The Walking Dead Season 8 Spoilers: 10 Things You Need To Know About All Out War
9. How Gregory Fits Into Things
As Rick and co unveil their plan to the Saviours, Negan reveals what he hopes will be a trump card: Gregory.
The Hilltop leader fled to the Sanctuary, telling him of Rick's plan. He's brought out by Negan and stands in front of the crowd, denouncing the war and stating that the Hilltop stands with the Saviours, and will not take part in any such revolt.
Unfortunately for him, and much to Negan's chagrin, only 8 members of the Colony actually leave the army to side with Gregory, causing Negan to kick the leader off the roof of the Sanctuary. He then has to make his way back to Hilltop with the fellow defectors, where Maggie punches him in the face, and when he continues to go against Rick's plan she eventually becomes the proper leader of Hilltop, backed by Jesus.
We've already started to see this play out on TV. By the end of Season 7, Gregory was slinking off towards the Saviours (presumably, anyway) after Simon's pointed message about visiting him, and he's already clashed with Maggie, Jesus, and Rick on a number of occasions, showing total resistance towards any sort of fightback against Negan.
Interestingly he went off with Kal, who is one of the members of the Hilltop in Rick's army to leave and side with Gregory/Negan, so we might see a bit more of him in Season 8, as well as Maggie becoming the official leader of Hilltop, even though she basically is already. If nothing else, we should get to see her punch him in the face, which is sure to be a highlight.