Top 25 Walking Dead Villains of all time
By Nir Regev
12. Gregory
Introduction: Gregory, a politician type king of akin to the Governor, was the leader of Hilltop until Maggie Greene arrived and slowly gained control. As time went on, Gregory would resent Maggie more and more, attempting to betray Rick’s group (and Negan’s Saviors when they’re losing) multiple times. Eventually, when he convinces a Hilltop resident to ambush Maggie at Glenn’s grave (which he told Maggie had been defaced) he is hanged by Maggie as an example of what happens when you repeatedly spit on your second chances.
Biggest moment of Villainy: Gregory is all about self-preservation, and his most memorable moment arrived when Gabriel returned to save him from walkers during Rick’s ambush on Sanctuary…only for Gregory to abandon Gabriel and steal his car to escape Sanctuary alone, with no remorse.
Everybody Hurts Sometimes: Gregory is no stranger to cowering for his life, seeing it as part of a larger game, and does so with Simon, Maggie, and Negan himself at times. However, when he has a noose around his neck, he begs for his life to no avail.
The Good Side: Cowardly or not, things at Hilltop ran smoothly with Gregory in charge. He was a people person, and knew how to manage personalities, good or bad, much like the Governor. Most of Gregory’s anger came when he lost power to Maggie.
First Appearance: “Knots Untie” (season 6, episode 11)
Last Appearance: “A New Beginning” (season 9, episode 1)
Cause of Death: Gregory is hanged by Maggie courtesy of Daryl in a public spectacle at the Hilltop. This would motivate Oceanside to extract revenge on the Saviors.
Memorable Quote: “What you’re doing isn’t right! Killing me in the dead of night, because you’re ashamed!”
Next: 11. Lizzie Samuels