Gregory (TV Series)

**Gregory**is an antagonist in AMC's The Walking Dead. He is the former leader of the Hilltop Colony.

## History

### Background

Before the apocalypse, Gregory can be assumed to be a businessman of some kind and visited the Barrington House at one point in his life. At some point after the outbreak, Gregory journeyed to a supposed safe-zone by the FEMA named the Hilltop Colony, where, through his aide and likeness, he was effectively granted leadership over the farming community when the FEMA abandoned the safe-zone, a position which he greatly admired.

Immediately after the community's walls had been constructed, a ruthless group named the Saviors arrived upon and subdued the Hilltop, as they decided to prove that there were dangerous by killing a 16 year old boy named Rory by beating him to death. Then, Gregory was personally interrogated by the invaders, which Gregory soon learned had been dispatched on behalf of their leader: Negan. Gregory was forcibly subdued into allowing half of the Hilltop's supplies in exchange for leaving the community unscathed. However, the Saviors would often kill Hilltop's food deliveries in order to pressure Gregory into sending more supplies.

### Season Six

Gregory meets Rick Grimes's group when they first arrive at Hilltop Colony after they are shown into the Barrington House by Jesus. He interrupts Rick while Rick is introducing him and his group to welcome them and to go wash up, remarking that he's trying to keep Hilltop clean and then retreats back into his office. He is later in his office when Maggie Greene enters and mistakes her name for "Natalie" while making introductions. Maggie then asks about the possibility of setting up a trade between Hilltop and Alexandria. However, while they are discussing this, he tries flirting with Maggie and will not listen to what she has to say. Maggie attempts to propose a trade of ammunition for food, but he keeps interrupting her, saying that he will give them food if they do labor for him, believing that 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 and then leaves his office.

When Ethan, Crystal and Andy, other members of Hilltop, return from a supply delivery to the Saviors, he approaches Ethan to ask what happened and where everyone else is. Ethan states that the others are dead, that his brother Craig is being held hostage and that Negan has a message for Gregory. When he asks about what the message is, Ethan places his hand on Gregory's shoulder, apologizes and then stabs him in the stomach. Gregory falls to the ground but is caught by Michonne while Dr. Harlan Carson rushes to his aid from his trailer as Rick's group intervenes. Abraham Ford is nearly strangled to death by Andy but Daryl Dixon rescues him and Rick stabs Ethan in the throat and kills him. Jesus calms astonished residents by pointing out Ethan 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 by ended up doing labor for 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 Seven

Gregory approaches Maggie, Jesus and Sasha Williams, confronting them about Rick's failure to wipe out the Saviors. He then tells Maggie and Sasha 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. He says that Rick's people were supposed to keep them safe, but Rick has only brought more harm. Gregory now denies any involvement with Rick and 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 disappears into his room. Gregory thanks Maggie and Sasha for saving the Hilltop but still refuses to let them stay however he offers to work something out with Sasha one-on-one with Maggie answering him to go to hell. They're interrupted by the sound vehicles arriving in the courtyard and Simon leads a large group of Saviors into Hilltop, so Gregory tells Jesus to hide Maggie and Sasha in the closet. He is then confronted by Simon into Barrington House and says they need to talk. In the study, Simon and Gregory are staring at a painting and 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 people in Hilltop probably forget about 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 they probably learned it all from the Saviors in the first place. He informs Gregory that the Saviors at the outpost were killed and asks him about cooperating with Rick and the Alexandrians taking down the outpost, but Gregory denies it. He tells Simon to tell Negan that he understands how to cross the aisle but 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 responds that there actually is. Gregory leads Simon to the 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 in liquor in Negan's truck. On his way out, Simon orders Gregory to kneel, which he does with little resistance and the Saviors then 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 allow Maggie and Sasha to stay. Jesus threatens to reveal his deal with Alexandria, stripping him of his 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 Hilltop is her home now and she says Gregory will call her by her real name: Maggie Rhee.

Gregory approaches Maggie who sits alone at the Hilltop's front gate with Eduardo and he warns her to not let her popularity with the 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's pregnant, and reluctantly gives his apple to Maggie and leaves.

Gregory is shown in his office met by Rick, Sasha, Maggie, Carl Grimes, Tara Chambler, Rosita Espinosa, Michonne, Daryl Dixon 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, saying in addition to ruling out any other connections. He is called out by Jesus for his cowardly behavior and for not helping to save Hilltop 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. He claims that his people grow things and they are not fighters. Tara insists people will step up if given a choice but Gregory stops her from finishing her sentence, though he admits they would be better off with the Saviors. Daryl calls him out for his big mouth and asks if he is on their side or not, and he makes it clear he wants nothing to do with it and has everyone leave Hilltop, pretending they never been there or had this meeting.

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 return 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 Hilltop, Gregory will come to the Savior's compound and they will take care of it. Simon also tells Gregory that Negan wants one of Hilltop's residents, Dr. Harlan Carson. In the medical trailer, Simon tells Carson that they need his services at the Sanctuary and Harlan correctly guesses that his brother, Emmett, 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 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 Carson 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 then enters the room and has Jesus leave.

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's gates. Gregory joins Maggie as she uproots the blueberry bush outside the community's walls. She asks him to keep watch while she finishes up but Gregory contemplates killing Maggie while her back is turned, however 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. 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 and studies a local road map before calling in Kal. He tells him to pack a bag and prepare to drive him somewhere.

### Season Eight

Simon greets Gregory in his holding room and Simon starts out that he came to see him but he was already away dealing with the 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 though it turns out, Gregory was going to reveal the alliance between Hilltop and the Kingdom but Simon was finding out at that point from someone in Alexandria according to Gregory.

Later, Gregory sits with Negan and his top lieutenants. He thanks them for listening to him and understands how hard it is to manage people in this environment and the "big scary u". He explains that he hates killing people but Negan tells Gregory that he likes killing people and killing the right people at the right time makes things fall into place. Negan justifies that killing one person can save a hundred, before stating 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 Hilltop who side with Rick, so Negan asks Gregory if he can exile people. Gregory then claims that he owns Hilltop and that he is still in charge there, however Negan questions it because Maggie is leading an army of his people. Gregory insists that he didn't know about Maggie until now before saying that Hilltop is his, explaining that it was a mistake that he allowed Maggie into Hilltop and that she and her people took advantage of his genorous nature. Gregory then says he sees his mistakes now and will fix it. The meeting is then interrupted by gunfire coming from outside and they step out and Gavin is disturbed upon seeing the militia.

Gregory is called outside of the Sanctuary where he states that Hilltop stands with the Saviors and threatens anyone who stands with the Militia from the Hilltop. However, the Hilltop memebers 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. However, Gregory steals Gabriel's car and escapes, abandoning Gabriel to die.

Gregory arrives at the Hilltop in the car he took from Gabriel and pleads to be let back in. 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 pleads that he doesn't know who Gabriel is and lies about finding the car empty, and arrogantly tells her that he built 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. However, he protests that he was trying to save lives but Maggie tells him the people are fighting for a better life. She calls him a coward, accuses him of looking after himself and she reveals that Kal informed them that Gregory wanted to warn Negan of the Militia's intentions to fight and Kal left him when he heard of his true plan. Kal overhears Gregory insulting him, gives him the middle finger, which Gregory called him delusional and argued over the little girl's pancakes Gregory has 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 they could win in a fight against the Saviors. He apologizes and makes a scene. After listening to his pathetic cries, she lets him, telling Enid that he isn't worth killing. Just then, Jesus' group arrives with the captured Saviors. Gregory immediately insists that 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.
Gregory and Maggie catch Jesus handing out food to the Saviors. Maggie orders him to stop giving away the Hilltop's food and Gregory suggests executing them before Maggie orders him away, so Enid escorts him in. Gregory and Maggie chat in Gregory's office, with Maggie sitting on his chair. He insists, again, that what he did with Negan was in the best interest of the community. Maggie accuses him of being scared however Gregory promises that his motives were pure and claims he can help her due to his experience as Hilltop's former leader, however she is not interested but he says he can tell her she needs someone to tell her to follow her gut. Gregory states he recognizes Maggie as the leader but they can't have "wolves" wandering amongst the "sheep". When Maggie has ordered the Saviors inside, Gregory says they shouldn't have people in Hilltop they can't trust. She agrees with him, which prompts Kal and Eduardo to put him in the same prison. Gregory is reduced to a sobbing wreck and later witnesses the exchange between Jared and Alden.

Gregory is later seen still locked in the cage with the captured Saviors. When Maggie returns, Gregory tries to talk to her about getting why she locked him in, but Maggie shuts him up. Maggie storms up to the fence and requests that Dean to 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.

## Personality

Gregory is a narcissistic, egotistical, cowardly and highly intelligent man who appeared to have enjoyed acting as a leader and having people under his control, and seemed to be a somewhat effective leader due to keeping many people alive during the apocalypse. Despite this, Gregory is a weak survivor who has cowered in the dark while others have risked their lives to protect him as he himself has not killed a single walker or human since the years in the outbreak, showing that he is completely ineffective in combat. He also allowed his people to suffer under the thumb of the Saviors, which has even cost some of his own people their lives and nearly cost him his own. He is also completely ignorant to the cruelty of the Saviors and is a completely selfish man who is only concerned about survival for himself. He is also an excellent liar, deceptive, unpredictable and deeply manipulative.

## Quotes

* "We are not letting them in! No way! With what they did, with what they do? They are monsters! This is not a sanctuary for killers. You'll be putting the safety of everyone in jeopardy!"
* "Our hippie-dippie kung fu fightin' friend may try and make you feel bad about it, but at the end of the day, you're the shepherd. And you can't have wolves wandering around amongst the sheep. It's as simple as that."
* "I know how it is...negotiating the slippery, steep terrain of managing resources and the population and the big, scary U. But you might know, it's called the unknown."
* "The Hilltop stands with Negan and the Saviors. Any resident of the Hilltop who takes up arms or supports this ultimatum against the Sanctuary or any of the Saviors, for that matter...they will no longer be welcome in the colony. Their families will be thrown out and will be left to fend for themselves. Go home now or you won't have a home to go back to!"