Simon

Simon is one of the secondary antagonists of The Walking Living and a high-ranking member of the Saviors as the right-hand man of Negan.

Personality
Simon is a sadistic, brutal and articulate man considered even by Negan too violent and psychotic. He has displayed extreme loyalty to the Saviors and is a highly trusted and valued member. Simon is not beyond using fear and intimidation to achieve his ends and is shown to be a completely remorseless, cold-blooded mass murderer and is not bothered at all by the excessive violence that the Saviors employ. Simon has become desentized by the acts of brutality and atrocities he has committed, often taking pleasure in the violence employed by the Saviors.

As the second highest ranking Savior, Simon held a large amount of power surpassed only by Negan himself, and is a capable leader and strategic thinker. In spite of being Negan's most loyal follower, Simon drastically differs in their views on how to deal with disloyalty and defiance on the part of their subjugated victims. Unlike Negan who chooses to kill a few to save many and get the rest back in line, Simon is more bloodthirsty and is willing to wipe out entire communities due to their disobedience to the Saviors. Simon is not bothered about causing harm to children or the elderly.

At the command of Negan, Simon assumes direct responsibility for the continued subjugation of Hilltop and takes pleasure in terrorizing the town when called upon to do so. He has demonstrated and verbally expressed his admiration for authoritian leaders, and those who lead by example, something which he himself puts into practice with his uncompromising methods, and strict obedience to Negan.

During the war, Simon has finally lost patience for Negan's methodology and when Negan believes it to be a principle of the Saviors to ultimately unite communities and only resort to keep people in line, Simon believes the Saviors should simply kill of all of the communities that oppose them and instead spare communities completely loyal to them. Simon eventually begins directly disobeying Negan's orders such as ordering massacres, displaying how little Simon values concepts such as morality or mercy. Simon is also willing to sacrifice his own fellow Saviors in his quest to exterminate his enemies

After Negan humiliates Simon in front of the Saviors and following being sent to prison, Simon reaches the end of his tether and attempts to lead a coup in order to get rid of Negan for good, showing that all respect he had for his leader is now gone and that he is desperate to take over the Saviors.

Negan
Simon and Negan had a strong relationship, with Simon befriending Negan and personally recruiting him into the Saviors, seeing how broken he was over his wife's death and thought the Saviors could get him a better and more thrilling life. Simon continued to have Negan's back when he was just a lowly Savior however when Negan witnessed that Simon personally killed every male at a village for retaliating, Negan became disgusted and horrified at what he had done, making Negan realize that John was a bad leader and had to be replaced for the Saviors' benefit. Negan enlisted Simon to help him kill John and take over the empire, which they were successful for.

After becoming the leader of the Saviors, Simon became Negan's top lieutenant and most trusted right-hand man. Negan vowed to assure Simon doesn't do anything like the Oceanside massacre again and kept him in the second highest position of the empire to both put his cruelty into productive means and to keep a close watch on him. As the second-in-command of the Saviors, Simon is entrusted with considerable power and authority, close to Negan himself. Negan trusted Simon extremely well that he put him in charge of dealing with and subjugating communities that retaliate against the Saviors. When dealing with enemies and subjugated communities, Simon often spoke on Negan's behalf and even sometimes introduced them to his leader, showing that he was given high authority.

Negan also views highly of Simon and claims without him there would be a whole lot more work to do. Though having a right-hand man is important, Negan shows his doubts, not believing Simon can be the leader of the Saviors and Negan also has his furious views against Simon's more extreme ideas and plans.

During the war, Simon shows extreme doubts in Negan's strategy for regaining control over the communities, believing they are far too rebellious to fall back in line and should simply be wiped out so the Saviors can begin anew with other settlements. Negan is infuriated by this suggestion, believing it is the easy way and that "saving" people through punishment is far more rewarding for them as people are resources. In response, Simon boldly states that Negan's warnings and punishments for done nothing for them lately but further motivating the communities to fight back. While Negan's right-hand man, it appears that Simon's true loyalties lie with the Saviors as a whole, wanting to do what he feels what is best for their survival and showing a great amount of concern for his people. Simon also assisted Negan in taking over the Saviors was not out of loyalty towards Negan himself, but because he thought Negan would be a better leader than John.

Simon begins directly disobeying Negan's orders and is inclined to his more bloodthirsty nature, instead giving in to his impatience and orders the Saviors to wipe out their enemies instead of trying to control them. Simon also attempts to look for members of their empire that despise or disagree with Negan's strategy, and even chooses to abandon him and become the leader of the Saviors himself when Negan is attacked and disappears. This shows that their relationship is completely severed.

Upon Negan's return, Negan proceeds to humiliate Simon in front of the entire Saviors however he seemingly forgives him for his actions and lets him continue to work as his top man even, but is less friendly towards him. Their relationship now however is completely and utterly severed, as Simon begins plotting against Negan and desires to kill him to become the leader. In prison, Simon and Negan are often seen together and having each others' backs and acting friendly towards each other, however Simon continues his plot against Negan and blames him for losing the war, wishing that Rick Grimes killed Negan instead of arresting him. Simon tries to kill Negan himself and abandons him with his own group of likeminded individuals, causing a civil war within the Saviors with Simon against Negan. Negan eventually brings down Simon's group and kills his former friend and right-hand man, but felt bad about having to do it.