10 Most Brutal Characters In The Walking Dead

For a long time, Simon was Negan's right-hand man, and a huge force to be reckoned with in the Saviors. He was in charge of ensuring the Hilltop fell in line and obeyed his every whim, scaring Gregory into complying with these demands.

What's interesting is even Negan was disgusted at some of Simon's actions. It is discovered through a meeting of the lieutenants that Simon was the one who ordered the killing of all the male residents of Oceanside (including children), and also slaughtered all of the Scavengers in the junkyard, leaving only Jadis alive. One of Negan's rules is that he would prefer to not kill if he can help it, and killing children is a huge violation of this code, yet despite this, Simon is forgiven and allowed to remain in the inner circle.

Simon's fate leaves him zombified and chained to the Sanctuary fence, after he tried to form a mutiny against Negan, resulting in his rival strangling him to death in a fist fight.