With the 1936 film Modern Times, Charlie Chaplin introduced a witty, scathing take on the effects of mass technology, and indeed, the type of life we forge with it has become a central preoccupation to our modern world. Film remains at the forefront of this conversation, not only for the speed and power of its own innovations, but also for its ability to provoke us to think. Plenty of films explore tech, but especially since the digital revolution, the theme of media enhanced surveillance often crops up. We decided to take a look a few recent films with their own distinctive take on tech and what it means these days to be watching and interacting with each other. 

Earlier I reviewed Zach Donahue’s The Den and Atom Egoyan’s The Captive. This time I’ve chosen Deep Web (2015), a documentary about the revolutionary potential of the Dark Net’s Silk Road.

“The Silk Road reflects where we are as a culture.” ~ Alex Winter

Greenberg's new book on crypto-anarchy

Wired’s Andy Greenberg was the first reporter to interview Dread Pirate Roberts. They carried out lengthy encrypted e-mail conversations about his libertarian philosophy and mission to use the Silk Road to reduce the violence caused by America’s War on Drugs.

Deep Web is the story of Ross Ulbricht’s trial and his family’s efforts to bring him justice. Ulbricht, aka Dread Pirate Roberts, was the mastermind behind the Dark Net’s infamous Silk Road, an online black market for drugs. In October 2013, the FBI caught Ulbricht at a public library while he was logged onto the Silk Road “mastermind” account. They seized his computer, tens of thousands of bitcoins and shut down the Silk Road. He was convicted in February 2015 of several crimes, including conspiracy to sell narcotics, conspiracy to launder money, computer hacking, and maintaining a criminal enterprise. On May 29, he was handed five sentences: one for 20 years, one for 15 years, one for 5 years and two for life, to be served concurrently with no possibility of parole.

“Ross Ulbricht is a fascinating character, he invented this brilliant thing. He had principles. He wasn’t just a cyber criminal or a drug lord or kingpin as he’s described in these charges. He was also an idealistic guy. I’m always going to be conflicted about the virtues of the Silk Road and Ross as a person. For the rest of my life I’m not going to be able to come to a conclusion about this.” ~ Andy Greenberg

Many people in Deep Web want to see Ulbricht as a crypto-anarchist hero, but he just isn’t that seductive. The judge who presided over his case, Katherine Forrest, commented that the Silk Road, “in its very existence, is deeply troubling, terribly misguided and very dangerous,” and I can’t say that I disagree with her.

The Dark Net arose out of the libertarian California Cypherpunk movement that began in the 1990s. Cypherpunk is a gathering of mathematicians, hackers and crypto-anarchists who believe that by encrypting the internet they can create a voluntary political-economy based on perfect free markets. Their goal is to undermine social and state control. When the Silk Road opened for business, it responded to the crypto-anarchist hope for a cypherpunk utopia. It was disruptive technology at its best. It combined internet encryption, the anonymity of cloaking browser TOR, and the crypto-graphic currency bitcoin to become a successful Dark Net version of e-bay. It is purported to have attracted almost 4000 sellers and 150,000 buyers who together did roughly $1.5 billion dollars’ worth of business in the short time it operated.

Ross Ulbricht

Ross Ulbricht. He announced in June 2015 that he is appealing his conviction and sentence.

The Silk Road came to public attention in 2011 when Gawker ran a story: The Underground Website Where You Can Buy Any Drug Imaginable. That’s when Greenberg jumped in. The Silk Road was a big F-you to “the system” and Greenberg wanted the next big story. He managed to interview Dread Pirate Roberts through lengthy encrypted e-mail conversations.  To Greenberg’s mind Dread Pirate Roberts was an idealist who wanted to reduce the violence in America’s War on Drugs. Just by dealing anonymously online and improving the quality of drugs sold through a competitive user review system like amazon’s, Dread Pirate Roberts convinced Greenberg that the Silk Road was doing the world a ton of good.

Bill and Ted's Excellent Adventure. Still the best movie for drinking games, dude.

Bill and Ted’s Excellent Adventure. Still the best movie for drinking games, dude.

Keanu Reeves, who narrates Deep Web, starred with Winters in Bill & Ted’s Excellent Adventure. I don’t want to make fun of these lovely guys, but for a lot of people unfettered access to the best drugs in the world is pretty “Awesome Dude!” It wasn’t long before at least one 14-year-old bought something heavy on the Silk Road and died, but, hey! Let’s get serious about the anti-foundational ethics of crypto-anarchy here.

Deep Web follows Ulbricht’s parents throughout his trial as they hope to show that Ulbricht is innocent, and in particular, innocent of  murder-for-hire. The DEA managed to infiltrate the Silk Road not long after it went public. In a sting, one of the agents negotiated $150,000 with Ulbricht to murder a site admin who threatened to share the real identities behind the Silk Road. The DEA staged his murder and sent photos to Ulbricht as proof of the hit. The FBI stayed the murder-for-hire charge at his trial, but still introduced it as evidence against him. Ulbricht’s parents believed the FBI didn’t have enough evidence to convict, but used the false accusation to prejudice the jury. Unfortunately for them, Ulbricht is now facing trial for that murder-for-hire, and the FBI has evidence of five more. Absolute freedom is a strange and twisted place to be.

Amir Taaki: genius hacker, bitcoin programmer, crypto-anarchist, spokesperson for a growing movement

Amir Taaki: genius hacker, bitcoin programmer, crypto-anarchist, spokesperson

The real revolutionaries of the Deep Web are millennial crypto-anarchists like Amir Taaki, an ex-game developer and internet gambler turned bitcoin programmer. At the beginning of Deep Web, Taaki’s voice floats over scenes of London until Winter’s camera finally locates him in an anarchist squat. It captures his melodramatic delivery of “The real base of power lies with us. We are the darkness.” Forbes listed Taaki as one of their top 30 under 30 in 2014. He created Dark Wallet, a fully anonymous bitcoin app. He also designed a browser, Dark Market, which facilitates a decentralized online market called Open Bazaar. Taaki comes across as a megalomaniac with an eye for the moment and a talent for inflated rhetoric, but he’s connected to people all over the world. He also has a reputation for building useful open source technology and not chasing mounds of bitcoin for himself.

Deep Web’s other shining light is Neill Franklin, an ex-cop who now heads up the group Law Enforcement Against Prohibition. He points out that it’s not just drug dealers making money under America’s War on Drugs. The Corrections Corporation of America, which runs private prisons sprouting up everywhere, returns $675 million in dividends to its shareholders, drug testing companies make billions of dollars testing prisoners, parolees and probationers, and the local police get whatever surplus military equipment they want under the Pentagon’s 1033 program to fight the War on Drugs.

Winter’s subject matter is interesting and his film’s got a lot happening on the floor, but he seems a little sucked in by Ulbricht’s surface philosophical polish. For me, Ulbricht is just an arrogant wiseacre. Still, I encourage you to watch Deep Web and draw conclusions for yourself.

About the Author

Megan Jones
Megan Jones
Hi. I'm a newcomer to Vancouver, working on a 2nd degree in Communications, film and video studies at Simon Fraser University. In my spare time, I can be found noodling on my guitar, exploring Vancouver, meeting people, working on Insight Meditation and writing for The Peak and Love it here, love the people, love my friends, love my family. Peace up everybody! And drop me a line :)