Fed up with their forced subjugation, the people of The Hilltop rally behind Rick Grimes and his declaration of war against the Saviors with Maggie Greene succeeding Gregory as their leader.

[volume & issue needed] Like his fellow survivors, he is helpless against the Saviors and relies on Rick to help rid them of the gang.

[volume & issue needed] However, his plan is foiled by Jesus who arrives in time to save Maggie, who requests that Gregory be jailed.

[volume & issue needed] In the episode "Knots Untie", Rick's group are introduced to Gregory, who leads the Hilltop Colony and is a former businessman on the Chamber of Commerce.

Gregory immediately belittles Maggie and asserts that the Alexandrians are in great need and attempts to use their food shortage as leverage.

Later, Rick says that they came all this way for food and they're going to get it, but Jesus calls for patience as he works to convince Gregory to instead show some goodwill to Alexandria and build a relationship that could pay back in the future.

They had been sent to deliver tribute to Negan, who said that it was "light" and killed Tim and Marsha while keeping Ethan's brother Craig hostage.

Daryl offers to kill Negan, take out his boys and rescue Craig if the Hilltop provides food and medicine along with "one of them cows."

In the episode "The Other Side", after Simon and an escort of Saviors appear again in Hilltop, Gregory welcomes them with open arms and tries to find out the reason for his previous arrival.

In the episode "Something They Need", when Maggie leaves the community to dig out a blueberry bush, Gregory follows her and apologizes for his behavior towards her.

As seen in the season premiere "Mercy" and the episode "The Big Scary U," Gregory makes his way to the Satellite Outpost and from there to the Sanctuary after abandoning the Hilltop.

Gregory meets with Negan and his lieutenants and promises that he can help to bring the Hilltop back into line before the Militia arrives to attack.

Alden then approaches the two, speaking up for the rest of the Saviors and attempting to come to an agreement, suggesting that the prisoners be allowed supervised freedom every once in a while for a few minutes each.

Gregory, while grateful for her decision, is worried about an impending attack by the Saviors and implores that Maggie consider an evacuation, fearing losing the war.

In the episode "Do Not Send Us Astray," after the Savior attack, Henry visits the pen in hopes of finding out who killed his brother Benjamin and exacting revenge upon them.

In the season premiere "A New Beginning," Gregory is revealed to have called for a vote to determine who the leader of the Hilltop will be in the eighteen months since the war with the Saviors and has lost in favor of Maggie.

That night, Gregory is strung up to a newly-built gallows and sat on a horse in front of the entire Hilltop Colony as well as Rick and Michonne.

"[4] Josh Jackson of Paste commented: "Gregory is indeed a strange one, and no matter how idyllic the Hilltop seems, I don't think he’s the leader I'd want for the zombie apocalypse.

"[5] Tim Surette of TV.com commented that Gregory "wasted no time being one of the most despicable characters the series has ever introduced by drooling all over Maggie and requesting some of her "services" in exchange for some carrots.

[8] Noel Murray of Rolling Stone ranked Gregory 24th in a list of 30 best Walking Dead characters, saying, "he's made quite an impression, thanks to Xander Berkeley's gruff performance.

More inclined to defer to the strong than to take action himself, Gregory has become the show's version of a weaselly politician: pretending to be in charge but always waiting to see which way the wind is blowing before making any decisions.