Well, he was prosecuted for running a website that allegedly facilitated sales of "illegal" drugs. Just like Alexander Vinnik was recently arrested for operating BTC-e, which allegedly facilitated "illegal money laundering". Such things are illegal just because governments say so. And the US and its client states seem to consider that their laws apply to the entire Internet, and everyone who uses it. Like it or not, moral or not, they can do it because they have the power.

The only way for individuals to opt out of that bullshit is through tools for privacy and anonymity. Using VPNs and Tor, Bitcoins and other cryptocurrencies, and so on. And in doing so, they must practice good OPSEC.

I don't mean to dis Ross, but he just made too many mistakes. Especially at the start, before he realized how huge Silk Road would become. Also, he was thinking like an idealistic activist. His OPSEC was sloppy. He used his real name on Stack Exchange to ask about onion design. He promoted Silk Road on Bitcoin Forum, then used the same account to invite developer applications, and included his real-name email address. He misconfigured Apache, such that some error responses included the public IP address of the onion server.

Anyway, we can all learn from those mistakes. And from mistakes of others that governments have pwned. And we can build stuff that won't get taken down.

As far as Ross goes, I doubt that he'll get out unless some President pardons him. Maybe Trump will flame out so badly that someone sane will win the next term. But even then, I'm not optimistic. Unless drugs, and drug dealing, are legalized, anyway.