Review: Alex Winter's "Deep Web" about Silk Road's Ross Ulbricht

Going in to see the movie Deep Web, which played yesterday and today at the Montclair Film Festival, I was most interested in the question "Who is Ross Ulbricht?" Is he the libertarian idealist who created Silk Road to let people do what the government doesn't want them to do? Or is he the scheming drug lord who put out contracts on associates who had betrayed him, as alleged by the government? Though the movie was fascinating, I left with my question unanswered.

This is no fault of the filmmaker, whose challenge was to make a documentary about someone he had little access to. Despite interviews with family, friends and business associates, Ross Ulbricht appears as a shadow in this movie. We see him in a few home movies, we see his LinkedIn profile, but we never really see or hear Ross Ulbricht talk about the subject at hand.

We hear more from Dread Pirate Roberts, a pseudonym that was at least partly Ross Ulbricht. We see many of his posts on Silk Road forums, with highlights to show the complexity of his motivations. DPR seems more interested in ideals than money, he wants to make the world a freer and safer place. But he's a businessman who values loyalty and doesn't tolerate people who don't make good on their promises.

The central voice of the film is that of Wired Senior Reporter Andy Greenberg, listed as "Consulting Producer" of Deep Web. Because much of the film surrounds Silk Road forum postings and the legal case against Ulbricht, it relies heavily on Greenberg to boil down and assess voluminous posts and complicated proceedings. Greenberg doesn't quite have the screen presence the film needs from him, but hey, that's not his job. But so we don't miss the point, there's always a poster of Edward Snowden behind Greenberg in his office.

The film has at least two narratives that make for a sometimes conflicted message. One narrative is the libertarian argument in favor of online drug markets, another is that the government has prosecuted Ulbricht unfairly, perhaps illegally.

The moral argument in favor of Silk Road is particularly resonant in this post-Ferguson post-Baltimore era, and I wish the film had followed this thread further. The gist of it is that real-life drug markets are violent scourges that ruin communities, and moving them online removes most of the violence associated with the illegal transactions. Silk Road succeeded by bringing accountability to these transactions; a transaction gone bad would result in a seller losing reputation instead of someone getting killed. In a sense, Silk Road functioned as a government beyond the reach of domestic law. By contrast, the War on Drugs results in police inflicting violence and punishment  on people and communities causing harm out of proportion to the benefit of extending the rule of law.

In the context of this war, it's small wonder Ulbricht doesn't get the benefit of the legal doubt. It's hard not to compare Deep Web with the film I saw last year at Montclair Film Festival, Brian Knappenberger's The Internet's Own Boy. Both films recount the story of a bright young man turned entrepreneur, who is driven by idealism to do something to which the legal system reacts with brutality. Both films prominently feature analysis by the eminently reasonable Cindy Cohn and the starker views of Chris Soghoian. Despite the emotional power of Knappenberger's film, Popehat's Ken White criticized it for its naive view of the legal system. White's cynical view is that we shouldn't be so outraged that Aaron Swartz was singled out for extreme prosecution, because that's what our legal system does to most people it turns its attention to today. This point would go double for Ross Ulbricht. The prosecution of Ulbricht was unfair, but that's exactly how most drug-related cases are prosecuted. "Drug kingpins" who complain about the feds hacking their computers can't expect much forbearance from judges who advance in the system by being "tough on crime", and rich white folks shouldn't expect to be treated differently.

Unfortunately for Winter, the most shocking revelation in the Ulbricht case came after most of the current film was shot, and is only mentioned briefly at the end - two of the agents investigating Silk Road were indicted for stealing over a million dollars worth of bitcoin from the site after they had infiltrated and taken control of the site. It's hard to imagine that this won't play a major role on appeal.

As far as I can tell, Deep Web get its facts right. It manages to avoid many of the silly characterizations of Bitcoin in the popular media (for example, bitcoin enables anonymity but it's not automatic). The only quibble I have is the title. "Dark Web" would have been more accurate, as well as more dramatic.

Over all, I found Deep Web an extremely engaging telling of an important story. But it ends in an unsatisfying place, with a shoe dropping. See don't miss it when it airs on May 31; you'll be able to enjoy what happens next.

Trivia note: Both Ross Ulbricht and I, in our past lives, published scientific articles on the incredibly obscure topic of adsorption-controlled molecular beam epitaxy of oxides. Yep.

• "Adsorption-controlled growth of EuO by molecular-beam epitaxy", Appl. Phys. Lett. 93, 102105 (2008); http://dx.doi.org/10.1063/1.2973180
• "Adsorption controlled molecular beam epitaxy of rubidium barium bismuth oxide", J. Vac. Sci. Technol. B 8, 332 (1990); http://dx.doi.org/10.1116/1.585064

Deep Web premieres on May 31 at 8PM EST on EPIX.

Here's the Trailer:

Ranganathan and the 5 Blind Librarians

It's "Choose Privacy Week". To celebrate, the American Library Association is publishing a series of blog posts; today they're running mine! I wanted to write something special, so I decided to have little fun with a parable. I'm reprinting it here:

I've heard it told that after formulating his famous "Five Laws of Library Science", the great Indian librarian S. R Ranganathan began thinking about privacy in libraries. Here's what I remember of the tale:

In India at the time, there were five librarians reknowned far and wide for their tremendous organizational skills, formidable bibliographic canny, and the coincidental fact that each of them was blind. It was said that "S" could identify books by their smell. "H" could classify a book just by the sound of the footfalls of a person carrying it. "T" was famous for leading patrons by the hand to exactly the book they wanted; the feel of a person's fingernails told him all he needed to know. "P" knew everything there was to know about paper and ink. "C" was quick with her fingers on a keyboard and there was hardly a soul in his city she had not corresponded with.  But these 5 were also sought out for their discretion; powerful leaders would consult them, thinking that their blindness made them immune to passing on their secrets of affairs and of state.

So of course, Ranganathan asked the five blind librarians to come to him so he could benefit from their wisdom and experience with privacy. The great librarians began talking among themselves as they sat outside Ranganathan's house.

"On my way through the countryside I encountered a strange beast", said librarian H.  "I can't say what he was, but he had a distinctive call like a horn: Toot-to-to-toooot..." and librarian H reproduced a complicated sound that must have had at least 64 toots.

"By that sound, I think I encountered the same beast." said librarian T. "I reached out to touch him. He was hard and smooth, and ended in a point, like a great long sword."

"No, you are wrong", said librarian P. I heard the same sound, and the strange beast is like a thick parchment, I could feel the wind when it fluttered.

"You fellows are so mistaken." said librarian C "You touch for a second and you think you know everything. I spent 15 minutes playing with the beast, she is like a great squirming snake."

"I know nothing of the beast except the smell of his droppings," said librarian S.  "But what I do know is that the beast had recently eaten a huge feast of bananas."

At this, a poacher who had been eavesdropping on the five librarians picked up his shotgun and ran off.

Just then, Ranganathan emerged through his door. Surprised at seeing the poacher run off, he asked the librarians what they had been talking about.

The librarians each repeated what they had told the others. When librarian S finally recounted the banana smell, Ranganathan became alarmed. The poacher had run in the direction of a grove of banana trees. Before he could do anything, they heard the sound of a powerful shotgun in the distance, and then the final roar of a dying elephant. 

With tears in his eyes, Ranganathan thanked the 5 librarians for their trouble, and sent them home. Though Ranganathan's manuscript on privacy has been lost to time, it is said that Ranganathan's 1st law of library privacy went something like this:

"Library Spies Don't Need Eyes".