Pando

As Ross Ulbricht is jailed for life, Alex Winter's "really fucking sad" Silk Road movie feels even more tragic

By Paul Bradley Carr , written on May 29, 2015

From The News Desk

Ross Ulbricht, the mastermind behind Silk Road, has been sentenced to life in prison. Prosecutors described Ulbricht as “the kingpin of a worldwide digital drug-trafficking enterprise.” During sentencing, the judge told him “what you did in connection with Silk Road was terribly destructive to our social fabric.”

In Alex Winter’s documentary, “Deep Web,” which airs Sunday night on Epix, the director paints Ulbricht as, at worst, a naive idealist who found himself at the mercy of an overzealous, even corrupt, prosecution. It also provides an introduction — an ode even — to Tor, the anonymous browsing protocol, the developers of which Pando has tussled with in the past.

It’s perhaps understandable why Winter thought Pando would hate the movie. “I know what you guys have written [about Tor], and I get it,” he told me as we waited for Deep Web's San Francisco screening.

The next day I call Winter at home in LA. I want to tell him that he was wrong. “Pando” didn’t hate his movie. For one thing, I can’t think of a subject on which the various writers, editors, and hangers-on that constitute “Pando” have ever fully agreed. For another, the movie is actually pretty good. At times excellent, even — in particular Winter’s access to Ulbricht’s heartbroken mother, who became a self-taught expert on the Deep Web, traveling the country, campaigning for her son’s release.

Winter describes Ulbricht's story as "really fucking sad." He's not wrong. I defy anyone to reach the final credits without feeling that, to at least some extent, especially after today's sentence,  Ulbricht has been unfairly treated by the American justice system.

Some of the other characters in the documentary come across less sympathetically. I congratulate anyone with a functioning brain who is able to resist yelling at the screen by the time the hundredth pasty-faced dipshit delivers a lecture on how Ulbricht was the perfect libertarian and how everything would be better if the government would just die already: “ULBRICHT WAS ARRESTED USING THE INTERNET INSIDE A PUBLIC LIBRARY.”

But disagreeing with characters in a documentary — even being unable to stand them, in the case of Tor’s mad-tin-foil-hatter Jacob Appelbaum — isn’t the same as hating the documentary itself. All that follows notwithstanding, you should see this movie.

When we speak on the phone, Winter tells a much more nuanced story than appeared on screen. Maybe he’s toning it down for Pando — I can’t know — but in any case, he insists he still doesn’t know exactly how he feels about Silk Road or Ulbricht.

“People assume you’re on one side or the other,” he says. Nor does he profess to be an expert in the underlying technology. “[Coming into the movie] I knew about the darknet, I had used Tor… but I’m not a computer scientist.” That said, Winter’s credentials put him way ahead of many filmmakers trying to comprehend a subject as inherently opaque as Tor and the deep web: he’s a long time supporter of the EFF and was active in the BBS and cypherpunk community before graduating to Usenet and the Internet.

That history, and the fact that his previous documentary was a love letter to Napster, might also speak to his biases. He insists however that he’s “not hugely into libertarianism” and nor is he someone who spends his days trawling the deep web for narcotics: “I didn’t think about the drug war until way into the movie… I don’t do a lot of drugs, don’t buy drugs online…” He also has a self-servingly old school approach to filesharing, explaining that he hasn’t distributed many review DVDs of the movie because he doesn’t want it to be pirated.

So, for the record, what is Winter’s position on Silk Road and Ross Ulbricht?

“Silk Road is a paradoxical thing… This was a crude but brilliant idea by a lot of naive idealistic young people, created by a bunch of postgraduates who were not good at operational security. It was, in a way, ramshackle.”

He takes issue with the way prosecutors tried to paint Silk Road as a billion dollar marketplace -- “It was totally penny ante, not billions of dollars. That was based on a brief bitcoin valuation.” -- and with how Ulbricht was originally accused of soliciting the murder for hire of Silk Road users who crossed him, accusations which mysteriously vanished from the final charge sheet. “I’m not saying Ross Ulbricht is Aaron Schwartz. He may be guilty. What I’m saying is that if he did [set up Silk Road], it’s all he did… [But] all we hear is that Ross was this Walter White style murderous kingpin. I have a problem with that narrative… I don’t know Ross from a hole in the wall but I do know he wasn’t charged or convicted of attempted murder.”

I tell Winter I agree with him, and I mean it. It is shocking that the murder-for-hire charges were used to frame the prosecution’s case with little to no evidence of guilt. And it’s outrageous that Ulbricht’s attorneys weren’t allowed to know precisely how their client had been caught. In particular they’re not allowed to know whether the seizure of Silk Road’s servers in Iceland breached Ulbricht’s fourth amendment rights. If they did, then it’s hard to see how that wouldn’t have hugely prejudiced the evidence in the trial.

On this question, too, Winter has a nuanced view, even betraying a sympathy for investigators who just wanted to get results, even if it meant bending the Constitution a little: “Everyone has a job to do. My gut tells me that [FBI agent Christopher Tarbell] used whatever means necessary to do his.”

Speaking of which.

Deep Web by no means tells the full story of Silk Road. Particularly jarring are some of the other questions left unanswered about Tor's security, perhaps because they might raise awkward questions about the relationship between Tor and its government funders. If the Iceland servers were located through an FBI hack of Tor, doesn't that suggest that the government-backed privacy network might not be as opaque to law enforcement as we're led to believe? Isn't it possible that vulnerability is the real reason the FBI didn't want to reveal its methods? Winter acknowledges the possibility, but insists the question of Tor's security was only left out of the movie to avoid complicating the narrative. "The more of that stuff we included, the more confusing it was," he says.

It's an unsatisfying answer, but not one that meaningfully undermines Deep Web. In fact, there are only two moments in the movie — both within the same minute or two of screen time — when it would be accurate to say I fleetingly, but deeply, disliked Deep Web. The first is when Winter’s narrator (his old acting partner, Keanu Reeves) tells us that, while Tor was originally funded by the US government, it is now “largely privately funded.”

As any Pando reader knows, that’s a flat lie: A glance at the Tor website confirms that a huge chunk of Tor’s funding in 2015 comes either directly from Uncle Sam — including the State Department and Radio Free Asia — or as a “pass-through” grant via one of his cut-outs. As reported by the Guardian, the most recent Tor financial statements available show that “the organisation received $1,822,907 from the US government in 2013. The bulk of that came in the form of "pass-through" grants, money which ultimately comes from the US government distributed through some independent third-party.”

The second is when, without citing a shred of evidence, Winter-via-Reeves tells viewers that Tor is “largely used for good”. That may be true, or it may not be: The department of Justice claimed that 80% of Tor traffic is child porn, a statistic that Wired dismissed as “baloney,” before clarifying that it’s 80% of Tor traffic to hidden services that involves child porn. The truth is, there is no reliable way of knowing what the vast majority of Tor users are up to: That’s the whole point.

Winter must know that Tor is still funded by the government. He must know that he can’t back up his “mostly used for good” argument. Right?

Right.

“The reason I [said Tor was mainly used for good] was to counteract the view that Tor is literally a hacking tool,” he explains. “I had one guy who saw [an early cut] who said ‘If my son had Tor on his computer, he’d be grounded.” But, he points out, “the line about Tor being good is delivered over a giant fucking picture of a gun on screen.”

His argument makes a kind of perverse sense: It’s not like Winter is pretending that there’s was nothing bad on Silk Road — the whole movie, and the giant fucking gun, tells us the opposite. By twisting the truth slightly to create turn a guess into a statement of fact — most of Tor is good — and by lying outright about the organization’s funding — Winter hopes to avoid losing mainstream viewers before they learn something important. It’s the old Wittgenstein's Ladder’s argument: Small lies are OK if they help the reader, or viewer, to eventually get to a more complex truth.

And yet… the same line of thinking is what led to the Tor community’s insane reaction to Pando’s coverage of their government funding: By telling the truth about Tor’s funding, Yasha’s reporting may well have spooked potential Tor users who could have benefited from the service. And so, went the logic of the Tor project, and those who put Yasha’s name on a deep web assassination list, he had to be silenced. For the greater good.

A few weeks have passed since my conversation with Winter and I still can’t decide if his two white lies are enough to damn the entire project. I know that Winter is right: Telling the full, unedited truth about Tor and Silk Road is likely to close more minds than it opens. But I know too that if anyone at Pando told me they’d lied to readers in pursuit of some higher purpose, they’d be fired before they’d finished the sentence. Winter’s white lie to viewers in no way compares, morally speaking, to the smear campaign against Yasha, but it’s cut from the fringes of the same cloth.

The result is that I’m almost as conflicted about Winter’s film as I am about Tor (the technology, not the organization) itself. It’s an important and sincere piece of filmmaking, and one that deserves a wide audience. As a piece of journalism, however, it is critically compromised for breaking the first rule: Always tell your audience the truth, no matter how few of them want to hear it.

Deep Web airs Sunday at 8pm on Epix.

[Illustration by Brad Jonas]