Originally Posted by Ron Temple
There have been hints of her character. She left Raylan for the realtor when he got transferred to Miami. She was supposed to sell the house, but instead took up with the realtor. When she was first introduced she told Raylan, she did it because she wanted the big house (which she is losing now). She always struck me as selfish and hard to deal with. This has been reinforced throughout this season. Ultimately, I get the feeling that whatever or whoever she's in to, she's more concerned about No.1. In that light, I see nothing illogical about this character going off the rails.
I think she's trouble for Raylan, certainly difficult. He just can't let her go. Most of us have been there in a relationship.
I can't fault your analysis because the facts would support the inferences you have made, although I come down in a somewhat different place. It seems to me that Raylan's problems match or exceed Winona's. He is almost insanely driven and reckless about his safety, so Winona's decision to move on wasn't entirely selfish, it seems to me. As we have seen again and again, Winona understands Raylan as nobody else does.
As to the motivation behind Winona's decision to take the $100 bill from the cash in the evidence locker, I think we simply don't know enough to draw a conclusion and I can't use her decision to leave Raylan as evidence that her motives were evil. I think we can agree, though, that Justified is smart television for grownups.