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- "Did you really think I'd just let you take over forever? You stupid fucking bitch. This is my town. I built this place."
- —Gregory menacingly gloating over Maggie Greene about the leadership of the Hilltop.[src]
Gregory is a main character and an antagonist first encountered in Issue 95 of Image Comics' The Walking Dead. He is a resident of and the former overseer of operations at the Hilltop, before having his position taken by Maggie Greene. Gregory acts as the main, but overall secondary, antagonist of Volume 23: Whispers Into Screams.
Gregory is the extremely vain and self-absorbed leader of the Hilltop Colony. His cowardly 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. His most notable time 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 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.
Nothing is known about Gregory's life before or as the outbreak began. He may have lived in or near the Hilltop.
Gregory is first seen in the hotel inside the Hilltop Colony, he interrupts Paul Monroe as he is guiding Rick's group around the Hilltop, saying he wants to speak to whoever is in charge of this group. Rick is pulled out of the group by Paul and sent with Gregory, who begins to immediately ask Rick many questions. However, their talk is cut short when a Hilltop resident, Wesley, interrupts to inform Gregory of Ethan's return, telling him that something is wrong. Gregory quickly rushes outside and confronts a traumatized Ethan, who tells Gregory that David and Andy are dead, and that The Saviors have Crystal hostage. He goes on to say that they will give her back if he delivered a "message" to Gregory. Gregory demands to know what the message is and Ethan apologizes before stabbing Gregory in the abdomen. Ethan was then tackled and killed by Rick, while Harlan Carson worked to heal Gregory's bleeding.
After his near death, Gregory wishes to speak to Rick again, this time about his proposition to deal with The Saviors. Rick offers to deal with The Saviors for the Hilltop in exchange for enough supplies to help his people. Gregory tells Rick how much of a pain Negan has been to the community and accepts Rick's offer, giving Rick the supplies he needs in exchange for the termination of The Saviors and Negan.
After the murder of Glenn, by Negan, Rick arrives at the Hilltop and informs Gregory of what had happened. Gregory starts to panic about it and demands to know if Negan knows of their agreement. Rick responds by punching him in the face, accusing Gregory of withholding information about The Saviors; Gregory defends himself by saying that no one in the Hilltop actually knew that Negan had really existed and claimed that The Saviors had made him up to intimidate the people of Hilltop.
Later on, he "accidentally" walked in on Maggie Greene while she was being examined by Dr. Harlan Carson. He introduces himself and says that Carson is one of the best, telling her how the doctor had saved his life from the stab wound he received from Ethan. He is also shown to try and get to know Maggie in a more than friendly manner, much to her dismay. Later, he encounters Paul and is asked how many people would be able to volunteer and join Rick and Ezekiel's forces in fighting against Negan. Gregory baulks at the idea, claiming that the deal set up between them and Alexandria Safe-Zone was off when Rick told them how merciless Negan was in killing Glenn.
Later on back at the Hilltop, it's shown that Paul went behind Gregory's back and began to round up people to join the fight against the Saviors. Gregory continues to remind Paul how uneasy he feels about this, but, Paul tells him that for all he knows, they defected. When Paul reminds him that if he had thought about the welfare of others over himself, Gregory takes offense and claims that his cautious nature was what prevented things from getting worse; he also says that HE was the one who's kept Negan at bay and that he isn't scared of The Saviors.
Sometime after this, Gregory snuck out to warn Negan of the attack, because he was terrified of the idea of going against Negan. When Rick, Paul, and Ezekiel arrive to the Saviors base with their army, Negan reveals Gregory and claims that the Hilltop's allegiance is with the Saviors and that anyone from the Hilltop who participates in the fight will be thrown out and will have to fend for themselves.
After this announcement, eight men leave Rick's militia. They apologize, but, nothing is held against them. Negan becomes furious that only eight men left after being told that the Hilltop's forces make up half of Rick's militia. Gregory apologizes and states that he didn't know the actual numbers. Negan then calls him pathetic as he kicks the man over the ledge and off the roof they are standing on.
Gregory returns to the Hilltop along with the eight who left and demands for Carson. When asked what happened, he claims that they walked the entire distance and his heart is racing; Kal corrects him saying that they actually drove most of the way back. Maggie asks if Negan is dead and if the war is over, but, Gregory feigns innocence and asks her if she knew about Rick and Paul's plan the whole time. Maggie talks back to him and questions why he's acting if he doesn't know, making Gregory angry and incredulously asks "who are you to talk to me like this?!" He goes on to say that what Paul did is to trick the Hilltop members into a suicide mission and claims that he saved the lives of those who came back with him, as well as smooth things over with Negan once more. Furious, Maggie questions why he sided with Negan, but, Gregory attempts to leave, stating that he laid his life on the line to save others and that he "won't take this from you!".
Maggie blatantly says that what Gregory's done is merely to save himself, but Gregory places the blame entirely on Rick, saying that Negan is reasonable and what Rick's doing is "tearing what we've built apart." Maggie punches him in the face, reminding him that Negan killed her husband, Glenn. Gregory tries to calm her down, calling her "ma'am", leading Maggie to lash out at him even further. When Maggie tries to rally the rest of the Hilltop to rebel against Negan, Gregory tries to interject, but, Maggie tells him to shut up.
After Maggie rallies the Hilltop residents and guards into fighting against Negan, they appoint her as the new leader of Hilltop, replacing Gregory and relegating him to a normal resident of the colony. As The Saviors attack the Hilltop Colony, he hurries out and helps Carl carry Rick inside the mansion, after Nicholas drops him when he was slashed on the back.
It is revealed by Maggie when talking to Rick that Gregory is still alive and living in the Hilltop. Maggie also states that he is still as ignorant as ever, and has not changed his ways.
After Dante's group goes missing, he insists that Maggie do something about it, to the point of offering to go find them himself. It is obvious, however, that he is bluffing. He's later seen with the two bullies' families, and proposes to kill Maggie due to her bad leadership. At first, the two families disagree. But later, while Gregory is in his trailer reading a book, Morton approaches him and concurs on killing Maggie and Carl Grimes.
Later, when one of the bullies wakes up, Gregory calms down the arguing parents and Maggie. He invites Maggie to his trailer to discuss the plans. Unbeknownst to her, he poisons her wine and she quickly succumbs and falls to the ground. As he stands above her triumphantly, Jesus appears at the door and witnesses what has just happened. Jesus kicks him back and lifts up the weak but still alive Maggie. He sets her down and is prepared to kill Gregory should anything happen to her, but Maggie protests and requests he be jailed instead.
A still imprisoned Gregory continues to protest his incarceration, despite Carson recognizing that the drugs stolen from his offices used to poison her were found in his trailer. With the influence of Jesus' and Tammy's words to her, Maggie later arrives (albeit reluctantly) to the conclusion that there is only one way to guarantee the safety of herself and her people: killing Gregory. Gregory is later hanged in a tree for all residents to see.
This list shows the victims Gregory has killed:
- Possibly numerous counts of zombies
After attempting to poison Maggie, she has him thrown in Hilltop's jail and later decided to have him killed. Presumably all of Hilltop witnessed the hanging.
- "Ezekiel is crazy. We can't trust someone so arrogant. Never liked him."
- —Gregory to Paul[src]
Ezekiel is shown to not care for Gregory too much, going so far as to call him a coward. According to Ezekiel, the Hilltop leader has more residents living there than all the other colonies combined and would be able to attack the Saviors, but, instead he spends his time in his house trying to hide the fact that he is too scared to stand up to them.
- "I think Gregory's sweet on you. He's sweet on every girl before they go tell him to fuck himself. Guy's a creep."
- —Brianna to Maggie[src]
Brianna doesn't like Gregory and thinks he is a creep for flirting with the women in the Hilltop. It is likely he tried to flirt with her sometime in the past.
- "I don't mean to offend, but that's just not acceptable. If you're going to lead these people, you need to recognize you have an obligation to keep them safe. "
- —Gregory to Maggie regarding Dante's patrol[src]
Gregory tried to get to know Maggie in a more-than-friendly manner, much to her dismay. After learning his position during the war between Rick's forces and the Saviors, Maggie called him a "selfish coward" outright. Gregory appears to be threatened by her. As of the end of All-Out War, Maggie fully usurped leadership from him, leaving Gregory to work for her, but he appears to continue questioning and challenging her abilities. During Volume 23, Gregory begins to persuade Tammy and her husband to rebel against Maggie and kill her, taking the leadership of the Hilltop. In Issue 137, Gregory leads Maggie into his trailer and poisons her wine, gloating over her as she passes out. This action ultimately seals his fate, as not only did he not poison her correctly and she never lost consciousness, but Paul Monroe caught him in the act.
- "Don't mistake my caution for cowardice. I'm not scared of Negan or anyone. I took a knife for these people! You want to see the scar? Where's your scar, Jesus?"
- —Gregory to Paul[src]
Initially, Paul seemed to be split on Gregory's methods. Although he thinks Gregory is suitable as a leader, he agrees that he is not the ideal man to face confrontations. When Paul comes to Gregory about rustling up the most able-bodied members of the Hilltop to help Rick fight the Saviors, Paul is shown to be disgusted by Gregory's extreme reluctance to help, the latter using Glenn's brutal death as an excuse to back out of the deal between the Hilltop and Alexandria. Their relationship is shown to have taken a severe blow when Paul brings up the fact that Gregory is scared of risking his life, which the latter firmly denies (although Paul's claim later turns out to be true.)
- "This "Rick" character is tearing what we've built apart. Negan is not a madman."
- —Gregory to Maggie[src]
Gregory seems to value having Rick and his group around, possibly feeling safer from the Saviors. He is also shown to have a moderate amount of respect for Rick, though he is unsure of Rick's overall plan on fighting the Saviors (and surviving.) The relationship between the two is severed when it's shown that Gregory sided with the Saviors instead of Rick and the other fighters. Gregory blames Rick for the arising conflicts.
- "The Hilltop stands with Negan and the Saviors... if you stand against us now, you will no longer be welcome."
- —Gregory to Rick's forces[src]
Gregory is shown to be terrified of Negan and his group, to the point where he avoids any confrontation as possible between The Saviors and the Hilltop. Eventually (despite what he told Paul), Gregory pledges allegiance with the Saviors against the survivors.
- Robert Kirkman revealed in Letter Hacks that Gregory is extremely vain and only really cares about himself. He also says that Gregory is a braggart, and even seems to believe his own lies.
- According to Jesus, Maggie, and Brianna, most of the residents of Hilltop Colony think that he isn't competent for being the leader.
- Gregory seems to be awful at remembering names and characteristics of his people. He calls Rick "Nick" and Maggie "Molly". Later, he calls Maggie "ma'am" and claims he doesn't know who she is. Kirkman mentioned that the ongoing joke about Gregory forgetting the names shows how much of a "shitty person" he is.
- In earlier copies of Issue 93, Gregory is identified 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.