Gregory
Well, how can we describe Gregory in just a few words? Arrogant? Selfish? Inconsiderate? Cowardly? Creepy? Heck, try all of the above, and then add a few more to the list.
The character first made his debut during the Negan saga as the Hilltop’s leader, but leader is a bit of a loose term because he didn’t do much leading. He just happened to be the man in charge who lived in the fancy big house, gave out orders to others and oversaw others as they held the place together. He was odious, self-serving and didn’t care about anyone else in the community. This much was clear when he was hostile towards Rick, Maggie, and the rest of the survivors when they first crossed his paths.
Gregory was particularly rude to Maggie and hated the fact that she was elected the new leader of Hilltop, and that would ultimately be his downfall as his attempt to have her killed resulted in his death at her hands.
It was impossible to root for Gregory. Every time he showed a little potential of goodness within him, he always chose the route that would allow him to weasel his way to victory or safety, irrespective of who he had to walk over to achieve it.
Verdict: WORST