Gregory

Gregory is the self-appointed leader of the Hilltop, a walled settlement that has survived largely by letting others do its fighting and dying. He drinks, postures, and speaks in the smooth, patronizing tones of a man used to being obeyed, more concerned with keeping his position than protecting his people.

Xander Berkeley plays cowardice as a kind of oily charm, never raising his voice because he doesn't need to — he's found other ways to survive. The show uses him as a study in leadership without courage, and Berkeley makes every flattering smile feel like a small betrayal in progress.