Many apologies for Sho being THE stick in the mud about everything. He doesn't trust a lot of people who are in charge - mainly because of in his personal experience, those in charge tend to try to kill/destroy anyone that doesn't play nice. And it is really against his nature to play nice with anyone. The time he was actually nicely asked to join up with a stronger group, his main response was to rob them, kill off their goons, and then lead a suicidal assault against the core group and the head of the entire organization all by himself. It also doesn't help that she seems to want to take the entire burden on herself and gets annoyed when people poke holes into her plans.

That being said, it might be interesting to see them come to an understanding as to how to relate to one another. It might take a bit of work to get that far though.