Jeffrey Dean Morgan’s role as Negan in The Walking Dead: Dead City season 2 has an ominous vibe after the recent trailer, and it’s made even more heartbreaking after Rick Grimes’ return. Having been away from the franchise for over five years, Andrew Lincoln finally reprised his role as Rick Grimes in his spinoff alongside Michonne. The Ones Who Live‘s ending paid off the character’s journey perfectly by having him reunite with his family, and given everything the protagonist has lost throughout his Walking Dead journey, it was satisfying seeing him finally have this touching moment.

Unfortunately, the franchise’s central character hasn’t had an easy time during the apocalypse, as he lost his wife, his best friend, and most importantly, his son. The bad reaction to Carl Grimes’ Walking Dead death made it a hugely controversial moment, but it all led to Rick sparing Negan as it was his son’s dying wish. Rick’s compassionate decision allowed Negan to become one of The Walking Dead‘s most crucial characters and even gave him a surprising redemption arc; however, his upcoming role in Dead City season 2 jeopardizes this, which is even more tragic now that Rick is back.

Rick Grimes’ Walking Dead Return Makes Negan’s Villain Arc Even More Heartbreaking

Negan’s Villainous Dead City Role Would Hurt Even More Now That Rick Is Back

Dead City season 2’s trailer suggests Negan is returning to his villainous roots in the spinoff, and Rick’s presence makes it incredibly heartbreaking. The Walking Dead‘s protagonist spent two seasons fighting Negan and trying to put an end to his evil ways, only for them to reappear now that he’s back. While the spinoff’s first season set up Negan’s return to villainy in Dead City season 2, hearing his iconic whistle is even more chilling than expected, and watching him embrace this dark side after spending years of his life trying to be a better man will be brutal.

Morgan’s performance as Negan is captivating, and he always puts on a great display as a villain, but after everything the character has been through, it will be tough seeing him revert to his old ways. Although Negan’s evil plans won’t necessarily impact any of the franchise’s central characters, it’s still a major revelation that will spoil Rick’s homecoming. Rather than being able to live a quiet life with his loved ones, Rick could potentially be dragged into another war with his oldest enemy, and with Negan getting a new Lucille, he could be more violent than ever.

The Walking Dead’s Timeline Means Rick Probably Reunited With The Redeemed Negan

The Ones Who Live’s Ending Took Place Before Dead City Season 1, Meaning Rick & Negan Likely Reunited

Rick would undeniably be disappointed to hear Negan had returned to his villainous instincts, especially since they probably reunited before the events of Dead City. The Ones Who Live‘s place in The Walking Dead timeline is pretty simple, as it seems to occur shortly after the main show’s ending, but Dead City is much harder to figure out. Given Hershel has grown up and Negan has left the central survivors, it is clear the spinoff is set sometime in the future, but it could really take place anywhere between three and six years after The Walking Dead‘s finale.

The spinoffs have definitely made the timeline messier, but assuming Rick joined the rest of the main characters directly after The Ones Who Live, an encounter with Negan seems likely. Even if Negan left the group before Rick showed up, the protagonist would want to track him down and look his former rival in the eye, especially since Negan helped his daughter survive. Sadly, this only adds to how tragic Negan’s upcoming role will be. Rick may have finally learned to trust Negan and found validation in keeping him alive, only to have this faith betrayed once again.

Negan’s Dead City Season 2 Villain Turn Could Be A Lie

Dead City Already Showed Negan Was Reluctant To Work With The Dama & The Croat

Although evil Negan is a huge selling point of Dead City season 2, it’s possible that Morgan’s character is only pretending to be a villain. The spinoff’s first season made it abundantly clear that Negan didn’t want to return to his past self and only did so to free Hershel. Dead City spent a lot of time exploring how much he regretted his past and focusing on the progress he’d made, allowing his sacrifice to feel genuine and authentic. Despite this, he looks happy embracing his villain side in the season 2 trailer, but this could be a double bluff.

Season 1 already showed Negan adopting some of his Savior characteristics when he smashes a man’s face through several bits of glass before slitting his throat. He turned this act of brutality into a performance – the sort of thing he’d do back when he was The Walking Dead‘s main antagonist. However, this appears to be a side of himself that Negan can tap into whenever he has to, even if he doesn’t enjoy it. Therefore, he may utilize that twisted charisma in Dead City season 2 to appease The Croat and The Dama, despite hating his actions deep down.