Silk Road Movie. PHOTO: Lionsgate.

Silk Road: Arc Of The Dark Web’s Biggest Takedown

Interview with director Tiller Russell on his latest film

David Braue

Melbourne, Australia – Mar. 3, 2021

Tiller Russell is still waiting to hear from Ross Ulbricht, the notorious cybercriminal who was jailed for life after an FBI operation shut down Silk Road, the anonymous dark web market that Ulbricht launched in early 2011.

With no response after several attempts, Russell — who plumbed a range of resources to get inside Ulbricht’s mindset as he wrote and directed his new movie Silk Road — accepts that his artistic accommodations may be the closest audiences get to the fantastic story that propelled Ulbricht from being an unknown hacker into the poster child for internet crime.

“I knew the odds of him being willing to speak with me were very low, but I figured it was incumbent upon me to take a shot at it anyway,” he told Cybercrime Magazine in the runup to the release of the film, which is available now on streaming services.

Russell began deep-diving into the history of Silk Road the day after Ulbricht’s arrest, collecting stories and bits of information about the “sketchy and sort of shadowy” activities of Ulbricht’s pseudonymous online twin, called Dread Pirate Roberts.

Silk Road was an innovation, combining the use of then-nascent bitcoin cryptocurrency and the Tor anonymity network to allow the completely anonymous exchange of goods — quickly making it a clearinghouse for drugs, weapons, and other unsavory behavior.

Cybercrime Radio: Silk Road Movie Director Tiller Russell

An invitation to Ross Ulbricht

Cybercrime Radio

“When bitcoin was barely a blip on the radar culturally, I remember having this visceral reaction,” Russell said, noting that the publication of a Rolling Stone article by David Kushner was the trigger for the decision to proceed with the production.

Russell’s contact with Kushner proved fruitful, with the like-minded writers working together to sort through the “very rich, archival historical record that [Ulbricht] had left in his wake.”

This included posts made on the website over several years, diary entries before and after the launch of Silk Road, exchanges between the journalist and people in Ulbricht’s life.

It was quite a life: long before he was arrested for money laundering, facilitating the sale of hundreds of millions of dollars’ worth of narcotics and even contract killings, Ulbricht was a keen surfer, comic-book fanatic, Warhammer fan and skateboarder.

That has all been overshadowed by the rapid rise and fall of Silk Road, which in just two short years became a masterclass in the way internet crime can have very real-world consequences.

“It’s almost as if he had a lifetime’s worth of drama, condensed into this very accelerated arc,” Russell said, “which I think is one of the things that made it so challenging for him to navigate.”

Art emulating life

Building an engaging story around Silk Road was no small feat — particularly given the need to represent the complexities of technologies like Tor and bitcoin to a general moviegoing audience – and “we were constantly trying to recalibrate,” Russell recalled.

“We were considering what is the minimum amount of expositional information that you need as an audience member to take the dramatic arc,” he said. “As a filmmaker you are trying to give the audience the tools they need to understand it.”

Russell also reached out to a range of security experts, including white-hat hackers whose expertise in dark web areas helped Russell “calibrate the line between being clear and accurate as to the facts, and being able to translate for a broader audience.”

Ultimately, the screenplay for the film includes a degree of creative license — something that Russell explained became necessary once it became clear a speculated pardon from former President Donald Trump was not going to eventuate.

“I’m always fascinated by these internal character conflicts that are in people,” he said, “the forces of light warring with the forces of dark.”

As a fellow Texas native, Russell said the other man’s story “felt relatable to me… I know the world that he is from… While I didn’t have access to the man, I had access to his voice in some regard or another.”

Recognizing the enormity of a potential life sentence for someone who is just 36 this year, Russell said, he wrote a letter to Ulbricht laying out his hopes that the portrayal in Silk Road would come off as personal and, as much as possible, authentic.

“In places where there were gaps in your biographical record,” he wrote, “I poured in pieces of myself and entered into it to the best of my ability, to hew to the spiritual truth of your story. But if you ever want to sit down with me, I’ll be there in a heartbeat.”

– David Braue is an award-winning technology writer based in Melbourne, Australia.

Go here to read all of David’s Cybercrime Magazine articles.