The Story of Dread Pirate Roberts

By Seth Ferranti 05/11/17

We interview the author of "American Kingpin" about Silk Road mastermind Ross Ulbricht and the events surrounding his arrest.

American Kingpin book cover next to picture of Nick Bilton
An interview with author Nick Bilton about his new book on Silk Road and its founder photo via Christopher Michel

Ross Ulbricht believed that drugs should be legalized. He thought the War on Drugs was a big waste of time, money, and effort. As an idealistic young man he figured that legalizing drugs would make the world safer. This was the thinking that led to the creation of the dark web online drug superstore, Silk Road. From an All-American kid from Texas to an international drug lord, the federal government would have you believe that Ulbricht-- in the form of his alter ego Dread Pirate Roberts -- was responsible for all the ills of the world. With the opioid epidemic at a raging pitch, drugs more available than ever, and the proliferation of online drug marketplaces, the story of Silk Road is more relevant today then ever before.

Investigative journalist Nick Bilton’s new book, American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Roaddocuments the story from start to finish. Ross Ulbricht was found guilty and sentenced to life in prison, but he maintains his innocence and claims that while he started Silk Road, he gave it away to someone else who took over the moniker of Dread Pirate Roberts. Everyone has heard of the Amazon of the drug world, but few know the twisting and turning true story. The Fix talked to Nick Bilton about how online drug marketplaces have impacted drug consumption in our country, why Silk Road’s founders used the DPR name from the classic Princess Bride movie, and how online drug retailers like Silk Road are still active today, shipping drugs ordered off the Internet into the United States.

How do you think online marketplaces like Silk Road have impacted drug consumption in the United States?

When I first started reporting the story of the rise and fall of the Silk Road, I had no idea where it would take me, how many people it had affected -- both good or bad -- and how it had impacted society, if at all. At one point I found myself touring the innards of the Chicago O'Hare International Airport, seeing where the mail comes in and the route it takes from an airplane to your mailbox, and that’s when I learned just how much the Silk Road, and other sites like it, had actually impacted society.

There’s a room in the mail facility, illuminated with bright halogen lights, where the drugs that have been found by customs officials are stored, and it’s now stacked from floor to ceiling with packages, almost all of which were coming into the U.S. through sites on the Dark Web. In short, the Silk Road enabled people all over the world to get access to drugs in the same way that Uber has enabled people to get a ride anywhere at any moment. As one agent told me, it was a turning point in drug distribution for everyday people.

Why do you think the government put so much effort into shutting down Silk Road and arresting the man known as Dread Pirate Roberts?

A lot of people believe that the government wanted to shut down the Silk Road for the drugs, but that isn’t entirely accurate. Sure, the drugs were important, and they wanted to stop them from coming into the country, but the Feds had no clue how many drugs were actually being bought or sold on the site. As I detail in American Kingpin, the more salient reason they wanted it shut down was two-fold: first, the site was using all U.S.-made tools to facilitate the sale of illegal drugs and weapons. Tor, the browser people used to shop on the Silk Road, was built by the U.S. government; the Internet was operated by the U.S. government; the U.S. Postal Service, which was used to ship illicit things, was part of the U.S. government; and on and on. Second, and perhaps more importantly, Jared Der-Yeghiayan of the Department of Homeland Security, feared that a terrorist organization- like Al Qaeda- would come into the country legally, perhaps on “vacation,” and then buy weapons from the site, and that was terrifying on a number of levels.

Is this case just another example of Drug War propaganda or is there substance to this arrest?

It depends who you ask. Ross Ulbricht’s mother, Lynn, believes Ross did not get a fair trial and that he was made an example of with such a terse sentencing of life in prison without the possibility of parole. Yet if you ask the law enforcement side, the site resulted in at least half-a-dozen deaths from overdoses or the sale of bad drugs, and harmed countless other lives.

Additionally, while the murders were a scam and presumably none actually happened, Ross, as the Dread Pirate Roberts, did commission and pay for the killing of several people. In the Federal system, in such an instance, you can be charged with Conspiracy to Commit Murder, which is punishable by any term of years to life in prison. The government did not charge Ross with this, but instead chose to charge him with the so-called “Kingpin” charge, which is used for mob bosses.

When you look at Ross Ulbrichts background and the infamous Dread Pirate Roberts they look like two different people, what did you find out in writing the story?

Actually, when you look closely, they are not all that different. They both wrote alike, read the exact same books, referenced the same quotes, wrote “yea” instead of the traditional “yeah,” even used the same emoji’s in their writing. Yes, Ross was a sweet and gentle person, and while the Dread Pirate Roberts could sometimes be terse, he was almost always gentle and kind too. There are moments when DPR is yelling at an employee for making a mistake, or discussing killing someone with his consigliere, Variety Jones, and he’s still using the word “fudge” instead of “fuck” because that’s how Ross spoke.

Can you explain the story of why the mastermind of Silk Road took on the name of Dread Pirate Roberts from the classic movie The Princess Bride?

The Dread Pirate Roberts moniker was pure genius, on so many levels. There were a lot of mistakes made in the programming and running of the Silk Road, including how Ross left his email address online pointing to him being the founder of the site, that he kept images of his employees’ IDs, and most of all, that he kept almost every single chat log- more than two million words' worth- and a slew of diaries on his laptop. The biggest mistake of all, of course, was that he was caught with his fingers on his laptop, logged into the Silk Road administration pages, with millions of dollars on his computer and on thumb drives next to his bed.

But, even with all that evidence, Ross was still able to say “hey, it’s not me” and have a lot of people believe him, simply by citing the folklore of the Dread Pirate Roberts from the movie, where the name would be passed along to different DPRs over the years. I can’t imagine Ross, or Variety Jones, the employee who came up with the nickname, ever imagined how important that movie would be to Ross’s defense. But it was, and in many respects, still is.

Was Ulbrichts transformation into a crime lord more government creation or actual truth in your opinion?

There is no doubt in my mind that Ross started the site with an idealistic goal, to show that legalizing drugs would make the world a better and safer place. But by the time he was caught, he had made some very harmful decisions. The judge who oversaw the trial and sentenced Ross said this to him at his trial, and it’s probably the most accurate summary of who he is and of what happened: “What is clear is that people are very, very complex and you are one of them. There is good in you, Mr. Ulbricht, I have no doubt, but there is also bad, and what you did in connection with Silk Road was terribly destructive to our social fabric.”

What is the state of the dark web today in regards to drug sales? Are there any new Silk Roads out there?

While the Silk Road was shut down, there are dozens of websites that took its place, all selling illegal drugs, and doing so in vast quantities. Some are now operated out of Russia, making them all but impossible to be shuttered by the Feds. Others are [in] Finland and China. I’m sure some are still being operated out of the United States, though it’s unclear where most are located. I don’t think it’s going to be possible to put the genie back in the bottle with these sites.

Please read our comment policy. - The Fix

After landing on the US Marshals Top-15 Most Wanted list and being sentenced to a 25 year sentence in federal prison for a first-time, nonviolent LSD offense, Seth built a writing and journalism career from his cell block. His raw portrayals of prison life and crack era gangsters graced the pages of Don DivaHoopshype and VICE. From prison he established Gorilla Convict, a true-crime publisher and website that documents the stories that the mainstream media can’t get with books like Prison Stories and Street Legends. His story has been covered by The Washington PostThe Washington Times, and Rolling Stone.

Since his release in 2015 he’s worked hard to launch GR1ND Studios, where true crime and comics clash. GR1ND Studios is bringing variety to the comic shelf by way of the American underground. These groundbreaking graphic novels tell the true story of prohibition-era mobsters, inner-city drug lords, and suburban drug dealers. Seth is currently working out of St. Louis, Missouri, writing for The FixVICEOZY, Daily Beast, and Penthouse and moving into the world of film. Check out his first short, Easter Bunny Assassin at You can find Seth on Linkedin or follow him on Twitter.