In the fall of 2008, during both the American financial crisis and the presidential election campaign, an older man named Johnny "Squirrel" Amato plans to rob an illegal poker game. He enlists two younger men to do the robbery: Frankie, a former business associate, and Russell, a heroin-addicted Australian expatriate who is stealing purebred dogs for money. They decide to target a game run by Markie Trattman, who is known to have previously orchestrated an inside job by paying two men to rob his own illegal poker room. Squirrel anticipates that the Mafia will automatically blame Markie for the heist because of this, and that once they have their local enforcer Dillon kill him the matter will be considered closed.
Frankie and Russell, though obviously amateurs, do the holdup and leave with the money. Afterwards, an emissary for the Mob named Driver hires a hitman and mob enforcer named Jackie Cogan to deal with the situation. Although Jackie correctly intuits that Markie was uninvolved in the recent heist, he believes he still needs to die in order to show people that the mob will not tolerate their games being robbed.
Upon completing the crime, Russell travels to Florida to sell the dogs. While in Florida, he inadvertently informs a man named Kenny Gill of his involvement in the heist while trying to recruit him as a drug dealer. Kenny informs Jackie, who deduces that Russell, Frankie, and Squirrel are the perpetrators.
Jackie carries out the hit on Markie himself but brings in another hitman named Mickey Fallon, who is on parole in New York, to kill Squirrel. Jackie explains to Driver how he prefers "killing them softly"—shooting his victims from a distance, without warning, giving them no opportunity to experience fear or despair—and that his acquaintance with Squirrel risks complicating this approach.
Mickey postpones going through with his assigned hit, instead indulging in drunkenness and sex with prostitutes in a hotel room. During conversation with Jackie, Mickey also reveals that he has violated his parole, and doesn't seem to care about or really comprehend the consequences; instead he goes off on drunken tangents. It becomes clear to Jackie that the respected hitman has lost his nerve and ability to do his job. Jackie eventually decides to carry out the hit on Squirrel himself. He convinces Driver to arrange Mickey's arrest before the job has been completed.
Russell is arrested on a drug possession charge and deported; meanwhile, Jackie confronts Frankie and convinces him to trade Squirrel's whereabouts for his life. Jackie has Frankie drive him to Squirrel; upon reaching Squirrel's apartment complex, he kills Squirrel with a shotgun. After confirming Squirrel is dead, Jackie has Frankie drive him to get his car several hours away. Frankie becomes very nervous and begins speeding. Unable to get Frankie to slow down, Jackie takes over driving. Once they arrive at the parking garage, Jackie shoots Frankie in the head without warning. Jackie then wipes down any fingerprints he might have left and leaves the scene.
On the night of the presidential election, Jackie meets with Driver to collect his fee for the three hits. On the TV in the bar, Barack Obama is giving his election victory speech. Jackie sees that he has been paid $30,000. He alleges that at $10,000 each, Driver has underpaid him for the jobs—on the argument that it would have cost $15,000 to have Mickey kill Squirrel. Driver responds that Dillon charges ten, and tells Jackie to take it up with Dillon. Jackie tells Driver that Dillon died that morning. Referring to Obama's speech, Jackie says angrily, "This guy wants to tell me we're living in a community? Don't make me laugh. I'm living in America, and in America, you're on your own. America is not a country; it's just a business. Now fucking pay me."Brad Pitt as Jackie Cogan
Scoot McNairy as Frankie
Ben Mendelsohn as Russell
Richard Jenkins as Driver
James Gandolfini as Mickey
Ray Liotta as Markie Trattman
Sam Shepard as Dillon
Slaine as Kenny Gill
Vincent Curatola as Johnny Amato
Max Casella as Barry Caprio
Trevor Long as Steve Caprio
Linara Washington as Hooker
Killing Them Softly is based on the 1974 novel Cogan's Trade by George V. Higgins, a best selling crime novelist whose works include The Friends of Eddie Coyle. Cogan's Trade, like Higgins's other novels, takes place in Boston; although filmed in New Orleans area, characters in Killing Them Softly make several references to Boston area suburbs from the original novel. The film was written and directed by Andrew Dominik, who chose to update the setting of the story, saying "as I started adapting it, it was the story of an economic crisis, and it was an economic crisis in an economy that was funded by gambling—and the crisis occurred due to a failure in regulation. It just seemed to have something that you couldn't ignore."
The project was first announced in November 2010, when Brad Pitt was reported to be in talks for the lead role. Pitt joined the project the following month, and production was scheduled to begin in Louisiana in March 2011. Additional roles were cast in early 2011. Dominik asked Pitt if he was interested in the role via a text message; he replied "yes" and the matter was settled over half an hour.
Pre-production began in Louisiana in January 2011, and filming was underway by March 2011.
According to Garret Dillahunt, the film's first cut was two-and-a-half hours long. Dillahunt, who had a cameo in the film, did not make the final cut for the theatrical release.
Killing Them Softly was scheduled to premiere on September 21, 2012; however, the US release date was delayed until November 30, 2012, to avoid competing with The Master and to improve its chances for award nominations. The film kept its original release date in other parts of the world, with the somewhat unusual result that it opened in the UK and India more than two months before the US opening.
The Weinstein Company distributed the film in the United States and Canada.
The film was released on March 26, 2013. The film was released in Australia earlier, on February 13, and on February 25 in the UK.
In its opening weekend, Killing Them Softly grossed a domestic total of $6,812,900. The film made $15,026,056 domestically and $22,904,409 internationally for a worldwide total of $37,930,465.
Rotten Tomatoes gives the film a rating of 74% based on reviews from 216 critics, with an average rating of 6.8 out of 10. The site' critical consensus reads, "Killing Them Softly is a darkly comic, visceral thriller that doubles as a cautionary tale on capitalism, whose message is delivered with sledgehammer force." At Metacritic, which assigns a weighted average score, the film received an average score of 64 out of 100, based on 42 critics. indicating "generally favorable reviews". However, on CinemaScore, audiences gave the film an average grade of "F" on an A+ to F scale.
Peter Bradshaw of The Guardian gave the film 5 stars saying the film is a "compelling comment on economic bloodletting in the real world". Tim Robey of The Daily Telegraph gave the film 4 stars describing it as "bleakly electrifying". Total Film awarded it 3 stars calling it "tough, stylish, violent and studded with stars" but countered that it "doesn’t quite get the job done".