Negan may have survived baseball bats, walker hordes, and the wrath of Maggie—but there are still ghosts from his past that won’t stay buried. As The Walking Dead: Dead City continues to explore the once-villain’s complicated path to redemption, one glaring omission in his evolution remains: a final confrontation with Dwight and Sherry.
Fans have watched Negan transform from the brutal, smirking tyrant who bashed Glenn's skull in to a begrudging antihero haunted by guilt and seeking some form of peace. Dead City season 2 ended with Negan and Maggie finding common ground (if only slightly), proving just how far he’s come. But one crucial chapter is yet to be written—and it’s not with Maggie, Rick, or Daryl. It’s with Dwight and Sherry.
Why Dwight & Sherry Matter More Than Ever
Introduced in Season 6, Dwight served as Negan’s loyal lieutenant while Sherry—his wife—was tragically forced into Negan’s twisted system as one of his “wives.” Their arcs became symbols of both the physical and psychological trauma Negan inflicted under his reign.
Sherry escaped the Sanctuary thanks to Dwight’s help, and Dwight was later exiled from Virginia by Daryl, a sentence that landed him in Fear the Walking Dead Season 5. The couple’s story there brought them full circle—returning to the ruins of the Sanctuary to rebuild a new life from the ashes of their shared pain.
Yet through it all, Negan has never faced them post-redemption. Never offered an apology. Never stood before the people whose lives he shattered.
And now that he’s on a path to change, that absence is more glaring than ever.
The Missed Opportunity (So Far)
Negan’s redemption arc has been meticulously layered through his relationships—with Carl, Judith, and most recently Maggie. But Dwight and Sherry represent unfinished business. They’re the ultimate test of whether Negan has truly evolved. Could he look into their eyes and admit he was wrong? Would they ever forgive him—or even acknowledge the version of the man he's become?
Bringing them back isn’t just about fan service—it’s a narrative necessity. Without this emotional reckoning, Negan’s arc remains incomplete. It’s like Rick never facing Shane again or Carol never confronting Lizzie.
How They Could Return
The good news? The pieces are on the board.
Negan remains in Manhattan in Dead City. While Dwight and Sherry were last seen returning to the Sanctuary, Fear the Walking Dead left the door wide open for their next move. A storyline twist could easily send them into Negan’s orbit—perhaps they’re seeking supplies, vengeance, or even refuge.
Alternatively, if Dead City ends and Negan ventures back to his old haunting grounds, a confrontation at the now-decayed Sanctuary could be the final scene he—and the audience—needs.
What’s at Stake?
Redemption arcs only work if they go all the way. Negan has made progress, but his journey can’t truly conclude until he looks into the eyes of those he destroyed. Dwight and Sherry don’t need to embrace him, but their presence would offer powerful closure—not just for them, but for the audience who lived through Negan’s tyranny.
Imagine a scene where Negan, stripped of ego and bravado, returns to the Sanctuary and finds Dwight and Sherry rebuilding it—not for war, but for peace. The man who once ruled with an iron bat now seeks forgiveness at the altar of his own sins.
It’s cinematic. It’s poetic. And frankly, it’s overdue.
The Future of The Walking Dead Universe
With The Walking Dead: Daryl Dixon returning September 7, 2025, and more spinoffs on the horizon, AMC has a chance to thread these narratives together in meaningful ways. Bringing Dwight and Sherry back into the fold—and directly into Negan’s storyline—would be a brilliant way to tie up loose ends while paying tribute to long-time fans.
One final reckoning. One more chance at redemption. The question is: will Negan take it?
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