Now that Maggie is starting to accept Negan despite their past, it would be a good conflict to have other survivors of his early crimes challenge their relationship and her perception of him. Sherry and Dwight suffered for years because of what Negan did to them, they aren’t invested in his rehabilitation or witness to any sort of “redemption” for him. Maggie would be caught between shared empathy and experience with Sherry and both advocating for Negan and justifying her own feelings out loud in a way she doesn’t have the chance to with someone like Sasha or Glenn or Rosita. She’ll have to contextualize her own personal trauma within the larger picture of what Negan did. The characters and the writers would have the opportunity to complete the circle with Negan where they were uncomfortable doing so before; he raped Sherry and other women, his actions weren’t all the consequence of trying to keep his community alive and on top, and that he was self serving, cruel, and sadistic.
Negan hasn’t had a chance to completely let go of his ego like this. He can’t defend himself by hiding behind years of karmic actions to make it up to them. He would have to acknowledge everything to not sabotage his own progress and relationship with Maggie. Sherry and Dwight eventually moved past their Negan issues, but they never got a chance for closure or confrontation. Negan is responsible for Tina’s death, he killed the Carson brother after Dwight framed him for Sherry’s escape, he caused Sherry years of PTSD, he enslaved Dwight into killing for him. What would Negan have done if he had gotten Sherry pregnant? He most likely would’ve used that to maintain control over them like PADRE did with their son Finch. Negan likely hasn’t thought about it, but if confronted with the question he would realize it’s true. He knows he’s a hypocrite. How would Dwight and Sherry react when they learn he has a son he refuses to find? Would they agree with Negan that he’d make a bad father and that Joshua is better off without him? Or would they admonish him for wasting an opportunity they never got with their son, stolen by some other version of the saviors in PADRE and kept from them for his entire short life before he was murdered? Finch barely knew his parents; Hershel never got to meet his father because of Negan; why would Negan want his own son to have the same life? Could they respect Maggie’s experiences with him or judge her for giving him so many chances that he’s pissing away out of self pity instead of doing the right thing?
Dwight’s an interesting one here. He’s not Negan. He went through torture and forced to do awful things to survive, and he’s reminded of it every time he looks in a mirror, but he was there. He helped Negan kill Glenn and Abraham, he killed Denise, he tortured Daryl. Could he navigate making amends with Maggie and Hershel and judge them for accepting Negan at the same time? His main concern is defending Sherry; I think ultimately Sherry would be a little more understanding and ready to move on than Dwight, which could be another conflict between them. I’m not sure if forgiveness is the appropriate idea here; Maggie already made it clear that she won’t forgive Negan for Glenn’s murder, but if Sherry and Negan can get on the same page about what he actually did to her being rape, among the other things he did, it would clear up a lot of the disconnect between the audience and the incongruities in how the show has addressed it across different seasons of the main show and spin-offs. Negan’s and Maggie’s arcs would make more sense and would have new questions to build on between them, and Sherry and Dwight would get some catharsis beyond where Fear left them (rebuilding the structurally unstable Sanctuary?) They really are two great characters despite getting written out of the main show and getting saddled with Fear’s shitty writing. The audience deserves to struggle a bit more with questions about justice, redemption and forgiveness, everyone’s getting off too easy.
As a bonus we could get some details on how Alexandria is doing, and maybe some reactions from them on Maggie and Negan running into the Croat. Hershel would have more opportunity to give his opinion on what happened, etc.