‘Deep Web’ questions the case against an alleged online drug impresario with libertarian leanings

April 14, 2015

By Matthew E. Milliken
April 14, 2015

Deep Web explores a variety of issues about the Internet and how it may shape our lives in the future. But Alex Winter’s new documentary is at its best by far when it dives into the prosecution of a man who became notorious for his links to an online drug market.

That individual is Ross Ulbricht, now 30, who was convicted in February on federal hacking charges. (His sentencing is scheduled for next month.) When he was arrested in 2013 at a San Francisco library, his laptop was linked to administrative functions of the covert Silk Road website, which sold all manner of illegal drugs.

Deep Web, which is narrated by Keanu Reeves, acknowledges that Ulbricht at the very least was one of the operators of the Silk Road and may actually have founded it. But the documentary raises serious questions about decisions made by law enforcement agencies, the prosecution and the judge in the case.

After Ulbricht’s arrest, prosecutors persuaded a judge to deny bail because they believed the defendant had attempted to arrange for six people to be killed, purportedly to protect the website and to prevent his identity from becoming public. Ulbricht was never formally charged with conspiracy to commit murder for hire, however, leading to speculation that the accusations may have been trumped up to tarnish the defendant’s reputation.

Ulbricht’s defense had to contend with numerous unfavorable rulings by Judge Katherine Forrest. She allowed the government to present evidence at trial that Ulbricht may have been involved in hiring hit men, despite the lack of charges, while barring the jury from considering a federal agent’s testimony that another man had been suspected of controlling Silk Road. Perhaps most significantly, she prevented the defense from contesting how federal agents accessed Silk Road’s web server.

This last ruling is important because the government apparently lacked a warrant to hack the server, which could nullify all the evidence collected from it. Such data collection practices are potentially as alarming as any that have been disclosed in recent years, including revelations that the government has monitored the phone calls and e-mails of Americans to with little to no legal authorization, oversight or limitations.

Unfortunately, few of the other matters explored in Deep Web get as thorough a treatment as Ulbricht’s case — perhaps because covert web activities raise so many different issues. For instance, the movie discusses the libertarian motivations of Ulbricht and of the Dread Pirate Roberts, the persona of the Silk Road administrator who may have been used by multiple people. According to the writings of “DPR” and his supporters, Silk Road simultaneously expanded individual freedom and reduced the fraud and violence that typically accompany black market transactions.

The documentary sketches a case against the war on drugs and suggests that online marketplaces such as Silk Road may indeed make drug purchasing less violent. However, I was dubious of the movie’s argument that seller rating systems and (as one Silk Road drug vendor says) seller scruples can actually make drug use safe. Instead, a more sensible policy change would seem to be drug legalization. This is a prospect that Deep Web never seems to engage, and one which the Dread Pirate Roberts and like-minded thinkers seem to have written off as unfeasible. (They may be right, at least for the moment, but I think circumstances could change over the next decade or two if the partial legalization of recreational marijuana usage continues to have benign or positive effects.)

Deep Web only touches on other aspects of dark net activity, mentioning, for example, that journalists sometimes use it to protect their sources. Winter also spends time with a group of London hackers who talk about the empowering aspects of privacy, but in retrospect, I couldn’t tell you what precisely these people were trying to do. (Granted, this may be due more to the lack of coherence and real-world grounding of their goals than to Winter’s framing.)

The ambition signaled by Deep Web’s title isn’t quite matched by the film itself. Still, the movie’s heart — the detailed examination of the Ulbricht prosecution — makes it very worthwhile viewing.

Author’s note: Please see the latter part of this post for details about my attendance at the 2015 Full Frame Documentary Film Festival, which is due to a generous gift from a friend. Also, although I always strive for accuracy, I did not take notes during 2015 festival screenings. I apologize in advance if I’ve muffed any dialogue, names or other details in my write-ups. MEM

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