Deep Web

The new fanboy doc on Silk Road provides a wealth of info, at a lickety-split pace.

As everyone in the tech-crazy Bay Area knows, the San Francisco arrest of Ross Ulbricht in October 2013 for allegedly operating the online drug-trafficking market Silk Road opened a public window on a number of engrossing subjects. Alex Winter’s provocative documentary Deep Web covers them, in one digestible and well-organized package, as a crime story that widens out into nothing less than a debate over who will control the future of the internet — for many people, that is the future itself.

On Silk Road you could buy hash oil, cocaine, Zoloft, or a new passport, among other contraband items (such merchandise as child pornography, stolen identities, and weapons were evidently prohibited), in complete anonymity through the machinations of the Deep Web and the Darknet, a murky online realm where encryption, utter secrecy, and the concept of “Do what thou wilt” bloom in the shadows.

Silk Road’s after-hours party got pretty crowded. It reportedly had 960,000 users and did $1.2 billion in business, in Bitcoin, before Ulbricht got busted — this in the context of the worldwide illegal drug trade, variously estimated at from $50 billion to $320 billion a year. Tried in federal court in New York City and convicted on seven criminal counts, including money-laundering, computer-hacking, and conspiracy to traffic narcotics, Ulbricht is scheduled to be sentenced on May 29.

Actor-turned-filmmaker Winter investigates Ulbricht’s case using a blue-chip cast of talking heads: Wired reporter Andy Greenberg, the first to interview Silk Road’s anonymous front man “Dread Pirate Roberts” (the pseudonym is a lift from the 1987 movie The Princess Bride); Ulbricht’s attorney Joshua Dratel; “crypto-anarchist” Cody Wilson, whose claim to fame is having developed a serviceable handgun that can be reproduced by a 3D printer; Bitcoin scientist Gavin Andresen; Andrew Lewman, one of the brains behind the “hidden” alternative internet, Tor; and the defendant’s parents, Lyn and Kirk Ulbricht. The notion is floated that Ross Ulbricht is being scapegoated in a power struggle between government and libertarians, when his real crime was providing “reduced harm” to guys (and maybe one or two gals) who otherwise would turn to the streets to satisfy their needs. This fan boys’ view of the world is bolstered by the voice of narrator Keanu Reeves, who starred with the doc’s writer-director Winter in the Bill & Ted’s Excellent Adventure series, a stoner favorite of the early Nineties.

Stoners, tech weenies, freedom-nerds, anarchists, conspiracy freaks, and anxious Main Street civil libertarians will find much to marvel at in Deep Web, although hardcore aficionados already know the story well. Winter’s businesslike digital doc provides only minimal scene-setting but a wealth of info, at a lickety-split pace. The most important unanswered question: How did the feds find Silk Road’s hidden servers in Germany and Iceland? Ulbricht’s “murder for hire” charge, still in court, is also highly questionable, as is the NSA’s role in rooting out the “national security threat” hatched under the cloak of the Darknet. A sequel beckons, both in real life and as documentary fodder.

Deep Web premieres Sunday, May 31 (8 p.m. PT) on EPIX, a network available on cable TV; online (; and via the EPIX app. EPIX, a joint venture of Paramount, MGM, and Lionsgate, launched in 2009 to provide content in the small-screen entertainment arena.


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