Doomsday
Rising Star
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That's the whole reason for it being a main person and it's one of the reasons Negan picks Glenn in the comic. He wants it to be someone that will really hurt Rick. Really hurt his group. Cause that's how he believes that these people will indeed do as he says, so they don't lose anyone else that really matters to them.
Not sure he wants to hurt Rick, the group yes, but how would he know Rick is the leader? That is why Glenn makes the most sense here to me. The group sold Maggie as the leader to the hill top people, so it feels appropriate that Negan would kill her husband to send a message.