#1. Just how slimy is Gregory?
Coming into this episode, fans knew that Gregory was a liar and a coward. The way he handled himself with Rick’s group, as well as every single interaction with Maggie, cemented that he’s not a good guy.
It was revealed in an earlier episode that Gregory was at The Sanctuary when the people from Alexandria, The Hilltop, and The Kingdom executed their assault on Negan’s home, but why he was there and what he was doing is still up for debate.
The hope was that Gregory would actually be doing what he said he was going to do: get Dr. Carsen back for The Hilltop to help Maggie and the Community after he was taken by Simon and The Saviors.
It turns out that Gregory revealed that the power dynamic was shifting at The Hilltop and he wanted to be on the winning side. Offering the help of the people of the community, to fight against Rick’s group…even though he knew that wasn’t a real possibility.