The Secret Life of a Silk Road 2.0 Mastermind
Illustrations by Shaye Anderson


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The Secret Life of a Silk Road 2.0 Mastermind

“At some point, you have to lie to someone. You have to deceive people.”

On one side of the kitchen, he was cooking for friends. On the other, he was running a multi-million dollar drug market from a laptop.

"Technically I was still at work while I was doing dinner," the man claiming to be Dread Pirate Roberts 2, the creator of the second Silk Road drug marketplace, recalled to me in a meeting. This social night with friends was one of the few moments when DPR2's personal life, and that of his illegal empire, came close to colliding.


"The laptop was open in the kitchen, which had stuff running on it. None of them are IT guys, they didn't understand it," DPR2 said. "But I knew what it was."


In court documents, an FBI special agent described Silk Road 2.0 as "one of the most extensive, sophisticated, and widely-used criminal marketplaces on the internet today." According to government figures, at one point it was "generating sales of at least approximately $8 million in United States currency per month."

But the site was ostensibly, at least in part, ideologically-driven by a desire for freedom. DPR2 assumed an often larger-than-life persona, and in posts to the site's forum, he made grand statements about the Silk Road 2.0 and what it stood for.

Shortly before the site was launched, in the wake of the original site being seized by the Federal Bureau of Investigation in October 2013, he said the news would "echo around the world."

"This isn't the end of our struggle, and I can hope we can all carry on fighting with the same vigor, courage and dedication as we have these past few weeks," he said.

"Dread Pirate Roberts is now immortal and if you devote yourself to that ideal, and our enemies cannot stop it, then the idea becomes something else entirely," he continued. "They may have sunk one ship, but now they have awoken the kraken."

That character crossed over into DPR2's daily life at points, and remaining free from imprisonment meant keeping secrets from friends and family. But DPR2 had a weakness.



Silk Road 2.0 ran as a Tor hidden service and only used the digital currency bitcoin. The site granted its users and administrators relative anonymity. It operated for a year with seeming impunity. Thousands of drug dealers used its digital shelves to brazenly sell heroin, methamphetamine, psychedelics, and a number of other drugs. It also stocked hacking tools and fake IDs.

It appeared as if the Silk Road had rebounded after the arrest of Ross Ulbricht, the convicted creator of the original site and the first Dread Pirate Roberts, named after a character from the novel The Princess Bride, as quickly as it was shut down.

"This new website—launched barely a month after federal agents shut down the original Silk Road—underscores the inescapable reality that technology is dynamic and ever-evolving and that government policy needs to adapt accordingly," Senator Tom Carper, chairman of the Senate Homeland Security and Governmental Affairs Committee, said in a statement published at the time.

"Once you hit that enter button, you've just launched something that you know there is going to be an absolutely fucking huge manhunt after you."

Then, in November 2014, Silk Road 2.0 was abruptly shuttered. The site was replaced with the FBI's signature seizure notice as part of the FBI-led Operation Onymous, which also targeted around two dozen other illegal dark web sites.

The FBI found its way to the Silk Road 2.0 server thanks to help from researchers in government-funded academia. Carnegie Mellon University's Scientific Engineering Institute, with funding from the Department of Defense, launched an attack on the Tor network that allowed it to unmask Tor hidden services. The FBI then subpoenaed the research institute for the collected IP addresses of dark web sites and users.


Blake Benthall, the administrator who worked alongside DPR2 as the main coder for Silk Road 2.0, was arrested in San Francisco. (Coincidentally, the same city in which Ulbricht was arrested just over a year earlier.) DPR2, meanwhile, has been described as one of the dark web drug lords that got away.

I met DPR2 while the Silk Road 2.0 was still up and running, and was generating hundreds of thousands of dollars in revenue a day.

"I don't doubt your abilities on security or that you have a genuine desire to protect those you work with, but in the past I have been in the heart of the same people now hunting me and I know what they can do," DPR2 told me in a message before we met. "No measure any journalist takes will be able to keep them off for more than a few hours."

"Quick note," he added. "The FBI [is] well aware of us planning to meet." I was not provided any evidence for this, however.

A section from the complaint of Blake Benthall, describing the scale of Silk Road 2.0.

Come the day of the face-to-face, I stood in a busy city street, and waited for the man I had exchanged dozens of encrypted messages with. No phones, or internet enabled devices, naturally. We had communicated beforehand with PGP signed messages—meaning I was in contact with whoever controlled the DPR2 encryption keys listed alongside the site's administrator account.

He was late, but as promised, appeared out of nowhere.

"Do you hear the people sing?" I asked, starting our pre-arranged phrase to verify each other's identity.


"Singing the song of angry men," he replied, completing the lyrics from Les Miserables, his words barely audible over the sound of traffic. I ushered him inside a small doorway and bolted the entrance shut. Dressed in a generically smart style, he never would have stood out from a crowd. He was invisible.

Before we spoke any further, DPR2 surveyed the edges of the room for hidden cameras and microphones, conscious that he was meeting me while some of the most well-funded and resourceful law enforcement bodies on the planet were likely trying to track him down.

The original Silk Road drew the attention of the FBI, the Drug Enforcement Administration, the Internal Revenue Service, and the Department of Homeland Security. New York Senator Charles Schumer even exhorted federal authorities to take the site down.

Parallel investigations had tried to identify the first Dread Pirate Roberts. One carried out by the DEA involved the elaborate, and fabricated, murder and torture of a Silk Road employee. The FBI, in identifying the location of the Silk Road server, seemingly carried out a legally questionable hack of a computer overseas, and undercover agents had penetrated the inner circle of the marketplace's staff.

It was likely that Silk Road's rebirth, which DPR2 was now at the helm of, would be met with a similar reaction.

DPR2 was nervous, only really spoke when spoken to, and exceptionally polite. But he did joke and make light of the bizarre situation we found ourselves in: of being face-to-face with a journalist, while under the assumption that a hunt into his location and identity was underway at that very moment. At one point, a police siren screamed from the street outside, making us freeze.


"They're always one step behind me," DPR2 said. He recalled walking behind a police officer who was totally oblivious to the serious criminal just a short distance away.


When the original Silk Road site's owner, Ross Ulbricht, was arrested, a small group of Silk Road veterans quickly worked on a replacement. DPR2, who took on the same title as his predecessor, was the technologically-savvy person and respected community member who spearheaded this relaunch.

Just over a month later, after a manic period of building along with a second administrator, Silk Road 2.0 was about to go live.

"I had the URL ready to launch," DPR2 told me. "I think I must have sat there for five minutes staring at the screen. Once you hit that enter button, you've just launched something that you know there is going to be an absolutely fucking huge manhunt after you."

"Upon launching the site, I just started laughing at one point, hysterically, for about 30 seconds," DPR2 said. "It's so many emotions combined into one." He said it was anxiety, excitement, and amazement at what he had just created and unleashed.

Clearly mocking law enforcement, the login page for the site contained an altered version of the seizure notice that authorities had placed on the first Silk Road. The new page read: THIS HIDDEN SITE HAS RISEN AGAIN.

The technical challenge of pulling together a fully functional drug marketplace in an incredibly short space of time was one attraction to the project. DPR2 and a co-administrator had to reverse-engineer the code that the original Silk Road had used, get DDoS protection in place to protect the site from being overwhelmed by traffic, and make sure that the site could handle a massive influx of users.


The original Silk Road had emerged underground, spreading via word of mouth before it was reported on by Gawker months later in 2011, and Ulbricht had developed and tweaked the site's code over years. The founders of Silk Road 2.0, on the other hand, sent embargoed press releases to worldwide media. It was to launch with a bang.

"No one had done it before on that scale, let alone in four weeks," DPR2 said. "A lot of people think we're sat there, hammering lines of code out constantly. It's nothing like that at all."

"I'd say about 70 percent of my time was reading—reading ideas of how can this be done better, how can we speed this up, how can this be made more secure, are there any theoretical limitations to that," he continued.

"At some point, you have to lie to someone."

While building the site, and during the subsequent months of its explosive growth, DPR2 had to maintain strict compartmentalization—that is, separate his normal, outward facing life with friends and family from that of his illegal enterprise. That involved choosing between working on the site or going to a birthday party, lying to people about what he was really up to, and making up elusive responses to everyday questions, so as to not reveal anything about Silk Road 2.0.

"You have to be very creative in how you describe mundane tasks," DPR2 told me. Instead of fabricating very elaborate lies that may eventually come back to bite him, he would remain vague, and simply say he was working on an IT project, for example. His computer-literate friends, however, were more of a challenge.


"At some point, you have to lie to someone. You have to deceive people," he explained. "Having a massive, multi-million-dollar drug operation in the background is quite a secret."

People noticed that he was more distant during Silk Road 2.0's launch, DPR2 said. Then again, he had always been the type of person who would often disappear for days or even weeks at a time when he was really into a project or an idea. But the influx of spam on Silk Road 2.0, or other "tedious" happenings, meant that DPR2 sometimes snapped at his family when they simply asked how his day had been.

"I felt like I was being a complete dick to them. They don't know about [it], they haven't done anything," he said.

Although keeping his mouth shut was obviously in the interest of staying out of prison, DPR2 was not always comfortable with having to constantly duck people's innocuous, and well-meaning questions: What are you up to? What are you working on?

"It does put a certain question mark on yourself. If I'm not saying the truth, if I'm hiding stuff from them, what kind of person does that make me?" DPR2 said. According to him, his co-administrator, who went under the handle Defcon, framed that lying for the sake of keeping the site running in a religious light.

"He likened it to [how] Jesus took our sins, and made everyone else better," DPR2 said.


Ulbricht was seemingly a lot more lapse in his handling of secrets. His ex-girlfriend Julia knew about the site, and Ulbricht confided in a friend who was ultimately forced to testify against him. That friend, while drunk, also told another person about Silk Road.


"Going out drinking was always a little bit risky, because of the chance that if you have too much to drink, you might say something," DPR2 recalled of his own experience. "There's always that level of paranoia that surrounded it all."

"People say 'I understand', or 'I know what it's like to have secrets,'" he went on. Yet they have no idea what it's like living with secrets on the level he has, according to DPR2. "It's isolating in the fact that one group of people you can tell some stuff to, and one group of people you can tell other stuff to, there was no one that you could tell everything to. It was far too risky."

"I think that was the only thing that bothered me with it," he admitted. "There was no one I could tell everything to."

While having to lie to friends who had known him for years, DPR2 was bonding with people he had never met face to face, and likely never would.

"There are people that I really trusted. You could say that they were friends, but I wouldn't go"—he paused. "It's not the same type of friendship that people think about."

In the real world, DPR2 explained to me, people often made judgments about others before a conversation had even started. But in the dark web, where most people act pseudonymously thanks to the protections offered by Tor, the only social cue to go on is people's actions.

"In this environment, you only heard what people were saying," he told me. "There was nothing to judge them on other than what they did."


Take Defcon, who offered his services as a programmer to DPR2 in a private message. DPR2 was intrigued by Defcon's calm tone among the chaos of Silk Road being shut down, and put him to the test.

Within a few hours, Defcon had put what would become the Silk Road 2.0 forum online, along with a host of security features that others often neglect.

"He knew what he was doing, I could tell instantly," DPR2 said.

Defcon did make a mistake, however. It would later be revealed that he registered a Silk Road 2.0 server with his personal email address.

Illustration: Shaye Anderson

Other characters DPR2 met didn't just help build the site, but destroy others.

In a secret, so-called "Geek" section of the Silk Road 2.0 forum, populated by a small group of technologists and hackers, DPR2 created long-running threads discussing how better to improve the security of the site. He also hired at least one in-house penetration tester to put Silk Road 2.0's defenses to the limits.

It was in this forum that DPR2 asked hackers to attack competing dark web marketplaces. TorMarket and Sheep Marketplace both became targets of attacks that included the theft of private messages.

"Agora is going down," he wrote to staff in March 2014, referring to Silk Road 2.0's main competitor. "I advise you all to stay clear of it."

"We want to keep all attacks separate from the Silk Road name," he wrote in another post.

As well as letting their actions speak largely for themselves, dark web users could be more truthful with each other than they might be in the real world.


"Because it was anonymous, a lot of people were more honest," DPR2 said. This was even the case with one security expert, who confided to a few Silk Road 2.0 members that he was a pedophile. Naturally, this is something that a person socialising in the real world is unlikely to publicly acknowledge.

"I think that level of comfort, where people can actually admit what they are, I think that would be a huge relief for him to be able to tell someone," DPR2 continued, who added that he didn't agree with what the pedophile did or believed in, but he was "an incredibly smart guy."

"When people are that honest, you get more of a connection to them, because it's no longer the whole thing of what society expects you to be, it's just what people are," DPR2 said. "I think knowing that he was a pedophile, but still seeing him as a good person, changed me as a person as well."


In December 2013, several alleged staff members of Silk Road 2.0 who had also worked on the original site were busted in coordinated arrests across the world.

"Libertas" was picked up in Ireland. "SSBD" was arrested in Australia. And "Inigo" was snatched in the US. DPR2 claimed he was given advance notice of an impending bust from sources inside law enforcement, including the European Cybercrime Centre, which is part of Europol, although the tip-off wasn't specific enough to warn particular members.

"Two entirely different personalities for the worlds, so one does not affect the other."


"If more than one source or different countries know about it, it's international, it's going to be big," he said. (In an email this week, a spokesperson from Europol told me, "Europol has no grounds to suspect that the scenario as described to you is correct." I also did not see any concrete evidence of DPR2 having a source in the agency.)

DPR2 told his remaining staff on the forum that, "right now it is still chaotic at best so I am not sure yet how to best respond long term. As a short term bit of caution both Libertas and Inigo are to be treated as hostile and all communications you receive from them must be forwarded to me immediately."

In response to the arrests, DPR2 went dark. He disappeared from the public-facing Silk Road 2.0 forums, leaving members of the community speculating that he had also been caught by the authorities.

"It has now been over 24 hours since we last heard from our Captain," Defcon announced on the Silk Road 2.0 forums. "He is most certainly in grave danger."

Instead, DPR2 was reading a young relative a Christmas story.

"His big concern [was] for Santa arriving with presents the next day, as he leans on me, where I am thinking of the possible ramifications of all I have done and the carnage it left behind," he told me.

"It's a moment that always reminds me of why I kept everything so distinctly apart. Two entirely different personalities for the worlds, so one does not affect the other."


DPR2 claimed this relative was battling an illness, and that he had to urgently visit this person. And at the same time, a security issue had arisen with the site, requiring his immediate attention.

"Some might say they would clearly go to their family in that situation, but don't forget a fuck-up with [Silk Road 2.0] could have meant hundreds of people spending decades behind bars in an unjust system, the very thing I spend my life fighting," DPR2 said. "Could I live with myself for ignoring the person who means everything to me [versus] can I endanger the very people I swore to protect come sunshine or hell?"

The decision wasn't the only hard one that DPR2 had been forced to make. But this one, he said, "was just soul crushing."

Ultimately, DPR2 made an incredibly risky compromise. He worked on the site while visiting his relative.

"Fucking awful security in retrospect," he said. "But emotion tears at logic from time to time."


DPR2 said Silk Road 2.0 "wasn't being done as a business, it wasn't an enterprise of any sort. It was people who genuinely believed in an idea, and they wanted to support that idea to some lengths that people don't usually go to."

Some of the benefits DPR2 saw of the marketplace included harm reduction for drug users and making the narcotics trade safer.

"It was pretty extreme," as far as activism goes, DPR2 continued. "It was founded on the idea of people putting their principles before what the law says, or what everyone else says about it, because that's what they genuinely believe."


Of course, even if a drug market is apparently run in the interests of helping users, there are significant side effects.

"I cannot deny the fact that some people have died from what they bought on what I've made, effectively," DPR2 said. During the trial of Ross Ulbricht, who supposedly created the Silk Road as a libertarian experiment, relatives of people who allegedly died from drugs bought on the site provided letters to the court.

"But, if I didn't act, what would be the consequences of that?" DPR2 said. "Would more people have died, would more overdoses have happened, would people have gone back into the habit of funding certain street dealers or something?"

These drugs, regardless of going to responsible users or those who would be harmed by them, were generating serious cash. Silk Road 2.0 was one of the most successful online drug markets of all time. Academic research indicated that at the site's peak in February 2014, Silk Road 2.0 was clearing around $400,000 a day, with the owners taking around a 4 to 8 percent cut of every transaction.

"After an hour or two of watching the money come in—you'd see a few thousand US dollars come in from a few trades—it didn't mean anything. There was nothing. After the first few ten thousand, everything else on top of it was just numbers. It didn't seem real," DPR2 said.

"I had no real outgoings. The server? A few hundred a month, at most."

In all, DPR2 claimed to have only made around four figures while working on the Silk Road 2.0.

This is because he says he donated hundreds of thousands of dollars to a wealth of different organisations and charities. Those included the Tor Project, the nonprofit that maintains the Tor software, and some entities with no immediate link to technology or drug policy, such as a children's home. (The Tor Project did not respond to multiple requests for comment.)

As many of these places didn't take bitcoin, "we found proxies to make the donations on our behalf," DPR2 claimed. In 2013 on the Silk Road 2.0 forum, DPR2 held a fundraiser for victims of the Philippines earthquake.

Illustration: Shaye Anderson

As I've gotten to know DPR2 better, what I see as his true motivation has shone through. When I suggested that his real drive wasn't the money, the ideology, or the technological challenge, but was instead a fierce enjoyment of breaking the law, he chuckled.

"There are some levels of entertainment that, once you've reached—it's like a drug, you can't get off it again, once you've reached it," he said, starry eyed, with a huge grin on his face. While his customers may have been reaching euphoria after their second bomb of MDMA, DPR2 was reveling in the chase, in the feeling of being one step ahead, and of disregarding the rules in the most audacious ways possible.

That adrenaline from being hunted is "something that most people will never really experience, because of the nature of it," DPR2 continued. "How many people can give the US government the two fingers, sat there, with just their laptop? There's nothing on Earth that you can really compare that to."

That fervent desire to push boundaries has been with DPR2 since childhood, he told me, and is part of his "whole personality." His family would often say he couldn't do something, and, in the same way many parents respond to their children, would not provide any explanation as to why.

"It annoys most people. I crack when people say that sort of stuff," DPR2 said. "Some people, like myself, just aren't satisfied with being law-abiding, calm people."