Will Gregory Keep Their Secrets?
Rick would be a fool to trust Gregory. Gregory is going to do whatever is going to benefit him the most. He doesn’t particularly care about Hilltop, except for what it gives him. But he does care about saving his own neck. He would cheerfully betray Rick, Daryl and Maggie to Negan if it would benefit him.
To be fair Gregory’s lack of trust in the survivors is justified. He did give them half of all the supplies that Hilltop had. Rick promised to wipe out the Saviors and he didn’t. So Hilltop gave Alexandria half their supplies then still had to give more to the Saviors.
Now Hilltop is harboring a fugitive and hiding Maggie and Sasha as well. Rick didn’t keep up his end of the bargain last time so Gregory isn’t going to put much stock in Rick’s promises now. Speeches aren’t going to keep the Saviors from attacking Hilltop if they find out about the survivors there.
If Rick wants to get Gregory on board with their plan to fight back against the Saviors it’s going to take some smooth talking. Maggie, Sasha and Jesus will need to rally the people of Hilltop to the cause as well. If the entire community wants to fight Gregory is going to have to commit Hilltop to the fight even if he doesn’t want to.