Check out Part 1 here if you missed it…

 Just after 3:00pm on October 2nd, 2013, Ross Ulbricht was working behind the screen of his laptop in the Glen Park branch of the San Francisco Public Library. In fact, he was logged in to the Silk Road Marketplace as an administrator under the handle “/Mastermind” (1). He chose the science fiction section of the library, since it was the most peaceful that day. That day would not, however, be an ordinary or peaceful day for Mr. Ulbricht. At exactly 3:14pm a young couple made their way past him, arguing. “Fuck you!”, the woman yelled as the man grabbed her and raised his fist. Ross turned around, one hand still on his laptop, but before he could act, the unassuming Asian woman sitting across from him snatched his laptop. She was an FBI agent, just like the young couple he had seen arguing. He never even had the chance to utter a word. By 3:17 he was in handcuffs and the FBI was in possession of his laptop; he was caught completely red-handed. As the agents looked at his laptop, they noticed he was streaming an interview with Vince Gilligan, creator of Breaking Bad. The series had actually just concluded, and for those who are not familiar, it is about a school teacher turned methamphetamine manufacturing kingpin. The irony here is pretty immense; arguably the biggest theme in the show is the descent of Walter White (the main character) from upstanding family man to base criminal. It’s a remarkable transformation, and for the main character of the Silk Road Saga, there are a lot of parallels that can be drawn. How did Ross William Ulbricht, the beloved son, Eagle Scout, charitable, outdoorsy all-American young man become Dread Pirate Roberts, the “/Mastermind” of the biggest drug market in history? In part 2 of our series on the Silk Road Marketplace, we’ll delve a little into the metamorphosis of Ross Ulbricht, and how exactly he fell so far from grace – and into a Colorado high-max penitentiary he resides today, serving multiple life sentences.

Catalyzing A Change

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        Every man or woman struggles with right and wrong. There is an age-old metaphor that exists in the depiction of an angel on one shoulder and a devil on the other. This doesn’t detract from the power of personal responsibility by any means, but the fact remains that one’s character can definitely be influenced by outside factors. Ross Ulbricht didn’t fall asleep a charitable Book Store operator and wake up in handcuffs in the Glen Park library. Dread Pirate Roberts didn’t inhabit the body of a young Eagle Scout and lie dormant for over a decade, plotting his move. The evolution of Ross Ulbricht into Dread Pirate Roberts was likely made possible by a variety of factors, one of which takes the form of a man you might recall from Part 1 of this article: Roger Thomas Clark, or as he was known to Ross, Variety Jones. It was his tutelage and also his radically shared views that I believe influenced Ross Ulbricht. Ross himself once described the Silk Road as an “economic simulation”, that was obviously rooted in his Libertarian beliefs. This aligns with the bright, non-violent, reasonable man everyone in his life knew Ulbricht to be. This is Walter White, agreeing to manufacture meth “as long as nobody gets hurt”. This is reminiscent of a young entrepreneur with radical political views and no ill-will, and that is surely how it began. As his ideas began to take flight however, Ulbricht seemed to become more involved, and almost intoxicated by his success and the fruition of his vision. Recall that he was not a man who sought money, he was a man who wanted to effect change and have an impact. He desired purpose. As a result, later postings by Dread Pirate Roberts became more grandiose, as his vision and ideals seemed to cloud his mind.

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“Some day, we could be a shining beacon of hope for the oppressed people of the world just as so many oppressed and violated souls have found refuge here already. Will it happen overnight? No. Will it happen in a lifetime? I don’t know. Is it worth fighting for until my last breath. Of course. Once you’ve seen what’s possible, how can you do otherwise? How can you plug yourself into the tax eating, life sucking, violent, sadistic, war mongering, oppressive machine ever again? How can you kneel when you’ve felt the power of your own legs? Felt them stretch and flex as you learn to walk and think as a free person? I would rather live my life in rags now than in golden chains. And now we can have both! Now it is profitable to throw off one’s chains, with amazing crypto technology reducing the risk of doing so dramatically. How many niches have yet to be filled in the world of anonymous online markets? The opportunity to prosper and take part in a revolution of epic proportions is at our fingertips!” (7).

While essentially harmless in and of itself, this transition seemed to open his mind to less idealistic enforcement of his views. Variety encouraged Ross Ulbrich, and shared many of his views, and in Ross’ own words, his “coming onto the scene [sic] reinspired me and gave me direction on the SR project.” (2). Eventually, the two started to sound very similar. Jones posted soon announcing his formal involvement, saying “I’m here to be involved with what’s going to become an unstoppable force that can work to break the ties that governments use to bind us,” (2.) Unfortunately, this was seemingly the beginning of the end for the old Ulbricht; Variety Jones’ influence eventually turned malevolent once it was discovered that one of DPR’s high ranking staffers (a person using the name Digital Alchemy) had all but disappeared. Jones then offered to track him down, saying he could “lay a finger on him in weeks, easy” (2), which Roberts eventually took him up on. This was a new development – Ross’ willingness to use his power for something other than the idealistic Libertarian values the Silk Road was founded on. In Ross Ulbricht’s trial, this offer, and its subsequent acceptance, would factor in.

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Another notable influence on Ulbricht was a user operating under the name Nob, whose relationship with Ross not only helped catalyze his full transition into the Dread Pirate, but also his ultimate demise in the Glen Park library. Nob claimed cartel ties and middle-man drug trafficking experience in Puerto Rico. He informed DPR of his ties to many different criminal enterprises. This information and more Ross Ulbricht took at face value; a friend in his world was rare and welcome. Nob welcomed this relationship too – in reality he was a DEA agent named Carl Force (1). Initially offering to buy the site in an attempt to capture DPR, Nob scoffed at Ulbrichts price tag of 1 Billion USD. “this is more than a business to me”, Ulbricht told Nob, “It’s a revolution and is becoming my life’s work.” (8) Clearly, Ulbricht’s desire for purpose remained unfaltered. Their back and forth banter continued, and while they never settled on a sale, “Nob” had made it that much closer to the man behind the mask. Their contact continued amicably and professionally, and when Force’s own DEA team busted one Curtis Green (aka Chronic Pain, Silk Road lieutenant) Nob was quick to Ulbricht’s aid. Green was busted in relation to the Silk Road of course, but his involvement was not fully understood until they seized his computer. In a stroke of good luck, Carl Force had found himself even closer to the Dread Pirate himself than he intended when he discovered that Green was not just a vendor, he was in direct dealings with DPR himself.

Carl Force then took control of Green’s admin account and drained $350,000 in Bitcoin from Silk Road accounts. Later, he would face trial and ultimately serve time for embezzling much of this money and attempting to keep it for himself, but in that moment his plan was to get Ulbricht’s attention, which he certainly did. Nob had solicited DPR for help with “enforcement” in the past, so after Roberts discovered that Green had been busted, arrested, and had (in Ross’ eyes) used his admin privileges to drain accounts, he contacted Nob explaining that he had a problem (8).

Ulbricht, with Nob’s encouragement, decided he would use his services to deal with this threat to his empire. It is impossible to know how Ross justified this; it could have been self preservation, but it also could have been simply to protect the Libertarian freedoms the Silk Road provided for its many users. Regardless of his intentions however, his decision to use violence to enforce them resulted in one of the biggest blows to Ross Ulbricht’s ultimate freedom. His good-natured, well-intended “economic experiment” had finally culminated into the assumption of his role of Dread Pirate. Ross Ulbricht was no longer a Walter White – he had finally become his own Heisenberg.

DPR worked with Nob, initially planning to have Green assaulted, and since Carl Force and his DEA team had gotten to Green first, he was able to use him in a torture sting to incriminate Roberts, even going as far as using props and fake blood to prove to Ulbricht that the job had been done. Eventually, DPR asked Nob if he could “change the order to execute rather than torture?”, saying that Green, “was on the inside for a while, and now that he’s been arrested, I’m afraid he’ll give up info” (8). Ulbricht wasn’t wrong about ChronicPain being on the wrong side of the law. When he used Nob’s “services” to act on this assertion however, he sealed his own fate. In trial, this “contract kill” would factor heavily into the judge’s decision to hand down Ulbricht’s life sentence. In another blow, he would be seemingly extorted by an entity of persons claiming they would leak personal information… Again, Ulbricht responded by paying to have said actors killed. While none of these “killings” actually took place, the precedent was set: Ulbricht was willing to kill to protect the Silk Road.

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Curtis Green, aka ChronicPain, smiling in front of the room where he worked together with Carl Force’s DEA task force to fake his torture and death to incriminate Ross Ulbricht.

And so was was the evolution of Ross Ulbricht, and the birth of Dread Pirate Roberts. Power has a strange effect on people, and the human conscience can be fickle. Even though the man had been altered, what of the enterprise? How did government agencies crack cutting-edge cryptography and high-level anonymity to bring down Ulbricht? How did they beat TOR? The short answer: They didn’t have to. The demise of DPR began with a process any layman could have executed – it all started with a simple Google search.

One of the very first mentions of the Silk Road found in this Google search was on “January 27, 2011, when a user under the handle “Altoid” made a post on a forum for users of magic mushrooms” (9). “Altoid” mentioned how he “came across” the website, and was considering using it to buy mushrooms. Another user named “Altoid” posted a similar message on (home of the 10,000 Bitcoin pizza!) describing a site he had found that was “like an anonymous” (9). In internet marketing this is called “astroturfing”, and if you couldn’t tell – it works. When the same user petitioned the community for an IT specialist who was involved with Bitcoin, he asked for those interested to send him an email. The email address he provided was [email protected]

Obviously these are not slip-ups we would expect from a “/Mastermind”. It is important to remember that our friend DPR was not really cut from such a cloth – clearly Ross Ulbricht shone from behind the mask of the Dread Pirate, and it attributed to his capture. In July of the same year he was busted, Ross Ulbricht was paid a visit by the Department of Homeland security when they intercepted a package at the Canadian border that contained nine different fake ID’s with separate names, all featuring Ulbricht’s face. Ross, who was known to his room mates at this address by “Josh”, almost laughed them out of the door. He refused to answer any questions about the ID’s and told them that, “hypothetically anyone could go on the Silk Road and purchase them” (9).

As agents later delved deeper into his online presence, the amount of incriminating evidence was pretty staggering. The user altoid had petitioned around the web for .onion server help, insiders in UPS, Fedex, and the like, and plenty of the same Libertarian rhetoric from von Mises that was so publicly lauded by Dread Pirate Roberts. Ross Ulbricht was clearly not anticipating the Silk Road’s immense success, and subsequently was far less careful during its meager beginnings. While the mask can never be chained, and an idea can never be broken or imprisoned, Ross Ulbricht was not afforded the same invincibilities. Through his carelessness and his sheer humanity, he proved time and time again to be his own worst enemy (1).

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The discovery of this online breadcrumb trail led to a vigilant surveillance of his activities in San Francisco. Task forces bode their time, watching his every move and how it aligned with the Silk Road, and especially that of Dread Pirate Roberts himself. As it were, “the activity matched; DPR and Ross were in lockstep. Every time Ross turned on his computer, DPR logged on to Silk Road. When he closed it, DPR logged out. Over weeks, the pattern was consistent. At his house, in cafés, in the morning or late evening, Ross and DPR were electronically aligned” (1). The government was watching closely, and the violence of oppression that Ross Ulbricht fought so adamantly was closing in on him. His world was tightening around him, squeezed by the hand of the very entity he sought to weaken. He would meet that entity a few short weeks later, face-to-face, in the science fiction section of the library near his rented home.

The fall of Ross Ulbricht from educated Texas Libertarian into contract-murderer extraordinaire is unsettling, and it should be. It speaks to the power of conviction and the poison of success. Many, myself included, align with the majority of the principles the Silk Road was founded on. Personal freedom, autonomy, reclaiming one’s life from entities with a monopoly on violence – these are all good causes in the eyes of a good portion of mankind. The problem with drawing lines is that it implies the world we live in is black and white, which couldn’t be further from the truth. We live in a sea of grey, where opinion is based on perception, and your personal perception breeds your own personal reality. Most can agree that to kill another person (or have them killed) is inherently wrong, but there are arguments people make. There’s the Trolley Problem, which asks if choosing to kill one is right if it saves many, and there’s also the Ulbricht problem – he believed he was saving an enterprise that bettered mankind. To him, at the time, this was worth more than the lives of those he set out to end. Dread Pirate Roberts, the result of a great education, loving family, and wholesome ideals, Ross Ulbricht. The Silk Road Marketplace was started as an economic experiment, and what a wealth of data it has provided. It shows how a man can be corrupted and a government can be tested. It started idealistically and ended… well, who’s to say it’s ended?



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