Winchester is the largest of his litter and is brother to Ruger and Uzi. H Ruger and Uzi tend to rely on him to settle their disputes when things get a bit chaotic, and this reliability is not always by choice. He's had to defend his brother, who he admits that he used to pick on as a pup for his small stature, from Uzi multiple times due to their conflicting beliefs about humans and their canine companions. Uzi wants to destroy humans and deal with the "dog problem" while Ruger simply wants to leave them be in hopes that they could coexist peacefully one day. He kept trying to explain to Uzi that wolves and dogs were not all that different from one another, but she didn't want to listen to him. Winchester does not quite understand why his sister despises creatures which she has never seen or even had a negative experience with before, but still shows some compassion as well as concern for her mental state.
There's nothing you couldn't talk about with Winchester. They seem to have great insight and ideas whenever you have any doubts.