"Things like Silk Road that Help Erode the Horrendous Drug War will Continue to Change Policy on a Big Level." Alex Winter on his New Documentary Deep Web

The documentarian chronicles the rise, fall, and importance of Silk Road.

Tomorrow, Ross Ulbricht is expected to receive his sentence for crimes he was convicted of in February connected with starting and operating the darkwebsite Silk Road, where people could buy and sell, using Tor anonymity and bitcoin, nearly anything they wanted—including drugs declared illegal by the federal government. I wrote a feature for Reason last year on the website, animated by classic libertarian agorist principles, and the government's misguided war on it.

The New York Times today has a useful summation of what might be at play in Judge Katherine Forrest's sentencing decision tomorrow, including dueling assertions that Silk Road both saved and cost lives by the access it provided to user-rated substances and dealers in an atmosphere mindful of harm reduction information and not requiring buyer and seller to meet in the real world where either could physically harm the other.

This weekend on May 31, a documentary film about Silk Road premieres on the Epix channel, Deep Web. It was directed by Alex Winter, best known for portraying Bill opposite Keanu Reeves' Ted in the 1989 classic Bill and Ted's Excellent Adventure. Winter has long been fascinated by electronic communities, including directing a documentary on filesharing, Downloaded (2012). 

Senior Editor Brian Doherty interviewed Winter by phone in early May about the film and the story of Silk Road.

Reason: Are you telling a story with an end—Silk Road gone, Ulbricht convicted—or one just beginning?

Winter: Of course it's just the beginning. The parallels between Silk Road and Napster are striking. You have this very simple but brilliant technological advancement with Silk Road combining bitcoin and Tor and growing into a scalable anonymized community.

Like with Napster, the essence was more threatening to government than the drugs, like that community ease of use with Napster was more threatening to institutional power than just piracy per se. The second big similarity is in Silk Road you had a central server with a point of control. Just like with Napster, that became a weakness because it's easier to shut down.

Like with Napster, copycats appeared, most of them terrible, but some are showing up that are very successful moving toward a decentralized markets like with BitTorrent, and that will be extremely difficult to stop. Silk Road is the beginning of the era, not the end.

And even with [Ulbricht's] story, revelations about [criminality on the part of] federal agents [investigating him] shows that what happened with Ross, there is more than we know now and other things might come out. The book might get slammed on him, but his family will work tirelessly appealing.

Reason: All those details about the federal agents' skulduggery, that came out publicly late in the game. Did you know about it while working on the film?

Winter: We all knew about this, that the indictments were going to drop, but there was a gag order on the defense. I did not know the full details of the indictment 'til it dropped. We certainly knew that there was malfeasance, and the defense had asked for a postponement until after the indictment so they could incorporate that into the defense, but they were denied.

I assumed from the beginning of Silk Road's existence that there was a pool of undercover law enforcement, some of whom are on the up and up and some weren't. That's just the way drug cases go in the physical world, and so it goes in the digital world. I was always highly suspect of the singularity of the charges [against Ulbricht], this notion there was one hoody-wearing naive youth who had entirely constructed this and run it by himself.

Reason: You got interesting stuff from FBI agent Chris Tarbell, the guy who allegedly found the Silk Road server via a security error on the site. Was there anything tricky about getting the government's side?

Alex Winter: I was happy that I didn't get clichéd table-pounding demonizing of the internet and privacy. I got a genuine examination of a conundrum.  You can say you want to dismantle privacy and encryption and anonymity but you are making yourself more vulnerable [as a society] if you do that. It's just a fact, [use of those technologies] requires more legwork for government and for law enforcement, in the same way it requires legwork if you go up to a house with a lock on the door. But that doesn't mean we shouldn't be allowed to have locks.

Reason: Are you optimistic or pessimistic about the future of the liberty Silk Road represented?

Winter: Andy Greenberg [of Wired] said it well in the movie: it will be a continual game of cat and mouse and in the end the mice will win but the cats will be well-fed. Despite the continual fist waving and invective [over change] from Napster through the Arab Spring through Wikileaks through [pseudonymous founder of Bitcoin] Satoshi and Silk Road, we have been expanding freedom and using technology to create social change, inform and change politics, and connect people together, whether in totalitarian regimes or in perceived free cultures like ours, and that is expanding. While institutional pressure against those technologies and movement has been increasing, those movement and technologies have been expanding regardless.

Things like Silk Road that help erode the horrendous drug war will continue to change policy on a big level. I'm not all rosy or Pollyanna about the Net. It's not all great. Horrible things go on, but I am supportive of using technologies to democratize culture and change policies that do need to be changed.