Crazed libertarian Ross Ulbricht fought the law, and the law won

American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road, by Nick Bilton

Ross Ulbricht is an extremist libertarian who wanted to live his life away from intrusive governments. He began by selling drugs on the dark web, rationalizing it would be safer for buyers, the drugs would be better, and somehow – without no social contract or icky government – we’ll all be free! Freedom to him meant drug sales would get so huge the government would be forced to legalize drugs. Then he, Ross Ulbricht, would be a libertarian hero! No, really, he actually believed this self-serving drivel. He started and ran Silk Road, which soon sold guns, fake ID, and lots more. His libertarian rants on the site, under the name Dread Pirate Roberts, got so grandiose he boasted Silk Road would bring down the government.

Pro tip to newbies who want to topple governments: If you loudly and publicly say you want to topple governments, law enforcement will take you at your word. This is especially true if you are illegally selling weapons and phony passports the feds think terrorists could use. This will make them cranky and they will hunt you.

So, our starry-eyed crackpot libertarian set out to change the world by allowing millions to break the law. He was soon making hundreds of thousands a week. Within a couple of years was ordering hits on people he thought were informants or untrustworthy. He justified these murders as being for the greater libertarian good of more freedom for all! (It’s unclear whether the murders actually happened. He may have been conned or the bodies were disposed of well. However, he did order them.)

Author Nick Bilton has voluminously researched Silk Road, Ulbricht, and how law enforcement tracked him down. It’s quite a tale. He talked to everyone except Ulbricht. His writing style makes American Kingpin read like a thriller. (It’s a little off-putting that he puts thoughts inside people’s heads. However they do not seem to be outlandish thoughts or could not have happened. His research is detailed. If he says a plane landed in heavy wind it’s because weather records showed the airport was windy when the plane landed.)

Dread Pirate Roberts made two rookie mistakes early on. He used a traceable email address, which helped the feds find him. A big takeaway on this book is maybe FBI cyber investigations were plodding and clueless some years ago. This is no longer true. FBI cyber agents can read and understand highly technical discussions on Stack Overflow now. They understand Tor, and how it works. You probably aren’t smarter than them. And it was an IRS investigator who provided the first clue because he was following the money.

Long story short: The combined forces of several government agencies tracked Ulbricht down. He was arrested, refused to take a plea deal, was convicted of being a drug kingpin (along with other charges) and was sentenced to life in federal prison. There is no parole or early release. He was sentenced at age 33 and will die in prison. A court of appeals has upheld the sentence.

The Politics of Bitcoin: Software as Right-Wing Extremism, by David Golumbia details how bitcoin and cryptocurrencies are rooted in right-wing libertarian extremism. Silk Road is just another example of this.