|This article is about the TV Series character. You may be looking for his Comic Series counterpart.|
"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.
Immediatly 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 deliveres 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 tris 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.
Gregory will appear in this Season.
This list shows the victims Gregory has killed:
- Possibly numerous counts of zombies
- The casting call name for this character was Rich.