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- "What you're doing isn't right. Somebody stop this, please. Killing me in the dead of night, because you're ashamed [...] Stop this! Please! For the love of God, stop it! Wait!"
- —Gregory's last words before being hanged.[src]
Gregory is a main character and later an antagonist as well as a survivor of the outbreak in AMC's The Walking Dead. He was the leader of the Hilltop Colony, before Maggie stepped in after he sided with the Saviors. He serves as an antagonist of the whole of Season 8 and the primary antagonist of the episode "A New Beginning".
Gregory is shown to be a narcissistic, egotistical, and cowardly man. He appeared to have enjoyed being the leader of the Hilltop and having everyone 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 revealed that he has killed not a single walker or human in the years since the zombie outbreak, showing that he is completely ineffective in combat. He has 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. Even after Negan ordered his own death, he still refuses to aid Rick and his group in fighting them and remains subservient to them fully, showing that he is completely ignorant to the cruelty of the Saviors.
Gregory is shown to be completely selfish as well and is only concerned about survival for himself as he leaves Gabriel behind following the attack on the Sanctuary even after the latter stopped and came back to rescue him. He's also an excellent liar: deceptive, unpredictable and deeply manipulative.
By the start of Season 9, Gregory is shown to be angered at losing his leadership over the Hilltop and is shown to have become even more unscrupulous and cruel as he attempts to use the grieving Earl to assassinate Maggie in order to reclaim his leadership position - claiming Maggie is a terrible leader who does not care for the people who die while attempting to fill out Rick's demands, ironically paralleling his own actions while leader of the Hilltop when attempting to fill out demands for Negan; this further exemplifies Gregory's arrogance and hypocrisy, which unfortunately proves to be his undoing when his assassination attempt fails miserably. He dies a selfish, horrible coward and meets a humiliating death at the hands of the woman who stripped him of the power he never deserved to hold over the Hilltop.
Nothing is known regarding Gregory's life prior to the outbreak, although it can be assumed that, judging by his apparel, Gregory may had been a businessman of some kind. He also visited the Barrington House at one point in his life.
At some point after the outbreak, Gregory journeyed to a supposed safe-zone put up by the FEMA named 'The Hilltop Colony', where, through his aid 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, and they decided to prove that they were dangerous 'right off the bat' by killing a 16-year-old boy called Rory. Then, Gregory was personally interrogated by the invaders, which Gregory soon learned had been dispatched on behalf of their leader, an individual only known as "Negan". Gregory was forcibly subdued into allowing half of the Hilltop's supplies to be taken 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.
Gregory first meets Rick Grimes' group when they first arrive at the Hilltop 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 tell them to go wash up, remarking that he's trying to keep Hilltop clean, and then retreats back into his office.
He is in his office later when Maggie Rhee enters and mistakes her for a "Natalie" while making introductions. Maggie then asks about the possibility of setting up a trade between the 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 tries 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, then leaves his office.
When Ethan, Crystal, and Andy, other members of the 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 what the message is, Ethan places a hand on Gregory's shoulder, says he is sorry, and then stabs him in the stomach. Gregory falls 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 rescues Abraham. Rick stabs Ethan dead. 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 that they 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.
Gregory is first seen approaching to Maggie, Sasha and Jesus, confronting them about Rick's failure to wipe out the Saviors. Then he tells Maggie and Sasha to burn Glenn and Abraham's bodies and orders them to leave the 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, plausible liability. 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 zombies 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 answering him "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 then confronted by Simon into 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 the 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 their asses off last night to provide him with an example.
Simon says 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 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 about him cooperating with Rick and the people of 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. "Actually, there is," he responds.
He 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 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 of power if they don't stay. Gregory reluctantly agrees, and approaches to 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 this is her home now, and she says Gregory will call her by her real name, Maggie Rhee.
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 gonna 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, Maggie, Sasha, Carl, Michonne, Tara, Rosita, 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. "We aren't trade partners," he says in addition to ruling out any 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. 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 "you either with us or you ain't", and he makes it clear he wants nothing to do with it and has everyone leave the 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. Suddenly, Simon and his men returned to the Hilltop Colony.
Gregory greets the Saviors in his foyer. Simon spends some time with Gregory and they both agreed that if there is any trouble in the 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 the Hilltop residents, Dr. Harlan Carson. In the medical trailer, Simon tells Dr. Carson that they need his services at the Sanctuary. 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 to 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 Dr. Carson. 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 him 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 enters and has Jesus leave.
At the Hilltop, Gregory observes Maggie and Eduardo's interaction. He overhears Eduardo refer to Maggie as "boss lady," 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 his 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. 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. He tells him to pack a bag and prepare to drive him somewhere.
When the Militia arrives at the Saviors' compound, Gregory is called outside where he states that the Hilltop stands with the Saviors and threatens anyone who stands with the Militia from the Hilltop. However, the Hilltop members 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 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.
Gregory arrives to the Hilltop in the car he took from Gabriel at the Sanctuary. He 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 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 the people are fighting for a better life. She calls him a coward, accuses him of looking after himself ans she reveals that Kal told 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 in, 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.
In a flashback, Simon greets Gregory in his holding room. Simon starts out. "You came to see me. Though I was already away dealing with that rank betrayal which was unknown to you." 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 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 according to Gregory.
Later, Gregory sits with the Saviors and Negan. He thanks them for listening to him. He understands how hard it is to manage people in this environment and "the big scary u". He explains that he hates killing people. Negan tells Gregory he likes killing people and killing the right people and the right time makes things fall into place. "You kill one and you could be saving hundreds more," Negan tells him. "We 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. "Can you exile people?" Negan asks.
"Hilltop is my house," Gregory said. He claims he's still "the guy" there. Negan questions it, though, because Maggie is leading an army of his people. Gregory insists he didn't know about Maggie until now. "The Hilltop is mine," Gregory said. "I let a fox into my hen house. She and her people took advantage of my generous nature. I see that now and I will fix it." The meeting is interrupted by gunfire coming from outside. They step out and Gavin is disturbed upon seeing the militia. The events of Mercy then take place.
Gregory and Maggie catch Jesus handing out food to the Saviors. Maggie orders him to stop giving away the Hilltop's food. Gregory suggests killing them but Maggie orders him away. 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. "My motives were pure," he promises. "I've sat in that chair. I can help. I'm already in the room." She is not interested but he says he can tell her she needs someone to tell her to follow her gut. "You're the shepherd," he said. "You can't have wolves wandering around amongst the sheep."
When Maggie has ordered the Saviors inside, Gregory says they shouldn't have people at the Hilltop who they can't trust. She agrees with him, which prompts Eduardo and Kal to put him in the same prison. Gregory is reduced to a sobbing wreck. Gregory later silently witnesses the exchange between Jared and Alden.
Gregory is still in the cage he is locked in with the captured Saviors. When Maggie gets back, 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 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.
Gregory speaks to Maggie through the barb-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 the Saviors and Gregory.
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.
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 in 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 he doesn't know any of the Saviors. Henry questions Gregory why he is a prisoner if he isn't a Savior.
Later, he 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 attacks one of the prisoners, allowing Jared to push Henry over and take his weapon, leading the other prisoners away. Gregory escapes with them as well.
Gregory is revealed to have gone straight to the Sanctuary after fleeing the Hilltop and tries to suck up to Simon and stands up to him which actually changes Simon's mind about killing him. He is spared during Simon's exposure and later tries to sneak away during the fight between Negan and Simon, but Dwight gives him the plans to warn Rick and gives him keys to a car so he can leave. Later, he arrives back at Hilltop and despite giving them the map to warn them of the attack he is placed back in the cell now alone.
When the Saviors attack 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.
During the year and a half that passed since the end of the war, Gregory called for an election at the Hilltop and lost, making Maggie the rightful leader. This left him spiteful and jealous, though he tried to move on and prove to be a changed man.
At Hilltop, Gregory gives a speech at Ken's funeral. He tells Jesus he is grateful for what he has. Gregory approaches Tammy and Earl with a bottle of whiskey. She drinks herself to sleep, leaving Earl and Gregory to talk, with Gregory breaking Earl's non-drinking policy and taking advantage of him. Through some cunning words, Gregory suggests to Earl that Maggie does not have to be in charge of Hilltop anymore.
Later, Gregory runs into Maggie, who takes Hershel out for a stroll and tells her someone may have defaced Glenn's grave. Upset, she rushes towards the grave and is attacked by a hooded stranger, who also knocks over Hershel's stroller. Enid intervenes but gets pushed to the ground hard and is knocked out. Alden and Cyndie grab the assailant and Maggie rips off his hood to reveal a drunken Earl.
Maggie rushes over to Gregory's place and accuses him of trying to get her killed. He angrily reminds her that he built this place and tries to stab her with a knife, but she overpowers him and holds it to his neck.
The next day, at night, the residents gather around the new built gallows as Maggie explains to her people that the punishment fits the crime. She looks on at Gregory, who has a noose around his neck and is sitting on a horse. Gregory pleads with her not to kill him. A couple of kids show up and Michonne yells for Maggie to stop, but it’s too late as Daryl smacks the horse and it rides off - leaving Gregory to hang to death to everyone's shock.
Gregory's body swings from the structure as he dies. Maggie then orders Daryl to cut off the noose, making his body fall to the ground.
After Gregory tries to have Maggie killed by Earl Sutton and then himself, Maggie decides to execute him as punishment in order to prevent this from happening again.
Despite Gregory's pleas, he is strung up to a newly-built gallows with a horse under him keeping him aloft. On Maggie's order, Daryl sends the horse away, hanging Gregory to death.
He is presumably put down before he can reanimate afterwards, likely by Daryl as he was the one to cut him down.
This list shows the victims Gregory has killed:
- Himself (Indirectly Caused)
- The casting call name for this character was "Rich".
- "Rich" is one of the names Gregory mistakes Rick for. Gregory also mistakes Maggie's names in a few occasions, similarly to his graphic novel counterpart, who also had problems remembering people's names. Robert Kirkman commented on this saying it was a way to show that Gregory ultimately doesn't care about anyone other than himself, not even bothering learning people's names.
- Gregory is the second character to go from being a group leader to an antagonist, the first being Shane Walsh.
- It is revealed in "Something They Need" that Gregory hasn't killed a single walker or human throughout the apocalypse's duration. Ultimately, the only death he causes is his own.
- Gregory's last name was said to be "Monroe" on the official Skybound website. This was most likely an error, given that his last name has never been mentioned in the show or comics and there is already a Monroe Family in the series that resides in Alexandria.
- Gregory didn't appear in any season finales during his time on the show. He is the second main character on the show to not appear in three consecutive finales. The first being Merle Dixon.
- Gregory is the second main character to die in a season premiere. The first being Glenn Rhee.
- Gregory is the seventh series regular to die while being credited under "Also Starring", the first being Gareth, the second being Bob Stookey, the third being Deanna Monroe, the fourth being Jessie Anderson, the fifth being Spencer Monroe, and the sixth being Simon.