The doc succeeds in some ways, fails in others
Deep Web is somewhat interesting documentary that succeeds in many ways but fails in others. My familiarity with the Deep Web itself is limited. I've never visited a site, used a TOR browser or had access to Silk Road itself. I've read the various articles online for the past few months. Some very supportive of Ulbricht that look at him as kind of hero. The filmmakers obviously fall into the category of people that feel Ulbricht is being unfairly prosecuted.
How it succeeds: The filmmakers do a good job of informing the viewing of the issues at hand. They do an excellent job introducing the deep web and Silk Road. It's quick and interesting.
They also do a very good job at questioning if the government violated the 4th amendment in their investigation of Ulbricht. That to me is the most compelling question in Ulbricht's defense against the government. Was the investigation itself legal? Also, did he get a fair trial from the judge? They make a compelling case that the government played dirty pool by disallowing witnesses and document dumps.
How it fails: Ulbricht's mother thinks he's a good boy who wouldn't do anything illegal. So what? Prisons all over the world are filled with guys that have sympathetic parents who think their baby is innocent. That means nothing.
Ulbricht is clearly at least one person that goes by DPR. Ulbricht wants you to believe that others are DPR as well. But they never provide any evidence that would prove that. We're supposed to just take his word for it. It's the equivalent of throwing something against the wall and hoping it sticks.
The doc outlines how the war on drugs has been a failure, which is clear to anybody paying attention. They outline Ulbricht's view that Silk Road is intended to provide a safer way to purchase drugs that he feels should be legal anyway. But here's the thing, it's irrelevant if Ulbricht or anybody else thinks drugs should be legal. They aren't. So if you traffic in drugs you're breaking the law. It's that simple. Your philosophy doesn't matter.
They also outline that many other things are on the deep web and not just drugs and porn. Again, so what. Nobody is being charged for the conversations about politics. They're getting busted for trafficking drugs. Whatever else they do is irrelevant.
Ultimately, I think Ulbricht has a solid case for his appeal based upon the possible violation of the 4th amendment in the investigation. Ulbricht is clearly guilty of being a drug trafficker but he might be able to get off on the illegal way that information was obtained. It should be interesting to see how it goes. Even with his crimes, getting a life sentence for what he did is ridiculous. Rapists and murderers get less time for more serious crimes.
There other issues discussed in the doc regarding privacy but I've provided enough of a word dump already. So I'll mercifully stop here.