The Walking Dead: Three weaknesses that might doom Negan in All-Out War
#1 Negan has WAY too many potential traitors inside his Sanctuary
This is probably the most obvious weakness of all. Apart from a few people like Arat (who seems to be Negan’s own Bellatrix Lestrange), Negan seems to have very few lieutenants he can really count on. His tactics to “convert” people mostly rely either on abuse, or on buying people’s loyalty with the promise of material comfort and/or power. Negan’s leadership relies on fear and on mutual interest, not love. This kind of leadership thrives as long as the person in charge appears to be strong, but can crumble at the first sign of weakness.
Dwight’s impending betrayal is already almost certain
We already know from season 7 of The Walking Dead that Dwight is almost certainly going to betray Negan and his betrayal could be key. Arguably, the only reason why Dwight was putting up with Negan’s abuse, and trying to pretend that he enjoyed being his henchman, was because he wanted to protect Sherry. Now that Sherry has fled, Negan has lost any leverage he had on Dwight. There is nothing Negan can take from Dwight that he hasn’t already taken. What’s more, Sherry’s goodbye letter was another motivation for Dwight to try and redeem himself.
Eugene is a very dangerous wild card
The other obvious “wild card” and potential traitor is of course Eugene. At this point, we have been shown enough evidence that Eugene had not been faking his conversion. Still, this doesn’t mean Eugene will not turn on Negan. His new position at the Sanctuary, which he seemed to actually enjoy, is already compromised by the Sasha incident. We also know that Eugene, although he can be callous and act in a purely selfish manner, is not immune to moral crises. The death of Sasha may have triggered something in him. His loyalty to certain members of the group, in particular Tara or Rosita, might bring him to try and redeem himself, just like Dwight.
The dubious loyalty of Negan’s workers
Apart from these two characters, many other groups of people would be likely to turn against Negan. The people who live in the Sanctuary as “workers” are probably happier inside than outside, and we have seen little of them, but the treatment they get seems to be quite harsh. It was bad enough to push several of them to try to run away: Dwight, Sherry and Tina, as well as the man Dwight killed on the road.
The more-than-dubious loyalty of Negan’s “wives”
And of course, the last group of people who could possibly rebel are Negan’s “wives”. We do not know many of them well, but we do know that several of them were coerced into accepting this position, and are not happy to be part of his “harem”. Sherry was one of them, and she has already betrayed Negan by setting Daryl free before running away. Amber seems to be in a similar position to Sherry’s, and we can assume that she hates Negan after he burnt her boyfriend’s face. We already know that the two women that Negan “lent” to Eugene for one night were trying to poison Negan. That already makes at least three wives who could potentially betray Negan, and given how close they are to him, that’s a lot.