15 of The Walking Dead’s most vile villains ranked
7. Gregory
Who is he: The self-appointed leader of Hilltop before Maggie stepped in to save the community from Gregory’s selfishness and poor political decisions. While Gregory started his arc as an apparent protagonist, he gradually morphed into a more villainous form. A lot of his decisions were fueled by his survival instincts. We all remember that he teamed up with the Saviors and willingly sacrificed precious food supplies to them. He also opposed any rebellion against Negan because he wanted to protect his own livelihood before Hilltop’s best interested, even though he desperately claimed to lead and protect the community. He might have thought he had a well-intentioned post-apocalyptic political agenda, but somehow, he even made the walker outbreak corrupt and self-serving. Additionally, he cozied up to Simon, who he thought would ultimately push Negan out of his leadership position. In short: Gregory is a coward and exploits his cowardice to survive the apocalypse, and he does little to nothing to benefit anyone else.
Worst act of villainy: Trying to get another Hilltop citizen to kill Maggie, who had just recently given birth. For what reason? Because Gregory couldn’t stand witnessing someone else lead Hilltop, let alone someone else lead Hilltop successfully. His only self-earned accomplishment on The Walking Dead is being the skeeziest and spineless villains in the history of the show. (Seriously, he couldn’t even attempt to kill Maggie himself.)
Weakness: Seeing as Maggie is a stronger leader and a stronger person (morally and physically), Maggie implemented a code of punishment to prevent Gregory from threatening her or anyone else’s wellbeing again — she hanged him. Honestly, he deserved it for a while.
Redeeming qualities: Before Rick, Maggie and company intermingled with Hilltop, he didn’t technically have a firm grasp on his survival skills. Although Hilltop had to give a certain amount of supplies and resources to the Saviors, his community managed to live peacefully and unharmed, even if it wasn’t really a realistic system for survival longterm. Granted, we still saw through his faux-charming personality.
First appearance: “Knots Untie” (season 6, episode 11)
Last appearance: “A New Beginning” (season 9, episode 1)
Death: Maggie ordered him to be hanged in public after he attempted to get someone to kill Maggie.