Dead City: Negan's motivation to squander the second chance given to him by Rick Grimes

Love him or hate him, Negan really did his best on his path to redemption in The Walking Dead. He was given a second chance by Rick Grimes, and by the conclusion of the series, he not only aided others in the fight against the Commonwealth, but he voluntarily removed himself from the communities. Years later, his story continues in The Walking Dead: Dead City. With his heartbreaking tale of being separated from his wife and son still hanging in the air, Negan will return to his wicked ways in the second season of the spinoff.

The teaser clip of the upcoming season of Dead City shared at the 2024 San Diego Comic-Con event is a quick glimpse into what viewers can expect. Maggie (Lauren Cohan), Negan (Jeffrey Dean Morgan), Hershel (Logan Kim), The Croat (Željko Ivanek), The Dama (Lisa Emery), Perlie Armstrong (Gaius Charles), and more will return for the continued story set in post-apocalyptic Manhattan.

By the end of season 1, Negan had been traded to secure Hershel's release from The Croat and The Dama, who wanted Negan to join forces with them so the Dama can reign over the gangs of New York. During a meeting with the ruthless woman, she threatens Hershel to ensure Negan will do as she wishes.

Why would Negan risk it all to revert to his villainous ways?

In The Walking Dead's season 8 episode "Wrath," Negan and Rick finally come to blows. Once Rick had the upper hand, he pleaded with Negan to listen to his plan of peace for Carl (Chandler Riggs), who had recently died. Negan agrees with tears in his eyes, mourning the loss of Carl, then Rick slits his throat with a shard of glass as his Savior looks on. Rick instructs Siddiq (Avi Nash) to save him as Maggie screams in disbelief in the background.

Rick went against everything he felt towards Negan to honor his dead son's wishes for peace. After everything Negan had done to the communities, there was no love lost between the two men. But, Rick, wanting to honor his son, and to prove he was different than Negan, allowed him to live. This was no easy feat for Rick, prompting him to say, "My mercy prevails over my wrath." Carl was right; the circle of violence had to be stopped.

For Negan, being put behind bars was a worse fate than death. The world continued to go on without him and he learned some valuable lessons going forward. This eventually led him to Annie (Medina Senghore), who would become the mother of his son Joshua.

Fast forward several years later, in Dead City, Negan is now separated from his wife and child and is called on to partner with Maggie, who then betrays him. While in the presence of the Dama, she produces a small box that contains the severed pinky toe of Hershel. She tells Negan that she can always go back for more. She had deep discussions with the boy before his release and learned much about the man who murdered Hershel's father. This also made her believe that because of his actions, Negan felt responsible for the boy and would do as she asked to keep him safe.

Is this the only motivation driving Negan to return to his former role as leader of the Saviors, squandering his second chance? Or, has he just suppressed his villainy for so long that it was bound to resurface?

The Walking Dead: Dead City returns to AMC and AMC+ in 2025 with its second season.