Ross Ulbricht (Nick Robinson) wanted to change the world. And he did. Whether you believe it was for the better (bringing the Dark Web and Tor into the mainstream via his anonymous marketplace Silk Road) or worse (using that marketplace to profit off illicit, criminal activities once selling designer drugs online quickly turned to hard narcotics, firearms, and even shadier “services”), the infrastructure he utilized coupled with the advantages afforded by Bitcoin ignited a firestorm of possibilities. Because at the center of it all was a desire to adhere to a Libertarian set of philosophies that shook the system and evaded the state. That the story has subsequently been reduced to “drugs-by-mail” is thus as much an in-road towards entertaining drama as a smokescreen away from governmental overreach.

It’s the latter that interested director Alex Winter enough to focus his documentary Deep Web on the whole issue rather than merely Ulbricht himself. The young man who went by “Dread Pirate Roberts” on his website was still a centerpiece being that he provided a human face to a world built upon anonymity, but his presence was less as a black and white “hero” or “villain” than it was a complex figure with ideas and motivations living in the gray area between. Whereas Winter was afforded the ability to embrace that nuance within his non-fiction deep-dive into the concept’s far-reaching applications, however, choosing to push all that into the background to tell Ulbricht’s story instead means picking a side. Silk Road writer/director Tiller Russell has chosen “villain.”

That’s his prerogative and probably the moral choice considering what ultimately transpired once Ulbricht’s ambition and paranoia took over (if all the liberties taken in a film that starts with the words “This is a true story … except for what we changed or made up” can be taken at even a quarter of face value). It’s one thing to shock the system so suburbanites can shop for marijuana and ecstasy without worrying about street violence, but another to actively assist in that violence by upping the ante once the allure of capitalistic enterprise beats idealistic anarchism into submission. So Russell doubles down on that shift to render Ross an unlikeable, hubristic opportunist who eventually pushes everyone who cares about him away—whether facts confirm it or not.

Who then is drawn as the hero? This is an interesting question where it pertains to the film because Russell’s decision to instead draw an antihero in DEA Agent Rick Bowden (Jason Clarke) inevitably renders the United States government as the de facto champion precisely because they’re given a pass. The great thing about Winter’s documentary is that he refused to ignore the danger inherent to our government’s carte blanche attitude where it comes to new online entities that exist outside their jurisdiction. Russell just glosses over the whole topic completely in order to let an FBI cybercrime task force operate without any judgment at all. They (through Jimmi Simpson’s Tarbell) are here to catch their guy and (through Will Ropp’s Shields) underestimate Bowden’s grizzled (and flawed) veteran.

The hope is that Bowden’s presence on both sides of the law (he’s recently been released from a psychiatric rehab stint and reassigned to cybercrime after botching an undercover narcotics operation while coked-up out of his mind) will give us the emotional thrust necessary to ignore Ulbricht’s devolution. Because while we don’t care about the friends Ross loses along the way (Alexandra Shipp’s Julia and Daniel David Stewart’s Max), we do care about little Edie Bowden’s learning disability and Sandy Bowden’s (Katie Aselton) desire to get her into an expensive school. We should therefore want Rick to succeed and show his new boss (who’s half his age) that good “honest” police work is better than MIT grads punching keys in an open floor plan office environment.

While some of it works (Rick’s genuine drive to learn despite being a technophobe and Darrell Britt-Gibson’s informant Rayford giving him a crash course), most of it comes across as a Boomer versus Millennial diatribe. There’s even a scene where Bowden and a veteran cop denigrate new hires as “vegetarians” who can’t be trusted like “red meat-eating” men such as them. A major narrative goal is proving Rick’s old school tactics (that Shields’ new school methods won’t pay to facilitate) are enough to break the case open if only someone would listen to him. Being that he was justifiably demoted to sit at a desk for nine months before collecting his pension, however, it’s tough to pull for his disgraced cop solely because he has a sob story.

My enjoyment in Silk Road is thus the fact that we can’t pull for him. That Rick will fall down a rabbit hole of “good” police work for bad reasons to become embroiled in the case at-large is what captivates the most since Russell would rather strip Ulbricht down to a two-dimensional douchebag than let us get invested in him or his work. Bowden ultimately becomes the lead simply because we’re unsure what he’s going to do (unless you’re familiar with the story and the DEA Agent the character is based upon). Will he save the day or exploit it? Clarke’s performance earned my focus precisely because his portrayal was elevating what was ostensibly an “old man yells at clouds” caricature. I wondered if he’d destroy himself.

That doesn’t mean Robinson is bad. He does a pretty solid job with a role that’s been intentionally written without redeemable qualities. Bowden being a father is clichéd and the bare minimum level of humanity, but at least it’s something to hold onto so his crisis of conscience (as opposed to Ross’ own) holds weight. It’s not enough to excuse the distractingly inconsistent freeze-frame dissolves or the rolled out red carpet for law enforcement still using the “War on Drugs” to ruin lives with draconian force rather than the subtlety necessary to actually make a difference, though. At the end of the day this is a hollowly reductive account of what happened with a weird subtextual rich punk against blue collar cop agenda falling woefully flat.

Silk Road hits Digital HD, VOD & Select Theaters on February 19 and Blu-Ray/DVD on February 23.

Grade: C-

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