Gregory (Comic Series)

"The Hilltop stands with Negan and The Saviors... If you stand against us, you will no longer be welcome. Your families will be thrown out and have to fend for themselves. Go home now, or you'll have no home to go back to."

- Gregory, being held by Negan, warning Rick and his army.

Gregory is a character first encountered in Issue 95 of Image Comics' The Walking Dead and is a resident and overseer of operations at the Hilltop Colony.

Overview
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 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.

Location Unknown
Nothing is known about Gregory's life before or as the outbreak began.

Hilltop Colony
Gregory is a resident of the Hilltop Colony. He is the leader of the large community and Gregory states that through his own hard work, he has helped make the colony's existence possible.

A Larger World
Gregory is first seen in the hotel inside the Hilltop Colony, he interrupts Paul as he is guiding Rick's group around the Hilltop, saying he wants to speak to who ever 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 Dr. 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.

Something To Fear
After the murder of Glenn, on the way back to the Hilltop, Rick informs Gregory of what had happened and then punches 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.

March To War
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.

All Out War - Part One
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, including Kal, 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 blatently 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.

Killed Victims
This list shows the victims Gregory has killed:
 * Possibly numerous counts of zombies.

Ezekiel
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.

Brianna
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.

Maggie Greene
"Oh dear...we have, haven't we. I'm sorry, you came here with that little girl. I remember now. Molly right?"

- Gregory to Maggie.

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 seems to be threatened by her.

Paul Monroe
"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.

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.)

Rick Grimes
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 (presumably) 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.

Negan
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.

Ethan
Ethan and Gregory relationship was never shown but it was assumed that it was stable before Ethan returned from his supply run.

Appearances
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Volume 20: All Out War - Part One

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Trivia

 * 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. He calls Rick "Nick" and Maggie "Molly". Later, he calls Maggie "ma'am" and claims he doesn't know who she is, in which Maggie responds her name is Maggie Greene.
 * Robert Kirkman revealed in Letter Hacks that Gregory is extremely vain and only really cares about himself.
 * In earlier copies of the issue, Gregory is identified as "Kenneth", a typo in the printing of the comics. Current copies of the issue have been corrected as it no longer says "Kenneth", but rather the actual name of this character, Gregory.