The sky is truly the limit for Negan, however, if The Walking Dead producers and AMC execs ever agree to give Negan a looking-forward sequel show that could possibly offer more context for what happened with Negan after he exited the main story in the comic book series.
After all, even if Negan and Lauren Cohan’s Maggie work together well enough during Season 11 that she makes it all the way through without putting a crowbar through his eye socket, that doesn’t exactly guarantee a happy and emotionally jubilant time for Negan as an Alexandrian, or even as a Commonwealth resident, should he ever make it there.