- “Silk Road,” written and directed by Tiller Russell, will be released on Feb. 19.
- It’s based on the case of Ross Ulbricht, the Westlake High grad who created the Silk Road.
- “Love, Simon” star plays Ulbricht, who’s currently serving a life sentence.
- “Silk Road” was partially filmed in Austin, including on South Congress Avenue.
Before he was the mastermind of a dark web drug marketplace, Ross Ulbricht was an Austin-area teenager. His path to creating the Silk Road — and the string of deaths and the millions in cryptocurrency on the way — became a national crime story, covered by outlets including the American-Statesman.
Now, it’s a feature film: “Silk Road,” written and directed by Tiller Russell. It’s out in theaters and available on demand on Feb. 19.
Ulbricht started the Silk Road online marketplace in 2011. Prosecutors later said he collected $18 million in bitcoin as commission on more than 1 million drug deals through the site. He operated under the alias Dread Pirate Roberts, a reference to “The Princess Bride.”
From the archives: Family, friends shocked by Ulbricht arrest
He was arrested in 2013 and currently is serving a life sentence, which a federal appeals court upheld in 2017. Prosecutors pointed to the deaths of people from drugs purchased via the Silk Road, and the sentencing judge took into consideration evidence that Ulbricht, who graduated from Westlake High School in 2002, tried to have five people killed because he deemed them a threat to the operation.
Russell, whose work also includes the docuseries “Night Stalker: The Hunt for a Serial Killer,” learned about the case from a Rolling Stone story by David Kushner and says he researched Ulbricht extensively.
“I never met with Ross, though,” Russell said when we talked on the phone recently. “I would very much love to — actually just sent him a letter yesterday with the movie now coming out, saying, ‘Hey, man, I’d love to sit down with you and hear your version of what happened and what it was like for you from the inside.'”
In the film, actor Nick Robinson (of “Love, Simon” and “A Teacher”) plays Ulbricht as an aimless idealist who finds an outlet for his radical libertarian philosophy in the Silk Road. The illicit project soon grows out his control, leading to conflict with his girlfriend, Julia (a version of Ulbricht’s real-life ex, played by Alexandra Shipp of the “X-Men” films), and an unscrupulous luddite of a federal investigator (played by Jason Clarke).
Russell thinks “there’s a bit of a Frankenstein element to the story.” As he understands it, Ulbricht went into the creation of Silk Road with the intention of changing the world and giving people freedom to do what they want. “But then at a certain point, he created this thing that entered the zeitgeist and became a monster and got out of his control and ended up grabbing him by the throat,” said Russell, who adds that he’s empathetic toward both Ulbricht and those who died.
We talked to the director about truth, fiction and filming in Austin. These excerpts have been edited for length and clarity.
You started out as a crime reporter, is that right?
Yeah, in the San Francisco Bay area, Berkeley.
A lot of people can get burned out on that subject matter. What keeps you interested in digging into the darker side of human behavior, now in the film world?
I was magnetized to this world a bit as a kid. My dad was in the DA’s office depicted in Errol Morris’ film, “The Thin Blue Line.” So as I grew up, he dragged me around to precincts and the courthouse and jails. I think his intention was that I would be scared straight, but instead, I kind of imprinted like a duck on the world and have been embedded in it ever since.
What about the Ross Ulbricht case spoke to you as something that would make a good movie?
I was fascinated by this story from the very first day I read about his arrest in the sci-fi section of the Glen Park Library in San Francisco. Even from the initial thumbnail reporting of it, I had a strong instinct, like there’s a movie behind this. Who is this guy? What was his arc and experience? Because it was this incredibly compressed story where he went from launching Silk Road in 2011 to getting arrested in 2013. So in the course of 18 to 24 months, he cycles through from dreamer to visionary to gangster to legend.
When the Rolling Stone article came out, it was a profile and portrait of Ross. At the time, the second half of the story had not yet broken, which was how law enforcement worked the case, and the malfeasance of some of the investigators. But I had pretty good connections via my background and source network into the D.E.A. and the U.S. Attorney’s Office, and so I had people giving me some inside information about what was going on.
Then I began to see it as the story of the collision course of these two characters who were on opposing arcs and were almost missiles that had been fired at one another.
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There’s this technologically savvy character in Ross, versus this really analog, kind of dinosaur character in the investigator, Rick Bowden.
I think that there are these very strong dualities that the movie is exploring. There is the generational divide between them, the millennial upstart and, what they call them in the D.E.A., “Jurassic narcs,” these sort of knockaround guys who know how the streets work and know how people’s psychology works and have that very old-school horse sense. …
They’re both obsessive. They’re both completely committed to what they’re doing. They’re both lying to the people around them and have this burning passion and desire that’s a secret at the center of their lives. It’s those conflicts and dualities that both separate them and unite them that made them both fascinating as characters for me.
The film begins with an epigraph that the story is “true, except for what we made up and changed.” Tell me a little about your approach to truth and fiction in this film.
In terms of methodology, I approached this like I do the documentaries on the front end, which is running down everything that’s in the public record: every article that’s ever been published, any of the court filings, everything that’s in the evidentiary record, from the chat logs, to statements at sentencing, to you name it. … Ross’ ex-girlfriend (Julia Vie) was a source and a contributor, in some ways, into him as a character.
Then there’s also, in an interesting fashion, these breadcrumbs that Ross had left behind, whether it’s his public postings as Dread Pirate Roberts, to the diaries that were later uncovered when his laptop was confiscated. There was a lot of source material to draw from. Then at the same time, there’s all these gaps in the public record, right? … I think one of the things that is fascinating about Ross as a character is that there were so many different vantage points and perspectives on him.
What are a couple of the biggest things that you had to change from the real events?
It’s a complicated question for me to answer in some ways, because you do all this very rigorous research and journalistic engagement with the story to begin with, so that you’re deeply steeped and mired in all of the facts and the data. Then at a certain point, you have to kind of set it all aside and re-enter the story emotionally, and make it make sense as a human being. What does it feel like to be Ross Ulbricht? What does it feel like to be Rick Bowden and make those decisions and pressures? At a certain point, the divide between what’s factual, what’s their story, what’s my story and what’s fictional becomes porous, I think.
I guess the simplest answer to your question is, the Rick Bowden character played by Jason Clarke, who’s an absolutely astonishing actor at the height of his power, he’s a composite character. There were several corrupt cops, people from law enforcement who were involved in, essentially, bilking and hustling as well as trying to bust Ross. That character is an amalgam of some of the actual folks who are out there and not based on any one particular source.
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You filmed in Austin. I caught shots of South Congress. How much was filmed here?
The bulk of the production was shot in New Mexico, and then we did a smaller splinter unit in Austin, in San Francisco, a little bit in Baltimore. It was really great filming in Austin. I’m a Texas guy; I grew up in Dallas. One of the producers is an Austin resident, too, Duncan Montgomery. …
I should say, when I first sat down to write the script, to the initial drafts of it, it was really important to me to soak up place in a fundamental way. I feel like it’s so informative of character, and so even before I ever began to write, I went to all of the places that I could find that were signature for Ross in some way or another. … We ran around and shot all over, everywhere from Jo’s to South Congress and Sixth Street to the San Jose. Some of them were particular places that were either mentioned by Julia or places that they had been or were just evocative of Ross’ world and the time he spent there. He went to Westlake growing up and then later went to (the University of Texas at Dallas). It was kind of getting a feel for his world, what it’s like to get the breakfast taco and a cup of coffee.
There’s a scene where Ross is at a bar, and he meets Julia. It really does have this sense of, like, being out on Rainey Street. It feels like a real time capsule of a certain youth culture in Austin. How do you think that environment that he grew up in informs him as a character?
Austin is this vibrant, youthful, kind of edgy but fun and open town. It’s a unique corner of the Republic of Texas, right, from the keep-it-weird vibe, which you could say is cliché at this point, but it’s true. It’s defining of Austin. There is this openness and this ability to be an outlier and be a weirdo and kind of find your own way. There is the breath of life that supports that, from the throngs of students at UT to the youth culture that spills over into all the bars. I think that fermenting hotbed of ideas and ambition and fun and dreams, right — it’s a bunch of young people with a dream, and Ross wants to make his mark in the world.
It’s a place where you can do that and where people believe, and are hopeful of the future. I wanted to capture that and to evoke that excitement and that freedom.
Eric Webb is the Austin360 entertainment editor for the American-Statesman. Email him at [email protected] and follow him on Twitter @webbeditor