Simon Philips

Simon Philips is an antagonist and main character in The Walking School, serving as the secondary antagonist of season six, season seven and season eight. He was the borderline psychopathic second-in-command of Negan and high-ranking member of the Saviors. However, Simon proved to be far more bloodthirsty, psychotic and ruthless than Negan and as a result, was willing to kill.

Personality
Simon Philips is a sadistic, brutal, and anticulate teenager considered even by Negan Morgan too violent and psychotic. He has displayed extreme loyalty and is a highly valued and trusted gang member, not beyond using fear and intimidation to achieve his ends and encourages the excessive violence and bullying that the Saviors employ. Simon shows no emotional reaction to the atrocities and crimes he and the Saviors had committed, taking pleasure in the violence.

As the second-in-command of the Saviors, Simon holds a large amount of power and influence within the gang, controlling his own set and has proven to be a capable leader and stategic thinker. In spite of being Negan's most loyal best friend and follower, Simon has disobeyed him a number of times and favors more bloodthirsty and violent methods and motives. Simon is also not bothered causing harm to children or the elderly.

On Negan's behalf, Simon commands his own set which controls Savior territory in Satellite Road and eventually temporarily taking over Hilltop Avenue, where he takes pleasure in terrorizing any non-Saviors. He has demonstrated and verbally expressed his admiration for authoritarian leaders, and those who lead by example, something which he puts into practice with his uncompromising methods, and strict obedience to Negan. Simon also enjoys smoking marijuana and his set business consists of selling drugs.

During the gang war, Simon becomes increasingly unhinged and loses patience, eventually emotionally breaking down and becoming much more borderline psychopathic and mentally unstable. Simon becomes a murderer and shows no regrets with anyone he kills, believing it is the greater good for the Saviors' sake. This makes everyone, even Negan and the thugs under Simon's leadership, realize Simon is a extremely dangerous individual and becomes greatly feared. Ultimately, Simon's thirst for blood and desire to eliminate his enemies due to his power hungry nature would lead to his own downfall and life sentence in prison. Simon

Background
Simon Philips grew up to a father who sold subprime mortgages to unsuspecting customers and was fully able to justify his immoral motives to other people even though he was fully aware of his own sinister motivations. However, when Mr. Philips lost this occupation, he turned to alcohol and became abusive to Simon physically and verbally. Due to this, Simon was driven to murder his abusive father in his sleep with his own switchblade and was arrested by the police as a result. However, Simon was released from jail after it was believed to be self-defense after he revealed the scars and bruises from his abuse.

Simon eventually met and befriended Negan Morgan and subsequently joined his gang known as the Saviors, upon where the two developed a firm loyalty toward each other and thus Negan later appointed Simon as his personal right-hand man.

Killed Victims

 * 1) Mr. Philips: Stabbed in the throat.
 * 2) Brion Murphy: Shot in the chest.
 * 3) Tamiel Gennaniro: Shot in the head.
 * 4) The Scavengers: Shot to death alongside his fellow Saviors.
 * 5) Jadis McIntoshi: Burned to death.
 * 6) Bruce Hucker: Stabbed in the stomach with a machete.
 * 7) Beth Greene: Shot in the stomach.

Other Victims

 * 1) Unnamed Man: Simon and his crew severely beat up the man to make an example of him to Rick and his group, then left him bleeding and barely conscious on the road for Rick to witness. Simon also left a note on the man, warning Rick of the future.
 * 2) Eugene Porter: Simon managed to kidnap Eugene to bring him to the woods along with Rick's group..
 * 3) Rick Grimes: Simon was responsible for capturing Rick and his group for Negan, he forced Rick to his knees and took his switchblade, even threatening to cut him with it. Simon also assisted Negan in breaking Rick by giving him a pen to use to threaten to cut Lori's arm off.
 * 4) Gregory Aktinson: Despite being an adult and principal, Gregory was a frequent bullying victim of Simon. Simon often threatened Gregory and cowed him into submitting to Negan personally, taking joy in it, and then treated Gregory like an ally when the Saviors required his services. Though when Gregory failed to make Rick and his group back down by using his power as principal while turning a blind eye to the Saviors, Simon attacked Gregory furiously for failing and making him look like a fool in front of Negan. This resulted in Gregory falling off a platform and injuring his leg, to which Simon only smiled at.
 * 5) Paul "Jesus" Monroe: When Jesus tried to stand up to the Saviors, Simon punched him in the stomach and left him to gasp for air.
 * 6) Alden McAuflie: For showing insubordination and standing up to Simon, Simon angrily beat up Alden in front of the other Saviors very badly. Alden was left with chipped teeth, bleeding and could barely breathe, and Simon remarked that nobody do what Alden did again. Alden was then taken hospital by Simon's thugs and forced to lie about who attacked him.
 * 7) Jerry Andrews: On his way to retake control of Hilltop Avenue, Simon encountered Jerry and beat him up along with his men to capture him. Simon had Jerry taken hostage to make Maggie back down and was ready to give the order to have Jerry killed, but Maggie managed to save Jerry by listening to Simon, resulting in Jerry being released on Simon's orders.
 * 8) Kal Chen: During another attack on Hilltop Avenue, Kal tried to attack Simon though was beaten down. Kal though managed to save himself from being killed by Simon and in turn, hurt his hand.
 * 9) Tara Chambler: During another attack on Hilltop Avenue, Simon attempted to murder Tara with his machete though she was saved and he was forced to retreat.
 * 10) Dwight Parker: Simon tried to attack Dwight after he betrayed him but was held back.
 * 11) Shawn Greene: While attacking the Greene Family Farm in an attempt to kill Rick, Shawn tried to stop Simon outside of the house though was shot by Simon. Shawn however managed to survive and was hospitalized.

Negan Morgan
Simon and Negan had a strong relationship, as he is Negan's best friend and most trusted right-hand man. As the second-in-command of the Saviors, Simon is entrusted with a considerable amount of power and authority, close to Negan himself. He often speaks on Negan's behalf and in turn, Negan highly values Simon and views highly of him. Though having a right-hand man is important, Negan shows his doubts, believing Simon isn't capable to lead the Saviors.

Simon eventually shows extreme doubts in Negan's leadership during the war, believing that Negan isn't truly capable of taking "real" action. Simon begins to argue and talk back to Negan, boldly stating his strategies are just not working. While Negan's best friend, Simon's loyalties lie with the  Saviors as a whole - wanting to do right by them and maintain the gang and shows a great amount of concern for his thugs. Simon starts to directly disobey Negan's commands and give in to his more bloodthirsty nature, which is murdering his enemies. Upon Negan's return to control the Saviors and realizing what Simon had done, Negan proceeds to humiliate Simon in front of the rest of the inner circle, forcing Simon down to his knees and taunting him. This results in Simon getting angry and raged at Negan, suffering from a mental breakdown. Simon then rounds up his most loyal friends from the Saviors and goes to the party at the Greene Farm to kill Rick, just to show Negan that he is better as leader and out of revenge for Rick and his group's actions. After Simon had killed Beth and Negan realized his actions, Negan was disgusted in Simon for the murder and eventually realized his wrongdoings because he didn't want to end up like Simon.

After the years had past with Negan being a teacher and Simon in prison, Negan decided to visit Simon. They had a civil conversation and Negan visits Simon because he wanted to end their relationship on a better note, with Negan forgiving Simon for his actions and admits he feels partially responsible for it. Simon though actually resents Negan, believing he ultimately betrayed him and while the two remember their good times as friends together, Simon mocks Negan for his teaching profession, believing he has gone soft. Negan in turn hopes Simon the best in prison and that he wishes Simon was one of the Saviors who reformed and finished school to make something of themselves, apologizing for not helping Simon and that he blames himself for Beth's murder and Simon's mentally instability and imprisonment. Simon though, despite seemingly being forgiving, promises to murder Negan one day for his betrayal.

Dwight Parker
Simon and Dwight have a neutral relationship as the highest ranking members of the Saviors, having a mutual respect for each other. While Dwight seemed to see Simon as a friend like the other Saviors and that he respected and trusted him, he actually hated Simon and saw him as even worse than Negan. Simon also had higher authority than Dwight but, despite this, Simon treated Dwight like an equal and even admired and greatly respected him. After Negan was arrested, Simon tried to convince Dwight to assist him in taking over the Saviors and personally dealing with Rick's group to "move on", Dwight went along with Simon, believing that he is an easier threat than Negan however this proved to be wrong as Simon was willing to exterminate the enemy.

Dwight was terrified of Simon and when Negan was released from jail due to lack of evidence, Dwight told Negan about Simon's plans and as a result, Negan punished Simon and Simon became extremely angered at Dwight, trying to attack him as a result though is held back. Dwight shows no remorse for betraying Simon While Negan visited Simon in prison, Simon still resents Dwight for what he did and even wants to kill him.

Gary Seal
Simon and Gary have a good relationship, as Gary often accompanies and assists Simon. Simon treats Gary like a close friend and trusts him as his personal number two man, often enlisting Gary to help him with various tasks. Gary shows no hesitation in following Simon's orders, no matter how extreme or heinous, even if it means murder. Toward the end, Gary showed his true loyalties when he sided with Simon over Negan, but this cost him being sent to prison.