Review: Two Men Put Everything on the Line in the Cat-and-Mouse Story of Silk Road

There are several films out this week about people who made a lot of money finding loopholes (usually legal, but not always) in the system and exploiting them (see also: Body Brokers and I Care A Lot). But the best of the bunch is Silk Road, telling parallel stories about real-life young internet mogul Ross Ulbricht (Nick Robinson) and Rick Bowden (Jason Clarke), the old-school DEA agent who ultimately brought him down but not without paying a steep price himself. Ulbricht was a highly motivated idealist who believed in pushing against authority every chance he could. As a result, he built an online service known as Silk Road, a completely anonymous, unregulated marketplace where people could buy and sell drugs (for starters) using bitcoin and have them delivered to their door via the U.S. Postal Service (or FedEx, UPS, or other shipping service).

Silk Road Nick Robinson as Ross Ulbricht in Silk Road. Cr. Courtesy of Lionsgate

Ulbricht has a great life even before creating Silk Road, with a ride-or-die girlfriend in Julia (Alexandra Shipp) and the ability to apply himself when he truly believes in something. He also sees his creation as a stepping stone toward something great in the world: freedom. But as the authorities move closer and closer to shutting him down, he grows more paranoid and obsessive about his work, pushing others away if they aren’t actively protecting him or working for him. Bowden has just come back to the DEA after a stint in work-related rehab—he got a little too into his last undercover assignment—and has been reassigned to the cyber crimes unit. He knows nothing about computers or the internet or tech in general, but once he finds out about Silk Road, he’s uses his old-school detective skills to track down Ulbricht and become online buds, painting himself as a loyal soldier, even willing to kill to protect the business. Naturally, Ulbricht eats this up and thus begins his own undoing.

Silk Road tells two versions of the same story: two men willing to sacrifice everything to win. Sadly, Bowden has more to lose, including a wife (Katie Aselton) and child who have already had to live without him during his last disastrous assignment. But Ulbricht has literally put the rest of his life on the line with this endeavor, and while he’s beyond cautious, at his core, he doesn’t believe he’s doing anything wrong. He’s only a facilitator and he stays far away from the actual criminal activity, or so he thinks. But it’s Bowden’s story that is more compelling because it’s rooted in the real world with real stakes. Some of the best scenes in the film involve his interactions with a former dealer turned sneaker broker, Ryford (Darrell Britt-Gibson), who teaches him all about Silk Road and the internet. By explaining this world to Bowden, he’s cluing us in on the practice as well, and that helps in getting through some of the denser portions of the organization and its set-up.

Based on the Rolling Stone article “Dead End on Silk Road” by David Kushner, and adapted and directed by Tiller Russell, Silk Road tells the story of someone whose flaw was not greed but ambition. I didn’t feel an ounce of remorse watching him flame out and crash to the ground, but it is a shame he couldn’t take his intelligence and ingenuity and apply it to something useful. Hell, some might say he did, I suppose. These two men display a succession of bad choices committed by smart people, and that combination is always fascinating and entertaining, even if it’s painful to watch it play out.

The film is out today in theaters and streaming via VOD.

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Steve Prokopy

Steve Prokopy is chief film critic for the Chicago-based arts outlet Third Coast Review. For nearly 20 years, he was the Chicago editor for Ain’t It Cool News, where he contributed film reviews and filmmaker/actor interviews under the name “Capone.” Currently, he’s a frequent contributor at /Film ( and Backstory Magazine. He is also the public relations director for Chicago's independently owned Music Box Theatre, and holds the position of Vice President for the Chicago Film Critics Association. In addition, he is a programmer for the Chicago Critics Film Festival, which has been one of the city's most anticipated festivals since 2013.