It's interesting. On one hand, if a leader of a traditional drug distribution network landed a life in prison sentence, I wouldn't have thought twice about it. With Silkroad though, I'm actually convinced by the defendants argument: that it provided safer, more trustworthy drugs to users. I've had friends who've died from purchasing bad drugs at raves from people who were looking to make money and run. In one situati…
Though I agree with you about the "safer drugs" argument, Ross' site was the worst possible thing that could happen to the supporters of safe, anonymous marketplaces- The evidence that he was willing to use brutal mob-style violence to support his business has yet to be disputed by anyone in a credible way.
I'm not saying this is the case for Ross, but it's a possibility, at least for one of the contracts. Using violence to protect innocents is not something bad. It's just unfortunate he created the situation in the first place - instead of an extortionist, he may have confided in a LEO, thus hurting his users. (Which is apparently what happened.)
Anyways, the big lesson is that when your startup has major security requirements, go slow and don't break things. There's no real reason he shouldn't be retired now, enjoying his life while enhancing others. Just technical incompetence.