that it reduced harm and crime in the drug trade.

There’s a lot of cypherpunks, crypto-libertarians featured in this documentary, who feel very strongly about the nature of the free market, the drug war, and the government, was that intentionally presented without criticism?

Let’s not call them crypto-libertarians. I know many of them would be horrified to be called that. They’re anarchists.

I would disagree people as crypto-anarchists are viewed as very threatening to many people. The DHS and spends a lot of time spreading fear, scary, and the way we present, is fairly threatening. They’re being seen as the darker side, for lack of the better word.

They’re aware that their views are provocative. It’s woven into their quotes, that they’re being provocative.

Going back to the trial, it seems any evidence the government presented and the case it made was not mentioned in the movie.

That’s now how I viewed it. It’s all laid out in the movie, and I don’t know how you perceived it…it’s all laid out in there.

Deep Web: The Untold Story of Bitcoin and Silk Road debuts on Epix at 8 PM on May 31st

(Photos: Epix/Deep Web)