Film Review: ‘Deep Web’

This intriguing documentary about alleged Silk Road website founder Ross Ulbricht may lack balance, but compels interest nonetheless.

Courtesy of SXSW Film Festival

Equal parts eye-opening backgrounder, cautionary chronicle and impassioned plea for the defense, “Deep Web” begins as an illuminating overview of the Internet’s non-indexed digital substratum, then narrows its focus to recount the arrest, prosecution and conviction of Ross Ulbricht, alleged originator and supervisor of the notorious Silk Road online bazaar. Even after touring several fests and airing on the Epix cable network, this latest cyber-centric effort by actor-turned-documentarian Alex Winter (“Downloaded”) could attract audiences in limited theatrical and noncommercial release, especially after the May 29 issuing of a life sentence for Ulbricht in a Manhattan federal court.

Winter shrewdly begins his slickly produced movie with a primer for those who tuned in late, explaining how groups ranging from banks and government personnel to cyberpunks and hacktivists operate undetected on the deep web, that vast area of the internet where search engines never roam. Various interviewees — including journalist Andy Greenberg, whose reportage more or less inspired “Deep Web,” and Cody Wilson, the crypto-anarchist who has helped enable the dissemination of guns through 3D printers — speak of the need for a surveillance-free zone where ideas and merchandise can be exchanged in unfettered fashion. “The fascists have the resources,” claims one enthusiastic cyber-libertarian. “But we have imagination … to take back our sovereignty.”

Still, even the most devoutly government-suspicious libertarians might be rattled by, say, the 3D printing of guns, or the online marketing of heroin, LSD and other illicit drugs (in some cases, to minors). The latter enterprise was a specialty of the Silk Road, a site located in the deep-web subset known as the Dark Net, where a freewheeling entrepreneur (or a team of such types) known either individually or collectively as Dread Pirate Roberts — an alias cribbed from “The Princess Bride” — peddled their illegal wares to users who paid in bitcoin cybercurrency.

Winter interviews what might best be described as Silk Road subcontractors (whose faces and voices are disguised) who make no excuses for their enterprise. Indeed, one insists that their service should be viewed as a noble attempt to take their customers out of the line of fire, enabling them to avoid violence attributed to drug cartel leaders and law enforcement agents.

“Deep Web” doesn’t go out of its way to dispute these and other claims by the Silk Road irregulars, and perceptibly tilts its sympathies toward Ulbricht, who was 29 when the FBI arrested him in 2013 on money-laundering and drug-trafficking charges.

According to Ulbricht’s loyal parents (extensively interviewed here) and defense team, the young man was, at best, one of several people operating under the Dread Pirate Roberts pseudonym — and that the other DPRs possibly conspired to frame him. But prosecutors paint a far different picture of Ulbricht, going so far as to claim that, as the one true DPR, he likely arranged the murders of potential betrayers — a charge, “Deep Web” duly notes, that was dropped only after being referenced during opening remarks to jury.

Even viewers who are profoundly skeptical of self-serving claims by individuals running unregulated online black markets might by troubled by certain elements of “Deep Web.” Winter makes a strong case that Ulbricht was railroaded by a judge who blocked introduction of mitigating evidence, and victimized by FBI agents who supposedly ignored constitutional safeguards, and even “hacked a foreign server.”

These and other claims doubtless will be raised during the inevitable appeals process, and certainly will be circulated by, among others, Fourth Amendment activists who insist the case against Ulbricht was built on unreasonable searches and seizures. “Deep Web” tells only part of an ongoing story, but it remains, however one-sided, a documentary worthy of attentive scrutiny and serious discussion. In fact, it would be fascinating to see how some presidential candidates (did somebody say Rand Paul?) would respond to the film’s depiction of anti-drug zealousness and possibly illegal invasions of privacy.

Keanu Reeves, all grown up since his days of clowning around with Winter in the “Bill and Ted” adventures, does a fine job of sustaining narrative momentum with his sobersided narration.

Film Review: ‘Deep Web’

Reviewed online, Houston, May 24, 2015. (In SXSW, Hot Docs, Full Frame, Brooklyn film festivals.) Running time: 90 MIN.

  • Production: (Documentary) An Epix presentation of a Trouper, Bond/360 and Zipper Brothers Films production in association with Exhibit A. Produced by Glen Zipper, Marc Schiller, Alex Winter. Executive producer, Seth Gordon
  • Crew: Directed, written by Alex Winter. Camera (color), Joe DeSalvo; editor, Dan Swietlik; music, Pedro Bromfman; sound, Joe Milner; associate producers, Damir Omic, Bree Polk-Bauman.
  • With: Andy Greenberg, Kirk Ulbricht, Lyn Ulbricht, Christopher Soghoian, Cindy Cohn, Cody Wilson. Narrator: Keanu Reeves.