Gregory (''The Walking Dead'')

Season 6

In the episode "Knots Untie", Rick's group is introduced to Gregory, the leader of the Hilltop Colony and former businessman on the Chamber of Commerce. Rick ominously says he should not be the one to talk to Gregory and tells Maggie to conduct trade talks. Gregory immediately belittles Maggie and asserts that the Alexandrians are in great need and attempts to use their food shortage as leverage. Later, Rick says that they came all this way for food and they're going to get it, but Jesus calls for patience as he works to convince Gregory that it would be better to show some goodwill to Alexandria and build a relationship that could pay back in the future. Three Hilltop residents, Ethan, Andy and Crystal, return and angrily confront Gregory. They had been sent to deliver tribute to Negan, who said that it was "light" and killed Tim and Marsha while keeping Ethan's brother Craig hostage. For Craig's release, Ethan delivers a message from Negan by stabbing Gregory in the gut. After Gregory is stabilized, Jesus explains that Negan is the head of a group called the Saviors. The Saviors came to the Hilltop, issuing a lot of demands and even more threats, resulting in a deal: half of the Hilltop's supplies, crops and livestock goes to the Saviors in exchange for peace. Daryl offers to kill Negan, take out his boys and rescue Craig in exchange for food, medicine and "one of them cows." Maggie closes the deal with Gregory, demanding half of everything from the Hilltop in advance.

Season 7

In the episode "Go Getters", Gregory approaches Maggie and Sasha and insists they need to leave and go back to Alexandria. Jesus tries to reason with him, but Gregory says they must leave by morning. At night, Maggie and Sasha wake up to loud music coming from a car parked on the Hilltop's interior, with the Hilltop gates open. Walkers are being attracted by the music and multiple fires that have been set inside the Hilltop. Gregory stares out the window of the house, but does not take action, while Maggie, Sasha, and Jesus intervene. The next day, Gregory and Jesus discuss what to do about Maggie and Sasha when some Saviors show up. Gregory tells Jesus to hide Maggie and Sasha in the closet. Gregory opens the door for Simon and the other Saviors at the Hilltop. Simon tells Gregory they should talk in private in the study. Gregory said the message last night was received loud and clear: He is the Hilltop's "Negan" now. Simon asks if there is anything else he should be made aware of and Gregory stays silent. He says that there actually is something and Gregory leads Simon to the corridor closest, opening the door to reveal bottles of classic scotch. Simon asks Gregory to kneel before they continue and Gregory instantly obliges. Simon tells him it's a solid kneel, and pats his head like a child. After the Saviors leave, Gregory finds Sasha and Maggie in his room, where they were hiding in a closet. Jesus puts his foot down and says the women are staying, and he will knock Gregory out of power if he disagrees. Gregory says the Saviors can be quite reasonable and Maggie punches him in the face. In the mid-season finale "Hearts Still Beating", Gregory warns Maggie not to let her popularity with the Hilltop residents get to her head.

Season 8

As seen in the season premiere "Mercy" and the episode "The Big Scary U," Gregory makes his way to the Satellite Outpost and from there to the Sanctuary after abandoning the Hilltop. Gregory meets with Negan and his lieutenants and promises that he can help to bring the Hilltop back into line before the Militia arrives to attack. Simon calls Gregory out to order the Hilltop to stand down, but the Hilltop members ignore Gregory's order, instead choosing to stand with Maggie as their leader over Gregory. An enraged Simon pushes Gregory down a flight of stairs, injuring him. As the attack begins, Gabriel Stokes spots Gregory in danger and rescues him from the herd of walkers. In return, Gregory steals Gabriel's car and abandons him to die.

In the episode "Monsters," Gregory returns to the Hilltop in Gabriel's car where he attempts to gain entrance. Kal is revealed to have abandoned Gregory after learning of his true plans and Maggie deduces Gregory's cowardice after they recognize Gabriel's car. Despite this, Maggie decides to allow Gregory to reenter the Hilltop, telling Enid that Gregory isn't worth killing. In the episode "The King, the Widow, and Rick," Gregory attempts to act as an advisor to Maggie, but she distrusts him. As a result, Maggie locks Gregory away in the new pen built for their Savior prisoners. Gregory spends several episodes as a captive in the pen, attempting to negotiate his way out but being largely ignored.

In the episode "Do Not Send Us Astray," after the Savior attack, Henry visits the pen in hopes of finding out who killed his brother Benjamin and exacting revenge upon them. Gregory introduces himself and alongside Alden attempts to talk Henry down without success. After a Savior prisoner suddenly turns and begins attacking, Jared overpowers Henry and most of the prisoners make a run for it. After appearing to briefly hesitate over whether or not to help out Henry, Gregory chooses to join the Savior prisoners in running rather than staying to help with the situation at the Hilltop.

In the episode "Worth," Gregory is revealed to have returned to the Sanctuary and the Saviors. Gregory tries to suck up to Simon again and actually stands up to him, causing Simon to change his mind about killing Gregory. Gregory participates in Simon's attempted coup and is spared when Negan and his loyalists kill Simon's soldiers. During the brutal fight between Simon and Negan, Gregory escapes the Sanctuary with the help of Dwight who gives Gregory a map detailing Negan's plans to give to Rick. Gregory returns to the Hilltop and hands over the plans before being locked up again. During the season finale "Wrath," Gregory is mentioned to have been left behind at the Hilltop when the residents evacuate rather than being taken with them.

Season 9

In the season premiere "A New Beginning," Gregory is revealed to have called for a vote to determine who the leader of the Hilltop will be in the eighteen months since the war with the Saviors and has lost in favor of Maggie. Now even more angry and bitter, Gregory takes advantage of a grieving father, persuading him make an unsuccessful attempt on Maggie's life. Maggie confronts Gregory, who tries to kill Maggie himself, but she overpowers him. Maggie decides to execute him to prevent such a thing from happening again. That night, Gregory is strung up to a newly-built gallows and sat on a horse in front of the entire Hilltop Colony, and Rick and Michonne. As he pleads for his life, Maggie has Daryl send the horse away, hanging Gregory. Daryl then cuts him down on Maggie's orders, and presumably puts him down before he can reanimate.