Tangled web

Alex Winter’s documentary “Deep Web” joins an expanding list of features concerned with the present and future of Internet freedom, privacy and the tensions between government encroachment and the evolving and seemingly limitless possibility of code. The film, which focuses on the case against Ross Ulbricht and the takedown of the Silk Road marketplace, balances esoteric tech-speak with the instantly recognizable but no less complex liberty-versus-regulation conundrum that shapes the underlying philosophical content of movies like “The Internet’s Own Boy,” “Citizenfour,” “We Steal Secrets: The Story of WikiLeaks” and several others. Winter raises challenging questions en route to a thesis highly critical of United States’ handling of the Ulbricht investigation, but regardless of one’s position on the morality of the Silk Road, “Deep Web” explores some of the most important digital issues faced by our society.

“Wired” writer Andy Greenberg, credited as a consulting producer on the movie, appears on camera as an authority on the messy politics of the Silk Road and its mysterious puppet master(s), the cleverly monikered Dread Pirate Roberts. While Greenberg and Winter are hesitant to identify Ulbricht as the only person behind the DPR handle – suggesting that any number of people were, are and will be associated with the role – “Deep Web” does acknowledge the prosecution’s smoking gun: at the time of his dramatic arrest at a branch of the San Francisco Public Library, Ulbricht’s unencrypted computer was logged in to Silk Road administration and contained financial records and other documents linking him directly to the site.

“Deep Web” spends significant energy on the vexing accusation that among his crimes, Ulbricht arranged six murders-for-hire, a bizarre rabbit hole that is dismissed by several of the film’s participants as ludicrous. Winter implies that the state’s inclusion of the assassination schemes sow associative doubt and guilt, even though the charges were ultimately omitted from Ulbricht’s indictment. For “Ars Technica,” Joe Mullin penned an essay excoriating Winter for his “obsequious” treatment of Ulbricht and his family members, who granted the filmmaker (so far) exclusive access, even though a number of other movies on the subject are supposedly in the works.

Running in parallel to the unfolding Ulbricht drama and the lurid black market intrigue of the Silk Road as a so-called eBay for illegal drugs are premises that have been explored more thoroughly in other contexts. One concerns the tenuous and perhaps illusory goal of anonymity and personal privacy for Internet users even as agents acting on behalf of “national security” seek to collect, collate, eavesdrop upon and access any and all of our online footprints without warrant. Digital rights attorney Cindy Cohn and ACLU technologist Christopher Soghoian are just two of the important voices Winter includes in the movie, and both speakers allude to stakes much higher than the operation of a website principally known for anonymous drug deals.

Echoing observations made by David Simon and others in Eugene Jarecki’s “The House I Live In,” reform advocate Neil Franklin articulates the economic realities of an enormous machine wholly dependent on the dubious War on Drugs, essentially concurring with the radical notion that the buyer-seller accountability inherent to the architecture of an agora like the Silk Road does in fact result in the violence reduction prized by so many technology idealists. Franklin’s observations merely affirm the government’s financial incentive to continue the “fight.” To change policy would jeopardize the very livelihood of huge branches of law enforcement and the prison industry.