The Deep Web

A 31-YEAR-OLD man made the news last month, when a US District Court judge in New York sentenced him to life in prison.

The crime of Ross Ulbricht, who held two college degrees, was operating Silk Road, an online black market that became a popular platform for people to buy and sell illegal drugs anonymously.

Prosecutors said since the secret website was set up in 2011, Silk Road generated almost $214 million in sales and $13.2 million in commissions before police shut it down in 2013. By that time, the clandestine marketplace listed some 10,000 items for sale, 7,000 of which were illegal drugs, from marijuana to black tar heroin.

Ulbricht, who went by the handle “Dread Pirate Roberts” (after a character in the 1987 movie The Princess Bride) before his arrest, was convicted in February of selling narcotics, money laundering and maintaining an ongoing criminal enterprise.

During his trial, his lawyers argued that the online drug market actually provided a safer alternative to buying drugs on the street.

Before his sentencing last month, Ulbricht also begged the judge to leave “a small light at the end of the tunnel” by giving him a lenient sentence. The judge was unconvinced, and handed him five sentences handed five sentences: one for 20 years, one for 15 years, one for five and two for life. All are to be served concurrently with no chance of parole.

“The stated purpose [of Silk Road] was to be beyond the law. In the world you created over time, democracy didn’t exist. You were captain of the ship, the dread Pirate Roberts. You made your own laws,” Forrest told Ulbricht at his sentencing.

For most people who followed the story on the mainstream media, Ulbricht was a drug kingpin who got what he deserved.

A new documentary, Deep Web, tries to shed light on sides on aspects of the story that the mainstream media ignored and portrays Ulbricht as being more of a libertarian than a greedy drug kingpin.

Directed by Alex Winter (who was Bill in the 1989 movie Bill and Ted’s Excellent Adventure) and narrated by Keanu Reeves (who played Ted in the same cult movie), Deep Web reveals the ignorance of prosecutors, judges and gives voice to the belief that society needs for a surveillance-free zone where ideas and merchandise can be exchanged freely.

Like the mainstream coverage, however, Deep Web is also one-sided—but for Ulbricht’s side. Here, Ulbricht is depicted as the victim of a government witch hunt.

His parents, interviewed extensively, believe he was only one of many people using the DPR handle, and that the others might have conspired to frame him.

The film also interviews users of Silk Road, protecting their identities by showing them in silhouette and morphing their voices. When one of these disembodied voices claimed that Silk Road was more than just a market for illegal drugs and was home to many philosophical discussions, I was reminded of how my friends and I, in our teenage years, claimed that we read Playboy for the interviews.

The documentary’s title is also a little misleading.

Silk Road did operate in the Deep Web, but it occupied only a small portion of it called the Dark Web, which is home to anonymous networks.

The Deep Web refers to the content on the World Wide Web that is not indexed by standard search engines, such as databases and academic journals. Even deeper from the surface is the Dark Web, the portion that has been intentionally hidden and is inaccessible through standard browsers.

To protect itself from prying eyes, Silk Road used TOR, an anonymous network that can only be accessed using a TOR browser, which masks a user’s IP address. While the network is portrayed in the media as home to criminals and a platform for illicit activities, it also protects political dissidents, activists and journalists from oppressive governments.

Silk Road also used Bitcoin, an unregulated payment system through which users can transact directly with each other without going through an intermediary.

All this is detailed as well in Winter’s documentary, which makes for interesting viewing despite its apparent bias. In the end, however, it is difficult to feel too much sympathy for a man who used technology in a way that arguably put people in harm’s way.

If you’re looking for a truly tragic online personality with a more heroic bent, 2014’s documentary The Internet’s Own Boy: The Story of Aaron Swartz does a far better job. Chin Wong


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