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Villain Overview
It occurs to me that I've not yet received the full definition of an apology. I feel like I've gotten some transgressional acknowledgment, the guns certainly cover restitution. But what I'm not yet feeling... Is the remorse. (...) SAY IT AGAIN! (...) Ohhh. No, no, no. *laughs* Ohh! Ah. I don't think you mean that!...Light it up, gents. LIGHT IT UP NOW!
~ Simon orders the massacre of Jadis' group.

Simon is a major antagonist in the AMC television series The Walking Dead. He was a high-ranking member of The Saviors and the right-hand man of their tyrannical founder; Negan. In Season 8, he temporarily acts as the de-facto leader of The Saviors after briefly usurping Negan's position.

He serves as the secondary antagonist from the second half of Season 6 to the first half of Season 8, the main antagonist of the second half of Season 8 (until Negan retakes that role for the finale) and a posthumous antagonist in Season 9.

He was portrayed by Steven Ogg, who also played Trevor Philips in Grand Theft Auto V, Professor Venomous and the Shadowy Figure from OK K.O.! Let's be Heroes.

Personality

Simon is a wildly unpredictable and brutally sadistic sociopath. Much like Negan, he is shown to be very charismatic and intelligent to a fault. Initially, he appeared to be completely loyal to Negan. As such, he was highly valued by Negan as a right-hand man, which was proven in the first episode he appeared in, where he single-handedly managed to divert Rick and his group into a trap through cleverly placed roadblocks preventing them from escorting a pregnant Maggie to the Hilltop, where he finally intimidates Rick into submission ready for extortion.

However, in spite of being an intelligent and dangerously effective right-hand man, Simon is in many ways a reckless and ambitious individual. Unlike Negan, Simon is much more destructive and bloodthirsty, and he appears to completely lack remorse. He is generally much more willing to resort to mass murder to achieve the Saviors' means of survival, which has resulted in hundreds of people from different communities dying by his hands. It is known that Simon is solely responsible for the massacre of the Scavengers, the library survivors and all of the male residents from Oceanside. This behavior appears to have clashed with Negan's ideology multiple times, who is more willing to kill at least one or a few people as a punishment to drive other communities into submission, as well as seeing that needlessly killing people is a waste of resources. This is first apparent when Negan scolds Simon for suggesting that they raid the Hilltop during their meeting for the upcoming war. Negan even goes as far as to admit from his perspective that Simon is "a demented, broken, god damned ghoul", making it clear that he is has been extremely wary of keeping Simon around as his right-hand man.

In addition to his dangerous presence and ruthless methods, Simon is shown to have a short temper, first seen when he lashes out at Gregory for failing to convince the Hilltoppers to surrender to Negan. As such, it is evident that his temper has heavily contributed to his cruel actions, especially with his action taken against the Scavengers and is shown trying to hold himself back after unexpectedly killing Neil in front of Maggie.

Over the course of the series, Simon gradually loses faith in Negan as a leader and openly criticizes his system of dealing with other communities, seeing it as ineffective and useless as they keep fighting back against the Saviors' tyranny. His lost patience with Negan is even driven to the point where he eventually betrays Negan and usurps his position of leadership by taking advantage of Rick's ambush on Negan, almost getting Negan killed in the process and later attempts to organize a plot to eliminate Negan with a group of Saviors under his command once Negan returns to the Sanctuary. His betrayal ultimately backfires and results in Negan personally beating him down and then strangling him to death.

In reality, his true loyalty lied with the Saviors rather than Negan himself, as he appears to be willing to do anything he feels necessary for the Saviors' survival as a whole and wishes to branch out to other outposts and communities, as well as to win the war against the Militia to keep the Saviors moving forward, even though his actions to achieve such goals were, in the end, rash and uncompromising.

History

Backstory

Simon was born in the late 1960s and grew up in Virginia, but extensively little is known regarding that of his early life. Simon grew to become a charismatic, efficient and hardworking man who sold subprime mortgages to unsuspecting customers and was fully able to justify his unmoral motives to other people even though he was fully aware of his own sinister intentions.

At some point during the apocalypse, he came across Negan and helped him and a group of people take over a factory. They fortify the factory and name it The Sanctuary and name their group "The Saviors", with Simon rising up in the ranks and becomes second-in-command. The Saviors become extortionists as a means to survive, and begin terrorizing other communities to force them into working for Negan by trading half of their supplies per pick-up in exchange for their lives. When one of their tributaries decide to retaliate against the Saviors for their brutal system, the Saviors overwhelm their efforts. As a punishment for fighting the Saviors, Simon callously singles out all of the community's male residents aged 10 and up from the rest and executes all of them. The surviving women and children decide to flee from their settlement and take residence in the "Oceanside Cabin Motor Court", where they isolate themselves from the Saviors.

Negan was particularly displeased with Simon's actions and has second thoughts about keeping him in such high authority over the Saviors, and made sure to keep a close eye on him until things cooled down.

Season 6

Trapping Rick's Group

Simon was first encountered when he and a band of others Saviors hunt down a man in the woods. They then mercilessly beat him and drag him to a road, intending to show him to Rick's group as a warning. When Rick and his group arrive at the scene in their RV on their way towards Hilltop, they are stopped by a roadblock made by Simon's group. He orders Rick to hand over their belongings and when refused, Simon says that they will not negotiate and their deal is the only deal. Simon then warns Rick about what will happen to those who oppose Negan and recommends him to treat his friends like it was their last day on Earth, knowing full well what Negan is going to do with them.

During their journey to bring Maggie to the Hilltop, Rick encounters more roadblocks orchestrated by Simon and he and his group are constantly forced to back up and find a different route. The final roadblock involved a mass of logs piled up on the road above an overpass. Once Rick and his group arrive at the roadblock, Simon has the man he beat up earlier thrown off the overpass and hanged by a chain and has his men set the logs ablaze. Simon taunts Rick from behind the burning log pile, reminding him that one of his people could still die today and advises Rick to leave. As the fire grows larger, Rick and his group rush back to the RV and drive away.

The Lineup

He is encountered once again in the climax, when a large group of Saviors led by Simon ambush Rick's group in the woods after scaring them into their trap by whistling at them. He then orders them to hand over their guns while threatening to shoot Carl. Rick, visibly intimidated, attempts to reason with him only for Simon to immediately refuse and demand their weapons. He also orders Dwight to go get the rest of the group that were captured earlier. After Rick and others are forced to line up and get on their knees, Simon knocks on the RV and summons Negan himself to make an entrance. When Negan asks which one is the leader, Simon points at Rick, telling him that he was the man responsible for the deaths of his men. He is present when Negan makes his speech and beats Abraham Ford to death with Lucille.

Season 7

Simon, along with the other Saviors, witness the execution of Glenn by Negan. When Negan captures Rick and brings him back to the clearing, Simon is asked by Negan if he has a pen, so he can draw the line of amputation on Carl's arm, to which he happily responds he does.

First Visit to the Hilltop

During Sasha and Maggie's stay in the Hilltop Colony, Simon orchestrates an attack on the community by opening the gates and luring a horde of walkers inside using a parked car with speakers playing music loudly, which is sealed inside with metal grates. A metal hand extending its middle finger is attached to the back of the car. With the help of Jesus, Maggie and Sasha manage to eliminate the walkers and close the gates.

Later, Simon appears at the Hilltop Colony, being in charge of a group of Saviors. Arriving at the Hilltop, Simon and his men enter the Barrington House where Simon invites himself into Gregory's office. There, he has an uncomfortable conversation with Gregory, speaking of the satellite outpost that was raided by Rick and his group. He explains that the incident the previous night was a reminder that the walkers are still a threat, and the Saviors provide a great service by killing them in exchange for the Hilltop's supplies. Due to Gregory being an awful liar, Simon senses that Gregory is hiding something and pressures Gregory to show him. Intimidated, Gregory leads Simon to the closet where he believes Sasha and Maggie, who have hidden from the Saviors at Hilltop, are hiding.

However, the two women were relocated by Jesus in time and Gregory is forced to improvise when the closet is revealed to be empty, instead begrudgingly gifting Simon with the scotch from his personal storage he was keeping in the closet. Simon is pleased, as, although he himself does not like scotch, knows Negan will be pleased. He orders the scotch to be brought to the truck delivering stuff to Negan and then orders the Saviors to spread out in order to take half of all the belongings of the colony. Before the Saviors leave the community, Simon publicly forces Gregory to kneel before him, both to undermine Gregory's authority and to reinforce his dominance.

Searching for Daryl

After Daryl escapes from the Sanctuary, Negan sends Simon and his men to Alexandria for a search. Rick, pretending that he doesn't know anything about Daryl gone missing, claims that he hasn't seen him ever since Negan took him. Simon then orders his men to turn Alexandria inside out just in case. After finding nothing, Simon then leaves Alexandria and advises Rick to take care of Daryl as soon as he sees him again and that he doesn't get away with his escape, the way Carl did.

Second Visit to the Hilltop

In the episode "The Other Side", Simon and his men returned to the Hilltop Colony and is still searching for Daryl. He spends some time with Gregory and they both agreed that if there is any trouble in the Hilltop, Gregory will come to the Sanctuary and they will take care of it. While there, he also took Dr. Harlan Carson from the Hilltop to the Sanctuary as a replacement for his late brother, Emmett Carson; whom Negan recently killed. In exchange for transferring Harlan to the Hilltop, Simon leaves behind a crate full of aspirin.

The War Begins

Later on, Simon, Negan, Dwight, Eugene and the rest of the Saviors drive to Alexandria with Sasha held hostage in a coffin while the people of Alexandria prepare for a fight. Prior to their arrival, they come across several trees chopped down and blocking the road, to which Simon and Negan assume that it was Rick's doing, unaware that it was Dwight who actually set up the roadblock.

Upon arriving, The Saviors unexpectedly outnumber Alexandria after Jadis and the Scavengers turn their guns on Rick and his group (who secretly made negotiations with The Saviors in exchange for spying on Rick). Simon and Dwight both reveal the coffin Sasha is kept in, and Negan announces that if Rick gives him all of their supplies and lets him kill one of his people, he will give them Sasha unharmed. However, a zombified Sasha tackles Negan after being let out of the coffin, which Alexandria uses as an opportunity to open fire on Jadis' people, starting a massive gunfight. After Negan pushes Sasha off him, Simon covers Negan and brings him behind cover. Simon then flees along with the rest of the Saviors back to the Sanctuary after people from the Hilltop Colony and the Kingdom turn up and join the fight against them. Afterwards, Alexandria, the Hilltop Colony and the Kingdom form an alliance between each other to put an end to the Saviors once and for all, collectively forming "The Militia".

Season 8

Attack on the Sanctuary

When the Militia arrive at the Sanctuary fully armed, Simon is present among the rest of Negan's lieutenants during the standoff. Rick announces that he will let the rest of the Saviors live if they surrender at the cost of Negan's life. In response, Negan boasts that the Militia does not have the equal numbers in a fight against the Saviors and orders Simon to bring out Gregory, who secretly left the Hilltop to seek help from the Saviors to keep his own people in check. In an attempt to sow distrust between the Militia, Simon brings out Gregory and has him announce that the Hilltop stands with the Saviors, and that anyone from the Hilltop who stands up against the Saviors will be evicted from their home. However, Jesus yells that the Hilltop no longer stands with Gregory, but with Maggie instead. Simon is visibly enraged by this revelation, and angrily voices his disappointment in Gregory before shoving him down a flight of stairs. Rick continues to urge Negan and his group to make up their minds and starts counting down from ten, but unexpectedly opens fire on the Sanctuary mid-way through his countdown, forcing Simon and the rest of the lieutenants to run back inside the factory while Negan dives for cover.

In "The Big Scary U", Simon is first seen in a flashback with Gregory. He mentions how he came to him when he needed him and Simon reassures him that he did the right thing. Gregory was going to reveal the alliance between the Hilltop and Kingdom, but Simon was "finding out at that point" from someone in Alexandria according to Gregory. Later, Simon is in the meeting that was mentioned by Negan in "Mercy". They discuss plans on how to stop Rick and the Militia and to try and subtract the Hilltop numbers from the Militia.

Simon suggests a strong raid on the Hilltop, which could end in killing everyone there if they don't cooperate, which would send a message to the other communities. Negan suddenly smacks the table with Lucille, "People are a resource", he furiously insists. "Money on the table. PEOPLE ARE THE FOUNDATION OF WHAT WE ARE BUILDING HERE!" He questions Simon and if he remembers who they are and who is in charge, and asks if him if things are "backsliding" (likely in regards to the incident involving the Oceanside community). Simon sternly pledges his allegiance. Negan declares that they have to capture Maggie, Rick, and King Ezekiel and kill them horribly in front of the Militia to force them back into submission. Suddenly, The Militia's gunshots ring out outside. Negan pauses and looks out the window to see Rick and his group are outside the door. He and the rest of the Saviors step outside.

Trapped in the Sanctuary

In the present, Simon is in the room with Gavin, Regina, Dwight and Eugene as they have another meeting. Regina mentions how if Negan is dead and they should send workers to distract the walkers while they alert the outposts. Eugene refuses to do that, as he insists they are valuable. Dwight agrees and says to Simon that if they are not gonna lead the Saviors out, he will. Simon has a angry grin on his face and compliments Dwight about his idea. He explains how when they find the traitor, they will kill him slowly in front of everyone. Simon is seen in another scene where Laura comes in the room and says the workers are outside.

Simon and the rest of the Lieutenants step out and he orders everyone to go to the factory floor. At first the workers refuse to listen to his order and ask the Lieutenants when the electricity is coming on, as well as pleading for food and water. As Simon attempts to calm them down, one of the workers draws a gun, prompting Regina to shoot him. At that moment, Negan and Gabriel walk in, with Negan explaining how he is going to take a shower, eat a sandwich and has to have a "talk" with Simon about the mole who caused the ambush and the herd.

Dealing with Maggie

In the episode "How It's Gotta Be", Simon and a group of Saviors cut off Maggie and the Hilltop members after escaping the sanctuary. It is revealed he has captured and brutally beaten Jerry and is keeping him as a hostage, he explains to Maggie that Alexandria and the Kingdom are going to be taken over by the Saviors but Hilltop will be allowed to keep producing for them as long as she surrenders. He then explains he will need to kill one of her people and immediately shoots Neil, killing him as a horrified Maggie breaks down in tears. Simon then orders Gary to shoot Jerry to which Maggie agrees to his terms with the request that she is allowed to take the coffin to the Hilltop to bury Neil in. Simon grants her request and leaves.

Arguing with Negan

Back at the Sanctuary, Negan is pleased to hear that Simon's mission with the Hilltop forces was a success, but Simon wishes to know where Negan wants him to be while the Saviors take action against the people of Alexandria and the Kingdom. Negan then orders Simon to head over to the junkyard to deal with the Scavengers, but sternly implores him that in spite of their double-crossing, that Simon should only kill one of their people to make sure they stay in line. "Just, one, Simon", Negan sharply reiterates. Frustrated, Simon expresses that Negan's system isn't working, pointing out that the opposing communities refuse to learn the lesson the Saviors have repeatedly tried to teach them and suggests that they should exterminate the Militia as a means to an end and attempt to find more communities willing to fall in line. Negan shoots down his suggestion, stating that massacring other communities is not what the Saviors stand for, reminding Simon that people are a resource, and that the only person they really need to kill to get things back to where they were is Rick.

At that moment, Gary, Norris and D.J. enter the room with a coffin containing a walker and a nail gun, explaining that they received it from the Hilltop and leave. The coffin reads "WE HAVE 38 MORE. STAND DOWN.". Simon pries open the coffin while Negan kills the walker with the nail gun, who happens to be a zombified Dean, who Maggie killed in retaliation after Simon killed Neil. Simon angrily expresses that Dean and the rest of the hostages at the Hilltop are his people from the Satellite Outpost, and wishes to kill every single person left at the Hilltop. Negan furiously smacks the table and yells at Simon to do exactly what he says.

The Junkyard Massacre

Later on at that point, Simon begins to defy Negan's orders. Simon brings Gary and a large squad of Saviors to the junkyard, standing off against the Scavengers. Simon politely asks Jadis to apologize for making a deal with Rick and taking up arms against the Saviors, but Jadis flatly denies that she made a deal with Rick, explaining that she made a deal with the Saviors to help turn Rick over to the Saviors. Simon angrily calls out her lie, but continues to deliver the standard message while struggling to maintain his composure. He states that Negan will forgive the Scavengers as long as they agree to the terms provided, but the Saviors need to confiscate their guns as a result of their betrayal.

However, after the Scavengers agree to hand over their guns, Simon still hangs around, questioning Jadis about their choice of home, and why it has the solar panels and a helipad. Simon then begins to demand remorse, not feeling a genuine apology from Jadis, for which Jadis says that there is. Suddenly, Simon draws his gun and shoots Brion in the chest, killing him before turning his gun on Tamiel. Shaken, Jadis expresses once again that there is remorse, but Simon shoots Tamiel anyway in spite of her protests. "SAY IT AGAIN", Simon yells before Jadis punches Simon, knocking over and spilling a can of blue paint. Simon, in retaliation, furiously orders his men to gun down the Scavengers. Jadis watches her people getting wiped out in horror as Simon sadistically smiles. During the slaughter, Jadis flees from the Saviors and wipes blood from a dead Scavenger on herself and plays dead. Gary briefly inspects her body before thinking that she is dead, spitting on her before rejoining the massacre.

Simon and his men return to the Sanctuary, lying to Negan about what really happened at the junkyard, reassuring Negan that the standard message was sent as planned. As Negan walks off to talk with Rick on a walkie-talkie, Simon looks down to see the blue paint from the junkyard on his boots and gives Gary a stern look.

Betraying Negan

After Negan establishes an attack plan on the Hilltop to the Saviors by tainting their melee weapons with the remains of walkers in order to infect people, Simon is among the many Saviors covering their weapons in walker guts. Negan gloats to Simon about how the plan will literally put the people at the Hilltop on their knees, with Simon appearing to agree. As soon as Negan walks away, Simon's smile immediately disappears. Simon relays Negan's orders to a group of Saviors: they are only going to infect a few people at the Hilltop and let them turn instead of killing them as a scare tactic. Simon then urges Dwight to ride with him in his truck, due to Negan taking his own car in the convoy, much to Dwight's protests.

On the way their way to the Hilltop, Simon asks, as mutual lieutenants serving Negan, for Dwight's honest opinion on the plan, to which Dwight responds that he doesn't get paid to think. Regardless, Simon vents his frustration towards Negan's leadership, explaining that he doesn't think the plan will work at all due to the opposing communities constantly fighting back every time the Saviors attempt to force them in line through fear and intimidation. As they pass through a town, Simon notices a car approaching through one of the alleyways and deliberately ignores it, resulting in the pursuing car, driven by Rick, to smash into Negan's car, which veers Negan away from the convoy while Rick chases after him. As the Saviors express shock at the situation, Simon begins to grin at what has happened to Negan before he and Dwight step out of the truck. The Saviors block the alleyways in case there are more people from the Militia ready to ambush them, while Simon orders the Saviors to stay where they are so him and a Dwight can search for Negan alone. Arat urges that they should back them up, but Simon continues to make excuses, explaining that Negan can easily handle one attacker alone and that the Militia will probably try and draw the Saviors out into a trap. Simon and Dwight then head out to find Negan.

Meanwhile, Rick continues to hunt Negan down in a building. Negan attempts to make a deal with Rick, but Rick questions why he should trust Negan after what he did to the Scavengers. Confused, Negan asks what Rick is talking about, to which Rick replies that Negan massacred them. Negan quietly seethes upon realizing that Simon massacred the Scavengers against his orders and quietly curses him while Rick continues to chastise him.

While Simon and Dwight search, Simon opens up to Dwight and asks if he ever considered wanting to kill Negan. Dwight sarcastically admits that he indeed has considered it due to Negan taking his wife from him and burning his face. Surprised and appearing to break through to Dwight, Simon then tells Dwight that he chose not to kill Negan as a means to survive the apocalypse just like everyone else has and appreciates him for doing so, and asserts that Negan on the other hand, isn't helping the Saviors survive at all and is jeopardizing the war even further by choosing not to exterminate the Militia. He further states that if he were the leader of the Saviors, he proposes that they should put their foot down and defeat the Militia so they can branch out to extort new communities as means of survival, and asks Dwight if he is on board (still unaware that Dwight has betrayed the Saviors in favor of the Milita's cause). Dwight dismisses the offer and says that they should just move on, much to Simon's disappointment. The duo eventually come across Negan's crashed car now leaking gasoline, with Simon concluding that they don't know if he is alive or dead, and gives Dwight two choices: they can either search for Negan and go back to how things are or leave him for dead and help the Saviors expand. Dwight, at first hesitantly, chooses the latter by lighting a cigarette and setting Negan's car ablaze, pleasing Simon.

Taking Over

The rest of the Saviors confront Simon and Dwight about Negan's whereabouts once they return without him, and announce that they couldn't find him and that the best course of action is to presume him dead. Simon then manipulates the Saviors with a speech: it doesn't matter if Negan is with them or not, the Saviors are all "Negan". Simon declares that although they were going to carry out Negan's original plan, they should instead avenge Negan by taking out the Militia once and for all after Rick's personal ambush on Negan, regardless if Negan survived or not, since they still won't learn from the Saviors' punishments, and the Saviors must accept that fact. "They are a mistake that we shall now erase! We are moving on. FOR NEGAN! YES?!", Simon declares and the Saviors cheer. With Simon taking full advantage of Rick's ambush on Negan, he has now become the de-facto leader of the Saviors.

Assault on the Hilltop

Simon and his convoy eventually arrive at the Hilltop, parking outside and pulling a spike trap out of the way. Maggie calls for Negan over a walkie-talkie, to which Simon responds, claiming that he is both speaking and acting on Negan's behalf that the Militia will have to pay by force for their lack of cooperation. Maggie threatens that she will personally execute all thirty-eight of his people from the satellite outpost if Simon refuses to stand down. Simon callously declares that he does not care about the prisoners, stating that they brought their mess upon themselves and begins his preparations to attack the Hilltop. Dwight interrupts and warns Simon that Negan could still be alive out there and asks if Simon really wants to eliminate the Militia at the risk of still being punished by Negan. Simon dismisses the warning by saying "Better to beg forgiveness than to ask permission".

Suddenly, Daryl ambushes the Saviors on his motorcycle, prompting the Saviors to get in their vehicles. Simon's convoy rushes through the gates of the Hilltop before they close before they are suddenly blocked by a school bus from the Kingdom as they enter. Under heavy fire, Simon orders his men to fire upon the Militia with bows and walker-tainted arrows, injuring and infecting a few members of the Militia and their prisoners, forcing Maggie to order them back inside the Barrington House. The Saviors then charge in with their tainted melee weapons and start to infect members of the Militia close by, including Tobin. Simon spots Tara and brings Dwight along with him in an effort to ambush her, sneaking past several parked vehicles. Just as Simon is about to attack Tara with a tainted hatchet, Dwight saves her life by shooting her in the arm with a non-infected arrow, which tricks Simon into believing she was infected. They are then forced back behind cover after being fired upon by Daryl.

The Militia suddenly ceases fire after shooting out the headlights on the Saviors' vehicles, leaving the Hilltop entirely in the dark. Simon emerges from his cover with the Saviors following behind him, splitting up and sharing his men between Arat and Gary. The Saviors slowly approach the Barrington House while Simon attempts to intimidate the Militia by whistling. However, the Militia tricks them by lighting up a row of headlights from vehicles parked in front of the Barrington House, briefly blinding them, and open fire. Rick then shows up with a squad and ambushes the Saviors, prompting Simon and the rest of the Saviors to flee from the Hilltop in their vehicles.

Despite receiving heavy casualties from their assault, Simon and his men successfully infect many members of the Militia, unexpectedly causing them to reanimate and kill more people from within the Hilltop. In the ensuing chaos, Gregory and many of the satellite outpost prisoners escape from the Hilltop.

Negan's Return

After escaping, Gregory makes it back to the Sanctuary and meets Simon, who is currently unaware that Negan has made a surprise return. Gregory sits with Simon hoping to make amends with Negan over his predicament with the Hilltop, but Simon informs him that Simon is now in charge of the Saviors due to Negan being presumed dead, and expresses that he wishes to maintain his control, without Gregory's help and wants him to leave due to seeing him as a liability. Gregory congratulates Simon on becoming the leader of the Saviors, but begins to arrogantly criticize him, seeing that the Saviors are unable to advise Simon on how to manage different communities and resources, while telling Simon that he can. Due to Gregory's botched plan to split the Hilltop numbers from the Militia through threats of eviction, which resulted in Simon feeling humiliated, Simon firmly states that their partnership has ended and doesn't need him anymore. Gregory angrily talks Simon down, ranting that Simon hasn't got what it takes to keep things managed around the Sanctuary and gloats that he has the leadership that Simon doesn't, which provokes Simon into violently throwing him to the floor. Simon explains that he had contemplated killing Gregory upon seeing him turn up to the Sanctuary again, but changes his mind and allows Gregory to work under him, but only to start him off by having Gregory make coffee to see how it lasts.

Once Simon realizes Negan is back, he attends a meeting between Negan and the rest of the lieutenants. Simon tells Negan that he thought Negan was killed by the Militia, so he took it personally by taking the assault a step further by changing the plans from infecting a few of the people there, to outright eliminating them in retaliation for his apparent death. Simon then asks for Negan to forgive him, taking responsibility for his thwarted raid. Skeptical of Simon after learning what he did at the junkyard, Negan openly expresses that after they took control of the factory and turned it into their home, he had his doubts about keeping Simon around as the second-in-command after Simon had killed all of the men and boys at Oceanside, deeming Simon to be too psychotic to work with at the time, but decided to keep an eye on him. Negan says at that point, things remained stable since then, until what has happened during the war with the Militia. Negan decides to force Simon on his knees with Lucille ready in his hand. Upon doing so, Negan asks if Simon is willing to make a move, with Simon asserting that he won't, convinced that Negan is ready to beat Simon to death with Lucille and accepts his fate. However, Negan forgives Simon and tells him to get back up. Negan then informs Simon of their plan to lay siege to the Hilltop with squads of Saviors in designated spots surrounding the community in hopes of forcing the Militia to surrender by sniping them. Simon goes along with the plan, welcoming Negan back.

While Dwight decides to make a copy of Negan's map and his planned siege on the Hilltop in order to hand the information over to the Militia, a knock is heard on his door. After he hides the map, Simon enters Dwight's room, visibly unhappy about Negan being back in charge. He tells him that they must find anyone in the Sanctuary who is unhappy with Negan's rule, and finally kill Negan in order to end the war and make sure the Saviors survive. Still noticing that Dwight is hesitant, Simon angrily tries to convince him that it must be done, reminding Dwight of everything Negan has done to him as reasoning to be on board. Dwight finally gives in and says he will help him in his plan, pleasing Simon.

After gathering a group of people, including Gregory and Gary, Simon meets Dwight outside and begins to discuss the plot to kill Negan. Simon declares that they must do it in at least a quiet and respectful manner and even offering if Dwight wants to be the one to take him out due to the personal issues Dwight has with Negan. He further states that they shall do it in a meeting and simply move on from there and rebuild their community after they finish the war, swiftly apologizing to Gregory about wanting to exterminate the Hilltop's residents. However, Negan suddenly interrupts the meeting and counts down from three. Once he does, all of Simon's men except Gregory are swiftly gunned down. As Simon's weapons are confiscated, he realizes that Dwight tipped Negan off about Simon's plan. Enraged, he lunges at Dwight before being restrained by D.J. and Norris. "Now there's the Simon that I know. Comes right at ya instead of that backstabbing bullsh-t", Negan taunts. Negan berates Simon for killing all of the Scavengers against his orders, but offers to give Simon a fair shot at killing him: in a one-on-one fight to the death to prove which of the two is truly in charge.

Death

Inside the Sanctuary, the Saviors form a circle around Negan and Simon as they prepare for their fight. Simon publicly brags that after the fight is finished, they will get back to work. He further explains that he didn't want it to come to this, but is willing to do what he needs to do to keep their community standing, and states that Negan is incapable of doing so. However, Simon suddenly punches Negan in the middle of his speech and the two engage in a brutal fist fight.

After landing several punches on each other, Negan eventually gains the upper hand and viciously beats Simon and pins him down. While this occurs, Dwight quickly brings Gregory aside and gives him his copy of Negan's map, urging him to take it to Rick immediately, giving him keys to one of the cars and lets Gregory escape. Negan begins to strangle Simon, angrily chastising him for assaulting the Hilltop and failing, and in the middle of his rage, vows to kill everyone at the Hilltop after Simon had ruined any chance for finding a peaceful outcome in the war. Negan then crushes Simon's larynx with his bare hands, killing him. Due to his brain not being destroyed, he eventually reanimates off-screen.

Later on, a zombified Simon is then chained to the Sanctuary fence with the rest of the walkers guarding the Sanctuary.

After the Militia defeat the Saviors, Rick convinces them that they will remain at peace as long as they drop Negan's system altogether. They surrender peacefully and clear the Sanctuary fence of all of the walkers guarding their home while the joint-communities trade supplies with them. Because of this, it is presumed that Simon's reanimated body was put down.

Killed Victims

  • Library Survivor (Caused, Alive)
  • Neil
  • Dean (Indirectly Caused)
  • Brion (Alive)
  • Tamiel (Alive)
  • Tobin (Caused)
  • Kurt (Caused)
  • Kevin (Caused)
  • Dana (Caused)
  • Wesley (Caused)
  • Katy (Caused)
  • Bruce (Caused)
  • Gary (Indirectly Caused)
  • All male Oceanside residents above the age of ten (Caused or Direct)
  • Many unnamed Library survivors (Caused or Direct)
  • At least 130 unnamed Scavengers (Caused and Direct, Alive)
  • Several members of the Militia
  • At least 14 unnamed Saviors (Indirectly Caused)
  • Numerous counts of zombies and unnamed people

Appearances

Usage

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Quotes

Season 6

Why the face? I hope you're not putting this on us... When we showed your people a way forward, we gave you rules. You broke the rules, so folks had to die. The one who fired the first shot we strung him up to make an example of him! Could've stopped there! But you people, you still didn't listen. You wanted to fight... us! So this, is how it has to be!!
~ Simon beats up a fleeing survivor in his first appearance.
Think about it - what if it’s the last day on Earth for you? For someone you love? What if that’s true? Maybe you should be extra nice to those people in that RV, ’cause you never know... just like that. Be kind to each other. Like you said... like it was your last day on Earth.
~ Simon to Rick Grimes, advising him to care for his fellow group members.
Simon: Good! You made it! Welcome to where you're goin'. We'll take your weapons. Now.
Rick: We can talk about it!
Simon: We're done talking! Time to listen.
~ Simon captures Rick and confiscates his group's weapons.
Alright! We got a full boat! Let's meet the man.
~ Simon introduces Negan to Rick's group.

Season 7

Sorry, I shouldn't ask... You wanna slide that one, back in, period.
~ Simon to Gregory.
Simon: One last thing, Gregory. Can I just get a kneel out of you?
Gregory: Excuse me?
Simon: Kneel.
~ Simon threateningly reinforces Gregory into submission.
Oh, and Rick! If Daryl does turn up here... two days from now, two months from now... hell, even two years from now, just know that there's no statute of limitations on this. Keep that hatchet handy! You're gonna need it if he turns up with you people! And it won't turn out the way it did for your boy.
~ Simon to Rick, threatening to kill Daryl should he return to Alexandria.
...I think my look may have conveyed the information. People say I have an expressive face. But if not, let me repeat your question: Why do we need two doctors? Answer: we don't.
~ Simon callously informs Harlan Carson of his brother's death.
Hey, you like ice cream? We have ice cream. We have a lady that makes cardamom gelato! Sh-t ya not.
~ Simon tries to cheer Harlan up before he takes him to the Sanctuary.

Season 8

I feel, like I invested a lot into you. And I am very, VERY, DISAPPOINTED!
~ Simon furiously shoves Gregory down a staircase.
Wakey wakey, eggs pancakey, Gregory!
~ Simon serves Gregory some breakfast.
Negan: Who the hell do you think you're talking to? Are you confused about who we are? Are you confused about who is in charge? Are we backsliding, Simon? Please, tell me we're not backsliding.
Simon: We are not, backsliding. This is a pronounced event, and a fragile moment.
~ Simon is scolded by Negan for suggesting the option to kill everyone at the Hilltop.
So, this can go one of two ways. One. I can kill this likable gent on his knees over there, drag you out of this car, and put you in this box! Hm? In which, you will not suffocate to death, like your friend. Sasha? Then...then we take you to Hilltop, gather everyone up and kill you in front of the whole place. And then drag you back to Sanctuary and put you on a spike in front of HQ. And then my people will lead the walker herd, to the Hilltop and pull off the same move, that your people tried unsuccessfully at our place. Phew, what a pain in the ass! Everyone concerned! Hm?...Or two. You turn around. Go home, start watering that sorghum. Save everyone, and most importantly me, a lot of trouble. And yeah, we're gonna have to kill one of your people, but then we're aces.
~ Simon offers Maggie an ultimatum.
I just really needed you to know what I was talking about. I need you to smell it! Now tell me, I don't gotta kill this gent with the lustrous mane, tell me I don't gotta go down the line, TELL ME MAGGIE!
~ Simon threatens to kill Jerry in front of Maggie after killing Neil.
Simon: Maybe we should cut our losses here. These people can't learn the lesson no matter how many times we teach it. Alexandria, Hilltop, Kingdom, these garbage rats. They're not seeming to understand the situation, not one, little, bit. So maybe we learn our lesson. Scrape the plates into the trash. Move further out. Find other communities too. Save.
Negan: *chuckles* Oh, I am doing my best to hold it together right now. You wanna cut your losses? Take your own advice. Killing everybody to solve the problem, that is the easy way, not our way. What we do? Saving people? It is hard! But it damn, well, works.
Simon: Not lately.
Negan: Once I clip Rick, everything's aces again, Simon!
~ Simon and Negan argue over what to do with the Militia.
Simon: That's Dean! That means the other thirty-eight people that the Hilltop are holding are from the satellite outpost. Those are my people! I'm gonna kill every last one of those farmers!
Negan: You will do exactly what I ask.
Simon: We can't let them get away with this sh-t!
Negan: YOU WILL DO...YOUR JOB!
~ Simon is angrily ordered to deal with the Scavengers properly.
BULL...SH-T!
~ Simon calls out Jadis on her lie about her deal with Rick.
Standard message and delivery. Showed 'em and told 'em. There was remorse.
~ Simon lies to Negan about what he did with the Scavengers.
We've thrown a lot, at Rick, the Widow, the King, and they just keep comin'. Keep fighting! You've seen it, I've seen it! Tallying it up, I keep seeing the same answer. They don't scare!
~ Simon openly complains to Dwight about the Militia and how their attack won't achieve the desired outcome.
Simon: You must've thought about it. Clipping him yourself?
Dwight: You mean when he took my wife? And burned my face? Nah! Never thought about that. Not once.
Simon: ...But you didn't because you chose to survive instead of focusing on past discomforts! You are an adult! You did what you had to, to live...And yet our leader is not doing the same! If it was my call, we'd say "enough"! We'd branch out, we'd find new places, we'd make new relationships. We'd make sure, the Saviors survive, as you chose to. And we'd move on from past discomforts, as you wisely chose to.
~ Simon converses with Dwight over Negan's leadership.
We can keep lookin', maybe find him more alive than dead, but then what? We could face a distasteful moment. Or we could walk away. Get back to our people, and make things even better. This is a critical point in our history, Dwight. This is something we could tell our grandkids about.
~ Simon proposes to leave Negan for dead.
Simon: Who are you?
Gary: Negan.
Simon: WHO?!
Gary: Negan! I am Negan!
Simon: DAMN RIGHT YOU ARE! We all are! Don't matter if the big man ain't here! We're still Negan! We don't if he's "gone" gone. He could very well be back. Our plan, Negan's plan, was to go on to Hilltop, and put the fear of God in these people so that finally once, and for all they get with the program! But after what just happened? What they did to Negan? That tells me, that what we need from them is beyond them. It's time we come to accept that. Then once we do, it'll become crystal clear there's only one thing left for us to do. We must expunge them! We must redact them! They are a mistake, that we shall now erase! We are moving on. FOR NEGAN! YES?!
The Saviors: FOR NEGAN!
~ Simon takes control of the Saviors and announces that they shall eliminate the Militia once and for all.
Well here I was, hopin' to give that gate a big ol', wet sloppy kiss, and there she goes, plain hard to get.
~ Simon upon arriving at the Hilltop armed and ready.
Well hello there, you are speaking to "Negan". But my birth certificate says "Simon", with whom do I have the distinct displeasure of speaking?
~ Simon greets Maggie through a walkie-talkie.
Better to beg forgiveness than ask permission, D. Future problems!
~ Simon dismisses Dwight's warning that Negan could still be alive.
Dwight: The rest of us?
Simon: The rest of us are making a house call. Wonder if anybody's home. It's time to do some proper slaughtering.
~ Simon and the Saviors move in on the Barrington house.
You made me look like an ass.
~ Simon bitterly reunites with Gregory after he had been previously humiliated by him.
I have that juice. I have that momentum. I want to keep it. Ergo, you go.
~ Simon tells Gregory he can control the Saviors without him.
You deliver, or get shipped!...He hasn't delivered. And that saddens me, but the time has come. Let us gather our like-minded individuals, draw strength from each other, and do what we need to do...Come on! I gotta sell this to ya?! Think about everything he's done to you! Every, little, indignity! Everything he's extracted from you, think about it, Dwight! You know what you have to do. You have to meet us in the courtyard, after rounds, and we begin what's next. I mean, Jesus! Right?!
~ Simon proposes to Dwight that they must kill Negan to move the Saviors forward.
Everyone! After this is done, we get to work! Just know that I didn't want this, but the Sanctuary must stand! This is not the man to prosecute this conflict. Just wanted to say, a grateful enclave thanks to you!
~ Simon's last words.

Trivia

  • When he was first introduced in the Season 6 finale, Simon was simply credited as the Lead Savior.
  • Simon is possibly the TV Series counterpart to the Savior that is seen in the comics in Issue 97 and 100. However in the comics, the Savior was not named and did not play a huge role in the comics as Simon does. He also has some similarities with Connor, a lieutenant of the Saviors in the comics, who orchestrated Rick's group to be captured and died before All Out War.
  • Simon is an original character and does not have a comic counterpart, similar to Daryl Dixon.
  • Simon shares some similarities to the popular character, Trevor Philips. Coincidentally, they were portrayed by the same actor, as well as the fact that Trevor's casting call name was Simon. The only difference between the two is that while Trevor may be more psychotic than Simon, Simon doesn't have any of Trevor's redeeming qualities, and/or loyalty.
    • The similarities between the two characters and the fact that they are both portrayed by the same actor is likely what increased Simon's popularity among viewers, as his role was changed from a recurring role to season regular.
  • The name Simon is derived from the Hebrew name "Shim'on" meaning ‘he has heard’.
  • Steven Ogg noted that he cited the film The Big Short as inspiration for Simon’s backstory.
  • Simon appears to hold an interest in art, as expressed by his admiration of a masterpiece portrait of Charles V owned by Gregory which he accurately described as 'management by example".
  • Simon enjoys alcoholic beverages most notably gin and tequila, however he dislikes scotch as he personally describes it as "ashtrays and window cleaner".
  • He is far more intelligent than the majority of the Saviors as seen in Season 6 finale, when he orchestrated the capture of Rick's group with an intriguing plan that involved several, carefully planned and elaborate road blocks.
  • Simon is far more ruthless than Negan as shown in his first appearance when he orchestrated the mass slaughter at the Library, and then goes on to exterminate the Scavengers in front of their leader: Jadis. It is later revealed that he orchestrated the mass murder of every male survivor from Oceanside. When he suggests that they should do the same thing at the Hilltop, Negan furiously reminds Simon to not start "backsliding", implying that their relationship has been strained ever since the Oceanside incident.
  • Despite his leadership skills, what sets Simon apart from Negan is that even he is not able to control the toughest of situations. During Negan's short absence, the workers started to revolt and none of Negan's lieutenants managed to calm things down as rationally as Negan. In addition, his violent methods are shown to be very reckless, in that he got many of Negan's men killed during the Hilltop raid in spite of dealing a large blow to the Militia, while his massacre of the Scavengers ended up backfiring after Negan had learned the truth of what occurred at the junkyard and made his promise to avenge Jadis' people for her.
  • Out of all of the secondary antagonists in The Walking Dead, Simon has the longest lifespan thus far.
    • Additionally, he is the only character to be the secondary antagonist for more than half a season.
  • Simon has killed the second largest amount of living people, having a total of at least 172 victims (including himself). Negan has the largest with a total of 225 victims.
  • Following both Negan's question about Simon "backsliding" and Simon's extermination of the Scavengers, it had been heavily theorized that Simon is responsible for wiping out all the male Oceanside residents aged 10 and above. Another supporting factor to this is how slow and stern Negan was when telling Simon to just kill one Scavenger, hinting that they have had issues in the past over an incident.
    • Furthermore, when talking to the Library Survivor, it was implied that he also had this group completely wiped out; something that was later confirmed in that same episode when Carol and Morgan came across and stayed in the library.
    • It is eventually confirmed in the episode "Worth" that Simon was indeed responsible for the Oceanside massacre.
  • As of Season 8, Simon is the second high-ranking Savior to turn against Negan, the first being Dwight.
    • However, their motives for betrayal are completely different. While Dwight acts as a double-agent to help the Militia overthrow and kill Negan out of revenge, Simon simply wants to take control of the Saviors to survive and take matters into his own hands by wiping out the Militia because of how he now sees Negan as an ineffective leader.
  • Overall, Simon is the third member of Negan's council to die during the war, the first one being Gavin and the second being Gary.
  • Simon is one of the most evil villains in The Walking Dead media and one of the only few villains to be considered Pure Evil, alongside Brian Blake/The Governor, Thomas Richards, Joan, and William Carver.

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