“[The] problem with the all-out libertarian argument of ‘anything goes’ is that we live in a world where everything you do affects someone else,” says Nick Bilton, former New York Times columnist, Vanity Fair special correspondent, and author of American Kingpin:The Epic Hunt for the Criminal Mastermind Behind the Silk Road.
Reason’s Brian Doherty called the book “a lurid cops-and-crooks story” in his recent review.
American Kingpin tells the gripping story of the manhunt for Ross Ulbricht and the “Dread Pirate Roberts,” a pseudonym used by the chief operator of the Silk Road, an online marketplace on the dark web that was used to buy drugs, weapons, and other illegal goods. The name was also a nod to the cult classic The Princess Bride, in which “Dread Pirate Roberts” is passed down from one character to another.
Ulbricht’s legal team claimed that this is exactly what happened with the Silk Road: Ulbricht started the site, but handed off the name—and control of the illegal marketplace—to another operator. The judge didn’t allow Ulbricht’s lawyer to present this theory in court, and Bilton doesn’t mention it in the book.
Ulbricht’s mother, Lynn, recently called American Kingpin a “media lynching.”
“I just don’t have a shred of a doubt that it was Ross,” Bilton told Reason’s Zach Weissmueller. “When I first started writing this book, I thought there were multiple Dread Pirate Roberts…Then I saw the evidence… [and it was like] a bullet train that started to point in one direction.”
Bilton also discusses drug prohibition, his own mixed feelings about his enigmatic protagonist, and the murder-for-hire accusations that Ulbricht was never charged with but that came up in the trial.
Produced by Zach Weissmueller
Camera by Justin Monticello and Paul Detrick.
Music by Blue Dot Sessions.
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This is a rush transcript—check all quotes against the audio for accuracy.
Nick Bilton: I came at it from a viewpoint of wanting to understand how Ross felt and why he wanted to do this. I didn’t know if it was monetary. I didn’t know if it was libertarian. I didn’t know what it was, and so I really wanted to understand, and that was probably the most important thing to me in the beginning of this reporting process. He had joined the libertarian club in college, and he had libertarian-leaning views prior to that, but at Penn State. I ended up talking to people who he was in the club with. I talked to people he met at conferences, libertarian conferences. I saw some of the transcripts from some of the debates he’d done, some of the quotes he’d given the local college newspaper, and spoke to people that he had debated with.
His arguments are incredibly relatable. He argues very succinctly, okay? Why is it that people are thrown in jail for buying weed or magic mushrooms? When it comes to that, I think I completely agree with Ross and his arguments and his ideas. Where I started to have a really hard time was with the idea of selling things like heroin and fentanyl which have led to more deaths in the last year alone than people who have been killed from firearms. I don’t see those as drugs. I see them as poisons.
One of the things I really tried to do in the book is I don’t offer a viewpoint at any point in time. What I do is I tell Ross’s side in the chapters about Ross from his point of view, from the things that I’ve read and reported and so on. Then I tell the law enforcement side from their point of view. Of course, there’s different versions of the law enforcement side. I want the reader to decide at the end. Do they believe that what Ross did was right? Do they believe it was wrong? Do they believe drugs should be legal? Do they not? I really hope that that’s how it comes across.
Zach Weissmueller: You get a little uncomfortable with things like heroin or fentanyl being sold on there, and certain people, certain characters in the book, also seem uncomfortable with that who are affiliated with the website. But the other side of that would be, well, still better here where there’s some sort of customer review process. There’s education happening on the forums to tell people how to take the drugs more safely, and also just the side effect of prohibition, all the violence that happens just because something that people want is prohibited. In the end, how do you think that all shook out?
Nick Bilton: I think that with all technology, whether it’s the Silk Road, Twitter, Facebook, driverless cars, you name it, with all technology, there is a good side and a bad. I think that one of the biggest problems in Silicon Valley, which is something I’ve covered for over a decade, is that people never ever think about the bad. They always think about the good, and the bad is something that happens. Then they have to kind of clean up the pieces afterwards.
For example, I was friends with the guys who built some of the early 3D printers, MakerBot and things like that. I remember saying, “What are you going to do with this? This is really cool. You can print objects out.” They said, “Oh, we’re going to make wall hooks and iPhone cases.” What was the first thing that people did was they built 3D-printed guns. Put aside the libertarian argument of that, whether guns should be legal or whatever. If there was something that they had thought about, they could have thought about ways to ensure that a five year old didn’t do that or whatever it is.
I think the same thing happened with the Silk Road. There are surveys and studies that came out in the past few years that have showed that buying drugs online makes people feel safer, makes them feel like they know what they’re buying because there are review systems, all the things that Ross set out to do. But then there are the negatives, and the negatives are that it has allowed fentanyl to come into the country more. There are other ways that it has come into the country, and people don’t understand.
This is a lab-based heroin that’s 50 to 100 times stronger, and people overdose on it. Where I have a problem with the all-out libertarian argument of anything goes is we live in a world where everything you do affects someone else, right? Every single, solitary thing you do has an effect on another human being. The way that I saw Ross arguing it was that, “Well, that’s not my problem.”
Zach Weissmueller: The libertarian viewpoint on the drug war is that it itself is so harmful that something has to be done to overturn it, and it’s not going to happen through normal, democratic processes. It’s been going on for over 40 years.
Nick Bilton: I completely agree.
Zach Weissmueller: A trillion dollars, countless deaths, incarceration.
Nick Bilton: Yeah. I completely 1000% agree that the war on drugs did not work, is not working, and I think that what’s fascinating is even the authorities that are chasing Ross in the book agree. The DEA agent ends up becoming a bad guy. He has a moment in the story where he’s like, “Wait a second, maybe, maybe this guy’s right. Maybe the war on drugs is broken.” But the argument that Ross was trying to prove was that let’s just make everything legal, and it will work itself out. I think that there are a lot of bad people in the world that try to take advantage of people by cutting up heroin with rat poison or whatever it is, and it kind of doesn’t think about the repercussions of those bad people.
Zach Weissmueller: I want to ask about the rather large group of federal agents who hunted down Ulbricht, because that’s a major part of this book. It’s about that manhunt. Could you just talk about the size and the scope of the investigation of Silk Road?
Nick Bilton: There’s a DEA team in New York. There’s an FBI team in New York. There’s an IRS agent in New York. There’s local police. There’s people in San Francisco that don’t even make it into the story. There are people overseas. Everyone is kind of hunting for this thing, because one, it was getting a tremendous amount of attention in the media because it was just fascinating that this thing existed and that no one had been caught and it hadn’t been shut down. Two, it’s because a lot of people wanted to be the hero that caught the guy.
But at the same time, you see the dysfunction of government. No one wants to share their information, because they’re afraid that if they do, someone will steal it, and go and catch this person and they won’t get credit. There are, of course, people that do bad things. Carl Force, the DEA agent, who starts stealing money and selling information to the Dread Pirate Roberts and all this insane stuff. There’s Sean Bridges, the Secret Service guy, who does the same thing, and is literally stealing money. It’s just mind-boggling just how dysfunctional this whole thing was.
Zach Weissmueller: Besides scrambling just out of pure ambition and media attention, there seemed to be, at least with some of these agents, a almost ideological motivation. We talked about Ross’s ideology, his libertarianism, but then there’s this Homeland Security agent who reads the writings of the Dread Pirate Roberts, which is the screen name of the administrator of the Silk Road. You describe him as being terrified at what he’s reading. Could you talk about the ideological motivations of some of the people involved in this?
Nick Bilton: For some of the agents, for one in particular, Gary Alford from the IRS, he seized the writings of the Dread Pirate Roberts, and they’re almost all incredibly anti-government. He is working on the task force where there are people who on 9/11 had run down to the buildings and spent weeks down there trying to pull bodies out of the rubble. He juxtaposes those two things, and is livid essentially that these people are now going to the hospital and some have died because of what their heroic efforts on 9/11, and then the Dread Pirate Roberts calling everyone in the federal government not very nice things.
Zach Weissmueller: I also sensed some of that in the sentencing statement of the judge in this case whose statements quite frankly infuriated a lot of Ulbricht’s supporters. She gave a full-throated defense of the drug prohibition. She said that his position was privileged and that what he did was terribly destructive to our social fabric, and then threw the book at him. What do you make of the judge’s comments and sentencing in this case?
Nick Bilton: Well, two things. The first thing I’ll say is that from my reporting, Ross was actually offered a plea deal in the beginning when he was arrested in New York. The plea deal was 10 to life. It would not have charged him with the kingpin charge. They said, “Okay, if you’re going to go to court, we’re throwing the kingpin charge at you,” which is everything, which is a really bad charge.
Zach Weissmueller: I will throw in that offering a plea deal of 10 to life is … I could see why someone might not jump on that.
Nick Bilton: I can see why someone might not jump on that, but when the amount of evidence that was on Ross’s computer, it also boggles my mind why he decided to take it to court and with the defense that he went with, he was caught with 2.1 million words of chat logs on his laptop, photos, videos, spreadsheets. All the same stuff was on thumb drives separately than his computer. It was a very difficult case to argue.
Putting that aside, one of the toughest questions that I’m ever asked around this book is if I agree with the sentencing. I can see it from both points of view. I can see people who look at it and say it’s ridiculous. It’s two life sentences plus 40 years for running this website, and I completely understand that argument. It makes complete sense. The other point of view is that there were at least six people who overdosed and died as a result of the site, that got bad drugs or had a bad reaction. You can say that the murders didn’t happen, but he thought that they were happening. The argument from that side is, “Well, of course that was a just sentence.”
As far as what the judge said, and this is one of the things that really upsets me the most about this whole story, this is a judge who not only hears cases like Ross Ulbricht’s but hears cases every single day from people in the Bronx and elsewhere that sell drugs because they don’t really have many options. What I took from her statement that it was a privileged argument is that Ross had a very lucky upbringing. He had a family that loved him. He had a lot of opportunities.
He went to school to be a physicist, and he chose to go down this path for the reasons he chose to go down. His argument that it was different because it was from behind a computer, I think, was what frustrated her the most. What frustrates me the most is you have everyone out there defending Ross, and I don’t see anyone out there defending all these poor people who are in jail for selling weed or magic mushrooms who are African American and Hispanic.
Zach Weissmueller: Someone like Ross who basically devoted his life to trying to stop the drug war from happening, and the people who support him who deeply believe that the drug war is immoral and wrong, think that this was a tool that could have disrupted that. Obviously they wanted to set an example of this guy who tried to do something to end this unjust drug war that throws all these poor people with these crazy sentences. To hear a federal judge who hands out those sentences sanctimoniously lecturing, I think probably rubbed people the wrong way.
Nick Bilton: I cannot speak for the judge. I am not the judge. If I was the judge, it probably would have been a different sentence. It definitely would have been a different sentence. But the everything goes mentality had repercussions. I don’t agree with the sentencing for these mild drugs. I do not believe that they should be illegal. I really think it’s just ridiculous, but when I see the results … I mean, go look. Go read the series in the Washington Post of people who have overdosed from fentanyl, and look at some of the stories and the videos of kids whose parents have died from it. It is harrowing. That shouldn’t be legal as far as I’m concerned, like in my personal opinion.
Zach Weissmueller: The argument for making something like heroin or even fentanyl legal would be that at least if it’s out in the open, we can treat the terrible consequences, the public health consequences, more effectively than when it’s totally underground, and again that something like the Silk Road would be a kind of crowbar to pry legalization open [crosstalk 00:14:39].
Nick Bilton: I mean, just I’m curious. Do you believe that they should be legal? Do you believe that heroin, that fentanyl, that all of these things should just be kind of open and …
Zach Weissmueller: I believe in harm reduction. I don’t think that harm elimination is realistic, but I think that making everything legal makes it a lot easier for information about these things to get out there and for treatment programs to flourish.
Nick Bilton: But I also believe that there are certain things that … Do you believe cyanide should be legal? I personally see fentanyl and heroin as the same thing. These are not drugs that we should be taking. I mean, tens of thousands of people now die a year from those drugs.
Zach Weissmueller: In a world where drugs were totally legal, who knows if fentanyl would even exist.
Nick Bilton: Yeah, I can see that. I think that, again, like for me it’s not all or nothing. It literally just boggles my mind that magic mushrooms are illegal and that even weed is illegal, MDMA and all these things. I don’t understand. It just makes no sense. But when it comes to these hard drugs that people overdose from on a daily basis if not an hourly basis, I just don’t understand why they exist, and I don’t think that we should be encouraging people to take them.
Zach Weissmueller: Obviously Ross is a sympathetic character to someone like me in a lot of ways, but there’s one area of this story that even makes his supporters uncomfortable, which is the supposed murder for hires that happened. There was one that was completely staged by a DEA agent, the one who was siphoning Bitcoins off the site. There were supposedly some five others that … where the Hells Angels were maybe contracted or maybe it was some sort of scam. In any case, no bodies ever came up, and it was not ever used in court against Ulbricht.
Nick Bilton: Well, it was used in court against Ulbricht. He was not charged with murder, but the kingpin charge, that was used both at the trial, chat logs around it, discussions around it, and it was used a lot in the sentencing.
Zach Weissmueller: Couldn’t you make the argument that that’s worse in a way, bringing it up in the trial but not actually feeling like you have enough evidence to charge him with it? You’re-
Nick Bilton: From what I can tell from the reporting I’ve done, the people I’ve spoken to, they didn’t not charge the murders because they didn’t have the evidence for the murders. They would never have charged him with murder. They would have charged him with some sort of commissioning to have someone killed or something like that, which is also a federal crime. But the reason is is because they wanted to prove a point about the website, and that was why they went after that kingpin charge, from what I can tell. The point was you run a website like this, that these are going to be the repercussions for those actions. That was the government point of view. I’m not saying I agree with it. I’m just saying that that’s what I heard during my reporting.
Zach Weissmueller: There’s been some criticism of the book from Ross Ulbricht’s mother, Lyn, who’s a very outspoken advocate. She’s called the book a media lynching, and says that you basically just presented the government’s side of the case.
Lyn Ulbricht: Nick Bilton has appointed himself judge, jury, and executioner.
Zach Weissmueller: Especially in relation to these commissioned murder charges where the defense side of the argument is that the Dread Pirate Roberts, who was the administrator who ran the site, might have been Ross at one point, but-
Nick Bilton: It was always Ross.
Zach Weissmueller: … he walked away.
Nick Bilton: It was always Ross. [crosstalk 00:18:20].
Zach Weissmueller: But you don’t buy that. Why don’t you buy that?
Nick Bilton: Well, first of all, you read the book. Do you think it’s a one-sided point of view from the government’s side?
Zach Weissmueller: I don’t think that, but you don’t raise this possibility that there might have been other people behind the DPR account.
Nick Bilton: Because there wasn’t. There is not a shred of a doubt in my mind that Ross ran that site from day one. The evidence, it is overwhelming, and I don’t need the government to tell me that. I went through everything. I went through 2.1 million words of chat logs. We went through social media posts, photos, videos, Ross in college arguing these things, saying the same exact things in college during debate class as the Dread Pirate Roberts said throughout the entire life cycle of the site. If you want to argue that the chat logs were hacked and changed, you would need a team of 1,000 people to pull that off. Imagine all you did for three years was talk online, and you didn’t really have many conversations in person. Now imagine that at the same time as talking online to your coworkers, you’re also posting on social media about things, right?
Let’s just say I have a few minutes while you’re in a library and I hack into your computer, and I’m going to place some documents there. How the heck am I going to get to the minute when you’re on a flight, telling your employees that I’m going to be on a flight, when you’re camping, saying I’m going to be away this weekend, when you meet a girl, telling people you just met a girl? To pull all those things off and to manipulate his social media, it would be impossible. If you read the book and you see how much of a mess the government was while trying to hunt this thing down, if you believe that the government could pull off manipulating all that stuff to throw this random kid in jail, it’s beyond delusional.
Zach Weissmueller: But does it necessarily prove that there were not other people with access to the login? Because one of the main alternative theories out there was that Mark Karpeles, who founded the Bitcoin exchange Mt. Gox, whose assets were seized in another investigation leading up to this, might have been the Dread Pirate Roberts.
Nick Bilton: So you’re trying to tell me that Mark Karpeles put together, manipulated those chat logs over almost three years, manipulated his social media feed, his emails, his text messages, the photos, right? Then not only that, took the entire Silk Road that was the exact version that’s on the laptop, snuck into Ross’s bedroom, and put the thumb drives next to his bedside the same day he’s arrested, and managed to get all those files on his computer in a library in a matter of about four or five minutes? It’s impossible, and so I just don’t believe for any moment that there was more than one Dread Pirate Roberts. I just don’t. There’s nothing that implies that other than the fact of that brilliant name, the Dread Pirate Roberts.
Zach Weissmueller: The defense is working on an appeal right now for Ross, and a couple of the things they’ve revealed are that they say they’ve discovered some deleted conversations between the Dread Pirate Roberts and someone who might have been another corrupted agent in the investigation. They also say that someone seems to have logged into the DPR account after-
Nick Bilton: Well, the DPR forum account, not the DPR account.
Zach Weissmueller: … Ross was arrested.
Nick Bilton: If someone logged into the DPR account, they would have taken off all the money and run away. Someone logged into the DPR forum account, and from what I understand, it was about seven weeks after. It was when the employees were taking the code from the site to build the Silk Road 2 and amid the code was a DPR forum login.
Zach Weissmueller: Given the complexities of this investigation and the nature of online identities and some of these anomalies, you still don’t think there’s any room for any uncertainty or doubt as to who was exactly behind the DPR account at all times.
Nick Bilton: I just don’t have a shred of a doubt that it was Ross. When you read the chat logs from the point in time when he supposedly handed it off to someone else, there’s no differentiation between them before and after, and the social media posts and so on. When I first started writing this book, I thought there were multiple Dread Pirate Roberts. When I first sat down and I started writing this book, I was like, “Okay, my job is to try to figure out who they are.” Then I saw the evidence, and I saw the diaries on his computer, and even before I saw the chat logs. It was the beginning of a bullet train that started to point in one direction.
Zach Weissmueller: Given the corruption that we know is involved with this case from people like Carl Force, you don’t have any doubts about anything being falsified in there?
Nick Bilton: I believe that there were things falsified from Carl Force’s DEA reports. I’m sure. He was not a very honest person. But I don’t believe that anyone got into Ross’s computer and managed to put in thousands and thousands of documents related to the Silk Road. There’s part of me that wishes, that really, really wishes, Ross would have said, “I did this. I believe that the war on drugs is stupid and wrong, and I did it because I believed this,” and become a martyr for the cause.
The other part of this that was so fascinating to me is the technological part. I meet people that will say on Twitter or Facebook, “You’re a piece of shit,” and, “Go to hell,” and this, that, and the other. I’ll meet them in person, and they’re the nicest, sweetest person in the world. We have a disassociation with what technology does and how it disconnects us from human beings. Even at Ross’s sentencing, he apologized for the things that had happened. After the parents of the people who had died stood up and spoke, he says that he didn’t intend for any of this to happen.
Zach Weissmueller: I want to finish talking about intentions versus reality, because you make it very clear in the book that he did start out with the idea of like, “I want my legacy to be the person who began the end of the war on drugs.” The Silk Road is gone. It’s been taken down, but as we know, dozens of imitators have popped up in its wake. What do you think his legacy will be, and what will people have learned from the Ross Ulbricht case?
Nick Bilton: His legacy will be both good and both bad. I think that there will be a group of people, mostly the people watching this, who will see that he has, if not started the conversation about how technology could be used to fight the war on drugs, will argue that and will see that from that point of view. You can’t deny that, but then there’s the other side of it, and that there are people who I’ve spoken to who say that these online drug marketplaces, whether it’s the Silk Road or others that are out there, have helped lead to the rise in fentanyl in America which have helped lead to the opioid epidemic, not exclusively, but have helped, and that there are repercussions for legalizing drugs on the dark web where there are still bad things that happen. I think that I see from my own personal point of view Ross’s legacy as being both a good one and a bad one.
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