American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road

by Nick Bilton

Asking kids what they want to be when they grow up is not good. It is, in fact, bad. Conflating who someone will be with what profession they choose is an abject failure of culture. Your career becomes your character, and a failure in business is a failure of personal worth.

The storyteller non-fiction genre abounds with “great person theories.” No surprise there, as it is a challenge to tell a pointed tale about real-life actions without shining a spotlight on a giant human face. For contrast, Shaolin does a good job of avoiding focusing all its energy on one person by creating a mood and letting you live it with someone who was there. Usually, that’s not an option. So the focus of non-fiction tends toward the biographic, on a single point-of-contact: Elizabeth Holmes or Steve Jobs or Jamie Diamond.

Part of the book is set in San Francisco. Here is some nice weather from July 2020.

Part of the book is set in San Francisco. Here is some nice weather from July 2020.

American Kingpin: The Epic Hunt for the Criminal Mastermind Behind the Silk Road does center the action on the guy who made the Silk Road website, but not exclusively. And it adds in a bunch of investigators and other law people. However, nearly all of the interesting parts are discussions of Tor, of Silk Road the website as a tangible artifact, not a digital simulacrum—how its servers were set up and hidden; with what it began; how many times it all almost collapsed. That the literal collapse of some bookshelves in a warehouse pivoted a point-and-click contraband-delivery site into a dotcom cultural monolith is a wild, wild ride.

The dramatic conclusion was more a series of general mistakes by Ross, the Silk Road guy, and of ceaseless on-the-ground investigative labor—rather than literature-inflected hamartia or celestial kismet—so the payoff is in the mundane details rather than in tropey dramatic flourishes. The scene where the Silk Road guy is telling the police all about Silk Road, and that his roommates know him by another name, and gives them an email address @tor.com, and they’re just like, “Oh, okay, have a good day, citizen” had me yelling:

“Before we go,” Dylan said, “we think you’re a smart guy—a clever guy—but it’s odd to us that you would order nine IDs; normal people, even normal criminals, don’t order nine fake driver’s licenses. It all just seems very odd to us.” Ross didn’t reply as Dylan kept talking.” So we’re going to need to talk to your roommates and your neighbors—” Dylan’s partner interrupted, finishing the sentence, “To make sure there are no dead bodies.”

Ross’s face scrunched up again, fear returning. “Well,” Ross said, “that’s going to be a bit of a problem.”
“Why?”

“Because my roommates know me as Josh,” Ross replied.

No one could write that and not feel like they went way over the top. He would definitely being going to jail at that point, right? 9 fake IDs? Same for the undercover cop that went corrupt and then double-dealt himself into a corner. And the other cops stealing money from a crime scene. Who then had to staging a fake hit on a Silk Road moderator to fool their target but also obfuscate their personal crimes. And then the founder’s constant G-rated swearing. All of these little tiny bits piled on top of each other, making each page just fly past. It’s like improv: There’s absolutely no way this is going to come together into any kind rewarding narrative structure, until *poof* somehow it just did.

Deciding to read American Kingpin was a direct result of me not getting what I wanted from Catch & Kill; there is no nuance here, only events that constantly move a plot forward. It’s the boiled distillate of what makes this genre addicting; because it is real, you probably know the rough draft of what happened. So there’s no twists to complicate events, or to fizzle out or feel tacked-on or too gimmicky. Banks fail; masterminds are caught; pyramid schemes collapse. No one comes to true crime non-fiction for surprising reveals. In the same way, it really doesn’t matter who the characters are. They could be named Subject A, Investigator 1, the Esteemed Mrs. W___, or Batboy Lives! Within these pages, they are only their careers, only as deep as their known actions allow them to be.

photo shoot take out: wind took it. i survived the recovery climb.

photo shoot take out: wind took it. i survived the recovery climb.

The book could benefit from including an index, as I believe most non-fiction books can, but I doubt American Kingpin considers itself a reference book. At all. And that’s okay, because it isn’t trying to be something in particular. And what it does, it does well.

David Dinaburg