Jackie Cogan (Brad Pitt) understands his fate in a way that the other smart guys don't quite, an understanding that makes him seem somehow smarter.
Love letters straight from your heart
Keep us so near while apart.
I'm not alone in the night
When I can have all the love you write.
-- Ketty Lester, "Love Letters (Straight from Your Heart)"
"We're not the only smart guys in the world." As Johnny (Vincent Curatola) speaks, the kid sitting across his desk nods. Indeed, Frankie (Scoot McNairy) agrees, they can't be the only guys who'll think of the scheme Johnny's just laid out. That scheme -- a robbery at a gangsters' card game -- sounds simple enough, as does the smart part of it, that the guy likely to be blamed for it is Markie (Ray Liotta), the guy who runs the game and who robbed it once before, years ago, and then bragged about it. The time is right. Smart guys need to make their move now.
And so Killing Them Softly cuts from the dreary office behind Johnny's dry-cleaning store to Frankie's thunderous muscle car, as he and his buddy Russell (Ben Mendelsohn) head toward the game, scene of their upcoming crime. They're going to net thousands of dollars, they're sure, a sureness that frames their conversation in the car, which has to do with sex, of course. While Russell, a junkie who's been stealing dogs for fix money, advises against sex with dogs ("From what I've heard," he says, his face grimy with perpetual sweat, It's very painful"), Frankie hasn't had much luck with girls. Russell insists they're available: "There's broads just as crazy as us too," he smiles, recalling one "who fucked like a fucking crazy alien from the Planet Gobble." He makes a noise to demonstrate, then wonders that, when the sex was done, she said she was going to kill herself. Again, Frankie nods: "They all say that."
These two conversations lay out Frankie's limited options. Even if he and Russell get their robbery done, his life isn’t going to be much different tomorrow than it is today. Still, he does it. Maybe he believes he's smart, maybe he doesn't give it much thought. Either way, he's like most of the other guys around him, Johnny and Russell and Markie included, making his way through each day with only the dimmest glimmer of a future in front of him. They're all inhabiting the same world, Killing Them Softly submits, a world where violence and sex are interchangeable, where money is the only thinkable point of any endeavor.
It's the same world inhabited by another smart guy, one played by Brad Pitt. Like the last smart guy Pitt played in an Andrew Dominik movie, Jesse James in The Assassination of Jesse James by the Coward Robert Ford, Cogan is here resigned to his fate. Which is to say, he understands his fate in a way that the other smart guys -- like Frankie -- don't quite, an understanding that makes him seem somehow smarter. Unlike Frankie or Johnny, Cogan (the film is based on George V. Higgins' 1974 novel Cogan’s Trade) sees limits and works within them: a hitman called in to clean up the mess made by Frankie and Johnny, Cogan keeps his focus tight, on the targets for whom he'll be paid. When he discovers that one of these targets knows him, he brings in his own contractor, Mickey (James Gandolfini), because he prefers to kill people "softly," from an emotional distance, without targets crying and begging.
Or at least this is what Cogan tells the organization rep (Richard Jenkins) with whom he's negotiating terms. They meet periodically during Killing Them Softly, in a car parked in the middle of nowhere (in a city that might be Boston), embodiments of management and labor, framed again and again by the film's historical moment, that is, the 2008 US presidential election. This framing extends to other meetings Cogan takes, with Mickey or with Frankie, background TVs offering speechy snippets, from George Bush and Hank Paulsen's declarations of Wall Street's needs to McCain and Obama's descriptions of the American character, uplifting or catastrophic.
This framing also makes Cogan connected to another protagonist, the one in Dominik's only other movie, Mark Brandon (Eric Bana) in 2000's Chopper. Brandon, like Jesse James and like Cogan, is a killer, brutal and cunning, with a perverse and intuitive grasp of the relationship between image and effect. This relationship is direct in Chopper and Assassination, as Brandon and Jesse James, both based on real life criminals, becomes celebrities because of their excesses, sensationalized by their respective media. In Killing Them Softly, the relationship is more indirect, but no less sinister: here Cogan is a corollary for the smart guys on TV, even if he's cynical about the stories they tell: "He's gonna say we're all one people," Cogan says, just before you hear Obama say pretty much exactly that. "America is not a country," Cogan sums up, "America is a fucking business."
Such cynicism is different in kind from Frankie's sadder, more intimate summary ("They all say that"). Cogan plies his trade, he gets paid. He sees what's in front of him, he doesn't expect anything other, doesn’t want to know his victims or have them know him. “Very few guys know me," he says more than once. But they know what he does. “It’s not what you been doing,” he tells Frankie, “it’s what guys think you been doing.” It's about the relationship between image and effect, again, even if that image isn't on TV. Or even if it is.