Movie Review: Alex Winter’s Documentary, ‘The Deep Web’

I should probably begin this with a disclaimer. I’m not new to the movie review genre. As a sort of hobby, I write reviews for IMDb. So, as a writer on cyber crime and security, I’m always looking for a good movie on the topic. Unfortunately, they are not easy to find.

In the usual cybercrime movie, there is always the scene where the hacker-hero sits down at a keyboard, begins typing frantically away, then turns to his eagerly awaiting colleagues and says something like, “okay, we’re into the Pentagon’s computer network”. None of his colleagues are surprised. If only life were so easy. Such movies may be good in other aspects, but the hacking scenes don’t usually hold up.

Documentaries on cybercrime are a bit different. Some of them are quite good, though they often come with an angle. By this I mean that they are not really trying to be objective; they are trying to make a case. This is fine as long as they don’t go to the Michael Moore extreme of sacrificing the truth in order to propagandize a political viewpoint. You can usually tell early on in a documentary when someone has an ax to grind and, for me, it detracts from the documentary genre. When ax grinding begins, filmmakers, like Moore, begin to lose credibility. I’d rather have someone put the facts on the table and let the viewer decide how they add up. The truth is that there are probably no truly objective documentaries because the director has to choose what and how the information in the documentary is presented. I suppose there is always some bias.

In The Deep Web, it is clear early on that Alex Winter has an angle. The angle is that the deep web, the Silk Road, and Ross Ulbricht have provided a valid, honest service that does not undercut social values and, in fact, may have re-invigorated them. On the surface, this might seem like a difficult case to prove, but, to his credit, Winter does a remarkable job.

Winter portrays the deep web as a new cyber nation where anonymity, freedom, and relief from the burden of government surveillance can thrive. It is, or can be, the true libertarian utopia. As Cindy Cohn puts it in the film, “an observed life is not a completely free life”. Although the film is hyped as being narrated by Keanu Reeves, he actually has a limited role. This is more of a marketing ploy than anything. In fact, a significant part of the film is carried by “consultant producer” and Wired tech site writer, Andy Greenberg. Greenberg was the first person to actually interview Ulbricht when he was only known as Dread Pirate Roberts. Greenberg admits to liking Ulbricht calling him “a super interesting guy with a real coherent philosophy”. He believes that Ulbricht was sincere in his libertarian philosophy and truly felt that an open drug market would reduce the violence that was connected to illegal drug use. Greenberg’s own sincerity goes a long way towards making the film credible. Since this is a film review, I don’t want to give anything away. You’ll have to decide for yourself if Greenberg and Winter makes a good case for Ulbricht or not.

Winter does try to balance his pro-Ulbricht stance with interviews of various law enforcement officers connected to the case. There is some good and somewhat rare footage here of interviews with Ulbricht’s lawyer, Joshua Dratal, Ulbricht’s parents, and some of Ulbricht’s friends and admirers. There are even some home movies of Ulbricht himself that show he was more than just a drug dealer looking to make quick money. The one interview lacking is the one of Ulbricht himself. Apparently, no one can interview Ulbricht because of what Judge Foster called “the severity of the charges”. Ulbricht was also denied bail because the judge thought he might put a hit on someone. Interestingly, the hit-hiring charges were dropped after the defense got the denial of bail that they wanted. It seemed like the classic bait-and-switch.

This brings us to the crux of the film, at least for me. This was the insinuation that Ulbricht received, to put it lightly, something less than a fair trial. I have already remarked on this in a post I wrote on the sentencing. Winter, however, takes this even further. He makes you wonder about two key points: the objectivity and competence of Judge Forrest and whether or not Ulbricht was railroaded. At times, Winter makes you wonder if there was not some sort of collusion between the prosecution and the judge; they just seemed to work so well together. Again, you can decide this for yourself.

If there is one weak point in this documentary, it is trying to portray Ulbricht in too positive a light. I have read his Tor chats, even the ones he released after his sentencing to show that he was  concerned about more than making money. From these alone, you can see that Ulbricht is not the aw shucks, golly gee, kid next door that Winter makes him seem to be. In short, like everyone, he has his positive and negative characteristics. That said, this is a good documentary and one that should be watched.

I would recommend The Deep Web to everyone, even those who do not know much about the deep web, Ulbricht, or cybercrime. Winter makes the viewer consider the basic values that have created America and whether they have been dismantled to build something other than a free society. It could be that the Ulbricht trial was the crucible in which these fundamental American values were put to the test. This is why I feel that the retrial, if it is granted, will be even more interesting than the trial. I will stick by the predictions I made in a previous post that the verdict, sentencing, or both will be overturned. If not, then, at the very least, you can expect the deep web to become more encrypted, more secretive, and more politicized; in short, a true libertarian refuge.

I treat the IMDb 1 to 10 scale for rating movies as being non-linear. A 6 is above average, a 7 is good, and an 8 is very good. I have only given out a few 9’s and never a 10. I give The Deep Web an 8. Go see it. It will certainly give you a lot to think about.

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