Gregory (TV Series)

"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 welcomed in the colony. (...) Their families will be thrown out and left to fend for themselves. (...) Go home now, or you won't have a home to go back to!"

- Gregory to The Militia

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 his disappearance.

Personality
Gregory is shown to be a narcissistic, egotistical, cowardly and highly intelligent 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.

Virginia
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.

Post-Apocalypse
At some point after the outbreak, Gregory journyed 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.

"Knots Untie"
Gregory first meets Rick Grimes's 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 Greene 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.

"Go Getters"
Gregroy 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 approches 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.

"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 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.

"Rock in the Road"
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.

"The Other Side"
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.

"Something They Need"
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. A resident 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.

"Mercy"
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.

"Monsters"
Gregory will appear in this episode.

Negan
It is shown that Gregory greatly fears Negan. Upon completion of the Hilltop's walls, the Saviors showed up and demanded half of the community's supplies in exchange they will leave the community unscathed. Gregory agreed on this and before leaving, the Saviors killed a 16 year-old boy named Rory as an example for everyone. Gregory would then send a group of supply runners every week to send half of their supplies to a nearby Saviors' outpost. Negan then takes advantage of Gregory's cowardice and begins to demand more. After some time, Gregory couldn't fulfill his needs and as a result they killed Tim and Marsha and held Craig as a prisoner. In return for his safe release, Negan orders Ethan, Craig's brother to kill Gregory and bring his head to him. At the same point, Rick Grimes and his group arrive at the Hilltop and are able to halt the situation, saving Gregory's life albeit taking a knife wound from Ethan.

Paul Rovia
During Season 6, Paul and Gregory's relationship isn't shown fully, but it is shown in Season 7 that Paul questions Gregory's leadership and threatens that he would tell the rest of the community about his deal with Alexandria. Paul greatly dislikes Gregory for his cowardly nature.

Rick Grimes
There wasn't much interaction between him and Rick and he seems he doesn't have much respect for him, since he was immediately telling him to clean himself up and that he is only communicating to him through Jesus.

In Season 7 there is a strong negative relationship between them, when Rick tries to convince him to fight the Saviors and Gregory brushes him off, for failing to take out the Saviors and he orders him to leave, pretending to not know him.

Maggie Rhee
Gregory and Maggie meet in Season 6 and Gregory seems to be impressed by her in Season 6 after she convinces him to give her and her community half of their supplies. In Season 7 there is a strong dislike between them due to the fact that Gregory doesn't call Maggie by her name, in fact he calls her Marsha, Dear and Honey, showing he doesn't care much for her and doesn't respect her. Maggie also dislikes him for being a coward and trying to sell her and Sasha out to the Saviors. Maggie punches him due to this and Gregory is shown to have taken Glenn's watch.

Sasha Williams
He seems to have some sympathy for Sasha, since he was offering her to work something out. Nevertheless he wants her to leave from the Hilltop too. When Gregory selfishless refused to help Rick fight the Saviors, Sasha told him she wants to knock his teeth out.

Simon
He met him first when Simon and some saviors came to take supplies from him. After Rick's people had killed every savior from one of the outposts, Simon is now responsible for the Hilltop and Gregory, being "his Negan". He tries to convince Simon about him not working with Rick, but Simon doesn't believe him. He later forced Gregory to kneel before him.

When Simon visits the Hilltop again, Gregory offers him a drink of Gin, but Simon declines saying he enjoys tequila and says that Negan wants one of the Hilltop residents. In exchange for taking Dr. Carson, Simon gives Gregory a crate of aspirin.

Gregory 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 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. Their relationship remains netural afterwards.

After Gregory attempts to sway the minds of the Militia to go home (which ultimately failed) Simon felt that his "investment" in Gregory was for nothing. Presumably, any relationship he had with Simon was now put to an end.

Season 6

 * "Knots Untie"

Season 7

 * "Go Getters"
 * "Hearts Still Beating"
 * "Rock in the Road"
 * "The Other Side"
 * "Something They Need"

Season 8

 * "Mercy"
 * "Monsters"

Trivia

 * 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.
 * It is revealed in "Something They Need" that Gregory hasn't killed a single zombie or human throughout the apocalypse's duration.