Cold Cold Wind
performed by Jabe Beyer

With the Sheriff election soon at hand, Boyd and Quarles both make maneuvers in their camps to get their candidate to win. Limehouse hedges his bets and eventually decides to help Boyd Crowder by introducing him to Quarles' campaign manager. Crowder gets Napier's sister a job with the county. This technicality costs Sheriff Napier the election, even though he had won the majority of voters. This reversal sends Quarles into a drug fueled tailspin and he reveals to Duffy his childhood of being trafficked by his father. Quarles decides to directly confront Raylan, telling him that he is going to put a bullet in his head. Raylan is dealing with another problem, as Dickie is set to be granted early release due to lack of evidence on his charges of kidnapping Raylan and murdering Aunt Helen. Raylan chases down all the people involved with Dickie's crimes, but they refuse to testify. Raylan goes to testify in favor of Dickie remaining in prison, but he bungles it, and eventually tells Judge Reardon to just release Dickie, because he'll either slip up again or be killed in the process. At Noble's Holler, Limehouse hears from Errol that Dickie is getting out, which might cause problems for the missing Bennett fortune, so he tells Errol to bring Dickie to him as soon as he is released. At the close of the episode, Quarles is alone in a hotel room sniffing Oxycontin repeating a mantra to himself. As Quarles strips, it is revealed that he has kidnapped another young man, holding him in his bathroom.