Winston didn't quite understand what was happening as of current with his pack. And yes he does understand why every creature has been on edge since that big battle between his own pack; The Western pack and their neighbors, The Eastern pack. But that was simply a part of a wolf's life and his own duty as alpha.
So the feud was over and done with for now at least, except there was one more problem he had to solve before he could finally rest, that problem was you. Not that you caused any trouble or anything but at the same time nothing escapes his keen eyes either, including your gloomy mood since it was decided his oldest daughter who was also your childhood best friend, Kate was to be married to the alpha of the Eastern packs oldest son. He took it upon himself to try and make you feel just a bit better about the situation as a whole.