Bill & Ted & the ‘Deep Web’: Alex Winter and Keanu Reeves Defend the Silk Road’s Ross Ulbricht
The documentary Deep Web, which premiered at SXSW, dives into the complicated story of Silk Road founder Ross Ulbricht, aka the Dread Pirate Roberts.
Call it Bill & Ted’s Hacktivist Expedition. The documentary Deep Web, a new film about the nefarious Bitcoin-fueled Darknet and its cyberhacker origins, is directed by Alex Winter and features the distinct vocal talents of narrator (and fellow Wyld Stallyn) Keanu Reeves. The Bill & Ted reunion also happens to be the most prominent defense to date of convicted Silk Road black marketeer Ross Ulbricht—aka the Dread Pirate Roberts—who supporters say was sent by the feds on a bogus journey of 30 years to life.
Back in the ’90s, Winter was best known as the curly-coiffed blond half of the slacker duo that tripped through history and gave Death a wedgie in service of a righteous utopian future. He later added director to his resume with the 2012 documentary Downloaded about the culture of digital media sharing fostered by Napster.
Deep Web, which premiered last week at SXSW, ventures beyond file-sharing and into the shadowy corners of the Internet where hackers, journalists, governments, activists, dissidents, and criminals trade anonymously in ideas and information—and also child porn, guns, drugs, and assassinations for hire—leaving behind untraceable trails of ones and zeros.
The film also pays tribute to the freethinkers, anarcho-capitalists, and cyberpunks who colonized and populated these unindexed reaches of the hidden Internet. But opening the digital floodgates to progressive off-the-grid cyber exchange also means it’s impossible to keep out certain evils.
Within the Deep Web lies the TOR-enabled Darknet, where paradoxical entities like the libertarian-minded black market the Silk Road represented the net’s new radical potential while collecting a reported 960,000 users and $1.2 billion in illegal drug sales. As Carnegie Mellon’s Nicolas Christin observes in the film, “It’s not so much about selling drugs as it is to make a political statement of sorts: ‘This shouldn’t be prohibited, we are free to do what we want, and we have the technology to do it. So there.’”
Some, like the Silk Road admin known as the Dread Pirate Roberts, claim to have spun the anonymous drug marketplace as a crime reduction tool that took narcotics transactions off the street and curbed violence more effectively than America’s actual War On Drugs. In Deep Web, an expert argues that Silk Road’s eBay-esque ratings system and marketplace philosophies even made drug sellers more accountable and product more pure, while one anonymous dealer tells the camera that he drew the line at selling heroin to customers he didn’t think could handle it.
That progressive spin was moot when Senator Charles Schumer blew the lid off the Silk Road in 2011, calling on the government to shut down the online bazaar fueling millions annually in sales of hard narcotics, including drugs mailed to teenage buyers through the post.
“It's a certifiable one-stop shop for illegal drugs that represents the most brazen attempt to peddle drugs online that we have ever seen,” blasted Schumer. “It's more brazen than anything else by light-years.”
“It’s about standing up for our rights as human beings and refusing to submit when we’ve done no wrong,” wrote the Dread Pirate Roberts on August 9, 2013. Less than two months later, 29-year-old Ross Ulbricht was arrested in the San Francisco Public Library in an elaborate FBI sting operation and charged with seven counts including money laundering, computer hacking, and conspiracy to traffic narcotics.
His seized laptop contained $28.5 million in Bitcoins and documents and chat logs that prosecutors said proved he was actively running the Silk Road. Ulbricht was indicted but never charged for six alleged contract murders for which no bodies could be found. A separate federal charge alleges that as Dread Pirate Roberts, Ulbricht paid $80,000 for a hit on an ex-admin who stole Bitcoins.
Deep Web opens with a Daily Beast headline that embodies the historic precedents at stake in the Ulbricht case: “The Most Important Trial In America.”
In court, Ulbricht’s lawyers admitted he had founded the Silk Road but insisted he then transferred its control to other admins. Those adoptive owners then set Ulbricht up to take the fall as Dread Pirate Roberts, a handle two to three other people might have shared, they argued.
But prosecutors and Judge Katherine Forrest ran a trial so one-sided, Ulbricht’s family and supporters say in Deep Web, that his defense team was denied the opportunity to try to prove other persons were responsible for Dread Pirate Roberts’s more heinous violations, including the alleged ordering of a hit on a dealer who ripped off Bitcoins. His fate was decided by a jury in under four hours.
Deep Web speaks extensively with Ulbricht’s parents, Kirk and Lyn Ulbricht, and friends who frame the trial’s outcome as a major miscarriage of justice. It also highlights still-unanswered questions surrounding just how the feds found their way to Ulbricht, and whether or not they illegally hacked into the Silk Road’s servers to find its IP address, the digital equivalent of a warrantless search and seizure.
“This was the trial that didn’t happen, because it was only the prosecution’s narrative that we heard,” Ulbricht’s father says. Deep Web all but stands in Ulbricht’s corner and suggests justice was trampled when the U.S. government went after the man they say was Silk Road’s No. 1 drug kingpin.
The film weaves in home videos that humanize the former Eagle Scout as he goofs around in a tutu and talks in a soft suburban Texas drawl. Ulbricht’s longtime bestie René Pinnell tells director Winter he hears once a month from him via email in prison, where Ulbricht teaches yoga to inmates. Interviews with Ulbricht’s supporters paint the picture of a gentle soul who literally could not hurt a fly desperately clinging to optimism from the clink.
More support comes from an unlikely source: Wired writer Andy Greenberg, a journalist who covered the Silk Road story and scored a rare early email interview with the Dread Pirate Roberts. He says he suspects there was more than one Dread Pirate Robert. Greenberg’s book This Machine Kills Secrets served as material for the docu, and he nabbed a co-producer credit on the film.
“The U.S. law enforcement hacked a foreign server, I believe, they didn’t have a warrant, and they completely got away with it,” says Greenberg, “and nobody even gets to ask any questions about it.”
It’s no coincidence that Neo himself is along to guide viewers through the vast and menacing matrix of the “hidden Internet.” What most analog plebes know of the Deep Web comes from the panicked mainstream news media, or that Season 2 hacker subplot on House of Cards. Reeves’s dulcet voice, perhaps the most trusted voice in cyber-storytelling for an entire generation, is here to navigate the uninitiated safely down the Darknet rabbit hole.
Reuniting 22 years after their last outing, Winter and Reeves have stepped up to give Ulbricht and the Deep Webbers of the world the mainstream defense their cause hasn’t yet gotten. Whether the pro-Ulbricht rally will help his request for a retrial remains to be seen. After all, Deep Web airs on May 31—two weeks after Ulbricht is set to receive his sentence.