(An-)Onymous – Ross Ulbricht: The Hidden Architect of the Cyber Caravan Route

This was the capstone project for my AP English Language and Composition class. Operation Onymous, the namesake of this article, is an international law enforcement operation against illegal websites on the Tor network.

Note: In researching for this project, I have used non-standard sources like Reddit posts from time to time as it is sometimes only through these sources that one can find firsthand accounts of interactions with Ross Ulbricht and Silk Road on the dark web. Moreover, quotes from Ulbricht post-arrest are not very telling as he is currently attempting to appeal the court decision.

Under the interwoven threads of the surface Internet, there exists another underworld. With two exabytes (1 Exabyte = 10,000 Terabytes = 10,000,000,000,000 Kilobytes) of information stored in encrypted network, over 90 percent of the Internet, including academic records, trade secrets, and personal information is jealously encrypted behind impassable barriers (International Business Times). Yet, within the deep web, a smaller, more notorious subset called the dark web lives as a crossroads of countless cyber-criminals. Like the back alleys of a dimly-lit street, it is dark and rife with crime. The vehicle of choice for infiltrating these dingy passageways is The Onion Router, also known as Tor. Tor is a free, open-source software facilitating anonymous communication (Tor Project). Although it has legitimate uses for protecting privacy, the tool is often abused by shadowy figures. There, the currency of choice is Bitcoin, abbreviated as BTC (Bitcoin.org). Bitcoin is a decentralized open-source cryptocurrency invented in 2009 that allows for secure, public, yet anonymous transactions that are difficult to trace for law enforcement agencies, making it the perfect conduit for criminal exchanges (ibid.).

One shadowy contour against the side of the back alley that is the dark web is Ross Ulbricht, often referred to by his The Princess Bride-esque pseudonym Dread Pirate Roberts (DPR). Growing up in Austin, Texas, Ulbricht worked his way up to become an Eagle Scout. DPR was no typical criminal, attending the University of Texas at Dallas with a full scholarship. At the same time, however, the countenance of this slim, scruffy, young man appeared to be more like a geeky, introverted computer nerd than the kingpin of a drug empire. Ulbricht’s mother commented in an appeal letter for a lighter punishment, “When he created Silk Road, Ross was a young idealist who was passionate about the concept of personal and economic freedom” (Southern District Court of New York). Though on one hand a libertarian idealist and supporter of Ron Paul, DPR was indeed convicted of money laundering, computer hacking, and conspiracy to traffic narcotics, and sentenced to life in prison without the possibility of parole. DPR’s unprecedented credentials and characteristics led to sensationalized media coverage, with Forbes calling him “no run-of-the-mill cybercriminal” and “a principled libertarian and cypherpunk” among the ranks of WikiLeaks’ Julian Assange and Bitcoin’s mysterious creator Satoshi Nakomoto (Forbes).

Dread Pirate Roberts launched the premier edition of Silk Road in February 2011, becoming the first black market on the modern dark web. Not long after he created the digital black market, Ulbricht commented, “Silk Road was founded on libertarian principles and continues to be operated on them… The same principles that have allowed Silk Road to flourish can and do work anywhere human beings come together” (Forbes). Ulbricht’s purported libertarianism was more a genuine belief than an excuse: on the site, he regularly published manifestos regarding his passionate thoughts on the morality of Silk Road in association with the formation of drug cartels, the importance of sharing one’s gains with others, and government stances on digital anonymity. His regular publications were rather paradoxical to public perceptions of him: he was neither an introverted computer nerd nor a money-motivated, unintelligent, greedy cybercriminal.

DPR was perhaps one of the most unconventional criminals ever. Sitting in the comfort of his home, working on Silk Road, he started the Dread Pirate Roberts’ Book Club. In one of the first posts of DPR’s Book Club, Ulbricht wrote commandingly, “We will focus on agorism, counter-economics, anarcho-capitalism, austrian economics, political philosophy, freedom issues and related topics.” Believing that knowledge is power, Ulbricht sought to proliferate his ideas within the Silk Road community not only because he believed in the principles, but also to consolidate his authority.

At the same time, he tread carefully, masterfully preventing the collective eyebrows of the community from being raised by appointing a third-party moderator by the name of “DoctaFeelgood” – which, if you haven’t noticed, evokes some rather criminal, druglord-ish connotations (Antilop.cc Silk Road Forum Archives). When conflicts erupted between users of his site, he attempted to mediate them carefully. In doing so, Ulbricht established a community atmosphere. This carefully calculated sense of exclusivity not only acted as a shield protecting Dread Pirate Roberts and his cult of personality from being discovered under the forensic searches of federal police, but also allowed the community to find a surprising form of solidarity that one would not typically expect from a community of criminals.

After all, as The Economist Mexico correspondent Tom Wainwright commented on his work as a journalist, “”I found that one week I’d be writing about the car business, and the next week I’d be writing about the drugs business” (National Public Radio). Ulbricht is one such example, utilizing his unique perspective derived from his activist background to integrate the principles seen in businesses – loyalty programs comparable to his book club – in the Silk Road community.

The Silk Road grew. By the time the servers were seized by the FBI in 2013, the online marketplace transacted an estimated amount of 9.5 million bitcoins, then worth US$1.2 billion and now over US$23 billion (Mashable). The dealers and buyers responsible for the millions of transactions that had taken place on the Silk Road were seldom punished or prosecuted, though the FBI was clearly intent on preventing Dread Pirate Roberts from ever making a return to society where he could potentially leverage his connections to restart his emporium.

One day in October 2013, Ulbricht sat in the San Francisco Public Library Glen Park Branch with his computer open while engaging in an online chat. Outside the building, federal agents were already following him (Business Insider). After all, what criminal mastermind, they thought, would put himself out in the open like this in a library without taking any precautions at all?

Two plainclothes agents acted as a bickering couple. Ulbricht turned around to look at them – and presto – his computer was seized while turned on – it turned out that the Silk Road employee he was chatting with was in fact an undercover FBI agent. Ulbricht himself made no effort to resist his arrest, once again contradicting societal expectations of criminals (Business Insider).

Soon after, he was taken to court. After requesting assistance to post bail from his friends, associates and family members, he surprisingly raised over a million dollars (Coindesk). During his bail hearing, the prosecutor strongly advocated against granting him bail, citing his possible involvement in murder-for-hire (these charges were eventually withdrawn) and the possibility that he could destroy evidence. The prosecution also raised the fact that he had applied for dual citizenship in the Commonwealth of Dominica, an island country, and portrayed him as a flight risk.

Ulbricht’s respectable defense lawyer, Joshua Dratel, started off by accusing the prosecution of giving them inadequate time to prepare as he had only received the new evidence at night the previous day. He also argued that the imprisonment of Ulbricht was preventing him from preparing a successful case, and that Ulbricht would not be a flight risk considering the fact that he had not fled during a Department of Homeland Security investigation a few weeks prior. Although Dratel claimed that Ulbricht was not directly involved in the production of transportation of the drugs, the prosecutor swiftly refuted the claim, alleging that Ulbricht had provided loans to help someone start a drug operation. The prosecutor also claimed that there was “another side” to Ulbricht that his family and friends were not privy to. In the end, after reviewing the facts, Judge Fox denied Ulbricht bail on the basis that he posed a significant flight risk. According to an observer, “[Ulbricht] seemed quite poised given the circumstances” and even had a faint smile on his face as he retired from the courtroom in green prison tops and beige bottoms (Reddit /r/SilkRoad).

Even while in prison pending trial, Ulbricht was not what the wardens and prison guards had expected: he tutored other inmates in math and science; he led a physics class and a yoga class; he tutored his cellmate for a GED, according to his mother’s appeal to the judge for lenient sentencing (U.S. District Court Southern District of New York).

In the end, Ross Ulbricht’s fate was sealed by an appeals court just three weeks ago: life in prison without the possibility of parole. Though Ulbricht’s case is indeed a hopeless one, it demonstrates the psychology of inmates from another perspective. The appellate court’s opinion to uphold the lower court’s sentence commented with a subtle criticism of the legacy of the War on Drugs, “It is very possible that, at some future point, we will come to regard these policies as tragic mistakes and adopt less punitive and more effective methods of reducing the incidence and costs of drug use” (Wired).

Afterword on retributive punishment

Harsh retributive punishment, as in Ulbricht’s and many others’ cases, doesn’t always make sense, and takes out critical societal and economic resources that could be used in deterring crime instead – often times, rehabilitation provides a more viable alternative. Inmates like Ulbricht have already shown remorse for their crimes and efforts to make amends. Life without the possibility of parole deters the inmate from making positive changes to their psychology. One confirmed escaped felon commented on an Internet AMA (ask-me-anything) session, “You might be against death penalty, but the justice system DOES kill people – just as a percentage” (Reddit).

What is the purpose of prison – is it to rehabilitate to prevent further offenses, or is it to give prisoners the worst possible experience as a deterrent? Rehabilitation, for one, allows criminals to re-enter society with legitimate skills for a legitimate career. According to Professor Lawrence Kohlberg’s Theory of Moral Development, there are six stages of moral development, and inmates often reside on the lower rungs of said ladder, and can be rehabilitated through education (University of Central Florida). Although Ulbricht is indeed a far more sophisticated criminal than many morally undeveloped criminals, programs like parole and supervised release would allow inmates like him to prove themselves through making meaningful changes in life after serving their deserved time in prison.

Moreover, one of prison’s most deleterious effects is its ability to function as a school of crime: surrounding criminals with criminals simply encourages more crime. Indeed, Ulbricht is again an exception as he is in fact offering assistance to other inmates, but what would happen when one is stowed away in prison for life? What happens to freedom deferred? Does it dry up like a raisin in the sun? Or fester like a sore and only hurt? Or does it explode?


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