When Simon showed up in Alexandria, Rick got to meet the only man in the apocalypse who might be more intimidating than Negan himself.
One of the big benefits of being a television viewer is that we get to see things that the characters onscreen either don’t know about or haven’t seen yet. In Rick’s case in “Rock in the Road” it’s the latter. Simon is a very bad guy, but Rick doesn’t know the full extent of Simon’s capabilities yet.
The Walking Dead introduced us to Simon during the season 7 premiere when Simon helpfully provided his boss with a pen so that Negan could draw a line on Carl’s arm. The line, as we know, was to help guide Rick in cutting off his son’s arm. While that didn’t end up happening, many people believed at that point in time that Negan was the biggest bad of all.
But then we met Simon in “The Go Getters.” Simon was the newly appointed overlord of the Hilltop, and Gregory quickly bowed down to prove his loyalty to the new overseer. Gregory didn’t hesitate in pledging loyalty to Simon because he knew that Simon was not someone to trifle with.
Rick hasn’t had a chance to meet Simon in those circumstances. Simon arrived in Alexandria looking for Daryl, but he didn’t do anything that could be considered worse than what Rick has seen from Negan.
The keyword is “yet.” Simon is much more intimidating than Negan because he doesn’t follow the same “rules” that Negan works with. Negan tells you the rules and expects you to follow them. Fall out of line and expect to be punished. Simon is a snake in the grass. He’s only interested in his own self-preservation and that makes him a lot more dangerous because he’s totally unpredictable.
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Rick will do well to keep a close eye on Simon. Negan may do bad things but Simon is a wildcard, and wildcards are not a good thing in the apocalypse.