During the American financial crisis and presidential election campaign in the fall of 2008, Johnny “Squirrel” Amato plans to rob a Mafia poker game. He enlists 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 game. Squirrel anticipates that Markie will be the obvious suspect because of this, and the Mafia will simply have him killed without investigating further.
Frankie and Russell, although obviously amateurs, do the holdup and leave with the money. Afterwards, a mafioso named Driver hires hitman Jackie Cogan to deal with the situation. Although Jackie correctly intuits that Markie was uninvolved with the recent heist, he believes Markie still needs to die since he looks guilty, and an example needs to be made to discourage further robberies.
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 were 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.