The road to Silk Road: How a story for our times captured the imagination of a Santa Fe filmmaker

Stills from the movie Silk Road, courtesy Lionsgate

The true-crime story of the Silk Road was just begging for a screenplay. No, this Silk Road wasn’t the historic network of trade routes connecting Asia, East Africa, and Europe, although that’s where it derived its name. It was a darknet black market where users could purchase thousands of items anonymously, including illegal drugs such as opioids, psychedelics, stimulants, ecstasy, and steroids.

Started by online entrepreneur turned criminal Ross Ulbricht in 2011, the site was eventually shut down after a federal investigation in 2013, although it later started up again. Under Ulbricht, the site used the cryptocurrency known as Bitcoin exclusively. And, as David Kushner reported in the Feb. 4, 2014, Rolling Stone article “Dead End on Silk Road: Internet Crime Kingpin Ross Ulbricht’s Big Fall,” it generated the equivalent of over $1 billion in revenue in its first two-and-a-half years.

Something about the story caught the attention of Santa Fe-based filmmaker Tiller Russell. It wasn’t just a tale for our times, in which the purchase of illegal narcotics was no longer a back-alley transaction. It was that Silk Road’s founder was nothing like what you’d expect of a criminal mastermind. He was a geek who grew up with a passion for comic books and a head for numbers. He studied physics at the University of Texas, Dallas, in the same city where Russell grew up. Even his Silk Road pseudonym “Dread Pirate Roberts,” was a nerdy reference to a character in the 1987 comedic fantasy film The Princess Bride. Ulbricht didn’t seem like the kind of person who would order hits on his enemies. But he did. And even though no murders were actually committed, the intent was there.

Russell is the co-director of the hit Netflix documentary series on the infamous serial killer Richard Ramirez, Night Stalker: The Hunt for a Serial Killer (2021), and director of the Netflix documentary Operation Odessa (2018), the saga of three friends who attempt to hustle the Russian mob and sell a nuclear submarine to a Colombian drug cartel. He’s no stranger to tales of true crime, no matter how strange. If anybody could bring the story of Silk Road to the screen, he could.

Silk Road, a narrative feature written and directed by Russell, premieres on Friday, Feb. 19. It stars Nick Robinson as Ulbricht and Jason Clarke as Rick Bowden, the old-school DEA agent determined to bring him down.

Russell tells Pasatiempo what drew him to the project and about his lifelong immersion in a world of cops and criminals.

Pasatiempo: The character dynamics in Silk Road are part of what makes it a compelling viewing experience, whether you’re interested in true crime or not. You have a likable, geeky young guy in Ulbricht, who becomes the head of a criminal enterprise, and a brash, hot-headed, take-no-prisoners type of DEA agent. That opens the door for ambiguity in terms of characterization.

Tiller Russell: For me, it’s all about the internal conflicts in these characters that make them interesting, and there are some unexpected card turns to it. What was fascinating to me was the transformations of these characters. When it starts, Ross [Ulbricht] is this idealistic dreamer who wants to change the world and kind of be a freedom fighter, so to speak, for his convictions and beliefs. Somewhere along the line, it becomes this kind of Frankenstein story. You’ve created this thing that has literally changed the world. But for this story, none of us would have heard of Bitcoin. It ends up becoming this monster that gets out of his control and ends up grabbing him by the throat.

Jason Clarke’s character, Rick Bowden, he’s almost like a Sam Peckinpah character. He’s out of step with the times. He’s being left behind as the laptop sort of supersedes the SIG Sauer, the tool of choice of a DEA agent. He’s becoming this antiquated Jurassic narc. For him, the case becomes this last shot at redemption. You have the opposing politics and generational divide between these guys. That’s what made the story so fascinating.

Pasa: Bowden’s disdain for the younger generation is so palpable. His breed was on its way out.

Russell: Depending upon who you are, coming into this movie, you’re either relating to the millennial upstart, who’s like, “Let’s change the world,” you know? Maybe you have to break a few eggs to make an omelet. Or you’re coming in and you’re like, “OK. The world has just shifted beneath me, and all of these skills that I’ve spent a lifetime honing, perfecting, and risking my life for, are suddenly devalued and tossed aside by the technological revolution.” As a culture, we’re reckoning with that divide. For me, it was a way to look at some of the conflicts that are roiling America right now through specific characters in a wild-ass crime story.

Pasa: What was it that drew you to this project?

Russell: I’m a sort of ravenous hunter of crime stories. Literally a day after Ross was arrested in the sci-fi section of the Glen Park Library in San Francisco, I remember opening the paper. Even though there was a very cursory description of who he was, I thought, That’s a movie. It may be a documentary. It may be a feature film. I don’t know what. But whoever this guy is, having mobilized like the entire U.S. justice system, and having categorically changed the nature of the war on drugs — instantaneously and irrevocably, overnight — I just thought there’s got to be an amazing story there. Then David Kushner published that brilliant Rolling Stone article, and I was so captivated by the character. I was fortunate enough to have some sources at the DEA and the U.S. Attorney’s Office who were quietly passing me information, before the story hit the public, about this whole other side about crooked DEA agents and law enforcement behind the scenes trying to get this guy. Once I had those two elements and saw the collision course between them, I was like, OK. Now I see the movie.

Pasa: I’ve seen pictures of the real Ross Ulbricht, and he really does look like Robert Pattinson, as Kushner mentions in his article. Was it tempting to approach Pattinson about playing the role?

Russell: I had actually talked to Robert Pattinson about it early on, and Pattinson is really at the top of his game, doing super interesting work. In the time it takes, though, from writing a script and going through the Hollywood machinery, to the time that you’re ready to shoot, I think he aged out of the part to some extent. I ended up meeting with a murderers row of amazing young actors in Hollywood. When I hit on Nick Robinson, what I loved about him was that he was so winning and likable. There was a sweetness and softness to him. Given the dark voyage of this character, you really need somebody that an audience can hook into emotionally in some way to take the ride. Once I sat down with him, I was like, “This is the guy.”

Pasa: He does elicit so much sympathy, and that creates a wonderful tension in the film as it becomes this cat-and-mouse story. A part of you almost doesn’t want him to get caught.

Russell: In the ways those characters were conflicted, as a storyteller, I was conflicted. At what point do you stop rooting for Ross and start rooting for Bowden? Both these guys are doing reprehensible stuff, and yet they’re relatable. They’re human beings with the complexity of being alive.

Pasa: I understand that you grew up immersed in the criminal justice world and even worked as a crime reporter for the Berkeley Voice. That background gives you a sort of insider’s perspective.

Russell: My dad was in the district attorney’s office that was depicted in Errol Morris’ film The Thin Blue Line. As a kid, he would take me to the jails and the courthouses and the precincts. It was a relatively natural segue when I moved to the Bay Area to become a cub crime reporter. I was comfortable knocking around with cops or knocking around with crooks, and investigating the sometimes thin and porous line between the two.

Pasa: How did you go from there to getting involved in filmmaking?

Russell: As a kid, I always dreamed about making movies. Once I got a press pass, I started doing some film reviews along with the crime reporting. I actually had the chance to sit down with Errol Morris, all those years later, and I get the last interview of the night with him. He was like, “I’m so sick of answering questions. You want to just go to dinner and get a steak and a bottle of wine?” There was nothing on Earth I would have loved more than the opportunity to do so. We went to the top of this hotel and had this fantastic drunken evening together. At the end of it, he put his hand on my shoulder and said, “You’re either going to spend the rest of your life writing about people like me, or you’re going to go try your hand at this.”

I literally called the paper the next day and was like, I quit. I’m moving to L.A.

Pasa: Over the years, you’ve gravitated between narrative features and documentaries. Was it a challenge to go from being a journalist to becoming a screenwriter?

Russell: In some ways, I feel like it’s a similar set of muscles but kind of exercised in different ways. At the end of the day, story is story is story, and dramatic arc is dramatic arc. So whether it’s a nonfiction story that you’re following, like the investigation of Richard Ramirez haunting Los Angeles, or the dramatic telling of a story, like that of Ross Ulbricht, the fundamental undertaking is the same, although the methodologies are kind of inverse in some ways. The time I spend knocking around with cops or crooks as I’m listening to their rhythms, patterns of speech, and motivations ends up informing me as a writer.

Pasa: Now that Silk Road is completed, do you have another project in the works?

Russell: I’m adapting my previous documentary, Operation Odessa, which is also on Netflix, and that’s going to be my next feature film to direct. I’m literally finishing the script as we speak, and then we’ll be pushing that out into the world and climbing on board to shoot before too long. ◀

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