Dread Pirate Roberts escaped development hell: Making Silk Road work as a film

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Trailer for Silk Road.In the last decade or so of Ars, two pre-COVID news stories stand out to me as the “biggest”—the kind of stuff that captivates a general audience in the moment and will attract the eyes of Hollywood eventually. The first one happened back in 2013, when former NSA contractor Edward Snowden leaked…

Dread Pirate Roberts escaped development hell: Making Silk Road work as a film
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Trailer for Silk Road.

In the last decade or so of Ars, two pre-COVID news stories stand out to me as the “biggest”—the kind of stuff that captivates a general audience in the moment and will attract the eyes of Hollywood eventually. The first one happened back in 2013, when former NSA contractor Edward Snowden leaked classified documents that showed the US had a secret surveillance program up and running that even monitored US citizens. To make the saga even juicier, Snowden ultimately had to flee the country for fear of legal retribution.

The second story largely unfolded in that same year. A young libertarian named Ross Ulbricht pondered why in the United States you couldn’t purchase drugs freely and openly on the Internet through some kind of one-stop repository like Amazon. Eventually, his Silk Road website sprang up and captivated the world… until federal authorities finally closed in on Ulbricht in a San Francisco library in October 2013. The arrest led to an eye-opening trial and a life sentence for the pseudonymous Dread Pirate Roberts.

Snowden’s story ultimately got the Hollywood treatment, via the Oscar-winning documentary Citizenfour in 2014 and a fictionalized account starring Joseph Gordon-Levitt two years later. And though it took a bit longer (unless we’re counting a made-for-TV documentary), the Silk Road odyssey has finally made its feature film debut, too.

After years of rumors and vetted projects, Silk Road had a February VOD run and arrived on Hulu this month. Previous attempts to get a film in the can included industry royalty as big as the Coen brothers (that one would have been based on coverage by our Condé brethren Wired). But time and again, these initiatives sputtered out during some stage of “development hell”—scripts that weren’t quite right, issues with casting and budget, etc. What actually got the job done was paring down rather than expanding the scope of this complex crypto crime thriller.

“There’s a long history of attempts to get this movie made—there were many competing projects at one time, I think there were four or five,” says Duncan Montgomery of High Frequency Entertainment, the production company that helped get Silk Road (based on this Rolling Stone piece) done. “[When we were finally brought on], we started giving our opinion directly to everyone: it needs to be a smaller film.

“[Screenwriter/director] Tiller Russell had interesting elements—the cat-and-mouse detective stuff that gets out of the box and has some entertaining aspects. But this was never going to be a $30 to $40 million-budget film,” he told Ars this spring. “So when Imagine Entertainment‘s deal with the other producer expired, we stepped in and got the rights. And I think Imagine was OK with that, because by then they understood it wasn’t going to be a fit for the kind and size of films they like to make.”

How to make a Silk Road film, step one: Narrow it

Anyone who followed even a tiny amount of the Silk Road news coverage can probably close their eyes and imagine how a studio might see this as a globetrotting blockbuster. It’s the Stefon of source material: the Silk Road had everything. Worldwide reach with major happenings in San Francisco, Austin, and DC. Bleeding-edge technology leveraged for lucrative crime. Drugs galore. An alleged murder-for-hire scheme. Dirty cops capable of major schemes and good cops capable of intricate investigation. And at the center of it all stood a stubbornly ideological kingpin who ultimately turned out to be more bluster and brains than brawn.

All that drama happens long before you even get to the tense arrest attempts and courtroom fireworks. But taking this huge story and translating it into a film that could be successful at the (before times) box office while keeping a normal runtime isn’t simple. Montgomery says the team started by identifying and then tackling two core challenges: the scope and the screens.

“To this day, there’s so much we had to leave out. Really, what this needs is a six-hour limited series,” he tells Ars. “So that was really hard, and it had to find a balance. Do we just tell Ross’ story? Do we even have enough time? Then we ultimately had a DEA agent who’s really an amalgamation of real people. We didn’t feel comfortable from a legal standpoint telling Carl Force’s story or using another guy, so we made a combination of several.”

To maintain this narrow focus, Silk Road unfolds in parallel storylines. On one side, the film follows Ulbricht, played by Nick Robinson (Jurassic World). Montgomery has lived in Austin, Texas, since the ’90s, and he remembers having friends that put him a degree of separation away from a young Ulbricht. But despite how captivating the team found Ulbricht’s backstory while working through the research, the film ultimately skips the Silk Road founder’s upbringing and college years, and it halts before the courtroom drama.

What’s covered, however, is extremely loyal to reality. Silk Road had Ulbricht’s former girlfriend Julia Vie as a consultant who also optioned her story rights. The film shows Ulbricht problem-solving early marketing and technical hiccups until he increasingly loses his grip on reality. He goes from philosophically driven entrepreneur with a life to a man whose site is his sole focus. And as nefarious as some of his choices and motivations ultimately become, Silk Road does sympathize with this character—a stubborn but personable young adult driven to a dangerous obsession that wipes out his humanity.

“On Ross’ side, that portion of the story is very, very accurate,” Montgomery says. “[Vie] lived with him during that time, so she more than anyone else—even more than his family, his friends—knew. We don’t always tell our parents everything. But it’s much harder to hide it from her, so he was very open with her story… The FBI had interviewed Vie and decided she was not a suspect, so she felt very free to talk with us. They had a relationship we could explore, and we could share their intimacy.”

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