Below are some ideas I had on how things would work out. Here is my commentary on how things did work out.
Rick-Ezekiel-Maggie
The Good Guys have just inflicted a defeat on Negan and his allies, the treacherous Scavengers, but as far as they know, the enemy leadership is intact. Furthermore, the Saviors have massive numbers and thanks to Morgan, the Kingdom has lost its most capable military leader.
First things first, bite off the low-hanging fruit. They know where the Scavengers are, they know the Scavengers aren't very numerous (120 tops and they took losses in the attempt on Alexandria), and the Scavengers are significantly weaker than the Saviors. March on the junkyard, leaving a screening force between the Sanctuary and any known Savior outposts to interfere with any relief or attacks on Alexandria, Hilltop, etc. while the army is gone, and wipe the Scavengers out completely. Put the head of Jadis (the leader of the group) on a spike and claim the junkyard's resources for the war. Punishing the Scavengers for their backstabbing also shows Negan cannot protect his subordinates and allies, a lesson the leaders of other communities under the Saviors' thumb would do well to learn.
(Speaking of subordinates and allies, now Alexandria has more guns from the Saviors killed in the battle in the finale, they should send a delegation to Oceanside to give them a few, with their old arsenal to be replaced in its entirety once Negan falls. Rick and friends took EVERY SINGLE ONE of Oceanside's guns, which was very Neganian of them and, in the immortal words of Negan himself, "not cool." Returning too many wouldn't be a good idea, since they'll probably need every gun possible for the coming war, but maybe two or three. Another "repayment on the gun loan" can be made once the Scavengers are dealt with. Not only would this be the right thing to do, but by showing Oceanside the Saviors can be defeated, it might be possible to recruit some of them.)
Destroying the Saviors' outposts in detail, hitting each one with overwhelming numbers before they can gather up into an overpoweringly large force, is a good idea, but Rick and friends don't know where all of them are. The Kingdom might know where the one they were paying tribute is, so that's a start.
One strategy to counter the Saviors' numbers would be to use the dead as a weapon like the Wolves did. Find ways to lure swarms of the undead onto Savior outposts or the Sanctuary itself. Rick and friends are probably too moral to use the dead to destroy surviving centers of civilization, but the outposts aren't large population centers like the Sanctuary and the zombies don't have to overrun them completely, just keep the Saviors busy and reduce their manpower. Considering how Rick and friends have stolen explosives from the Sanctuary's explosive anti-zombie defense, this wouldn't be that hard to implement. Even if the Sanctuary can repel a zombie swarm a few guys with bullhorns can funnel through the gap in their defenses, it'll definitely interfere with Negan's mobilization.
A high-risk high-reward strategy would be to do to Negan what Caesar did to Vercingetorix at Alesia and lay siege to the Sanctuary while laying an outer line of defense to keep reinforcements from the outposts away. A murderous donut, if you will. A strategy this aggressive would put Negan on the back foot and allow for re-establishment of contact with the traitorous Dwight or the weak Eugene, who'll probably flip back to the good guys if it can be done safely. Dwight mentioned joining forces with the workers at the Sanctuary, so it might be possible there are more allies to be found.
(One problem with trying to get help from Eugene is the fact that they tried to blow him up in the season finale and Negan knows this.)
However, Alesia was a pretty near-run thing (it took Caesar himself leading the last of the Roman reserves to prevent a breakthrough at one point) and Negan has shown himself able to think two steps ahead of Rick and friends. This is on full display when he used his superior numbers to progressively block the routes to Hilltop in "Last Day on Earth" before trapping Rick and his crew outright and again in the season finale when he had the Scavengers turn traitor at the worst possible time. A strategy that aggressive might be too risky.
Negan and the Saviors.
Negan knows that Hilltop, Alexandria, and the Kingdom are in open rebellion against him. He also has the Scavengers as allies.
If I were in Negan's position, I would start by keeping a very close eye on Eugene. Negan is clearly suspicious of him, based on the conversation they have at the end of the episode. He might need Eugene's technical skills and so isn't going to throw him into the oven or take Lucille to him yet, but he's clearly not trustworthy. I would have someone who is definitely loyal, like Simon, keep an eye on him.
(Negan would be insane to trust Dwight, given how he raped Dwight's wife Sherry and, as far as he knows, she ran away and got eaten by zombies. If I were Negan I wouldn't know Dwight was a traitor but I'd be a bit more careful with him on principle.)
I would also emphasize to Eugene that Rick tried to blow him up when the latter tried to negotiate Alexandria's surrender and save lives. Eugene is weak and cowardly, so using this as a lever to set him against his friends is doable.
Secondly, I would provide military support to the Scavengers. You don't win wars by letting your allies hang and the Scavengers are vulnerable, given the losses they took in the failed attack on Alexandria and the fact Rick and friends know where they are. It might also be the perfect chance to ambush a significant part of the allies' army, if they go for the Scavengers first and don't guard their flanks.
As far as the first target for an offensive, I'd go for Hilltop. The Hilltop community doesn't seem to be particularly large (unlike the Kingdom) and it's not the primary base of operations for the rebellion's leader Rick (unlike Alexandria), so it'd be a relatively easy first target. Furthermore, Negan knows that Maggie is still alive and that Rick had gone to great lengths to conceal her from him (the whole fake grave thing). If the Hilltop in general and Maggie in particular were under threat, that might be a way to draw out the rebels for the type of battle that favors Negan's superior numbers.
(Plus if Maggie were taken alive, she could be useful as a hostage or bait given how important she obviously is to Rick and friends. A postcard or radio broadcast of Negan's typical gross sexual comments about Maggie and Rick might do something stupid. Negan doesn't even have to abandon his policy against--forcible--rape to do this. In the comics, he made comments about some of his goons "running train" on Carl only to return him to Rick unharmed, so it's in-character.)
Alternatively, going for Alexandria again in order to cut the head off the snake (kill Rick) and this time make sure of it, is a viable strategy. The longer the war goes on, the more likely other communities under Negan's thumb or the workers in the Sanctuary might get restless, so this would be a chance to end the rebellion early. With Rick dead, Hilltop might surrender (Gregory can be restored to power for status quo ante--just blame Maggie and her entourage for the whole situation) and the Kingdom can be negotiated back into line. Throw on the blame on Rick, claim he and his troublemakers deceived Ezekiel to let the King save face, and try to get status quo ante there too.
As far as broader policy is concerned, I would lighten up on "half your shit." It's my understanding that Negan regularly taking half of Hilltop's supplies was driving them toward extinction and pushed them to ally with Rick in the first place. A tax rate that extreme is killing the goose that laid the golden egg. The communities under Negan's thumb could have lived with a much lower tax rate, or a tax payable in something less precious than supplies. A group of workers from a community for a day or two corvée labor restoring old roads, clearing out zombies from strategic sites, etc. instead of the supplies they need to survive would be much more in Negan's interest than taxing communities to the point it's rebellion or death. It could also provide evidence for Negan's claim that he's "bringing civilization back to this world" as opposed to just extorting everybody.
Finally, I would take pains to deter treachery by vassal communities. One article said it made no sense for Negan to leave existing leaders in place, or at least not have garrisons in towns under his rule. Negan can spare a few soldiers to keep whatever other equivalents of Gregory he has out there in line while maintaining a solid defense of the Sanctuary and a mobile force to deal with Hilltop-Kingdom-Alexandria.
As far as broader policy is concerned, I would lighten up on "half your shit." It's my understanding that Negan regularly taking half of Hilltop's supplies was driving them toward extinction and pushed them to ally with Rick in the first place. A tax rate that extreme is killing the goose that laid the golden egg. The communities under Negan's thumb could have lived with a much lower tax rate, or a tax payable in something less precious than supplies. A group of workers from a community for a day or two corvée labor restoring old roads, clearing out zombies from strategic sites, etc. instead of the supplies they need to survive would be much more in Negan's interest than taxing communities to the point it's rebellion or death. It could also provide evidence for Negan's claim that he's "bringing civilization back to this world" as opposed to just extorting everybody.
Finally, I would take pains to deter treachery by vassal communities. One article said it made no sense for Negan to leave existing leaders in place, or at least not have garrisons in towns under his rule. Negan can spare a few soldiers to keep whatever other equivalents of Gregory he has out there in line while maintaining a solid defense of the Sanctuary and a mobile force to deal with Hilltop-Kingdom-Alexandria.
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