Dear Linux Pro Reader,

On May 29, Silk Road founder Ross Ulbricht received a stern sentence for his involvement with building and operating the world's first global anonymous supermarket for everything. Some were surprised with the severity – life in prison without parole for the 31-year-old "Internet entrepreneur." But the Silk Road led its wayfarers way out beyond the cutting edge, and if you live your life as a pioneer, sometimes you get surprised.

The recent history of the Internet is littered with tales of technology leading out in front of the legal system. It is pretty obvious the law allowing a life sentence for a criminal boss was not created for a guy like Ross Ulbricht. One gets the vision of Ulbricht as an extreme libertarian who also happens to be an entrepreneur, who also happens to be a computer whiz. Still, he didn't get $13 million in bitcoins on his laptop by reprising his childhood role as an Eagle scout.

The grim sentence reflects the fact that the law doesn't have a place to put what Ulbricht did. In one sense, he can argue the same thing that social networking sites argue: We just provide the platform, and blaming us for what people do with that platform is like blaming the phone company for a robbery that gets planned over the phone. Nevertheless, he knew these deals were going down, and Silk Road took a percentage for every sale, so he was actively putting drug money in his own bitcoin wallet.

It is possible to acknowledge the ambiguity of the law and still not give Ross Ulbricht a free pass. Ulbricht didn't believe selling drugs should be illegal, so he built a business model around the assumption that selling drugs isn't illegal. Our Internet sensibilities would view that act as a political statement, as if he were somehow ahead of his time and guided by the infallible moral compass of technology. But what drug dealer, big or small, street creep or kingpin in a tinted limo, wouldn't want to claim, "Oh, yeah, that's right. I'm doing this for political reasons."

Much of Ulbricht's tenuous public reputation seems to balance on the question of whether he is actually guilty of conspiring to murder some of his enemies, as prosecutors have alleged. The murder conspiracy charges were strangely missing from the completed proceedings, prompting some to doubt whether the prosecutors have the case (although the transcript of messages from a guy using Ulbricht's Dread Pirate Roberts name and talking cheerfully about murder-for-hire is truly alarming) [1].

Ulbricht's family certainly believes he is a non-violent offender. The Free Ross website [2], which calls itself "The Official Legal Defense Fund of the Ulbricht Family," depicts Ulbricht as a kind and sympathetic young man who wouldn't hurt anyone and was always trying to help. They decry the fact that Ulbricht's sentence is "… beyond what murderers, rapists, and child pornographers get. It is a harsher sentence than given to Charles Manson: Manson is eligible for parole."

Innocent facilitator or venomous agent of moral decay? Which is Ross? The friends who know him and love him wonder, "Is it possible that someone could do hard prison time simply for the crime of being naïve and trusting the wrong people?"

And that's where it all gets real: Yes – actually, it is possible. In fact, it happens every day.