24Departs - Simon
Next to Negan, Simon is the show's resident "bad guy." In other words, he's Negan's No. 2 in command, and you can tell as he's picked up a lot of Negan's most heel-like qualities. He too is charismatic and constantly smiling in that evil not-going-to-do-anything-admirable kind of way. Therefore, when
he gets what's coming to him, fans will feel a sense of gratification.
Our prediction is that Daryl gets his hands on Simon and does him in this season. After all, Simon has been on the lookout for Daryl since midway through Season 7, and when he finds Daryl, he won't like what's waiting for him.
Simon's death will be one of those where you think the show might put some buildup into it, but our guess is it comes by surprise and happens in the heat of battle.