The Walking Dead, Vol. 28: A Certain Doom

What is effectively the Part 2 of the Whisperer War is where the bigger punches are felt, when Beta (who unlike a lot of villains doesn't actually die just yet) unleashes the Horde against Alexandria, doing far more damage than what happened in No Way Out, that results in the deaths of Andrea, Rick's now wife who has been around since the first several issues. It's drawn out in a single issue and it really is devastating. Dwight's ex wife, Sherry, also meets a kind of comedic end, as she attempts to clean up the scraps and take charge of the communities. We can't forget she's not a good person, so her death is more of a relief than anything, outside of Dwight not taking it too well. He's far more loyal to Rick than his ex wife though, so that bait and switch was phoned in.