Gregory

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".

Overview
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 is 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.

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 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.

Death
Killed By 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.
 * Himself (Indirectly Caused)
 * Earl Sutton (Indirectly Caused)
 * Maggie Rhee (Caused)
 * Daryl Dixon

He is presumably put down before he can reanimate afterwards, likely by Daryl as he was the one to cut him down.

Killed Victims
This list shows the victims Gregory has killed:
 * Himself (Indirectly Caused)

Relationships
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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. Gregory threatens to kick Paul out of the Hilltop on numerous occasions when Paul sides with Maggie and Sasha over him. Gregory eventually says to Paul that they are not friends, showing their lack of a relationship.

Kal
Kal and Gregory were not shown to interact much but it was strongly inferred that Kal is among Gregory's right hand men. When Gregory returns to the Hilltop after trying to sell them out to Negan, it is revealed by Maggie Rhee that he told Kal about his plans to betray the Hilltop to Negan and the Saviors, which resulted in Kal leaving him behind after the shootout, Kal then gives Gregory the middle finger after he calls Kal delusional, not knowing he was on top of the gate. In "The King, the Widow, and Rick", Kal and Eduardo drag him into a makeshift prison with a bunch of saviors captured by Paul Roviaand Morgan Jones, but not before Gregory tries unsuccessfully in vain to escape before getting thrown against the barbwire by Eduardo.

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 neutral 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.

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.

Maggie Rhee
Gregory and Maggie meet in Season 6 and Gregory seems to be impressed by her 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, Maggie takes it back. Maggie eventually usurped his leadership of the Hilltop, which angers Gregory. He goes to the Saviors to rat Maggie and the others out, but is too late.

When he arrives at the Hilltop after the attack on the Sanctuary, Maggie shows him mercy by allowing him back inside the Hilltop, saying that he wasn't worth killing.

Later, Gregory is thrown in the prison with the other Savior prisoners due to Maggie not being able to trust him because of his deceptive and cowardly behavior.

Eighteen months after the war with the Saviors, Gregory has lost an election for leader of Hilltop to Maggie and is bitter about it. Gregory attempts to get Maggie assassinated and then to kill her personally, both of which fail. As a result, Maggie executes Gregory by hanging to prevent such a thing from happening again.

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.

Rick was present at Gregory's execution, and after that, Rick does not feel upset or sad about Gregory's death.

Sasha Williams
Upon first interacting with Sasha, Gregory thought that she was one of his people. When he learned that she was with Maggie, he wanted them both to leave the Hilltop because of his cowardly nature. He offers to let Maggie and Sasha stay if she were to meet with him in private, which demonstrated his pervertedness. When Gregory selfishly refused to help Rick fight the Saviors, Sasha said she wanted to knock his teeth out. Sasha believed that Maggie was the future of the Hilltop, and believed Maggie should be the leader over Gregory.

Gabriel Stokes
Due to not being a member of the Hilltop, Gabriel and Gregory don't interact much. In "Mercy", Gabriel drives back to sanctuary to save Gregory from a horde of walker after he was left to die by Kal and the Saviors, but Gregory betrays him and drives off in his car, leaving Gabriel behind and eventually locked up in a caravan with Negan for several days. While they haven't crossed paths since, it can be assumed that any respect Gabriel had for Gregory is long gone.
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Appearances
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Season 6

 * "Knots Untie"
 * "Last Day on Earth"

Season 7

 * "The Day Will Come When You Won't Be"
 * "Go Getters"
 * "Hearts Still Beating"
 * "Rock in the Road"
 * "The Other Side"
 * "Something They Need"
 * "The First Day of the Rest of Your Life"

Season 8

 * "Mercy"
 * "Monsters"
 * "The Big Scary U" (Flashback)
 * "The King, the Widow, and Rick"
 * "How It's Gotta Be"
 * "Dead or Alive Or"
 * "Do Not Send Us Astray"
 * "Worth"

Season 9

 * "A New Beginning"
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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.
 * 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 revealed 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.[1]
 * Gregory is the first main character to die in a season premiere.


 * 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.