I think his original sentence was absolutely deserved—even though the charge of hiring a contract killer to assassinate his business competition may have been dropped, I think it's clear he did many things in the same vein. Even if you support his original pursuit of a free and open online marketplace, I think most people would agree he took it a bridge too far in the end. That said, I do think he absolutely deserved…
"he took it a bridge too far" is a massive trivialization. The guy operated a marketplace for illegal goods in order to enrich himself. The illegality wasn't just incidental, it was literally his business model -- by flouting the law, he enjoyed massive market benefit (minimal competition, lack of regulation, high margins etc) by exploiting the arbitrage that the rest of us follow the rules. Said a different way, he…
The illegality of drugs is a government reaction, since governance failed to do anything with the problem by action. No-one deserves a life-long sentence in prison for that. This market, as well as minimal competition, lack of regulation, and high margins was created by the same power which sends people to jail.