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Alex Winter on The Head-Spinning Challenges of Making ‘Deep Web’

Alex Winter on The Head-Spinning Challenges of Making 'Deep Web'

READ MORE: Alex Winter Kickstarts Doc About Bitcoin and Silk Road

In October of 2013, a young man named Ross Ulbricht was arrested in San Francisco, accused of creating and running the Silk Road, a massive black market on the Dark Net. A few weeks later I launched a Kickstarter campaign for my documentary on the story of Ross and the Silk Road. Thus began an 18-month journey that would end on May 31st of 2015, the day of the film’s release on EPIX and only two days after Ross Ulbricht was sentenced.

My previous documentary, “Downloaded,” was about the rise and fall of Napster. While I had begun work on this project many years before, when Napster was still up and running, I did not make the film for over a dozen years after Napster closed its doors. “Downloaded” was a purely retrospective examination of the Napster saga, with full access to the core participants. “Deep Web” was the opposite; a real-time exploration of a cyber-criminal case where little was known, turns and revelations occurred at a dizzying pace. While the immediacy of the story set an exciting tone for our narrative, it also presented some head-spinning challenges.* The first hurdle was sifting through the facts in a world of unknowns.

Thematically, I wanted to make a movie about unknowns. The Silk Road was unprecedented in scale for a Dark Net online service. Add to that the unknowns around the Silk Road itself; all participants used anonymous handles and transactions were enacted with an anonymized crypto-currency. Everything about this story was cloaked, anonymized and designed to obfuscate and deceive. This played perfectly to my theme, but it raised enormous practical challenges in the execution of the film.

I was able to penetrate the contraband community of the Dark Net using some prior connections to that world and PGP encryption, which utilizes a verification process that makes it possible to be certain that the people on the other end are who they claim to be. So within a few months of early production I had a network of verified and highly placed sources within the Dark Net and Silk Road. This access allowed me to construct a genuine inside view of why the site was created and how it ran, but it was only part of the story. Specifically, I wanted Ross Ulbricht’s own story, but I was denied physical access to him. In the end, I was able to gain unprecedented access to Ross’s family and defense team but not the man himself. This perceived obstacle turned out to be a gift, as it allowed me to focus on my theme of what little was truly known about Ross Ulbricht and who actually ran the site. And so we cleared our first set of hurdles but immediately ran into another, more formidable obstacle.

Ross had only just been arrested when we began production. The story was breaking and new information was spewing forth at a rapid and constant pace. Where the story was leading and what ultimate fate awaited Ross was many months or years away from resolution. How do you build a foundation and set a course for a story that has only just begun?

While it’s somewhat necessary to roll with the punches while making a documentary, there remains a need for structure and a workable plan that allows the day to day labor of building something. It was imperative that we make structural decisions based on what we presumed would be the ultimate outcome of the case and the eventual trial. In other words, we had to guess about many of the impending outcomes; of the criminal investigation, the public and media response and Ulbricht’s trial itself, or if there would even be a trial as many assumed Ross would strike a plea deal. And then we had to be lucky enough to be largely correct as to how these outcomes would play out. 

Several factors guided our hunches. I had seen the intense level of anger and the desire for punishment directed towards Shawn Fanning and Sean Parker over Napster, and more recently had witnessed the extreme response to the cases of Aaron Swartz, Barrett Brown and Jeremy Hammond. So I suspected that the response to Ross would be even greater, given that he was caught at the intersection of the three most prosecuted legal areas in our country: Cyber, the Drug War and Financial Markets.

I felt certain that Ross would not be offered a workable plea deal. He had been caught red-handed logged onto the Silk Road admin page and a diary of involvement and a great deal of Bitcoin were found on that unencrypted laptop. From the government’s perspective a public trial and stiff sentence was of great use both politically and to send a message of deterrent. It also seemed highly probable that there were rogue law enforcement agents working within Silk Road, something I had seen occurring in the drug markets that existed online back in the BBS era of the early ’90s. This guesswork allowed us to form a plan and forge ahead, but it also presented a kind of Catch-22. If we we were right, we would be able to work effectively but it would also mean the downfall of an individual and his entire family. If we proved incorrect and the narrative took an unexpected turn, at any point, our entire structure would be rendered useless. 

In the end, somewhat incredibly in retrospect, all our major hunches proved correct and played out in even more outrageous fashion than we had imagined. Ross Ulbricht was sentenced to two life sentences without parole, a truly staggering ruling, and the level of corruption on the part of some law enforcement was far more pervasive than I could have predicted. Our structure held firm and we were able to release a completely cogent narrative only days after the sentencing. But that doesn’t mean the process was easy, it was without doubt the most stressful project I’ve ever taken on. Every morning when I fired up my computer I had to process a deluge of new developments that did not relent, all the way up to the morning of our broadcast premiere. Making the film had been an enormous gamble, and succeeding was bittersweet, as it cemented our view that this entire story is a terrible tragedy, a situation in which everyone lost.

A few weeks ago I received a letter from Ross in prison. This was our first direct communication and he has not seen the film. He wrote that he has received many letters from people who have seen the film and are now aware and activated by the many civil rights issues raised by his case. Ross thanked me for this, but was clear that he did not believe the film would have an impact on his chances for appeal. He was not condemning the film, there was nothing remotely resentful about his perspective.

The most slippery challenge we faced from the beginning was to make this movie without having an impact on the case itself. That would have crossed a line for me both ethically and artistically and we took great pains to stay on the right side of this line. In closing his letter, Ross asked me what it was like to make a movie about someone I did not know. It was a shrewd and nuanced question, and impacted me emotionally. Whatever you think of Ross, here was a young man, sitting in prison, possibly for the rest of his life. A brilliant mind that had invented a game-changing technology, whatever you think of Silk Road.

In my response, I wrote that it was better for everyone that I didn’t know him, and ultimately, it was better for the film. But after mailing the letter, I felt nauseous and depressed. The hard truth is that making this film was incredibly taxing. I feel some degree of guilt at being relieved that my journey with this story is over, as Ross and his family’s journey is, in many ways, just beginning.

“Deep Web” is now available on iTunes and VOD. A deluxe edition will be released at DeepWebTheMovie.com.

READ MORE: As Silk Road’s Ross Ulbricbht Gets a Life Sentence, Alex Winter Says ‘Nobody Expected It’

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