The Dumbest of Elmore Leonard’s Many, Many Dumb Criminals

The man knew how to get inside dumb criminals’ minds.

Photo by Vince Bucci/Getty Images

Elmore Leonard, who died Tuesday morning at the age of 87, specialized in dumb criminals who thought they were smart. Nobody did better than the prolific crime novelist at getting inside the heads of his irrationally confident villains. Here are five of his dumbest. Oh, and spoilers abound.

Richard Edgar Monk, The Switch. A neo-Nazi peeping tom who is repeatedly referred to as “the fat policeman,” Monk is the dumbest member of the kidnap crew in this 1978 novel—and that’s saying something. Like many of Leonard’s antagonists, Monk has an overinflated sense of his own competence. “Richard wanted to go to California to look for his wife and boy and believed he could do it himself because of his interest in police work and procedures,” Leonard writes. “He read books on it, watched police shows on TV and, until recently, had had a job with Alert Security Services—patrolling shopping centers, rich neighborhoods and construction projects—which Richard felt was good training.” His scheme to rape the kidnapped woman gets foiled when the woman “drove her foot into the sagging pouch of his Jockeys.” Later, he dies in an unnecessary shootout with police.

Nicky Testa, Pronto. “This guy was so dumb you could say anything you wanted to him,” Leonard writes of Nicky Testa, and it’s more or less true. The muscle-bound mob enforcer serves as comic relief in this book, which features one of Leonard’s best-known heroes, Raylan Givens. Testa’s always getting insulted, or slapped around by his fearsome mob associate, the Zip:

[T]he Zip arranged to have a talk with Nicky and brought him out to the lanai, the open sitting room that faced the patio, saying, “Follow me, stronzo.” This time calling him an asshole.

Stronzo,” Nicky said, fingers caressing his bare chest, “what’s that mean, strong? Like referring to how I’m built?”

“Something like that,” the Zip said.

But Testa gets the last laugh, when, as one of the only mobsters left alive, he ends up in charge of the entire operation. It’s a twist that has no chance of ending well for anyone involved.

Ordell Robbie, Rum Punch. The fast-talking Robbie first appeared in The Switch, as the nominal brains of that novel’s failed kidnap scheme. When he returned as the main antagonist in 1992’s Rum Punch, which Quentin Tarantino adapted for the screen as Jackie Brown, he was much more successful, thanks to a gun-running scheme, but not much smarter. As the novel’s hero, bail bondsman Max Cherry, puts it, Robbie’s “the kind of guy who worked at being cool, but was dying to tell you things about himself.” What kind of things did he have to tell? Namely, that he, Ordell Robbie, was cooler and smarter than you, his interlocutor. But a truly smart person doesn’t end up dating three women at the same time, because a truly smart person would know that at least one of those women will always be looking to double-cross you at the earliest possible opportunity. Rest in peace, Ordell Robbie, and your unnecessarily complicated schemes.

Richie Nix, Killshot. This tremendously stupid fellow, who wears a T-shirt reading “It’s Nice to be Nice” and harbors ambitions of robbing a bank in every state (except Alaska), is a motormouth psychopath who kills for no reason. But he shows his stupidity by underestimating his partner, a laconic crook whom he insists on calling “the Bird.” “The Bird was Indian and they were a weird bunch anyway, believing you could get turned into a fucking owl,” Leonard writes from Richie’s perspective. “Donna didn’t know what kind of bird she’d be. Richie believed he’d be an eagle. Shit, be the best.” But when the Bird finally shoots Nix in the face as he’s blowing a gigantic bubble with his chewing gum, the talkative gunman doesn’t turn into a bird. He just dies.

Bo Catlett, Get Shorty. A Hollywood limo driver and drug dealer who wants to break into the movie business, Catlett is another of those smooth-talking Leonard characters whose stupidity derives from his overconfidence. Ultimately, though Catlett’s overconfidence proves fatal, when he fails to realize that an associate has tricked him into falling to his death. I’ll always remember Catlett for the Blake Snyder-worthy screenwriting advice he gives the novel’s main character, Chili Palmer:

It isn’t like having to learn how to play the piano, like you have to learn notes. You already learned in school how to write, didn’t you? I hope so. You have the idea and you put down what you want to say. Then you get somebody to add in the commas and shit where they belong, if you aren’t positive yourself. Maybe fix up the spelling where you have some tricky words. There people do that for you. Some, I’ve even seen scripts where I know words weren’t spelled right and there was hardly any commas in it. So I don’t think it’s too important. You come to the last page you write in ‘Fade out’ and that’s the end, and you’re done.

Words to live by.