Gregory

**Gregory**is a main character and later antagonist in *AMC's The Walking Dead.*He was the leader of the Hilltop Colony, before Maggie Rhee stepped in after he sided with the Saviors.

## Biography

### Post-Apocalypse

#### Season 6

##### Knots Untie

Gregory first meets Rick Grimes's group when they first arrive at Hilltop and they are shown into the Barrington House by Jesus. He interrupts Rick while Rick is introducing him and his group to welcome them and tell them to go wash up, remarking that he's trying to keep Hilltop clean, and then retreats back into his office.

Gregory is in his office later when Maggie Greene enters and mistakes her for a "Natalie" while making introductions. Maggie then asks about the possibility of setting up a trade between Hilltop and Alexandria. However, while they're discussing this, he tries flirting with Maggie and will not listen to what she has to say. Maggie tries to propose a deal of ammunition for food, but he keeps interrupting her, saying that he will give them food if they do labor for him, believing Rick's group has nothing despite Maggie repeatedly saying otherwise. He becomes flirtatious with Maggie again when she interrupts him, getting more frustrated, and states that the groups will help each other. At this point he abruptly ends the conversation, bids goodbye, then leaves his office.

When Ethan, Crystal and Andy, other Hilltoppers, return from a supply delivery to the Saviors, Gregory approaches Ethan to ask what happened and where everyone else is. Ethan states that the others were killed, his brother Craig is being held hostage, and that Negan has a message for Gregory. When he asks what the message is, Ethan places his hand on Gregory's shoulder and apologizes before he stabs him in his stomach. Gregory falls to the ground but is caught by Michonne while the community's doctor, Harlan Carson, rushes to his aid from his trailer as Rick's group intervenes. Abraham is nearly strangled to death by Andy but Daryl saves Abraham. Rick then stabs Ethan dead and Jesus calms astonished residents by pointing out Ethan is initiated the bloodshed.

He is later seen recovering in his bed when Maggie comes in to propose the new deal. Maggie states that the trade is that Rick's group will deal with the Saviors in exchange for food, to which he responds they ended up doing labor for the Hilltop anyway, when Maggie interrupts him. She states that they will take care of the Saviors for half of the Hilltop's supplies, to which he reluctantly agrees.

#### Season 7

##### Go Getters

Gregory is first seen approaching Maggie, Sasha Williams and Jesus, confronting them about Rick's failure to wipe out the Saviors. Then he tells Maggie to burn Glenn and Abraham's bodies and orders them to leave Hilltop. Gregory tells Jesus that if they leave, he has plausible deniability, and the Saviors won't think they colluded to take down their outpost. Jesus tries to reason with him, but Gregory fires back and he says Rick's people were supposed to keep them safe, but Rick only brought more harm. Gregory now denies any involvement with Rick: plausible deniability. Gregory says they can stay the night, but must leave in the morning. Jesus says he'll take them back and that it's settled. He walks away without hearing any more.

During the Saviors' attack, drawing walkers with music inside the walls, Gregory is just watching and disappearing in his room. Gregory thanks Maggie and Sasha for saving the Hilltop but still refuses to let them stay. He offers to work something out with Sasha one-on-one with Maggie telling him to go to hell. They're interrupted by the sound vehicles arriving in the courtyard. Simon and the Saviors arrive, he then tells Jesus to hide Sasha and Maggie in the closet.

He is confronted by Simon into the Barrington House and says they need to talk. In the study, Simon and Gregory are staring at a painting. Simon tells Gregory they unleashed the walkers on Hilltop to remind its residents that walkers are still a threat and the Saviors provide a great service by killing them. He says it was management by example, and Gregory agrees. Simon says they worked hard last night to provide him with an example.

Simon says the people in Hilltop probably forget what the walkers look and smell like, and they were going to clean up the mess so they could show the service they provide. Gregory says probably they learned it all from the Saviors in the first place. He informs Gregory that the Saviors at the Satellite Outpost were killed and asks about him coorperating with Rick and Alexandria taking down the outpost, but Gregory is denying that. He tells Simon to tell Negan that he understands how to cross the aisle. Simon says there's no need, and that he is Hilltop's Negan now. The two come to an understanding, and asks if there's anything Gregory wants to tell him. Gregory cracks and says there actually is.

Gregory leads Simon to a foyer closet and opens it with the intention of handing over Maggie and Sasha. Instead, he finds boxes of scotch. Simon says Negan will be pleased and orders a nearby Savior to put the liquor in Negan's truck. On his way out, Simon orders Gregory to kneel, which he does with little resistance. The Saviors leave.

After Jesus released Maggie and Sasha from Gregory's closet, he yells at Jesus for hiding them there instead of the foyer closet. Jesus stands up to him and forces him to let Maggie and Sasha stay. Jesus threatens to reveal his deal with Alexandria, stripping him out out power if they don't stay. Gregory reluctantly agrees, and approaches Maggie saying the Saviors can be quite reasonable and suddenly, Maggie punches him in the face, reaches into his pocket and takes Glenn's watch, which he stole from the grave. Maggie says that Hilltop is her home now, and she says Gregory will call her by her real name: Maggie Rhee.

##### Hearts Still Beating

Gregory approaches Maggie who sits alone at her post at the Hilltop's front gate with Eduardo. He warns her not to let her popularity with Hilltop residents get to her head. Maggie asks if Gregory is going to eat his apples, he says yes, but Eduardo berates him telling him Maggie is pregnant, and he reluctantly gives his apple to Maggie and leaves.

##### Rock in the Road

Gregory is shown in his office by Rick, Maggie, Sasha, Carl Grimes, Michonne, Tara Chambler, Rosita Espinosa, Daryl and Jesus. He denies Rick's attempt to bargain with him and fight the Saviors. He tells them their previous agreement is null and void. Gregory says they aren't trade partners in addition to ruling out other connections. He is called out by Jesus for his cowardly behavior and for not helping save the community when Maggie and Sasha did.

Rick insists the group can win and questions how Gregory wants to live. Maggie jumps in and Gregory has been calling them by the wrong name and insists his people don't want to help. They grow things, they don't fight. Tara insists people will step up, given a choice. Gregory stops her from finishing her sentence, though he admits they would be better off without the Saviors. Daryl calls him out for his big mouth, and asks him he's either with them or he isn't, and Gregory makes it clear that he wants nothing to do with it and has everyone leave the Hilltop, pretending they never been or had this meeting.

##### The Other Side

Gregory is at his office window, suspiciously watches a group of Hilltop residents congregate in the courtyard. He downs a drink and, suddenly, Simon and his men returned to Hilltop. Gregory greets the Saviors in his foyer and Simon spends some time with Gregory and they both agreed that if there is any trouble in the Hilltop, Gregory will come to the Saviors' compound and they will take care of it. Simon also tells Gregory that Negan wants one of the Hilltop's residents, Dr. Harlan Carson.
In the medical trailer, Simon tells Harlan that they need his services at the Sanctuary and Harlan correctly guesses that his brother, Emmett Carson, the Sanctuary's former doctor, was killed. In exchange for taking Harlan, Simon gives Gregory a crate of aspirin.
Gregory is reluctant and pulls Simon aside and assures him that he's an ally of Negan. He explains that he needs to hold on to his people's trust; otherwise, someone less cooperative (Maggie) could take over. He hints that he might eventually need Negan's help quelling insurgents within the community. Simon gives Gregory a hand-written note that will grant him entry into the Sanctuary should he ever need to seek their help. The Hilltop residents gather at the gates and watch the Saviors leave with Harlan. Gregory, sensing their disappointment, shifts around uncomfortably.

Gregory later summons Jesus to his office and hands him job assignments for the newcomers. Jesus accuses Gregory of letting the Saviors take Harlan and splitting up groups to protect himself. Gregory warns Jesus against talking back to him and says he's realized they're no longer friends. Kal enters and has Jesus leaves.

##### Something They Need

At the Hilltop, Gregory observes Maggie and Eduardo's interaction. He overhears Eduardo refer to Maggie as the boss, and hears Maggie's plan to transplant a blueberry bush from outside the Hilltop gates. Gregory joins Maggie as she uproots the blueberry bush outside the Hilltop walls. He proposes they present a united front to the community and Maggie agrees to consider the offer. She asks him to keep watch while she finishes up. Gregory contemplates killing Maggie while her back is turned, but ultimately decides against it. A walker emerges from the woods and Gregory charges at it but backs away at the last minute. Maggie kills the walker as a second walker attacks Gregory. A passing group of Hilltop residents witness Maggie saving Gregory however she defends him and says it was his first time. Oscar remarks that's not what Gregory told them.

Back in his office, Gregory takes Simon's hand-written note from his shirt pocket. He studies a local road map then calls for Kal and he tells him to pack a bag and prepare to drive him somewhere.

#### Season 8

##### Mercy

When the Militia arrives at the Sanctuary, Gregory is called outside by Simon where he states that the Hilltop stands with Negan and the Saviors and threatens anyone who stands with the Militia from Hilltop. However, the Hilltoppers make it clear that they don't see Gregory as their leader anymore but Maggie. Enraged, Simon shoves Gregory down a flight of stairs. As the walker herd attacks the compound, Gabriel Stokes notices an injured Gregory in danger and climbs out of his car to rescue him. Gregory returns the favor by stealing Gabriel's car and escaping, abandoning Gabriel to die.

##### Monsters

Gregory arrives at the Hilltop in the car he took from Gabriel at the Sanctuary. He pleads to be let back in and the gate opens halfway and Maggie meets him at the gate and asks him what he's doing back at the colony after what he did and what happened to Gabriel, Gregory pretends he doesn't know who Gabriel is and lies about finding the car empty, and arrogantly tells her that he built the Hilltop long before Maggie arrived. Maggie furiously tells him to shut up and stop pretending he didn't try to sell the community out to Negan.

He protests that he was trying to save lives, but Maggie tells him that people are fighting for a better life. She calls him a coward, accuses him of looking out only for himself and she reveals that Kal told them that Gregory wanted to warn Negan of the Militia's intentions to fight and Kal abandoned him when he heard of his true plan. Gregory calls Kal delusional, but Kal overhears him insulting him and gives Gregory the middle finger before arguing over the little girl's pancakes Gregory had eaten, which Gregory himself remarked that he didn't. Maggie makes to leave Gregory on his own outside the walls, but changes her mind when he desperately pleas for mercy, saying that he was scared and unsure if he couldn't win in a fight against the Saviors. He apologizes and makes a scene. After listening to his pathetic cries, she lets him in, telling Enid that he isn't worth killing.

Just then, Jesus' group returns to Hilltop with a large group of captured Saviors. Gregory immediately insists they can't stay, but Maggie shuts him up and orders him to leave while she talks to Jesus. Gregory reluctantly complies and walks away.

##### The Big Scary U

In a flashback, Simon greets Gregory in his holding room in the Satellite Outpost. Simon starts out, saying he came to see him though he was already away dealing with the rank betrayal which was unknown to Gregory. The tone in Simon's voice indicates he is giving Gregory instructions on what to say should anybody ask, which he quickly abides by, but also indicates that there is a mole in one of the groups. As it turns out, though, Gregory was going to reveal the alliance between the Hilltop and Kingdom but Simon was finding out at that point from someone in Alexandria to Gregory.

Later, Gregory sits with the Saviors and Negan. He thanks them for listening to him and he understands how hard it is to manage people in this environment and the scary unknown. He explains that he hates killing people however Negan tells Gregory he likes killing people and killing the right people and the right time makes things fall into place. Negan tells him that killing one person could be saving a hundred and that the Saviors save people. Gregory continues, describing the conflict and claiming he can stop it before it gets started. He offers to kick everyone out of the Hilltop who side with Rick. Negan asks him if he can exile people.

Gregory claims he owns Hilltop and that he is still in charge there. Negan questions it, though, because Maggie is leading an army of his people. Gregory insists he didn't know about Maggie until now and that Hilltop is his, saying it was a mistake letting Maggie in Hilltop and that she took advantage of his generous nature. Gregory insists that he'll fix it. The meeting is interrupted by gunfire coming from outside and they step out and Gavin is disturbed upon seeing the Militia. The events of Mercy then take place.

##### The King, the Widow and Rick

Gregory and Maggie catch Jesus handing out food to the Savior prisoners. Maggie orders him to stop giving away the Hilltop's food and Gregory suggests killing them but Maggie orders him away, so Enid escorts him in. Gregory and Maggie chat in Gregory's office, with Maggie sitting in his chair. He insists, again, that what he did with Negan was in the best interest of Hilltop. Maggie accuses him of being scared but Gregory promises his motives were pure and says he can help her run the community because he was once in charge. She is not interested but he says he can tell her she needs someone to tell her to follow her gut. Gregory calls Maggie the shepherd and that she can't have "wolves" wandering around amongst the "sheep".

When Maggie has ordered the Saviors inside of a makeshift prison, Gregory says they shouldn't have people at the Hilltop wandering around who can't be trusted. She agrees with him, prompting Kal and Eduardo to put him in the same prison. Gregory is reduced to be a sobbing wreck and struggles, causing him to hit in his head on a bar. Gregory later silently witnesses the exchange between Jared and Alden.

##### How It's Gotta Be

Gregory is still in the cage he is locked in with the other Savior captives. When Maggie gets back, Gregory tries to talk to her about getting why she locked him in, but Maggie shuts him up. Maggie storms to the fence and requests that Dean be fetched from the prison. Gregory is angered that he gets to come out, but is shocked that Maggie brought him out to execute him.

##### Dead or Alive Or

Gregory speaks to Maggie through the barbed wire fence, reasoning that he should be released for good behavior, but Maggie refuses to set him free. Alden then approaches the two, speaking up for the rest of the Saviors and attempting to come to an agreement, suggesting that the prisoners be allowed supervised freedom every once in a while for a few minutes each. Again, Maggie refuses, and reveals that they are removing their rations for a few days, much to the shock of Gregory and the Saviors.

Later, Maggie returns to the holding pen and agrees to Alden's deal, allowing a maximum of two Saviors at any given time out of the pen for work, exercise, and if the need arises, medical attention. Gregory, while grateful for her decision, is worried about an impending attack by the Saviors and implores that Maggie consider an evacuation, fearing losing the war. She remains strong, telling Gregory that with all they have now, there is little possibility for loss.

##### Do Not Send Us Astray

Gregory appears when Maggie is speaking on the radio with Simon, Gregory questions Maggie's decision to fight the Saviors, she says it will ultimately work. During the attack, he is taken to Maggie's office and later on back to the pen. The night after the attack, an armed Henry arrives to the pen and confronts Gregory, asking who killed his brother. He tells him that he doesn't know any of the Saviors and Henry questions Gregory why he is a prisoner if he isn't a Savior.

Later, Henry opens the gate, demanding to know which Savior killed his brother and threatening to kill everyone if the killer doesn't step forward, when suddenly an injured Savior reanimates and bites one of the prisoners, allowing Jared to push Henry over and take his gun, leading the other prisoners away. Gregory escapes with them as well.

##### Worth

Gregory is revealed to have gone straight to the Sanctuary after fleeing Hilltop and tries to suck up to Simon however stands up to him which actually changes Simon's mind about killing him. He joins Simon's coup against Negan until all of Simon's followers are executed on Negan's orders however Gregory is spared and later attempts to sneak away during the fight between Negan and Simon, but Dwight gives him the plans to warn Rick. Later he returns to Hilltop and despite giving them the map to warn them of the attack, he is placed back in the prison alone.

##### Wrath

When the Saviors attacked the Hilltop, Enid reveals that Gregory was locked in the Barrington House when asked about his whereabouts. Since the Saviors were wiped out by the Oceansiders before they could get inside the settlement's walls, Gregory was unharmed.