Hot Docs ’15: Alex Winter delves into “Deep Web”

Downloaded director Alex Winter took the stage at the Bloor Hot Docs Cinema for the festival's 'Big Ideas Series' (pictured) to discuss his latest entry, Deep Web, which investigates a criminal case around the online black market Silk Road.
April 29, 2015

For director Alex Winter (pictured below), the same impetus behind his 2013 documentary on online music service Napster propelled his latest film Deep Web, which investigates a criminal case around the online black market Silk Road.

Billed as “the inside story of one of the most important and riveting digital crime sagas of the century,” Deep Web – which bowed at SXSW and will premiere on VoD service and premium cable and satellite net Epix on May 31 – chronicles the arrest of 30-year-old American entrepreneur Ross Ulbricht (pictured below, right), who was in February convicted of being ‘Dread Pirate Roberts,’ the creator of the Silk Road, which is known as an online portal used to buy and sell drugs using the digital currency, bitcoin.

The film centers on Ulbricht’s involvement in the Silk Road, but also debates the legitimacy of the “new Internet” through interviews with cryptographers and whistle-blowers who maintain the deep web and the anonymity it affords online is necessary in a culture of increasing government surveillance.

Winter – who views Deep Web as a “continuation of the same conversation” he started in Downloaded – was on hand to discuss the film at Toronto’s Bloor Hot Docs Cinema on Sunday (April 26) as part of the festival’s ‘Big Ideas Series,’ in which filmmakers engage in extended discussions, along with subjects from their films.

Joining Winter on stage was Wired writer Andy Greenberg, who is interviewed in the film and also credited as a producer, as well as Ulbricht’s parents Lyn and Kirk.

alex winter

Alex Winter

“The shift from the industrial age into the digital age we’re experiencing now is the very, very beginning,” Winter told the audience following the screening. “We’re going to look back on this as a very crude infancy, and the fabric for how certain laws are created and certain things function is going to have to be torn down and completely rebuilt. There’s so much resistance to that, and fear and ignorance.

“That’s what made me want to tell the Napster story,” he continued. “You couldn’t talk about downloading without being shouted down for music piracy. There was just so much more to that story – it wasn’t to say it was good, because you wanted to look at the nuances, but it was to say, there’s more here than this and we need to be looking at the ‘more.'”

Winter says the same conflicts inherent to the Napster case continue today, but with bigger implications, and points out that in the case of Internet hacktivist Aaron Swartz – who was profiled in Hot Docs’ 2014 opening night doc, Brian Knappenberger’s The Internet’s Own Boy – it became a matter of life and death. Swartz, a proponent of making information accessible online and open to the public, was indicted in 2011 on federal computer crime charges and killed himself in 2013, shortly before his trial was slated to begin.

“In the Swartz case, somebody’s life was on the line,” said Winter. “It’s not to say they’re all martyrs; it’s to say there’s a lot more here than we’re getting an opportunity to look at.”

Wired’s Greenberg – who was among the first reporters to cover the Silk Road and is interviewed extensively throughout the doc – said he came on board for the film because of Winter’s unique perspective on the case.

“I was attracted to Alex’s telling of this when he approached me about it, because he saw it as more than just a cyber-criminal conspiracy, the way that you see the television coverage of this case,” he said. “I think the Silk Road began with such immense idealism. This was a story about a libertarian philosophy and a guy seeking to carve out a place where people could be free to buy and sell what they wanted online.”

Currently, Ulbricht stands convicted on seven charges, including drug trafficking, criminal enterprise, computer hacking and money laundering. At his sentencing on May 15, he faces a potential sentence of life in prison.

During the discussion, Winter maintained it was important that audiences keep themselves informed about cases such as Ulbricht’s, and that individuals should be conscious of the impact technology, and its advances, has on their daily lives.

“We don’t live in a world anymore where you can just pretend you don’t care about technological issues,” said the director. “All of your information is already out there, that’s how technology works. So what you have to do is be aware of these things and take them seriously.”

  • Deep Web next screens on Thursday (April 30) at Toronto’s Kingsway Theatre at 9 p.m. For more information, click here.
About The Author
Justin Anderson joined Realscreen as senior staff writer in 2021, reporting and writing stories for the newsletter and magazine. During his 20-year career he’s filled a variety of roles as a writer and editor at a number of media organizations, covering news and current affairs as well as business, tech, the film and music industries and plenty in between. He’s also spent time behind the scenes in television production, having written everything from voiceover scripts for documentaries to marketing copy. He has a degree in Journalism from Toronto Metropolitan University (formerly Ryerson University).