"Hershel sees Maggie's relationship with Negan as a very big issue because of his own relationship with his mother. The only person standing in the way of that, in Hershel's mind, is Negan. He has a lot of malice and a lot of hate towards Negan because he's in the way of Maggie, and he just wants Maggie to be free of him."
"Hershel kind of constantly thinks about Negan, because he knows that he’s the only thing that’s really in between his relationship with Maggie. And [he thinks that] if he was gone, then all these other problems would be somehow resolved."
"Ever since he was little, she would always focus on Negan. […] Hershel's view on Negan is the only way to get Maggie to really let go completely is to let Negan go from life. … Then he'll have a happy life with his mother." --Logan Kim (ScreenRant, TV Insider, Collider)
Geez, the Oedipal vibes, lol (esp considering my interpretation of negan as a pseudo godfather to hershel). Anyway, I really like that Dead City gave Hershel his own perspective on and feelings about his and Maggie's connection to Negan and his own relationship with it, instead of just keeping it an extension of Maggie's, like when he was little. As he never got to know his father and wasn't around for the events of his murder--apart from his father's absence he only knows about all that completely second-hand--I totally buy that he would've reckoned with and processed it by now, in his own way, so that that's not the crux of his beef with Negan, actually. Actually his issue is that man taking up way too much of his mom's emotional and head space "rent free", lol (as Negan himself called Maggie out on in early s11 of TWD). Which then puts him in Hershel's mind rent free, and sheesh, what a cycle.
The fact that this whole show basically boils down to these three characters trying to reckon with and figure out how to live with this surreal bond they share is truly something... Even the fact that Hershel is such a major part of it, which I was not at all expecting before I started the show. Then turns out he's like, the lowkey centerpiece, the link that connects the tethers between Maggie and Negan (he'd hate to hear it, lol, but it's true). It was Hershel the Dama and the Croat used to lure Negan to NY, so it was Hershel that got Maggie to reunite with Negan. Now Negan's saving him from certain death left and right so he's gotta be putting 2 and 2 together that Maggie must be back in NY, too.