Gregory (The Walking Dead)

Appearances

Gregory, the leader of the Hilltop Colony, fancies himself a capable administrator, often described as someone who keeps things running smoothly. In truth, he is vain, forgets people’s names, makes unwelcome advances toward new women, and consistently prioritizes his own safety over anyone else’s. When the Saviors take Craig hostage, a Hilltop resident named Ethan stabs Gregory in the gut as a message from Negan, though Gregory survives. Like everyone else in the colony, he is powerless against the Saviors and must turn to Rick Grimes for help.

Over time, his poor leadership becomes obvious. In the comics, Maggie Greene eventually takes over as Hilltop’s leader. Later, after Carl Grimes moves in and nearly beats two boys to death, Gregory tries to poison Maggie. Jesus stops the plot just in time, and Maggie has Gregory jailed. After thinking it over, she decides he must die, and he is hanged in front of the entire community.

In the television episode “Knots Untie,” Rick’s group meets Gregory for the first time. He is a former businessman who once served on the Chamber of Commerce. Rick decides he should not be the one to negotiate and sends Maggie instead. Gregory immediately talks down to her, pointing out that Alexandria is desperate for food and trying to use their shortage to his advantage.

Rick later insists they came for food and will get it, but Jesus asks for patience, hoping to convince Gregory to show goodwill and build a future relationship. Then three Hilltop residents—Ethan, Andy, and Crystal—return angry. They had delivered tribute to Negan, who called it too light, killed Tim and Marsha, and kept Ethan’s brother Craig hostage. As a message from Negan, Ethan stabs Gregory in the stomach.

After Gregory is patched up, Jesus explains that the Saviors are a brutal gang that forced the Hilltop into a deal: half of all supplies, crops, and livestock go to them in exchange for peace. Daryl offers to kill Negan, rescue Craig, and take out his men if the Hilltop provides food, medicine, and one cow. Maggie closes the deal, demanding half of everything up front.

Development and reception

Gregory is portrayed by Xander Berkeley on The Walking Dead television series, beginning with the sixth season. In his debut appearance in the season six episode 'Knots Untie', Ed Powers of Telegraph.co.uk called Gregory 'a cowardly creep' and 'slithery', commenting that Gregory was painted in broad strokes by veteran television actor Berkeley, a further example of The Walking Dead telegraphing to the audience how it should feel about a character.

Josh Jackson of Paste commented that Gregory is indeed a strange one, and no matter how idyllic the Hilltop seems, Jackson did not think he is the leader he would want for the zombie apocalypse. Tim Surette of TV.com commented that Gregory wasted no time being one of the most despicable characters the series has ever introduced by drooling all over Maggie and requesting some of her 'services' in exchange for some carrots. Ed Gonzalez of Slant Magazine called Gregory 'some kind of perverse caricature of the Southern gentlemen.

By which I mean he scarcely qualifies as one.' For the seventh season, Berkeley was promoted to a series regular. Noel Murray of Rolling Stone ranked Gregory 24th in a list of 30 best Walking Dead characters, saying he has made quite an impression, thanks to Xander Berkeley's gruff performance, and that Gregory has become the show's version of a weaselly politician.