The documentary starts off as a primer on Tor (a crafty bit of anonymizing communications software), the web of secretive and mostly inaccessible "dark" sites like Silk Road and the sentiments that led to their creation. Where it really shines, though, is the second act, which explores the long, transformative path that helped turn Ulbricht from a brilliant student and book seller into the Silk Road's owner, Dread Pirate Roberts, who would eventually be caught red-handed in a San Francisco library. The events surrounding the collapse of the Silk Road have been recounted and retold from just about every perspective, which left Winter the unenviable job of finding an objective, nuanced thread to wind through his work.
"I think that the media does the best they can with these kinds of stories, which, first and foremost, are incredibly confusing to the average journalist," Winter told me over the phone. "They have to be very tech-savvy to get the ins and outs of what's going on, and they will generally go for the easy or salacious headline. Whatever you think of Ross Ulbricht, I think it's fairly evident the motives for creating Silk Road were more idealistic, even if they were reckless and naive."
That recklessness and naïveté can be spotted again and again as the film traces the growth of Ulbricht's masterwork. The Silk Road first started as a sort of economic experiment, one that balanced allowing its members to sell whatever they damn well pleased with an adherence to an ethos that sought to reduce harm where possible. "We don't allow the sale of anything that's main purpose is to harm innocent people, or that it was necessary to harm innocent people to bring it to market," Ulbricht wrote in an interview with Forbes. According to Winter, who interviewed a number of vendors and dealers who peddled on the Silk Road, most present just ate it all up.
"I kind of expected to find the Walter White or the Jesse Pinkman of the internet, and that's just not what I found," he said. "It wasn't there. What I found were tech-adept, politically active people pretty much across the board. Obviously some were there strictly for criminal purposes, but I'd argue they're not the primary architects or vendors on the Silk Road. Some of the people I encountered were even involved in the drug trade since the '80s, in the Usenet and BBS era, on alt.rec.drugs, but none of them were that significant."
"The core architects," he went on, "were -- pretty much to a man -- more interested in it for more libertarian reasons, or crime- and harm-reduction reasons, or combating the drug war or changing policy through technology."
The system worked, and perhaps too well. During its years of operation, Ulbricht had to protect -- desperately -- not just the sanctity of what he'd created, but also his own identity. The evidence unearthed in the FBI's investigation alleged he was even willing to have lieutenants like mild-mannered Mormon Curtis Green killed after he was arrested by the DEA in his Utah home. Green is still alive, as are the handful of other people Ulbricht supposedly paid to have killed too. These hits were eventually deemed a hoax by authorities and dropped from the official charges against him, but it seemed in those dark, desperate moments, Ulbricht might have turned his back on his cherished harm-reduction principles. That, or there were yet other people clamoring behind the mask of Dread Pirate Roberts, a contention that continues to this day.
It'd be simple enough to chalk Ulbricht up as yet another man turned corrupt by the power he grew to wield, but Deep Web endeavors to make us remember he was just a person, thanks to videos provided by his friends and family. Behind the fierce libertarian rhetoric and his dedication to building a marketplace for potentially dangerous unmentionables was a guy who occasionally strapped on a tutu and sang, "I'm a little teapot," for laughs. Watching him in a StoryCorps booth with his best friend reveals the faintest hint of native Texan drawl. Winter says Ulbricht's loved ones knew he wasn't in this to craft a work of advocacy, but they were at least comforted by his hesitance to go with the typical "table-thumping rhetoric" being wielded by other media outlets.
His portrayal in Deep Web even surprised his mother, who's all too used to seeing the media jump to salacious conclusions about her son. "I read things by people who don't have a clue who Ross really is," his mother Lyn said in the film while bold-faced headlines inched across the screen. "He's been tried and convicted in the media. Nothing has been proven at all. I don't know what's happened to the presumption of innocence in this country."
Winter doesn't try to answer her question. Amid dueling narratives, Winter can't quite decide if he likes Ulbricht/DPR either. Fair enough: The two have never met and Ulbricht declined to be interviewed for the film. What Winter was more concerned with was painting a nuanced portrait of a man facing charges and a trial that only could have happened "in the digital age," even if the result can be less than satisfying. "It's difficult to get concrete answers when you're dealing with anonymized marketplaces and anonymized currencies," he said. Of course, there's only so much one could squeeze into an hour and a half, and Ulbricht's odyssey absolutely refuses to taper off. As such, Winter's work isn't complete, at least not in the sense that it wraps up nicely at the end. Between the film's premiere back in March and the present day, exhaustive in-depth stories have cropped up to shine additional light on what played out on the Silk Road. A television show and at least one nonfiction book are in the works. There's still plenty more in this story to tell, but when asked if he planned to continue his exploration on film, Winter was pointed.
"I don't," he said, laughing. "The film is about unknowables. It's about the way the media covers digital issues. It's about the way the federal government deals with digital crimes. It's about anonymous communities. It's about fighting the drug war. It's not about wrapping the story up with a neat little bow."
How appropriate. With a sentencing on the horizon, and a near-guaranteed appeal from Ulbricht's defense and family to follow, there's no neat little bow in sight here in real life either.