Good question.
Also where is he is going? Does what happened with Maggie have anything to do with him deciding to go there?

 

I think he is planning to visit Simon. He took out that little piece of paper (that Simon wrote down the contact address) and had it on the desk just before he tool out a map.
What happened out there with Maggie further confirms to Gregory that his leadership position is slipping away to Maggie (eg his inability to kill a walker, the dialogue between the patrol team and Maggie) and so he decides to get Simon to do the dirty job of removing Maggie for him.

 

I wondered if it was Simon . What made me have doubts about it was Gregory saying to pack an overnight bag . How far away does Simon live do you think ? If it is relatively close, why does Gregory want to stay overnight? I dont know.

 

I guess Simon's base (a saviours outpost) is quite far. My rationale: Gregory needs a map in order to locate that 'town'. I suppose he is a locale and should know most, if not all, towns nearby and should not need a map to look it up (or to find a route to reach there). Or, maybe, he does not expect Simon to respond to his plea and accompanies him back to the Hilltop on the same day (thus, spending a night there)?

 

I assume he was planning on staying the night, so he wouldn't be at the hilltop when Simon and company arrived to get Maggie.

 

They are going to drink tequila together, and the driver probably gets something to drink too, obv Gregory adheres to 'Don't drink and drive. ' That's why they are staying overnight, the hang over they will have.

 

I think that's exactly what he is doing. He knows Maggie will supplant his ass as the leader of that community. He contemplated on killing Maggie but he couldn't kill a walker without her saving him. After her saving his lowsy hyde you'd think he'd look at Maggie differently. But with the citizens witnessing that, he will probably be more determined to get rid of her. Which is why I think he will slither his way to Simon.

 

Just my thought, I think Maggie's comments to the group walking by were meant to cover the fact that she killed the walker and not Gregory. To me it seemed that she gave the impression that Gregory had killed it in order for him to keep respect with the group.

 

My guess is that he told his cronie to pack an overnight bag because he knows that once he gives up Maggie, and essentially the Hillside, Gregory knows they won't be able to come back.

 

The only reason he didn't kill Maggie is because he lacks beach-ball size balls. I thought that was clear as immediately after he couldn't even do it to the walker.

 

Somebody on the good side is going to have to take that weasel out.

 

You know, I thought Gregory took out a map of Argentina, and I was wondering how he planned on getting there and why he thought Cal would agree to accompany Gregory to South America! I guess I need to re-watch that scene.

 

Were you drinking tequila or gin at the time?

 

Gregory is the embodiment of me in school right now.