The Dread Pirate Roberts from The Princess Bride, a man named Westly, also known as the Man in Black, took his name and reputation from his predecessor to strike fear in his enemies and maintain the loyalty of his crew. Similarly, Ross Ulbricht chose the same pseudonym of the Dread Pirate Roberts while engineering and running the most notorious online drug enterprise the world had ever seen. It was called the Silk Road.

Renee Pinell : “Do you think you’re going to live forever?”

Ross Ulbricht: “I think it’s a possibility. I honestly do, I think I might live forever in some form…”

– From StoryCorps Interview with René Pinnell and Ross Ulbricht

“You had to admire a guy who called his own new book a classic before it was published and anyone had a chance to read it.”

– William Goldman, The Princess Bride

Wow! Just wow. What a fascinating book. I only have a vague memory of seeing this story in the news. It was less than five years ago after all and I almost have to wonder how I could have missed a story this big. I have to imagine the coverage was extensive but you never know. It certainly was covered to some extent or another and from the searches I have done after having read the book, it has definitely been talked about after the fact. I found an interesting article dated just two days ago about Bitcoin and was surprised to see Dread Pirate Roberts referenced and even speculated in the article to be one of the persons possibly responsible for a recent sell-off of Bitcoins resulting in Bitcoins plunging value.  Keep in mind that this guy is in jail, for life, yet people are speculating that he could be having an impact on one of the world’s most interesting and volatile markets today. It is just speculation though and I suspect just for the purpose of drama and intrigue. The story of Ross Ulbricht, AKA the Dread Pirate Roberts, is a fascinating one and I have to believe that it will go down in history with the likes of Al Capone, El Chapo, and Pablo Escobar. Not to say that the Dread Pirate Roberts (DPR) caused as much death and destruction as these famous criminal figures but rather instead because DPR’s criminal enterprise represented a cultural shift in what is a very old and traditional drug enterprise.  This is a criminal enterprise after all that in only a few short years was reportedly worth billions and taking in a half million dollars a day and was revolutionizing how drugs were bought and sold all across the world.

“Inconceivable!”

– Vizzini from The Princess Bride

The author of American Kingpin describes his book as a work of narrative non-fiction and if researched as well as reported creates a incredibly deep and intricate look at a real-life criminal enterprise like nothing the world has ever seen. The author concludes the book with a description of said research and the amount is staggering in scope and detail. This enterprise after all took place almost exclusively online and as such the records left behind are both numerous and transparent. In fact, many of the conversations that take place in the book are taken directly from transcripts of the actual conversations between DPR and his associates as well as conversations between law enforcement agents and agencies. It’s almost surreal that something of this scope is even possible in this day and age.

“Her heart was a secret garden and the walls were very high.”

– William Goldman, The Princess Bride

To add to the intrigue of the story, the Silk Road takes place on what is known as the “Dark Web.”  Now I’ve heard of the so-called “deep” and “dark” web but it’s always seemed almost like a urban myth. Not that I didn’t believe it existed, just that tales of this hidden web seemed exaggerated and melodramatic. With just a little research though I learned that the web that we all use on a regular basis, full of incredibly vast and seemingly limitless information, is literally just the tip of the iceberg in terms of the information on the internet. It is said that the surface web represents only around 5% of all the information on the internet. Meaning that somewhere around 95% of the information on the web is generally hidden from public viewing. That fact is staggering. And scary. Some of that information I understand is not buried so deep, and includes things like documents and records, but that leaves still quite a bit to the imagination in the deeper levels of the web.

“I have no one to share my thoughts with in physical space. Security does not permit it, so thanks for listening.”

– Ross Ulbricht, the Dread Pirate Roberts (3/20/2012)

So what’s the story? Simple. A young Libertarian by the name of Ross Ulbricht starts an online drugstore with some home grown mushrooms. His website the Silk Road grows exponentially almost overnight and Ross must manage this worldwide criminal enterprise almost entirely by himself while always trying to stay one step ahead of every major law-enforcement agency in the USA as well as many around the world.  Ultimately a task force with members of the DEA, Homeland Security, FBI, and possibly most importantly, the man from the IRS, track the Dread Pirate Roberts down and catch him with his fingers on the keyboard.  It could have gone the other way. If Ross had taken his namesake more literally the Dread Pirate Roberts may have retired wealthy and gotten off scot-free, passing on his name and reputation to the next Dread Pirate Roberts and disappearing into the sunset. Not surprisingly, only a month after being shut down the Silk Road was back online with a new Dread Pirate Roberts at the helm. Ross Ubricht may indeed live on in infamy as the first of his namesake and to many a pioneer and hero in the battle to legalize drugs. American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road by Nick Bilton is a fascinating story. Read it.

Inigo Montoya: You are ready then?

Man in Black: Whether I am or not, you’ve been more than fair.

Inigo Montoya: You seem a decent fellow… I hate to kill you.

Man in Black: You seem a decent fellow… I hate to die.

– The Princess Bride