In October 2013, a 29-year-old strict-libertarian, yoga-enthusiast named Ross Ulbricht hunched over his Samsung laptop in the science fiction section at the Glen Park library in San Francisco when he was swarmed by FBI agents. Knowing the contents of his PC would be crucial to making the arrest stick, they seized it before Ulbricht hit the kill switch. Upon examination, the agents discovered what they presumed: He was logged in as “Mastermind” on the notorious black market website called the Silk Road. A chat window showed him using the Dread Pirate Roberts alias that was used to helm the site.

Three years prior, the nearly free-for-all bazaar that would later be deemed the “eBay of vice” seemed more like an heady dream of Ulbricht’s rather than something that would logistically work. He wanted to create something that could subvert the war on drugs but felt it was too risky. Things changed, however, when he discovered it could be buried on the dark web. By limiting its accessibility via the anonymous browser called Tor and avoiding easily traceable funds by using the cryptocurrency Bitcoins, Ulbricht surmised the two technologies would keep him from being linked to what was soon dubbed the Silk Road. When the site debuted in Feb. 2011, Ulbricht was not only its sole coder (his close friend would later help, among others) but also the site’s first merchant (with him hawking high-grade magic mushrooms he grew himself).

Within weeks, new vendors trickled in, offering up marijuana, MDMA and cocaine by way of the U.S. Postal Service. To help protect buyers and sellers, the decentralized digital funds were held in an escrow system that wasn’t accessible until the transaction was deemed successful. More and more illicit drugs and services — from LSD to heroin to hacker tools — poured in. Silk Road’s listed terms of service did forbid, however, such things as child pornography and stolen credit cards. And, just three months after its launch, the site garnered its first press coverage, with Gawker blogger Adrien Chen publishing an article about the dissident startup. Shortly thereafter, Senator Chuck Schumer of New York urged authorities to take down the site. Before it was finally shuttered, Ulbricht alone was able to amass around $80 million in sales, according to FBI estimates.

During his trial, Ulbricht conceded through his lawyer that he did in fact build the online black market but ultimately gave it away long before Dread Pirate Roberts surfaced as the site runner. They argued that Ulbricht was framed by this new owner who went by the DPR handle. The jury, however, disagreed. Ulbricht was found guilty of all seven counts he was facing, including the so-called “drug kingpin statute.” He’s currently serving life in prison.

Knowing Ulbricht’s fate doesn’t diminish the suspense of American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road, the new book by journalist Nick Bilton chronicling the rise and fall of Ulbricht and his darknet creation.

The central question is how someone who was nearly universally viewed by his peers as thoughtful, kind hearted and even reserved (a person, for instance, who “always used the word ‘fudge’ instead of ‘fuck’ in e-mails and in conversations”) could also allegedly commission multiple murders for hire under his online persona. (The murder for hire charges didn’t stick.)

Bilton tracks not only Ulbricht but his employees and the agents (many who were corrupt and also ended up in prison) that eventually brought down his $1.2 billion enterprise. Bilton, a special correspondent for Vanity Fair and former New York Times columnist, uses his meticulous research as a springboard into a stranger-than-fiction page-turner.

I spoke with Bilton about how the Silk Road shared similarities to tech titans like Google, Ulbricht’s ultimate undoing and whether there is any doubt in his mind about who the sole mastermind behind the darknet site.

This conversation has been condensed and lightly edited for clarity.


You’ve went from writing the founding of Twitter in your previous book, Hatching Twitter, to something as outré as the Silk Road. Can you talk about that transition and connection?
In a lot of ways both books tell a story about people with similar outlooks. People who are ambitious. And what ambition can do to people and how they want to execute an idea at all costs. So the stories have similar paths in that respect. When I started I came at it with a somewhat of a fresh perspective. I had covered hackers and even written about the Silk Road for the New York Times, but I hadn’t covered it to the degree that some other journalists had. Anyway, for me, I really wanted to understand Ross’s views on why he started the site, why he believed drugs should be legal and why law enforcement agents were so hell bent on stopping it. It took me down these interesting paths that were very eye-opening. One thing that struck me is that Ross ran the Silk Road like Travis Kalanick does Uber or Sergey Brin and Larry Page run Google. With the Silk Road, people had to clock in, it had marketing strategies, support issues and all these different things. And all these people, including Ross of course, have to make decisions that could harm the livelihood or even lives of other people but will help their businesses get to the next level. Those are the decisions that people have to make every day that run these billion dollar companies.

How did your views of Ross change during the course of writing the book?
I started the reporting by going to his trial. I sat in the courtroom, watched him come in, watched his parents. I felt terrible for his parents and I felt bad for Ross. And as I read his writing, his diary entries and so forth, I got the point of why he wanted to make drugs legal. Especially marijuana and magic mushrooms, which, reality be told, have barely killed any human beings on the planet earth. Obviously, countless more people have died from alcohol or cigarettes. But the more I did the reporting, and talked to people and read his chat logs, things became more complex. I ended up speaking to the parents of a 15-year-old kid in Australia who had died from the drugs he got on the Silk Road. When I looked at the reality of what this had done and how people got access to things they wouldn’t normally be able to get their hands on—specifically bad drugs from Chinese labs with no regulations—I started to feel very differently about Ross. By the end of the reporting, two years in, I started learning about how the opioid economy was starting to kill more people than guns. That’s when I came out on the complete opposite side. I think that drugs like marijuana and magic mushrooms should be legal but heroin and things like that are poison, and the government has a responsibility to prevent them from getting in the hands of people.

Ross would argue that the rating system on Silk Road was making drugs safer than what individuals could buy off the streets.
When Ross was creating the site, his then girlfriend didn’t believe that hard drugs should be sold on it. Ross would say, “But we have a rating system.” And her retort was, “What if someone overdoses and dies? They then can’t rate the drug.” I see the argument that if you make drugs legal, just like alcohol and cigarettes, you can regulate it. People don’t buy a certain brand of whiskey at the liquor store that has rat poison in it. That doesn’t happen because it’s regulated. And that does happen with illegal drugs and darknet sites are helping facilitate these substances. People may disagree and say, “It’s your body, you should do what you want,” but I truly believe that the repercussions are disastrous. And we, as a society, have a responsibility to make sure that people don’t overdose and die from these drugs.

One thing that was interesting about the Silk Road was its message board. The community on there—the “tribe of Silk Road” as you call them—so many of them believed in Ross’s philosophical outlook and what he was trying to accomplish.
The Silk Road was Ross’s baby. He had this idea and truly believed he would make society a better place. And I’ve spoken to people who sold and bought on the site and they believed in their cause. The thing I’ve learned from covering technology for so long is there’s a good and bad side of every single technology. Take live streaming. It’s great to communicate with your friends across the ocean but individuals will also kill people while filming it for the attention. Look at 3D printers . They were designed to help make an iPhone case or wall hook or whatever but the first thing people created were 3D-printed guns. The Silk Road allowed people to buy drugs through the internet, but there were alternate repercussions, such as kids were buying drugs and overdosing, it helped fentanyl to come into the US, and the site itself sold things it never intended to sell initially, like hacker tools and weapons. Do we allow anthrax to be listed? When the question was posed to Ross whether it was fine for people to sell livers and kidneys on the site, he mulled over the issue but in the end replied that it should be fine as long as they came from someone consensually. But how do you know? One of Ross’s downsides was he trusted people too much.

One of those people he trusted perhaps to a fault was his alleged mentor who went by the alias Variety Jones. And, yet, he was also someone who pushed back against Ross on a lot of these issues regarding consent. A man named Roger Thomas Clark was arrested in Thailand in Dec. 2015 for being Variety Jones. What’s interesting is there is still theories over whether there was more than one Dread Pirate Roberts that helmed the Silk Road or if Clark without certain is who is accused of being.
First off, I don’t have a question in my mind that the people they arrested are the right people. I spent hundreds of hours with law enforcement, and interviewed numerous people who were on the site and worked on it. On top of that, I read 2.1 million words of chat logs, and Ross’s diary entries. So, yes, There is not an ounce of a question that these people are who we think they. One of the genius things Variety Jones did was suggesting to Ross that he take the name Dread Pirate Roberts, which was borrowed from the movie The Princess Bride. More specifically, it presented this concept—just like in the movie—that DPR is not one individual but several people who keep passing the moniker to a successor. For Ross, it was a way to erasing his past and to make the claim he gave the Silk Road to someone else after going from the name Admin to DPR. And that was the entire defense in Ross’s court case! That there were multiple DPR’s.

There was a line the judge said during the sentencing of Ross. That “people are very complex.” The same thing was true with Variety Jones. He’d sit there on chat logs and say things like “We should have this person killed for stealing money” or whatever. And yet he was adamantly against heroin on the site. He told a story about how he was in jail in England, and there were these things called “hell days,” which was when people would get access to heroin and took as much as they could over the weekend, before the drugs tests began on weekdays. He was horrified about how sick this people would get from withdrawing during the week. He thought it was the most destructive drug in the world and wanted nothing to do with it. So it was fascinating how people who worked on the Silk Road and sold on it had all these different philosophies. The weed people didn’t want to be associated with the people who sold guns, and the gun people didn’t want to be linked to heroin, and the heroin guys didn’t like the fentanyl sellers. There were all these dynamics. And Variety Jones was an embodiment all these things. And without question he was the most important person on the Silk Road besides Ross.

What do you make of the argument that there must had been more than one DPR since someone logged in as DPR on the Silk Road message board, which stayed up after the site was brought down, weeks after Ross was arrested?
It interested me, when I first started reporting this. But then when you see the stuff that they got on his computer and his writings, it’s impossible to make that claim. And if you go through the chat logs, it would take a team of hundreds of people several months to manipulate that many words. What my researcher and I did was. So for instance, you see in the chat DPR say , “okay I’m going away for the weekend.” And then literally 10 minutes later there is a picture of Ross with friends as they sat up for a camping trip. And then, come Monday, he would log on and say he met this beautiful girl on the camping trip. These things happen over and over. There is not a doubt in my mind, whatsoever, that Ross was Dread Pirate Roberts from the beginning to then end. There was a defense that when he was in the library that day when he was arrested, that the real DPR had hacked his computer and put all those chat logs on there and manipulated things. It is impossible that much information could have been planted on his PC in that short of time.

In regards to the login on the Silk Road message board, from what I’ve gathered from my reporting is that the team that had been working for him were working on the Silk Road 2.0 and they took all the code from the first one and it turned out that the code allowed them to log in as DPR.

What do you think was the biggest mistake that led to him being arrested?
In the beginning, he was confident that he built the site in a way that could never be traced back. After the Gawker article came out about the site and put it on a lot of radars, and Chuck Schumer said he was going to make sure the site was shut down, right after that, if you’re not caught immediately after that, in your mind you think, “I’m good.” But the biggest mistake was working on the project with his friend who testified against him in court, who said they had programmed the site together. It wasn’t necessarily a coding error on his end. And, also, when the Department of Homeland Security showed up at his door over the fake IDs he ordered. He was asked about where you could buy fake IDs, and he told them you could buy them on the Silk Road. That boggled my mind that he would have the audacity to do that. He thought he was unstoppable. He thought there was nothing he could do or say that would trace back to him.

Do you believe Ross deserved a life sentence?
A life sentence is incredibly harsh. I wouldn’t want the responsibility or burden to come up with a sentence for him. I asked a lot of people in law enforcement, some said yes and others said no. Whether or not people were killed was irrelevant—people died. Some said he was naive. If he had just said “i screwed up,” he would’ve gotten 10 to 20 years and that would’ve been the end of it. For the families affected by the site. Some thought it was justified, some thought it was a little much. I can see all sides of the argument.