25 most polarizing The Walking Dead characters

10. Simon

Simon has all the charm of a psychopath and the murderous intentions of one, too. Sadistic, unstable, and vengeful, Simon even turned on Negan toward the end. Simon was the second in command to Negan but often went off script and ignored Negan’s wishes like he did when he slaughtered all of The Heapsters except Jadis because they helped Rick and the others.

Simon was also the one responsible for the massacre of the Oceanside people. Before Negan had come along and taken charge, Simon ordered that all men and boys over the age of 11 be killed as a punishment for the rebellion of the people of Oceanside.

Simon’s charming demeanor could flip to murderous in a second. While he did have some great one-liners and it was fun to see him and Gregory interact, ultimately, Simon was a truly dangerous and polarizing character. It was fitting that he ended up on a pike outside the fence at The Sanctuary as a walker. After he tried to stage a coup and take control of The Saviors, Negan killed him with his bare hands and put him on the fence as a warning to others not to try that kind of rebellion.

Simon’s cruelty and cunning made him extremely dangerous. It says a lot about that character that even a character as brutal as Negan couldn’t keep Simon in line. If Negan hadn’t killed him, Simon would have kept trying to seize power until he managed to overthrow Negan and take control of The Saviors again. Maybe someday fans will get a Saviors spinoff to see how Negan took power from Simon in the first place.