The Fate of The Man Behind The World's Largest Underground Marketplace

Was Ross Ulbricht a naïve idealist running an anonymous digital marketplace or an online Walter White who built the equivalent of an Amazon for bad guys?
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Was Ross Ulbricht a naïve idealist running an anonymous digital marketplace or an online Walter White who built the equivalent of an Amazon for bad guys?
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Bill & Ted have yet to reunite on screen for another excellent adventure, but the actors who played the time-traveling slackers — Alex Winter and Keanu Reeves — are back together again, collaborators on their first film in a little more than two decades.

Only this time around, unlike their previous lighthearted romps through time, the new work is a documentary that’s both weighty and urgent.

Deep Web, narrated by Reeves and directed by Winter, is a look at the underground, hidden corner of cyberspace that exists beyond the reach of search engines and mainstream awareness, a clandestine Web that’s as much a haven for anonymity and privacy advocates as it is a playground for criminals. For evidence of the latter, the film turns its attention to the drug-trading website Silk Road and the downfall of its creator — 31-year-old Ross Ulbricht — convicted in February of running the site under the alias “Dread Pirate Roberts.”

Winter, who left acting in the '90s to pursue a new career turn as a filmmaker, had already been thinking about the documentary project that would become Deep Web when the authorities nabbed Ulbricht in 2013 in a San Francisco public library. The more he learned about Silk Road, the more he says it seemed to be a “watershed moment in online community” and that a film about the story could also be used to tug on the threads of crime and privacy to reveal deeper truths about the digital age.

Questions also abound in the film, by design. It’s up to the viewer, for example, to decide whether Ulbricht was a naïve idealist running an anonymous digital marketplace or an online Walter White who built the equivalent of an Amazon for bad guys.

“I maintain the truth lies between those two opposing poles,” Winter said in a phone interview less than 24 hours before Ulbricht was set to be sentenced Friday in a federal courtroom in New York.

In a sentencing memo filed earlier this week, prosecutors depict Ulbricht as a drug kingpin and are seeking a lengthy prison sentence. Ulbricht wrote a letter of his own to the judge who will sentence him, begging for some measure of leniency.

“I’ve had my youth, and I know you must take away my middle years, but please leave me my old age,” he wrote.

In thinking about what he hopes viewers take away from the film, Winter pointed to its myriad ambiguities. While there’s something familiar about listening to Neo take viewers to the Internet’s dark spaces, for example, viewers may also walk away unsettled by things like the unprecedented capabilities of the federal government to pursue digital crimes. Or about the efficacy of the drug war (drugs being one of the prized goods bought and sold via the Silk Road). Or by the way unindexed, inaccessible spaces on the Web that promise a higher degree of privacy don’t always attract the better angels of our nature.

“I want people to be faced with the conundrum we live in today,” said Winter about the film, which will be part of this weekend’s Brooklyn Film Festival and premieres on EPIX on Sunday, with video on demand to come this summer. “I hope they’re faced with many unanswerable questions and about how difficult it is to enforce the law in an online world.”

Why was he attracted to Silk Road as subject matter for a film? It was, as Winter puts it, the “brilliance of the innovation” — combining the anonymity of the Deep Web with the anonymity of the digital currency Bitcoin to create a black market that was, in many respects, the first of its kind.

“And it was the first large-scale wholly anonymous Internet community,” says Winter, whose previous film “Downloaded” tracked the birth and flameout of Napster. “I’ve spent a lot of time and always had great interest in burgeoning online communities and have been following them since the 80s. Napster was something that had never been seen before in terms of community and changed many, many things. That’s why I did ‘Downloaded’ and why I was drawn to this. I’m interested in the social and moral implications of the Internet, and how we as humans respond to them.”

Deep Web was made in part through the support of a Kickstarter-backed crowdfunding effort, the campaign page of which shows 1,222 backers pledged $78,700. Winter stresses, though, that the use of Kickstarter wasn’t intended as a way to come up with the budget for the movie. It was, instead, a move to build community around the film — and, Winter says, working through Kickstarter gave him the added bonus of helping him find many of the sources for the movie.

Look for the film on EPIX this weekend and VoD later this summer. 

Photos by REX USA