Raylan goes to see Boyd Crowder in prison. He’s still angry at his father Arlo and wants to know if Boyd has any dirt on him that could put him away. Boyd agrees to look into it.
The next morning, Raylan’s in his hotel room with Ava when his boss Art comes to the door. Raylan’s careful Art doesn’t see Ava when he slips out, but later, in the car, he all but admits he’s sleeping with Ava. Art’s furious, sleeping with a witness in a shooting involving himself, this could be a real black eye for both Raylan and the marshals.
Raylan and Art are on their way to visit an art dealer in Cincinnati as part of an ongoing case against Owen Carnes, a crooked Madoffesque money manager. Owen is trying to sell some valuable paintings, and as the marshals are very close to confiscating all of Owen’s possessions, any proceedings from this art sale also belong to the Marshals Service.
Raylan and Art show up at Owen’s sprawling ranch along with the art dealer, Karl Hanselmann. As Karl analyzes the paintings, Raylan and Art discover to their shock these paintings are supposedly by Adolf Hitler! Karl owns dozens of Hitler paintings, and will purchase these if they turn out to be authentic.
While Karl looks at the art, Raylan takes a stroll through the property and meets Owen’s much younger wife, Caryn. Caryn was just a riding instructor for Owen’s kids before Owen left his first wife for her. Now she’s clearly broken up about the prospect of losing her newfound life of ease and riches if Owen is convicted.
Raylan returns to the house to find Owen furious. Karl says these aren’t real Hitler paintings, but fairly poor forgeries.
That night, Owen’s summoned Caryn’s art dealer, David Mortimer, to the house. He’s chewing him out about selling him fake Hitler paintings when Greg, the horse trainer, sneaks up behind him and kills him with an antique Luger. David is shocked, but Caryn and Greg quickly go about making the death look like a suicide. Caryn’s been having an affair with Greg, and she figures the marshals can’t convict a dead man, or confiscate his money and estate. Owen discovering the Hitlers were fakes was only a slight hiccup. Caryn had indeed enlisted David to sell her husband fakes, splitting the profits with him, but she’s got David over a barrel, because if he tells anyone about the murder, she’ll reveal he swindled Owen.
The morning the police discover Owen’s body, Luger in hand, and the fake Hitler paintings gone, apparently burnt in the fireplace. Raylan’s not so sure it’s a suicide, though. Normally in suicides the gun falls from the victim’s hand, but in this case Owen’s still got a pretty firm grasp on it.
Later that day, Raylan’s ex-wife Winona comes to his office to ask for a favor. She wants him to run some names, but she won’t say why. Raylan agrees. After looking into the names, Raylan sees something suspicious enough to warrant a visit to Winona’s husband Gary’s real estate office. Raylan insinuates to Gary that he knows Gary might be up to something not quite ethical, and if Gary endangers Winona in any way there will be consequences.
As he continues to investigate Owen’s death, Raylan discovers those weren’t the fake Hitlers in the fireplace, after all. The remains aren’t the right kind of paint. Raylan figures something fishy is going on, and he confronts Caryn, spooking her.
It turns out, Caryn kept the paintings in order to always have some blackmail material on David Mortimer. She goes to Greg after Raylan confronts her and tells him they’ll have to kill David, just in case. Not long after Caryn leaves Greg, though, Raylan shows up to talk to him. He encourages Greg to ask himself “where does it end?” Once you’ve killed one person, and then you’re forced into killing another… Does it ever end?
That night, Caryn and Greg lure David to the barn. Greg puts a gun on him, ready to take him out, but hesitates. He asks Caryn the same thing Raylan asked him. “Where does it end?” Angry, Caryn tries to convince Greg to go through with it, incriminating herself in the process. That’s when Raylan and the police step out of the shadows. Greg was wearing a wire.
The next day Raylan goes to see Karl, the Hitler art collector, to tie up some loose ends. At Karl’s urging, Raylan reluctantly agrees to take a look at Karl’s Hitler collection. Karl takes him into a back room containing no paintings, but instead shelf after shelf of jars with what looks to be ash inside them. Karl explains that his father was part of the Third Reich, and that one of his fondest memories was of going throughout Germany on behalf of Hitler and buying up the art he had produced in his youth. Karl hated his father, and now he buys Hitlers wherever he can find them, then he burns them.
Later, Raylan goes to Boyd again and tells him he’s changed his mind, he doesn’t want anything on Arlo. Boyd wants to know if he’s sure, because he’s found a something out that could put Arlo away for the rest of his life.
Raylan doesn’t answer right away…