If I was with Hilltop I sure as hell would want another leader besides Gregory.
His attitude alone with Maggie was pure horsecrap. It not only was extremely rude, but she bent him over HARD when the tables were turned. That isn't in Maggie's character normally. It was her natural response to being called Natalie (more than once) along with the other degrading treatment.
A leader has to lead his/her own people, but he/she also has to be diplomatic with others. His total lack of diplomacy cost his own group far more than it should have, and in the long game may well have poisoned relations between Ricks group and his own.
They don't need a leader like that. That is more harm than good in my opinion.
Doug
I was also not impressed with writing a character like that as a leader. He's not charismatic, he's not intimidating. He's just full of crap and full of himself. Did he make the group think he was more intelligent? He just strikes me as someone the residents would have given the finger to immediately.