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 the army of survivors.

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

Location Unknown
Nothing is known about Gregory's life prior to the outbreak 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.

Gregory was stabbed in the abdomen by Ethan, but was brought inside and nursed back to health by Dr. Harlan Carson. As Rick tackled Ethan and cut his throat, everyone in Hilltop watched in horror.

Gregory survived and was recovering when he wanted to speak to Rick about The Saviors and Negan. After hearing Rick's proposal to fight off The Saviors in exchange for supplies, Gregory agrees to the arrangement.

After the killing 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.

Later on, he accidently 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 balks 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.

The War Begins
Sometime after this (possibly in retaliation of what happened at Alexandria), Negan had Gregory kidnapped by the Saviors and held inside their base. 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.

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.

Paul Monroe
"Don't mistake my caution for cowardice. I'm not scared of Negan or anyone. I took a kinfe 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.

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 after being kidnapped (and 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

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Trivia

 * According to Jesus, Maggie and Brianna, many residents of Hilltop Colony think that he isn't competent for being the leader. Brianna even calls him a 'creep'.
 * Gregory seems to be awful in remembering names. He calls Rick "Nick" and Maggie "Molly".
 * 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.