Gregory was facing extortion from Negan (supposedly). Lets remember, Gregory is a douchebag. Gregory didn't even ask for Rick's help. Rick came in and offered to broker a deal, actually Maggie did because Rick knew he couldn't work with Gregory. So, Rick agreed to get rid of Negan merely to take his place. Had it been a one time thing then fine, but apparently it wasn't. It was taking Hilltops stuff for killing off the Satellite people.
So, to use your recap....
So, Rick came to Gregory, not the other way around. As Gregory says, they're doing fine. Moving on....
OK, Negan didn't kill them randomly. Did Gregory try to screw over Negan or was Negan getting greedy? We don't know, but we do know Gregory is a douche.
So, Negan is offering protection for half their stuff. Typical Mob move.
More Gregory douchebaggery.
So Maggie demands the exact same thing Negan is getting. Again, I thought it might be a one time thing, but Rick comments in another episode of his plan to just take stuff they want from Hilltop (guess you can look in the recap for that) Here ya go, from Rick....
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