Dwight has had quite the storyline on The Walking Dead so far, and the more we learn the more we believe he’ll be playing a big role in the fight against Negan.
Dwight was first introduced on The Walking Dead when Daryl was separated from Sasha and Abraham by a group of Saviors in episode 6×06. Dwight, his wife Sherry, and her sister Tina were all on the run from the Saviors themselves and mistakenly believed that Daryl was one of them. They got off to a rough start, but once Daryl realized that Tina is diabetic he decided to help them.
However, after Tina was bitten by a walker things started to go bad again. After Daryl invited Dwight and Sherry to Alexandria they instead looted his things and motorcycle. Instead of going to the new community, they decided to go back to the Saviors. What wasn’t shown was that once the pair got back Negan was furious and wanted to kill Dwight. Sherry offered to become one of Negan’s wives in order to save Dwight’s life.
The next time Dwight appeared on The Walking Dead was in 6×14 when he attempted to kill Daryl but accidentally killed Denise with an arrow instead. Eugene ended up saving the day after he bit Dwight in the crotch and allowed the others to kill some of the Saviors. But in the following episode Dwight succeeded in capturing Daryl, Glenn, Michonne, and Rosita.
In season 7, Dwight became much more prominent as the Saviors storylines expanded. It quickly became clear that he has worked his way into high position among the community he had once fled. With Daryl captured, his main priority is to break the captured man down to an obedient servant. However, there are still glimpses of the man with compassion.
In episode 7×02 Dwight was sent after a friend of his that escaped the Saviors and was supposed to bring him back. However, in a moment in humanity he killed the man instead of forcing him back to base at his request. That was the first time fans saw Dwight putting someone else before himself since returning to the Saviors.
The Walking Dead 7×07 revealed that Dwight was definitely still harboring feelings for Sherry, who had been living as one of Negan’s wives and yet is still drawn to Dwight. Despite being forced to watch what happens when someone tries to interfere with one of the wives, Dwight and Sherry still shared moments alone together.
When Sherry escaped the Saviors in 7×11, Dwight was sent after her and he knew just where to go. In a heartbreaking moment, it was revealed that Sherry went back to their former house but didn’t wait for Dwight. Even she couldn’t tell if he had fully succumbed to Negan and would have forced her back to base. In actuality, Dwight had been ready to flee with her. Instead, he had to go back to Negan alone with the knowledge he’d probably never see Sherry again.
Dwight’s storyline has deviated some from the comics but the writers still seem to be setting up the character to become a double agent. With his distaste for Negan and having nothing left to lose it’s definitely possible that Dwight will turn against the leader of the Saviors. In volume 18 of The Walking Dead comics, there was a similar situation where Negan burned a man for messing around with one of his wives with the others looking on. It served as a reminder to Dwight and Sherry of what happened to them.
Dwight also heard Negan talking about having sex with Sherry and decided to travel to the Kingdom to speak with King Ezekiel. There he agreed to inform Ezekiel and Rick about Negan and the Saviors. He became their inside man to help bring down Negan. Although Sherry is out of the picture now on the television series, Dwight could still head to one of the communities and offer to help them.
He may not go to Ezekiel, however, since the Kingdom has never received the Saviors inside their community. At this point in the television show, Ezekiel is still resistant to fighting the Saviors. With Rick seeming more open to getting help from outsiders, it seems more likely that Dwight would approach Rick about it. He’d also have a better chance at getting in touch with Rick than Ezekiel. Another option is Maggie and Jesus, Dwight could reach out to them at the Hilltop.
Most likely, Dwight’s biggest role in helping Rick and the other communities would be to relay information to them. Since they’re outnumbered, it would be a great advantage if they knew Negan’s plans ahead of time. Another way Dwight could help is by trying to sabotage Negan’s plans from the inside.
There was a bit of that in the comics, for example in volume 20, Dwight was able to help his new allies when they attacked the Saviors. He did so by causing a delay in getting help from the Saviors outposts. This made the numbers a little more even for Rick and the others in the fight. Later, Dwight was also able to kill a group of Saviors himself and he also supplied Rick with some unused grenades.
I would not be surprised if the show also had Dwight trying to recruit others to help him bring down Negan. As fans have seen on the series, many of those living with the Saviors are suffering and hold animosity towards their leader Negan. It wouldn’t be hard to find others that want to bring him down, given that Dwight is careful about who he speaks with. If Eugene isn’t too far gone, it’s possible they could team up together. In the comics, Dwight also teamed up with Dr. Carson. But of course that can’t happen on the television series since he’s already been thrown under the bus for Sherry’s escape.
Dwight also basically saved Rick’s life in volume 21. Negan came up with a plan to kill those in Alexandria by shooting them with arrows contaminated with bacteria from walker guts. The hope was that it would have the same affect as getting bitten by a walker. When Rick was vulnerable, Negan ordered Dwight to shoot Rick with one of the arrows.
Dwight did shoot him, but he used a normal arrow instead of an infected one. Instead of being killed, Rick was only wounded. The shock of finding out Rick didn’t die, gave him the chance to slash Negan’s throat and ending the battle. This was quite a big moment in the comics so I’m assuming that the tv series would show it in a similar way.
Following Negan’s downfall, Dwight also paves the way for the Saviors to become allies with the rest of the communities. They no longer act against the others or try to control them, instead they all begin to trade together. Dwight and Rick also form a friendship that allows them to help each other going forward as other problems arise.
Dwight will definitely have a hand in Negan’s downfall, it’s just up to the writers of The Walking Dead on how much of a role he will play.