While the series introduces plenty of new stories and characters, it also continues his redemption arc while addressing his strained relationship with Maggie. Dead City season 2 ended with the pair on the same side, albeit begrudgingly. His past's continued focus in the present emphasizes how he should reunite with two characters he hasn't seen since before his reformation.
Negan Should Face Dwight & Sherry Again Before The Walking Dead Ends
The Couple Haven't Met Negan Post-Redemption Yet
Before The Walking Dead franchise ends, Negan should be forced to face Dwight and Sherry one last time. Introduced in season 6, Dwight was one of Negan's most trusted allies in the Saviors, while Sherry was his wife. However, Sherry had been forced to be one of Negan's "wives" at the Sanctuary, escaping with Dwight's help in season 7.
After the war with the Virginia communities in season 8, Dwight was banished, later joining the cast of Fear the Walking Dead in season 5. By the end of Fear the Walking Dead, he and Sherry had returned to the ruins of the Sanctuary, hoping to build a new life among the rubble of their old home.
How Dwight & Sherry Can Meet Negan Again
Someone Would Have To Change Locations
While Dead City season 3 hasn't been confirmed as of writing, Negan's story continuing in Manhattan means Dwight and Sherry could find him in the city. Although the pair were originally headed for the Sanctuary during Fear the Walking Dead, it's possible a detour led them elsewhere. This would also allow more legacy characters to tie into the spinoff's story.
Another option is for Negan to find them at the Sanctuary post-Dead City, directly following up on where they should be. Whatever reckoning would come from the three of them meeting again, The Walking Dead could use it to continue bolstering Negan's storyline while giving some missing faces a chance to shine again.