What do a sexy stewardess, a street-tough gun runner, a lonely bail bondsman, a shifty ex-con, an earnest federal agent, and a stoned-out beach bunny have in common? They're six players on the trail of a half million dollars in cash! But, who will end up getting played, and who will actually make the big score?

Season three introduces a new main villain, Robert Quarles of Detroit. The parent criminal organization connected to the Frankfort mafia has exiled Quarles to Kentucky. Quarles begins to muscle in on the local criminals, successfully supplanting them until Raylan begins investigating. Simultaneously, Dickie Bennett, the lone survivor of the Bennett clan, seeks the aid of the black residents of Noble's Holler and their leader Ellstin Limehouse in recovering...

Jack is a small-time con man trying to lead an easier life in Hawaii. Trouble is, he can't keep out of trouble, and when he does stay clean, trouble finds him. Trouble, in this case, comes in the bikini-clad form of Nancy, the mistress of a local real estate developer. She lures Jack into a scheme that ultimately involves complicating Jack's moral dilemma when Nancy asks Jack to help her double-cross the developer out of $200,000.