Gregory

The Walking Dead
Gregory was a middle-aged man who became the leader of Hilltop Colony. It is unclear exactly how he gained this position, but it is possible that he just assumed authority unopposed. Though he was committed towards safeguarding the community, Gregory was a weak and spineless man. He had little connection to the people under his care, and had difficulty even remembering their names. He was a bit of a misogynist and had little regard for women, offering them almost no respect at all. When the Saviors began extorting supplies from Hilltop, Gregory fell in-line, giving them whatever they wanted. Rick Grimes and his group came to Hilltop, and Maggie Greene attempted to establish a trade arrangement between Gregory's people and their own at Alexandria. Gregory began flirting with Maggie, who brushed him off. One of the Hilltop colonists, Ethan, returned from a meeting with the Saviors. His brother Craig was being held hostage and he was ordered to give a message to Gregory. The "message" ended up being a knife between the ribs. Rick tackled Ethan and stabbed him in the throat. Gregory recovered and during his convalescence, Maggie proposed a new deal: Her group would take care of the Saviors in exchange for food and medicine. They succeeded in wiping out all of the Saviors at one particular compound, but had no idea just how many people were actually part of the group. Following a harrowing encounter with the Saviors, Maggie and her friend, Sasha Williams, returned to Hilltop. Gregory wanted nothing to do with them, and felt that they now presented a threat to their existence. A contingent of Saviors, led by a man named Simon, came to Hilltop and antagonized Gregory. They left after taking half of all of their materials. Gregory told Maggie that the Saviors could be reasonable, which earned him a punch in the jaw.