|This article is about the TV Series character. You may be looking for his Comic Series or Road To Survival counterparts.|
"Narcissistic, egotistical, quick to braggadocio and anger, his own skin is his principal concern. He feeds off the superiority of being in control, but he plays it off with Senator-like charm. He’s vibrant, and has the charisma of a car salesman."
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.
At some point after the outbreak, Gregory journyed 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.
Gregory first meets Rick Grimes's group when they first arrive at the Hilltop after they are shown into the Barrington House by Jesus. He interrupts Rick while Rick is introducing him and his group to welcome them and to tell them to go wash up, remarking that he's trying to keep Hilltop clean, and then retreats back into his office.
He is in his office later when Maggie Greene enters and mistakes her for a "Natalie" while making introductions. Maggie then asks about the possibility of setting up a trade between the Hilltop and Alexandria. However, while they are discussing this, he tries flirting with Maggie and will not listen to what she has to say. Maggie tries to propose a trade of ammunition for food, but he keeps interrupting her, saying that he will give them food if they do labor for him, believing that Rick's group has nothing despite Maggie repeatedly saying otherwise. He becomes flirtatious with Maggie again when she interrupts him, getting more frustrated, and states that the groups will help each other. At this point he abruptly ends the conversation, bids goodbye, then leaves his office.
When Ethan, Crystal, and Andy, other members of the Hilltop, 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, that his brother Craig is being held hostage, and that Negan has a message for Gregory. When he asks what the message is, Ethan places a hand on Gregory's shoulder, says he is sorry, and then stabs him in the stomach. Gregory falls the ground but is caught by Michonne while the community's doctor, Harlan 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 in exchange 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.
He is first seen talking to Maggie, Sasha and Jesus, confronting them about Ricks failure to wipe out the saviors. Then he tells Maggie and Sasha to burn Glenn and Abraham’s bodies and orders them to leave The Hilltop by morning. Gregory tells Jesus that if they leave, he has plausible deniability, and The Saviors won’t think they colluded to take down their outpost.
During the saviors' attack, drawing zombies with music inside the walls, Gregory is just watching and disappearing in his room.
Gregory thanks Maggie and Sasha for saving The Hilltop but still refuses to let them stay. He slyly offers to work something out with Sasha one-on-one with Maggie answering him “Go to hell”. They’re interrupted by the sound vehicles arriving in the courtyard. He then tells Jesus to hide Sasha and Maggie in the closet.
He is then confronted by Simon about him cooperating with Rick and the people of Alexandria taking down the outpost, but Gregory is denying that. Simon says he’ll be his new liaison and asks if there’s anything Gregory wants to tell him. “Actually, there is,” he responds.
He leads Simon to the foyer closet and opens it with the intention of handing over Maggie and Sasha. Instead, he finds boxes of scotch. Simon says Negan will be pleased and orders a nearby Savior to put the liquor in Negan's truck. On his way out, Simon orders Gregory to kneel, which he does with little resistance. The Saviors leave.
After Jesus released Maggie and Sasha from Gregory's closet, he yells at Jesus for hiding them there instead of the foyer closet. Jesus stands up to him and forces him to let Maggie and Sasha stay. Jesus threatens to reveal his deal with Alexandria, stripping him of his plausible deniability. Suddenly, Maggie punches him in the face, reaches into his pocket and takes Glenn’s watch, which he stole from the grave.
Gregory approaches Maggie sits alone at her post at the Hilltop’s front gate with Eduardo. He warns her not to let her popularity with Hilltop residents get to her head. Maggie asks if Gregory is gonna eat his apples, he says yes, but Eduardo berates him telling him Maggie's pregnant, and reluctantly gives his apple to Maggie and leaves.
This list shows the victims Gregory has killed:
- Possibly numerous counts of zombies
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.
During Season 6 is isn't shown fully Paul's and Gregory's relationship, 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.
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.
Gregory and Maggie meet in Season 6 and Gregory seems to be impressed by her in Season 6 after she convincing 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 her calls her Marsha, Dear and Honey. Maggie punches him due to this and Gregory is shown to have taken Glenn's watch.
He seems to have some sympathy for Sasha, since he was was offering her to work something out. Nevertheless he wants her to leave from the Hilltop too.
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 outpost, 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.
- 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.