Carolyn is known to have put Raylan on his heels many times when he’s stepped outside the line. A notable example was their first meeting in court. Winona would have been happy to use this kind of strategy, showing how much she is willing to tolerate, even if Raylan was a charming lawman. It is inevitable that opposite forces would attract. However, Winona, like an old flame in Raylan’s past, was more willing to dig her heels into the dirt.
She’s trying to be good, but her duty to Sweet (Vondie curtis-Hall), has placed her in an unsavory position. Carolyn has been drawn into an area she’s supposed to avoid, like Ava Crowder at both the beginning and end of ‘Justified, before falling in love with Boyd Crowder. Rule breakers clearly get Raylan’s attention, but in this case, it will only make things more dangerous. Clement’s character is as explosive as any Raylan has encountered, and when Raylan finds out that his own attorney is sleeping with an enemy, he will be concerned. Isn’t romance complicated?