The Walking Dead: Dead City is a spin-off of The Walking Dead focused on the ultimate frenemies, Negan (Jeffrey Dean Morgan) and Maggie Rhee (Lauren Cohan), set in New York City. The two characters concluded their stories on The Walking Dead on relatively good terms, only to find themselves on opposing sides once again by the end of Dead City’s first season.
With season 2 set for a spring 2025 release, teasers hint at an Escape from New York-style power struggle in the Big Apple, with Negan rising to power once again—this time with help from The Croat (Željko Ivanek). AMC has already announced several new cast members, including Keir Gilchrist (Atypical), Dascha Polanco (Orange Is the New Black), Jake Weary (Animal Kingdom), Pooya Mohseni (Law & Order: SVU), and Kim Coates (Sons of Anarchy). But could we also see surprise cameos from some fan-favorite TWD characters?
More than likely, the answer is yes
Season 1 of Dead City already delivered a shocking return with fan-favorite TWD villain Simon (Steven Ogg). Negan’s former right-hand man and eventual usurper was put down by Negan in The Walking Dead, but Dead City brought him back for a flashback sequence, revealing more about The Croat’s time in the Sanctuary.
Given that precedent, it’s not at all far-fetched to expect more familiar faces in season 2 of Dead City. Here's a list of all possible returning characters.
(Warning: Spoilers across all TWDU content below.)
Lydia
Lydia (Cassady McClincy) is one of the most likely candidates to appear in season 2. Introduced in season 9 of The Walking Dead, Lydia was the daughter of Alpha (Samantha Morton), leader of the Whisperers. After breaking away from her abusive mother, she found a home in Alexandria and later at the Hilltop.
Lydia shares a unique bond with both Negan and Maggie—Negan acted as an un-appointed guardian after she became an outcast due to her Whisperer ties during season 10, and later, she became a close confidant of Maggie’s at Hilltop in season 11. The first season of Dead City revealed that Hilltop was reformed as The Bricks at some point in time, with Maggie still leading. Lydia (along with her love interest Elijah, played by Okea Eme-Akwari) could easily return if season 2 expands on Maggie’s new community, which we've already seen glimpses of in the show's first season.
Dwight & Sherry
A reunion between Negan and Dwight (Austin Amelio) has been brewing for a long time in The Walking Dead Universe. Their history is complicated, to say the least—Negan stole Dwight’s wife, Sherry (Christine Evangelista), and Dwight later betrayed him to help Rick (Andrew Lincoln) take him down in Season 8 of The Walking Dead. Since then, Dwight found his way to Fear the Walking Dead, where he reunited with Sherry. By the end of Fear, Dwight and Sherry had plans to rebuild the Sanctuary—the former stronghold of Negan and the Saviors.
Dwight’s return in Dead City Season 2 could be enticing for a number of reasons. He and Sherry are still ghosts from Negan’s past, having only known him as a ruthless, tyrannical dictator. They weren’t there to witness any of his redemption arcs. Seeing their reaction to this new, supposedly softer Negan could be compelling. On top of that, the new and improved Sanctuary could play a key role in Negan’s upcoming power struggle.
Lucille (The Real One & The Bat)
'Here's Negan' is one of the most acclaimed episodes in The Walking Dead Universe. The episode finally gave fans the long-awaited backstory of Negan’s wife, Lucille (Hilarie Burton), whose tragic fate became the catalyst for his entire arc. Played by Jeffrey Dean Morgan’s real-life partner for added chemistry, Lucille succumbed to cancer in the early days of the apocalypse, pushing Negan past the point of no return and leading him to create his infamous barbed-wire bat in her namesake and memory.
Now, with Dead City Season 2 on the horizon, teasers and production stills confirm that Negan will be reunited with his bat, Lucille. This could stir up unresolved emotions, opening the door for Hilarie Burton to return through flashbacks or dream sequences, giving us another glimpse into Negan’s past and the woman who shaped the man he became.
Annie
Speaking of Negan’s wives—where is Annie?
Annie (Medina Senghore) was introduced in season 11 of The Walking Dead as Negan’s newest wife and the mother of his child, Joshua. When Dead City begins, Negan is separated from both, and we later learn Annie was attacked and robbed off-screen. Negan retaliated, killing every single one of her attackers, before apparently putting Annie and their son on a "train to Missouri." (Doesn't that sound like code for "they're dead?")
Negan abandoning his wife and child feels really out of character, especially given his aggressively paternal instincts throughout the series. He was a school teacher after all. There’s likely more to the story, and season 2 could finally give us some answers.
Rick Grimes
Okay, this one’s a long shot—but not impossible.
After the events of The Ones Who Live, Rick and Michonne (Danai Gurira) safely made their way to The Commonwealth in Ohio where they were reunited with Judith (Cailey Fleming) and RJ (Antony Azor) thanks to their new alliance with the Civic Republic Military (CRM).
Given Dead City’s season 2 setup with various groups battling for control of NYC, this could attract attention from the CRM, whose main base is in Philadelphia, not far from New York! If word reaches them about Negan causing trouble (and Maggie being involved), Rick could take an interest. The last time Rick saw Negan, he was locked in an Alexandria jail cell, so seeing them face to face again would be one of the most exciting TWD moments in years.
Of course, these are just a few possibilities. We could also see more of Simon through flashbacks, Morgan (Lennie James) could show up after hitting the road at the end of Fear The Walking Dead, or even Gabriel (Seth Gilliam) could make an appearance, given his relationship with Negan and Maggie, and his role in The Ones Who Live.
One thing’s for sure, Dead City season 2 is shaping up to be one of the most exciting Walking Dead spin-off seasons yet. We’ll just have to see what's in store for us when the anticipated second season premieres later this year.
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