5. Dwight and Sherry choose to go back to Negan
Dwight and Sherry’s decision to go back to the Sanctuary instead of taking Daryl’s offer to join Alexandria deserves, without a doubt, to make this list of the worst decisions ever made by characters on The Walking Dead.
To begin with, turning on Daryl and stealing his bike and crossbow after he’d saved them wasn’t really a classy move, to say the least. But going back to Negan? The kind of guy who takes betrayal super personally, and has plenty of imagination to torture you while smiling and pretending that it’s all fun? That’s not smart.
Dwight and Sherry may have thought that without Tina, whose illness basically made her a liability (poor Tina), they would have a chance to fare better in the Sanctuary. And indeed, they certainly moved up: Sherry became Negan’s favorite wife, and Dwight his first lieutenant. Still, the price was high, and it was far too much to bear for both of them.
The most obvious horror they had to suffer as a result of their decision was Dwight’s disfigurement, but Negan actually did something worse to them: he destroyed them both, as a couple, and as people. He took away their moral integrity, forcing them to be complicit in various morally questionable actions in exchange for positions of power that were really gilded cages.
As a couple, it seems that Dwight and Sherry are truly finished, but as individuals, can they still be redeemed? We don’t know if Sherry will ever be seen again, but Dwight will almost certainly play a crucial part in bringing down Negan. In any case, they probably both wish they had followed Daryl to Alexandria.