Silk Road founder Ross Ulbricht is currently serving a double life sentence, with no possibility of parole, for being the alleged mastermind of the notorious dark web online marketplace. Operating under the alias “Dread Pirate Roberts” the Texas native facilitated the sale of hundreds of millions of dollars worth of illicit drugs, paid for in the crypto-currency bitcoin, racking up USD $80 million in commissions in the process.

His case was featured in the documentary Deep Web, directed by Alex Winter, and both A&E and BBC are working on film adaptations of Ross’s story. Ulbricht’s mother, Lyn Ulbricht, has emerged as a tireless advocate for her son’s release. She notes that many extremely violent and sadistic criminals such as murderers and rapists get far more lenient treatment. Ulbricht after all, despite the illegality of hosting a site that allowed drug transactions, never directly hurt anyone.

Furthermore, if merely hosting a website that in any way facilitated illegal activities was illegal, then such tech captains of industry as Jeff Bezos of Amazon, Mark Zuckerburg of Facebook, and Craig Newmark of Craigslist would also be subject to prosecution.

Ulbricht, in fact, spoke of the principle of “harm reduction”…the idea that it would be better to purchase drugs from the safety of one’s home via the mail, than to do so in person, putting oneself at risk by traveling to dangerous and crime-infested neighborhoods. And shutting down Silk Road did little to nothing to stop online drug trafficking. In fact, the federal government has acknowledged that such activity has increased in the wake of the dismantling of Silk Road.

Judge Katherine Forrest specifically cited Ulbricht’s libertarian ideology in imposing a life sentence, noting that if he were to be released, he would likely return to participate in activities seeking to elude the scope of government control.

Indeed, Ulbricht’s rationale for launching the site was as ideological as it was commercial. While pursuing graduate work at Penn State Ulbricht became disillusioned with natural sciences, and began engrossing himself in libertarian economic theory. He worked on Ron Paul‘s presidential campaign and enthusiastically read the works of Ludwig von Mises, the founding father of the Austrian School of economics which greatly influenced such figures as F.A. Hayek and Murray Rothbard. He envisioned an online marketplace where human beings as rationale actors would be free to make their own choices, beyond the stifling controls of federal, state, or local regulatory authorities.

Ulbricht is now paying a severe price for his vision of an online marketplace. On May 31 of this year, Judge Gerard Lynch of the Second Court of Appeals, upheld Ulbricht’s life sentence, rejecting objections made by Ulbricht’s attorneys on Fourth Amendment grounds.

It appears that Ulbricht’s only hope at this point remains an appeal to the Supreme Court. Regardless of your perspective on Ulbricht’s crimes, the case presents extremely interesting questions about Fourth Amendment rights, prosecutorial overreach, privacy, and the intersection of law and technology in an age where the law routinely fail to keep up with technological advances and are generally written and applied to the technology of the previous generation.