> After all, he's kind of like us, spending a lot of time coding in front of his computer and he doesn't look that stupid.

He doesn't look stupid?

Ulbricht was not a smart guy. This was obvious from his various writings, examples:

http://www.forbes.com/sites/andygreenberg/2013/08/14/an-inte...

http://www.forbes.com/sites/andygreenberg/2013/04/29/collect...

He talks at length about his philosophy in a way that seems superficially intelligent, until you actually scratch the surface and discover that what he was saying was internally contradictory and had no intellectual merit.

For example:

Firearms and ammunition are becoming more and more regulated and controlled in many parts of the world. We actually had a site up called “The Armory” ... if we can find a model that works where people can get the equipment they need to defend themselves and their families despite what the state wants and often in defense of the state itself, I would be more than happy to provide that.

The Armory, lest we forget, sold bazookas and RPG launchers. The awful oppression he is rallying against here ("in many parts of the world") is usually a highly popular policy that's completely uncontroversial. From the perspective of people living in these places being able to buy sub-machine guns online and have them delivered to your door is not some kind of non-violent libertarian utopia. It's just horrible.

Just a few paragraphs later he is saying

We don’t allow the sale of anything that’s main purpose is to harm innocent people

His deep lack of technical knowledge was revealed by this sentence:

I’m not one hundred percent on this, but I don’t think it’s possible to do a DDoS over Tor

Ulbricht routinely conflated libertarianism, agorism and anarchism as if they are all the same. His knowledge of economics was as flaky as his knowledge of political systems:

There is also nothing morally wrong with [cartels]. If a cartel were to form, I would not attempt to break it up unless its members were breaking other rules. If you want an explanation for why cartels are nearly impossible to maintain in a free market environment, please read “Man, Economy and State” chapter 10, part 2, section D

I was curious what kind of economics textbook would state that cartels could not form in a free market. It turned out to be a book written by "the founder and leading theoretician of anarch-capitalism" (quote from wikipedia). The chapter he refers to is available online. It is a tedious text that contains no references to real world examples at any point. In fact the entire thing is abstract philosophical argument, without any attempt to cross-check against data, yet it purports to explain real economies.

Nobody smart would actually make such an absurd claim or cite such a text to support it.

Finally, for all you people who think Ulbricht was some heroic martyr for the war on drugs, here is what he had to say about it:

If prohibition is lifted, most people here will go away. You’ll go back to your lives and get your drugs from whatever state certified dispensaries are properly licensed to sell to you. Drug use will be as interesting as smoking and drinking .... If prohibition is lifted, and the drug industry is placed under the yoke of the state, then we won in a small way, but lost in a big way.

Ulbricht didn't actually want the war on drugs to end because ultimately what he wanted was anarchy.