Killing Them Softly makes it official that writer-director Andrew Dominik and Brad Pitt (no title needed) should always collaborate together. Based on a 1974 crime novel by George V. Higgins called Cogan's Trade, Killing Them Softly is transformed into a gangster story with the tumultuous political setting of 2008 as the backdrop. The film follows the sketchy life of Frankie (Scoot McNairy, who has the voice of Mark Wahlberg and who you hopefully know—but probably don’t—from 2010’s In Search of a Midnight Kiss) as he struggles to make a living in the crime underworld. The fact that even criminals are suffering in the wake of the 2008 financial crisis is just one of the many ways that illustrates, to quote hitman Jackie Cogan (Brad Pitt), “America is fucked.”
As Frankie sets out to meet a shyster-type gangster named Johnny “Squirrel” Amato (Vincent Curatola), one of Obama’s campaign speeches plays in a disjointed manner in the background, setting the tone for the fragmented and polarized nature of the United States at this moment in time. The point is solidified as Frankie walks past a billboard with John McCain and Obama ads right next to each other—proving that the only real motive in politics is getting the same amount of exposure.
On the way to Squirrel’s, Frankie meets up with his friend and fellow criminal, Russell (Ben Mendelsohn, who also showcased his knack for crime dramas by appearing in 2011’s Killer Elite). Slightly less put together than Frankie, Russell is an overt junkie with a slew of harebrained schemes, the current one being selling purebred dogs. In spite of knowing that Russell isn’t exactly the most silver-tongued when it comes to representing himself, Frankie takes him to meet with Squirrel, who immediately hates his irreverence. Russell then fucks off to have sex with a prostitute (whose attractiveness he describes as, “I wouldn’t rape her, but the plumbing still works.”) while Frankie listens to Squirrel’s latest moneymaking proposition. The heist involves a poker game run by Markie Trattman (Ray Liotta, because, honestly, what would a gangster movie be without him?), who, several years prior, set up one of his poker games to get robbed and then drunkenly admitted it to his fellow crime bosses during a private card game. The crime bosses laugh it off and allow bygones to be bygones, but another fuck-up from Markie will assuredly signal his demise.
And so, with this in mind, Squirrel promises Frankie that if they rob Markie’s next poker game, Markie will undeniably be the one to take the fall for it. Feeling confident, Frankie gets Squirrel’s permission to use Russell as his partner. In costumes evoking the ghetto times of 2008, Russell and Frankie roll up to the poker game wearing rubber gloves on their hands and much too tight trouser socks over their heads. While Frankie aims his gun at the poker players, Russell leads Markie into the back to get the money. As he reluctantly hands Russell the suitcases, Markie urges him to reconsider, promising that if he goes through with this robbery, he will most certainly die. Russell appears briefly tempted to oblige—indicating his somewhat dubious loyalty—but then ends up leaving with the money without incident.
Not wanting to be tied to the robbery in any way, Russell and Frankie part ways for awhile, leaving the mafia bosses to investigate with their own cruel methods. Enter Jackie Cogan, a ruthless, old school hitman, who, ironically, says that he prefers to kill people softly—meaning from a quick, painless distance so they don’t know it’s about to happen. Enlisted by a button-down, obsequious in-between referred to only as Driver (Richard Jenkins), Jackie tracks down the true masterminds behind the robbery after Russell’s friend, Kenny Gill (Slaine, you know, the rapper), mentions that Russell had been bragging to him on their way down to Florida about the crime he recently got away with.
Now knowing who to target, Jackie insists to Driver on the need for an additional hitman, preferably a classic go-to by the name of Mickey (James Gandolfini, yet another actor that no gangster movie is complete without). Driver grudgingly agrees based on Mickey’s reduced price (fifteen grand) and gives Jackie the approval to kill Squirrel, Frankie, Russell and Markie (who has to be killed in order to restore faith in any high-stakes poker game).
When Mickey arrives in town, Jackie is less than pleased to see that he’s become an alcoholic hot mess. As they sit at a hotel bar discussing their plan, Mickey continuously chastises their waiter for his slowness at bringing the drinks. The waiter apologizes, citing that they are short-staffed (another indication of the recession and inability for businesses to afford hiring people). Jackie, already irritated with Mickey’s self-pitying sob stories (his wife wants to leave him and he recently had to be bailed out of jail for a felonious gun possession charge), begins to grow concerned over the success of the job.
Jackie quickly realizes that he’s going to have to handle everything himself as even the mafia’s usual go-to hitman, Dillon (Sam Shepard, yeah the playwright/Patti Smith’s ex), has been killed—proving Frankie’s recently acquired belief that “The world is just shit. We’re all on our own.” With Mickey as an added liability, Jackie arranges for him to get in a fight with a prostitute so he’ll be charged for violating the terms of his bail. Everything comes to a culmination on election night as Jackie goes to meet Driver in a bar and resolve the final matter of his payment.
As Obama makes his acceptance speech espousing the concept that every American is capable of achieving his dreams, Jackie spurns the idea, telling Driver that Thomas Jefferson is the asshole responsible for making us believe that “all men are created equal.” The reality, of course, is that all wealthy people were created equal. Jackie’s unyielding commitment to this idea is solidified when Driver tells him that the mafia bosses are paying him a “recession price” fee for the services rendered. In one of the most biting, salient and abrupt lines in cinema history, Jackie responds, “America’s not a country. It’s a business. Now fuckin’ pay me.”