The advent of the World Wide Web has brought seemingly endless information to

everyone with access; however, with everything just a click away comes ethical dilemmas on a
unprecedented scale. Everything includes countless cat videos, educational lectures, and photos
from far away lands, but it also includes access to drugs, hitmen, illegal weapons, fake
documents, and hacking equipment. In February of 2011, Ross Ulbritch launched a website
called the Silk Road to host exactly these kinds of transactions and in doing so pitted anonymity
and freedom against safety and legislation (USA v R. Ulbricht). The Silk Road has brought back
the century old dilemma of security verse freedom in a dramatic fashion. To explore both sides of
this argument, the Silk Road and the methods used to seize the site are examined.
Accountability helps to keep people from committing illegal acts. This is why laws work
so well. If someone is caught stealing they must deal with the consequences as defined by the
laws. Without laws and enforcement, people couldthough not necessary wouldcommit
terrible acts. In the physical world accountability has been firmly established through legislation
and refined over years, but establishing accountability within the framework of the world wide
web is much more difficult. In the United States, the National Security Agency (NSA) lays the
foundation for World Wide Web accountability by monitoring for, Someone searching the web
for suspicious stuff or someone who is using encryption. (NSA.gov1.info). The fear of having
federal agents arrive at your doorstep in response to your web searches is a powerful deterrent.
Especially when innocent searches, like pressure cookers and backpacks, can result in a terrorism
task force at your front door (Catalano). However, despite the efforts of the NSA, the World
Wide Web has parts that are not catalogued by search engines (Chandran). This subsection of the
World Wide Web is called the deep web and it is home to the notorious dark web: where
anonymity reigns supreme and everything goes (Chandran).

Anonymity provided the platform for the Silk Road. Users activities were encrypted and
bounced between a network of computers thus making them largely invisible to law enforcement
surveying the webs traffic. Still, as a marketplace, the Silk Road needed a method of payment
that was untraceable to be truly anonymous. The Silk Road found their solution in the digital
currency Bitcoin. Created in 2009, Bitcoins are a currency mined, assigned and used within the
framework of the internet (Bitcoin.org). They also provided the final piece of anonymity to the
Silk Road: a currency for their illegal marketplace.
By and large the World Wide Webs traffic is not used for illegal transactions. An
uncountable many positives have come from the World Wide Web: email, banking, charity,
crowd-funding, social media, sale and purchase of legal goods, and entertainment, to name a few.
Are we to believe that all of this should be regulated or be subjected to heavy surveillance
because of the Silk Road? The scale of the Silk Road operation was concerning though. In
November of 2012, Carnegie Mellons Nicholas Christin evaluated that the Silk Road had 1.2
million US dollars in monthly sales. This was in the Silk Roads infancy and by the time the Silk
Road was brought down by the FBI the court filings place the sites total sales at 1.2 billion US
dollars (USA v R. Ulbricht). Weed, cocaine, prescription pills, narcotics, LSD, and other drugs,
illegal documents were all sold on the Silk Road (USA v R. Ulbricht). The site was also used to
solicit murder (USA v R. Ulbricht). Perhaps more concerning is that the founder known as Dread
Pirate Roberts at the time, intended the Silk Road to be accessible by all, including children
(Wired.com). In Rosss mind, the idea of any restrictions would taint the immaculate concept of
the Silk Road.
The Silk Road sold billions of illegal items to anyone interested, including children, but
just how bad was it? Taking a step back helps put the scale of the Silk Road into perspective. The

United Nations estimates that global illicit drug sales is near 320 billion US dollars per annum,
which dwarfs the total sales of the Silk Road (World Drug Report 60). The Silk Road was
operational for two-and-half years, putting it responsible for less than 16 basis points (or .16%)
of the global drug trade per annum. This alone shows that stopping the Silk Road would have
little effect on reducing global drug production, usage, or consumption. Using federal funding
and allocating anti-drug resources towards stopping .16% of the global industry seems foolish as
those using the Silk Road could get their drugs from any number of other sources. In late 2012,
The National Drug Research Institution (NDRI) surveyed nearly ninety-five hundred drug users
across the United States, the United Kingdom and Australia on the usage of the Silk Road. The
study relieved that the most common reasons for not using the site were: adequate drug access
and fear of being caught (Barratt et al.).
While the Silk Road was comparably small, it had the potential to become a massive
player in future drug sales. When the Silk Road was seized it had a small footprint in the world,
but it was laying the groundwork for the worlds most convenient drug marketplace. The NDRIs
study also showed that those who used the Silk Road used it mainly for its convenience and the
quality of drugs (Barratt et al.). When someone buys drugs from a dealer offline the purchaser is
limited to the drugs the dealer has. They are further limited to the quality, and quantity the dealer
has. On the other hand, the Silk Road had everything from heroin to MDMA and LSD to
cannabis each with detailed reviews of the product and distributor (USA v R. Ulbricht).
Consumers could even purchase insurance for their drugs, just in case the package was
intercepted, destroyed, or damaged (USA v R. Ulbricht). The problems associated with typical
drug dealing were not problems for the Silk Road and others took notice. It wasnt long before
the Silk Road had competitors (Economist.com). Today online drug marketplaces like Agora,

Nucleus, Black Bitcoin Bank, and Alphabay have picked up exactly where the Silk Road left off
(Economist.com). The Silk Road was only a small fraction of the worlds annual drug sales but it
planted the seed for online marketplaces to dominate future drug sales.
Despite the decryption capability of the NSA and all of their surveillance of the World
Wide Web, they had nothing to do with the seizure of the Silk Road or the arrest of Ross Ulbritch
(Wired.com). Ironically the government agency monitoring the web for suspicious searches and
encryption missed a massive perpetrator. A mistake on this scale calls into question the
effectiveness of web surveillance. Picking up the NSAs slack, the FBI was responsible for both
seizing the Silk Road and arresting Ross Ulbritch. Yes, the FBI monitors the web too, but
recounting the seizure and arrest shows that the FBI relied on detectives infiltrating the top ranks
working for Dread Pirate Roberts (Wired.com). The story of the Silk Roads down fall only
further obfuscates the dilemma of security versus freedom. On one hand, the NSAs whiff may be
one in million (not unlike the Silk Road itself). On the other hand, undercover work that respects
freedom was ultimately what brought the Silk Road and its founder Ross Ulbricht down. So, how
should the NSA and FBI be surveying the web and using the decryptions tools when they are a
direct headwind to anonymity and freedom? The creator of the World Wide Web, Tim BernersLee, has openly criticized government agencies like NSA for decrypting code on the World Wide
Web (Pilkington). Encryption is extremely important to keeping sensitive information hidden
such as credit card numbers, social security numbers and much more (Pilkington). By decrypting
such security the NSA, ironically, opens the door for hackers to do the same (Pilkington).
Lastly, the dark web is not only used for criminal activity but also for whistle blowers.
Whistle blowers often publish sensitive material that could cause them to become a target, thus
they often wish to remain anonymous. Edward Snowden is just one example of a whistle blower

who made use of the dark web to publish his findings (Wired.com). The civil use of the dark web
in combination of the ineffectiveness of web surveillance begs the question: are the effects of
securing the World Wide Web worth the consequences of the method of implementation? If it
takes a greater evil to eliminate a small evil is it truly worth the endeavor?
In summary, the Silk Road has brought the ethical dilemma of security and legislation
verse freedom and anonymity into the digital age. The Silk Road hosted many evils from drugs
to soliciting murder. While it was a relatively small operation when it was brought down, many
question the growth potential of the site and the idea of an online drug marketplace. The methods
we have today to ensure web security are flawed. The agency set up to catch such suspicious
activities played no role in bringing an end the to Silk Road, but does endanger the freedom and
anonymity of those surfing the web (Wired.com). Furthermore, the act of decrypting the web in
hopes of finding malicious activity in and of itself aids future hackers gain access to personal
information of innocent web users. There is no clear answer or end to this ethical dilemma. Just
as it has plagued politicians for years it will invariably plague computer scientists in the years to
come as they search for solution that respects both.

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