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Gregory is a fictional character and recurring antagonist in The Walking Dead.
He is the leader of the Hilltop Colony and a survivor of the outbreak whose cowardly, selfish nature makes him an antagonistic character towards the series's protagonist, Rick Grimes, and the Alexandrians, particularly Hilltop's would-be-appointed leader, Maggie Greene. This is further proven when he himself is secretly revealed to be conspiring with Rick's archenemy, Negan, and his faction, The Saviors, against the Alexandrians.
In the comics, he serves as the secondary antagonist of Volume 23: Whispers Into Screams. In the TV show, he serves as a supporting antagonist in Season 8 and later becomes the main antagonist of the Season 9 premiere.
Gregory is extremely vain, arrogant, and self-absorbed. He is the selfish leader of the Hilltop Colony. His vanity and arrogance is evident in his rude habit of forgetting and misremembering many people's names. His cowardly and pusillanimous nature is known by many people at the Hilltop, yet they still believe him to be the best leader they have. Gregory refuses to believe himself a coward, saying his actions keep the people of Hilltop safe and that every decision he makes is for the good of the Colony, when they are rather for his own well-being.
He also tends to crack easily in tense situations. He starts to panic and cry when Rick Grimes tells him that he could not stop the Saviors and immediately asks if Rick told Negan about their deal, worrying about his own life, rather than even feeling sorrow for Glenn's death. He is content with the Hilltop living under the subjugation of the Saviors if his safety can be ensured. His most notable act of cowardice is when he betrays Rick and Ezekiel's alliance and plans to The Saviors, in exchange for the Hilltop's safety and more so, his safety. He later explains these actions to Maggie Greene, saying that they saved the Hilltop and that Rick Grimes is tearing down what he built, going on to say that he believes Negan can be reasonable.
Another noticeable trait of Gregory's is his flirtatious and sleazy nature around women. He goes out of his way to "accidentally" bump into attractive women like Maggie Greene and flirt with them. However, he is generally rejected and many of the Hilltop's women see into his true nature and want nothing to do with him.
Following the timeskip, Gregory continues to be a nuisance to the Hilltop community. Even more villainous aspects of Gregory's personality are revealed when his jealousy of Maggie compels him to make a failed attempt on her life, resulting in his execution.
War with the Saviors
Gregory played a big part in Rick's war with the Saviors acting as an advisor to Negan.
2 Years Later
Gregory is reduced to a citizen since Maggie became the leader of the Hilltop. After Dante's group goes missing, he insists that Maggie do something about it, even saying that he'll do it himself. But she ignores him, as he was obviously bluffing. He is later seen persuading 2 families to help him kill Maggie, but they decline. However, one of the fathers, Morton, comes to Gregory's trailer and tells him they agree, and want Gregory to kill Carl. Gregory then poisons Maggie's drink but it doesn't work. At that moment, Jesus sees what Gregory's done and beats him up. Gregory is then locked up in a cell. Gregory is later hung.
Gregory first meets Rick's group after they first arrive in hilltop once they enter Barrington House with Jesus. He interrupts Rick while Rick is introducing him and his group to welcome then and to tell them to go wash up, remarking that he's trying to keep Hilltop clean, then he retreats back into his office.
While in his office later Maggie enters, and after getting her name wrong, and introducing himself to her. Maggie then asks about the possibility of setting up a trade between The Hilltop and Alexandrea, however while they are discussing this, he tries flirting with Maggie and wont listen to what she has to say. While Maggie is trying to propose a trade of ammunition for food, he keeps interrupting her saying he will give them food, if they do labor for him, thinking that Ricks group has nothing despite Maggie repeatably saying otherwise. He starts to get flirty with Maggie again when she interrupts him, starting to get pissed, states that the groups will help each-other, after which he abruptly ends the conversation, says bye, then leaves his office.
When Ethan, Crystal, and Andy 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, and Craig is being held hostage, and that Negan has a message for Gregory. When he asks what the message is, Ethan says hes sorry, then stabs him, he then falls the ground but is caught by Michonne while Carson rushes to his aid from his trailer as Rick tackles Ethan.
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 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 Hilltops supplies, to which he reluctantly agrees.
- According to Jesus, Maggie and Brianna, most of the residents of the Hilltop think that he isn't competent for being the leader.
- Robert Kirkman stated in Letter Hacks that Gregory is extremely vain and only really cares about himself. He also says that Gregory is a braggart and even believes in his own lies.
- Kirkman mentioned that there's also an ongoing joke about Gregory forgetting the names which shows how much of a "shitty person" he is. For example, he calls Rick "Nick" and Maggie "Molly". Later, he calls claims he doesn't know who Maggie is.
- In the app The Walking Dead: Road to Survival, Gregory is given a rush attack named "Selfish Heal" as a homage to his personality in the comics.
- In earlier copies of Issue 93, Jesus introduces Gregory as "Kenneth", a typographical error made in the printing of the comic. Current copies of the issue have been corrected as it no longer says "Kenneth", but rather the actual name of this character.
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