Simon (TV Series)

"Don't matter if the big man ain't here. We're still Negan. We don't know 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 and once we do, it'll become crystal clear, that 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!"

- Simon to the Saviors about killing all the people in the Hilltop

Simon is a main character and an antagonist as well as a survivor of the outbreak in AMC's The Walking Dead. He is a former high-ranking member of the Saviors, serving as Negan's right-hand man, and was the secondary antagonist of the second half of Season 6, and the whole of Season 7 and Season 8. He was eventually exposed for trying overthrow Negan and was put into a fight to the death to declare who should leave the saviours unfortunately for Simon, Negan come out the victor.

Personality
Simon is shown to be a sadistic, cruel, brutal, cunning and highly intelligent sociopathic man. He has displayed extreme loyalty to his leader, Negan, and as such is highly valued and trusted by the latter. Like Negan, 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 at all bothered by the excessive violence that the Saviors employ as seen when Negan casually asked him for a pen to mark where he would cut Carl's arm off. Simon simply grants Negan's request and shows no emotional reaction to the situation, which seems to imply that Simon has committed similar acts of brutality and has become desensitized to it. Unlike Negan who chooses to kill a few to save many, Simon is shown to be even more bloodthirsty and is willing to destroy entire groups due to their disobedience to the Saviors, as seen when he had the Scavengers, except for Jadis, exterminated due to their betrayal of the Saviors for siding with Rick and Jadis' lack of remorse.

He is shown to not be bothered by causing harm to children or elderly as proven by a comment to Rick in which he claimed that Carl was not punished hard enough for killing two Saviors in an attempt to kill Negan. Simon also executed the elderly Brion without any hesitation, and had adolescent members of the Scavengers massacred.

As the second highest ranking member of the Saviors, Simon has a large amount of power, and also seems to be a capable leader and strategic thinker as he cleverly organized the capture and ambush of Rick's group by predicting which roads they would travel on and constructed barricades accordingly to lead them into an ambush.

In Season 7, at the command of Negan, he assumes direct responsibility for the continued subjugation of the Hilltop Colony after the elimination of one of the Saviors' outposts and takes pleasure in terrorizing both the Hilltop and Alexandria when called upon to do so. He has demonstrated and verbally expressed his admiration for authoritarian leaders, and those who "lead by example", something which he himself puts into practice with his uncompromising methods, and strict obedience to Negan.

During Season 8 and the war, Simon has lost patience for Negan's methodology of only killing when an example is to be made. While Negan believes it to be a principle of the Saviors to ultimately unite communities and only resort to violence to keep people in line. Simon believes the Saviors should simply kill off all of the communities that oppose them and instead only spare communities completely loyal to them. Shortly after having this disagreement with Negan, Simon travels to the Junkyard and eventually orders his men to gun down the Scavengers. Simon merely grins in satisfaction as he watches unarmed men, women and even children get killed on his orders, displaying how little Simon values concepts such as morality or mercy, while at the same time defying Negan's orders. Upon Negan being kidnapped by Jadis, Simon takes advantage of the situation to assume leadership over the Saviors and manipulates them all into destroying the Hilltop for Negan, even though this is directly against Negan's wishes. Simon is even shown to be willing to sacrifice his own fellow Saviors in his quest to exterminate his enemies as seen before he launches his attack on the Hilltop in which he makes it clear that he does not care about the 38 Savior prisoners that Maggie has inside and is willing to sacrifice them in order to launch his assault. Simon is shown to not be that much of a strategic leader as during the Hilltop assault he leads his people up against machine guns with bows and arrows and tainted walker weapons and as a result loses nearly half of his soldiers.

Virginia
Simon was born in the late 1960s and grew up in Virginia, however, 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 immoral motives to other people even though he was fully aware of his own sinister intentions.

Washington D.C.
At some point after the onset of the outbreak, Simon somehow came into contact with Negan and subsequently joined his group named "The Saviors", upon where the two developed a firm loyalty towards each other and thus Negan later appointed Simon as his personal second-in-command. At some point later, The Saviors discovered an abandoned factory where together they managed to seize control over where Simon took residence inside, which Negan later established as their central headquarters as well as their personal home which became titled ‘The Sanctuary’.

Throughout the following months, Simon aided his leader in terrorizing other survivors and communities they encountered into subjugating to Negan's will; during where he committed several brutal atrocities in order to do so, including murdering innocent people, displaying gruesome acts to implement superiority and fear to other survivors, as well as orchestrating several raids and ambushes to whoever opposed them. undefined

At some point he came across the Oceanside when they were at their original location. After the Oceansides' rebellion, it was Simon who orchestrated the deaths of every single male above the age of 10; something that Negan did not approve of at all.

At some point after discovering the Hilltop Colony, they demanded half of their supplies in exchange for leaving the farming community unscathed, demonstrating their methods and bringing their intentions to light by executing Rory, a 16-year-old member of the colony.undefined Roughly during the same period, The Saviors discovered another commnuity known as The Kingdom where upon meeting with the community leader they demanded a portion of supplies to be produced in exchange for leaving the commnuity unscathed.

Season 6
Some time later, Simon led a group of Saviors on a hunt for Rick Grimes' people, following several attacks that left many Saviors dead. They soon discovered a small group of survivors who had taken refuge in the Viskocil Public Library; the Saviors soon terrorized the group by implementing their strict rules upon them. However, after the group retaliated, the Saviors hanged the member who first initiated the firefight inside a tower before ruthlessly executing each member of the group and allowing them to reanimate. One survivor managed to evade their attacks and escape, prompting the Savior party to chase after him.

"Last Day on Earth"
Simon is first seen when he and his small party of Saviors hunt down a man in the woods, following an attack staged by the Saviors on the lone survivor's group. He drags the man from the woods to a road, where he and the other Saviors stand and create a roadblock, waiting for Rick Grimes' group to arrive. He stands over the captured man and taunts Rick and his crew in their RV as they pull up. Asking for their belongings on behalf of the Saviors, the leader states that negotiations cannot be made and that their proposal stands, prompting the Alexandrians to return to their RV and take an alternate route to the Hilltop. Before they leave, Rick and Simon discuss the possibilities of their days on Earth being their last, with the latter warning Rick that he should be "extra nice to those people in [the] RV", should their days on Earth be numbered.

After a number of subsequent roadblocks en-route to the Hilltop, the Alexandrians come across yet another barrier created with fallen trees. They witness the Saviors' prisoner's execution as he is hanged with a chain over the side of an overpass, before the roadblock is set ablaze and Simon reminds Rick to look after his people with utmost care. This display startles the Alexandrians, and they make a quiet retreat in search of another route.

Following a failed diversion by Rick's group, Simon greets them after they find themselves surrounded and outnumbered by dozens of Saviors in a small clearing in the woods. Once again demanding their belongings, he declares that the time for negotiations is now over and that the Alexandrians are simply required to listen. Simon lines the group up on their knees before commanding Dwight to present the captured search party (Glenn Rhee, Daryl Dixon, Michonne and Rosita Espinosa). All are brought together in the line-up before Simon introduces Negan to the group.

As Negan paces up and down the line-up, Simon points Rick out as the leader of the Alexandrians after he enquires. He is present for the entirety of Negan's monologue, alongside Dwight and the rest of the Saviors, and watches as Negan gruesomely beats one of Rick's group to death with Lucille.

"The Day Will Come When You Won't Be"
After Negan kills Abraham and Glenn, he asks Simon what weapons Rick had with him. Simon reveals that Rick was carrying a Hatchet with him. Simon is seen giving Rick's hatchet to Negan after he orders him to, further proving his loyalty to his leader. Negan reveals to Rick that Simon is his right-hand man, and without him, there would be a whole lot of work. Simon stays behind and watches the survivors of Rick's group as Negan grabs Rick by his shirt and drags him inside the RV.

After Negan returns with Rick in the RV and calls Carl to him Negan asks Simon for a pen to which Simon replies that he does and tosses him a pen to draw on Carl's arm. After Negan succeeds in breaking Rick and taking Daryl captive, he and the rest of the Saviors take their leave.

"Go Getters"
Simon is shown leading a group of Saviors into the Hilltop. Gregory opens the door for Simon and the other Saviors at Hilltop. He tells them to make themselves at home, and Simon says it isn't a social call. He tells Gregory they should talk in private. Simon tells Gregory that the people he used to deal with are out of play, and takes him into the study.

Simon and Gregory are staring at a painting. Simon tells him they unleashed the walkers on The Hilltop to remind its residents that walkers are still a threat and the Saviors provide a great service by killing them. Gregory said the message last night was recieved loud and clear, and Simon questions him. He says it was management by example, and Gregory agrees. Simon says they worked their asses off last night to provide him with an example. Simon says people in Hilltop probably forget what the walkers look and smell like, and they were going to clean up the mess so they could show the service they provide. Gregory says they probably learned it all from the Saviors in the first place.

Simon informs Gregory that the Saviors at the Satellite Outpost were killed by Rick and the people of Alexandria, but Gregory pretends this is news to him, and Simon says the people that killed them work for Negan now. Gregory tells Simon to tell Negan that he understands how to cross the aisle. Simon says there's no need, and that he is Hilltop's Negan now. The two come to an understanding. Simon asks if there's anything else he should be made aware of, and Gregory stays silent. “Actually, there is.” says Gregory.

He leads Simon to the foyer closet and opens it with the intention of handing over Maggie and Sasha. Instead, he finds boxes of scotch. Simon says Negan will be pleased and orders a nearby Savior to put the liquor in Negan's truck.

He then has the Saviors go through the entire house and take half of thier supplies. He also notes that he will take the painting. Simon asks Gregory to kneel before they continue, and Gregory instantly does with little resistance. Simon tells him it's a solid kneel, and pats his head like a child. He and the Saviors leave.

"Rock in the Road"
When Negan discovers that Daryl escaped The Sanctuary and murdered Fat Joey, he orders an operation to track, capture and kill Daryl by visiting Alexandria, his assumed destination. Simon immediately volunteers to lead the mission. He later arrives with a group of a dozen Saviors, moments after Rick’s group returns to Alexandria. Rick innocently wonders why they are back so soon for tribute. Simon tells him they’re looking for Daryl.

The Saviors ransack Alexandria but come up empty. Simon notes that the pantry shelves are bare. Aaron explains that they’re having a hard time scavenging, and Simon mocks the community. As the Saviors leave, he apologizes for messing the place, and hops in a truck. Before driving off, he tells Rick that if Daryl shows up here there is no statute of limitations on the punishment and that the next supply pick-up is nearing. “Tick-tock, chop-chop!” he reminds Rick.

"The Other Side"
Simon and his men returned to the Hilltop Colony and are 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 Savior's compound and they will take care of it. While there, Gregory takes Simon in the medical trailer, Simon tells Harlan Carson that they need his services at the Sanctuary. Harlan correctly guesses that his brother, Emmett Carson, the Sanctuary’s former doctor, was killed. In exchange for taking Harlan, Simon gives Gregory a crate of aspirin.

Gregory pulls Simon aside and assures him that he’s an ally to Negan. He explains that he needs to hold on to his people’s trust; otherwise, someone less cooperative (Maggie) could take over. He hints that he might eventually need Negan’s help quelling insurgents within the community. Simon gives Gregory a hand-written note that will grant him entry into the Sanctuary should he ever need to seek their help.

The Hilltop residents gather at the gates and watch Simon and the Saviors leave with Harlan Carson.

"The First Day of the Rest of Your Life"
Simon is among the men out on the road to inspect the fallen trees blockade and as several Saviors are clearing them out, he asks Negan the possibility of Rick and his group doing it to delay them. After The Scavengers have betrayed the Alexandrians, Simon is seen with Dwight and Eugene with dozens of other Saviors listening to Negan's monologue to Rick. He and Dwight are later instructed by Negan to lift up the coffin. As Negan opens the coffin, Sasha emerges a walker and tackles Negan, nearly killing him, but is pulled off by Roy who is then killed by the reanimated Sasha. Simon then quickly runs to Negan's aid and brings him to cover as Negan roared at his opponents.

After the Saviors have seemingly won the battle, Simon is present among the group of Saviors inside Alexandria as Rick and Carl are lined up and as Negan is about to hit Carl with Lucille, Shiva is released by Ezekiel and jumps on a Scavenger, catching all of them off guard and another commotion ensures as Simon and the rest begin to retreat and find cover. Due to the overwhelming forces of Alexandria, The Kingdom and Maggie's troops from the Hilltop, Simon hops back into the truck he drove in on, along with Negan and Dwight, and drives them away from the battle, making their retreat. Back at the Sanctuary, Simon, Dwight and Eugene are standing on a podium alongside Negan in front of hundreds of Saviors as Negan tells them they're going to war as chants "Yes Sir!"

"Mercy"
When the Militia arrives at the Saviors' compound, Simon was seen among the rest of the Savior Lieutenants as Rick and the Militia attempted to convince them to surrender. Simon calls Gregory outside where he states that the Hilltop stands with the Saviors and threatens anyone who stands with the Militia from the Hilltop. However, the Hilltop members make it clear that they don't see Gregory as their leader anymore but Maggie. An enraged Simon pushes Gregory down the stairs after deciding he’s no longer useful. Rick then opens fire at Negan and the lieutenants. Simon quickly dove for cover and retreated inside.

"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 complaints him how he did what he was told with the other Saviors. 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 how people are resources and how they are going to stop Rick and 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 disagrees with him saying, "People are a resource," "Money on the table. People are the foundation of what we are doing here!" He questions Simon and if he remembers who they are and who is in charge. Simon pledges his allegiance. Negan says they have to capture Maggie, Rick and Ezekiel and kill them horribly in front of their people. 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 steps out with the other Saviors.

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 complaints Dwight about his idea he explains how when the find the guy they will kill the guy 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 electrify is coming on, as well as plead for food and water. As Simon attempts to calm them down, one of the workers pulls out a gun to shoot him, but is saved when Regina immediately guns down the worker. Negan and Gabriel walk in, explaining how he is gonna take a shower, eat a sandwitch and he has to have a “talk” with Simon about the Mole who caused the ambush and the herd.

"How It’s Gotta Be"
Simon first appears when he and the Saviors apprehend Maggie, Jesus, and a large convoy of Hilltop residents. Simon jumps out of the truck and states what a "damn nice night" it is. He orders Maggie and all Hilltop members for their weapons, and to coordinate he threatens Maggie if she doesn't, they will kill Jerry, who has been taken hostage.

Maggie asks Simon how the Saviors managed to escape their predicament. Simon doesn't respond directly, but eventually explains that it was Eugene who made it all happen as music begins to play from a distance, stating he was skeptical about the man at the beginning but saw that Eugene proved himself worthy in the end.

Simon tells Maggie that a group of Saviors is taking over the Kingdom, and another is taking over Alexandria. He says that she's lucky because the Hilltop is useful and he will keep them alive to help make things right. He also says that Negan prefers to keep people alive, but he is concerned only with the result and will not hesitate to kill them even if he is disobeying him.

He then gives Maggie two choices; either the Saviors kill Jerry on his knees, drag Maggie to the Hilltop in the wooden box, which the Saviors have made sure won't suffocate whoever is in it, then kill Maggie in front of everyone and finally place her head in front of the Sanctuary as a warning to other troublemakers. Then the Saviors lead the walker herd to the Hilltop and pull off the same trick Rick and Maggie's people tried to do against the Saviors. Or, Maggie and her convoy can head back to the Hilltop, unharmed, however, with the cost of one of their people's lives.

Even if she cooperates, they will have to kill one of her people. Simon stops Gary from killing Jerry and Simon then kills Neil sitting in the backseat of her car. She says she will cooperate but asks him one favor first. She wants to borrow the box that he was going to use on her so that she can bury Neil. He grants her favor and leaves.

"The Lost and the Plunderers"
Simon is ordered by Negan to confront the Scavengers, but to only deliver the standard message: kill one of their own to force the others to fall in line. Simon lets his frustration show and suggests they cut their losses and kill them all, because Negan’s way hasn’t been working as of late. Negan doesn't like the idea. He reminds Simon that what they do is hard, they don't take the easy way, they save. Once he kills Rick, everyone will fall in line again.

Their conversation is interrupted when Gary enters with a gift from Hilltop: a wooden coffin containing the zombified Dean who Maggie killed. Negan puts him down. Furious, Simon realizes that the remaining 38 Saviors mentioned on the crate cover are his men from the Satellite Outpost. Simon sounds off about going to kill every last one of the Hilltoppers, but Negan screams and yells at him to “do your job.” Simon reluctantly agrees.

Simon shows up with a group of Saviors at the Junkyard to confront Jadis and the Scavengers. His composure begins to crack as he and his men stand off against the Scavengers. He relays Negan’s message of forgiveness: As long as Jadis can honor the original terms of their deal, all will be swept under the rug. Jadis says she had no deal with Rick but was, instead, delivering him. Simon doesn't believe her, though. Simon offers them a chance to divert back to the original deal along with handing over all of their weapons. Jadis agrees. Simon calls for his men to take the guns. Simon goes on to question Jadis' art and the choice of living in the Heap.

Simon then wants to feel assured that there is remorse on Jadis’ part for her role in aiding Rick. She claims there is, but he swiftly pulls out his gun and kills Brion and Tamiel. Jadis punches Simon in the face, knocking over a can of blue paint. Simon stands up and in retaliation has his men kill all of the Scavengers except for Jadis.

Simon returns to the Sanctuary with Negan waiting outside. They still haven't heard from Gavin, who are unaware that he is dead, but Negan already sent a team. Simon shows Negan the guns they took from the Scavengers. Negan asks how it went with the Scavengers. Simon lies and tells Negan the message was delivered simply. Simon looks down at the paint smudge on his boots, the only clue to what really happened at the Junkyard.

"The Key"
Simon is seen collecting walker guts with the rest of the Saviors, after they are finished loading the guts into the trucks he confronts Dwight to ride up with him to catch him up on the plan. On their way to the Hilltop, Simon questions Dwight's perspective of it. Dwight supports it but Simon wants to "get weird" and honest. He questions whether or not the Hilltop will ever actually fold and behave but Dwight deflects by saying he doesn't get paid to think. It prompts Simon to express his doubts of the desired outcome.

Suddenly, Rick rams his car into Negan’s car, then chases him down city streets. Simon instructs the rest of the Saviors to stay behind and set up a perimeter while he and Dwight search for Negan.

Simon and Dwight search for Negan. Simon presses Dwight into admitting his resentment of Negan. Dwight sarcastically says that he never thought about killing Negan even after he took his wife and burned his face. Simon expresses a desire to move on from Rick’s group and find new communities. Simon and Dwight find Negan’s wrecked car. They decide to abandon their search and return to the Saviors. Dwight lights the car on fire.

Simon and Dwight inform the Saviors that Negan is gone. Simon reminds them that with or without their leader, the plan goes on. They're all Negan. He proposes they attack Hilltop, and kill everyone. The Saviors raise their guns in solidarity.

"Do Not Send Us Astray"
Simon and the Saviors arrive at the Hilltop. Simon notices she has barricaded and orders his Saviors to move the blockade. Maggie radios to him and Simon informs her that Negan received her care package in the box which he gave to her. He tells her she and her people are gonna die because of it. Maggie tells him she will execute the thirty-eight Savior prisoners if he does not leave. Simon does not appear to care for them anymore and tells her to "screw them" and he proceeds with his attack.

Simon mobilizes the Saviors for battle. Dwight warns that Negan might still be alive and will punish Simon if he kills everyone at Hilltop. Simon ignores him, saying he rather beg for forgiveness than ask Negan's permission. Suddenly, Daryl rides up on his motorcycle and opens fire with his machine gun. Simon's convoy follows Daryl through the gate. Hilltoppers block the convoy with a bus and fire at the Saviors. The battle begins in earnest. The Saviors start firing back, striking several people with mucked up arrows.

Simon spots Tara and orders Dwight to hunt her down. Simon and Dwight both sneak up on Tara while she's distracted and Simon is about to kill her, but Dwight shoots Tara in the arm with an arrow.

Hilltop goes silent and dark. Simon now wants to go inside and "do some proper slaughtering." He starts to whistle as they prepare to enter the Barrington House. As they ready their attack, a row of headlights turn on and blind the Saviors as the house's windows light up with gunfire directed at the Saviors. Angered that his plan is failing, Simon orders everyone to retreat as they race to their trucks and he and the remaining Saviors flee from the Hilltop.

"Worth"
Simon meets with Gregory who tries to convince Simon that what happened with the Hilltop isn't his fault. The two argue about what will happen next before Simon changes his mind about killing Gregory.

After Negan's unexpected return, Simon is forced to fall back into line, but is visibly unhappy with Negan's new plan. Negan forces Simon to his knees and contemplates killing him with Lucille, but suddenly forgives Simon. Simon later approaches Dwight with the intention to lead a coup against Negan. Dwight reluctantly agrees to meet with Simon's loyal followers in the courtyard and join the coup.

In the courtyard, Simon makes his pitch to a group of Saviors, including Gary, Gregory and Dwight. Everyone agrees to join Simon who decides to allow Dwight to kill Negan as Dwight has the biggest grudge against Negan. Suddenly, Negan arrives, having been tipped off by Dwight. Simon's followers are killed and Simon is shocked by Dwight's betrayal, leading Dwight to simply claim that Negan would win. Negan then challenges Simon to fight for leadership. Once all the Saviors and workers have been gathered around, Simon fights Negan and initially gets the upper hand before Negan eventually overpowers him. He then strangles Simon to death, all the while Negan furiously rebukes his right-hand man for ruining what chance they had left of making peace with Rick and the rest of the communities - asserting that he'll now have to kill them all just like he is killing Simon right now.

Following Simon's death, he reanimates as a walker and is chained to the Sanctuary fence.

Killed by
After Simon attempts to lead a coup against Negan, he is betrayed by Dwight leading Negan to challenge Simon to a fight for leadership. Though Simon initially got the upper hand, Negan ultimately wins and defeats Simon by strangling him to death. Rather than prevent Simon from reanimating, Negan chains him to the Sanctuary fence with the other walkers.
 * Himself (Caused)
 * Dwight (Caused)
 * Negan (Alive)

Killed Victims
This list shows the victims Simon has killed:
 * Library Survivor (Caused or Direct, 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)
 * Himself (Caused, Alive)
 * 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)
 * 13 unnamed Hilltop residents and refugees (Caused)
 * 1 unnamed Alexandria resident (Caused)
 * 14 unnamed Saviors (Indirectly Caused)
 * Numerous counts of zombies and unnamed people

Negan
"You went for it all at the Hilltop. You got Saviors killed. And then you ran away like a coward! You got shown up one too many times. Those people are always going to know there's a loophole, a way to escape, they are always going to be looking for that chance to push back, SO NOW I'VE GOT TO KILL ALL OF 'EM, JUST LIKE I'M GOING TO KILL YOU!"

- Negan berating Simon for his betrayal before killing him

It is unknown whether Simon and Negan had known each other prior or after the outbreak but they seem to have a strong relationship, as he is Negan's lieutenant and most trusted right-hand man. As the second-in-command of the Saviors, Simon is entrusted with a considerable power and authority, close to Negan himself. He was most likely the leader in charge of orchestrating each roadblock on every possible route to the Hilltop Colony from Alexandria, preventing Rick Grimes and his group from reaching the Colony. When Rick and his group have finally been cornered and captured, he spoke on behalf of Negan by demanding them to surrender their weapons and to kneel down before introducing his leader, showing that he was given high authority.

Negan also mentions to Rick about Simon being his right-hand man and without him "there would be a whole lot of work" proving that he views highly of him.

Though having a "right-hand man" is important, Negan shows his doubts, saying that considering he isn't in the Sanctuary (due to being stuck in a walker-swarmed RV) people will die under Simon's command. After escaping the RV, he arrives back at the Sanctuary and to his disappointment, realizes that someone indeed died due to Regina, showing that Simon can't handle tough situations such as the small "revolt" at the Sanctuary. Negan is also furious with Simon's suggestion that the Saviors eliminate the residents of Hilltop and angrily tells Simon "who do you think you're talking to!"

Simon eventually begins to show extreme doubts in Negan's strategy for regaining control over the communities of Alexandria, the Hilltop, and the Kingdom, believing that 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 to be the easy way out and that "saving people" through punishment is far more rewarding for them as people are a resource. In response, Simon boldly states that Negan's warnings and punishments have been doing nothing lately but further motivating the communities to fight back.

When instructed to kill one Scavenger to keep the rest in line, an order that goes against his more bloodthirsty inclinations, Simon initially does as he is told, but eventually gives into his impatience of the group for their betrayal and odd mannerisms and orders his men to wipe out nearly everyone, leaving only Jadis alive. Negan later learns of Simon's actions via Rick Grimes, and is furious at this. Simon, meanwhile tries to look for Negan alongside Dwight, when they come across his flipped over car, instead of continuing the search, Simon suggests they leave and move on, showing that his relationship with Negan is now all but severed.

Upon Negan's return, Negan proceeds to humiliate Simon in front of the rest of his inner group, having Simon get down on his knees and taunting him, asking him if he's going to make a move. When Simon responds that he has no move to make, Negan seemingly forgives him. After this Simon begins plotting against Negan, showing that their relationship has been completely and utterly severed. Negan eventually puts down the plot and fights Simon one on one in front of all the Saviors, ultimately overpowering him and then strangling his former right hand man to death.

While Negan's second in command, it appears that Simon's true loyalties lie with the Saviors as a whole - wanting to do what he feels is best for their survival and showing a great amount of concern for his people.

Dwight
Simon and Dwight have possibly known one another in the past. They share a neutral relationship as they are both high ranking members of the group. However, Dwight's brief escape from the Saviors might have affected their relationship somehow, although nothing has been seen so far. Even though both he and Dwight are Negan’s top men, Simon is shown as the secondary commander of the Saviors; his higher authority is shown when he orders Dwight to take out the rest of the captured members of Rick's group. During the meeting at the Sanctuary, Dwight's remarks to Simon about leading the Saviors out of their current predicament if Simon is incapable of doing so actually impresses him, showing the level of respect he has for Dwight and that he is unaware of his double-agent role. In "The Big Scary U", he stops Simon from fighting a worker who angered him. Simon seemed comfortable with talking badly about Negan with Dwight, indicating that Simon somewhat trusts him. After Negan's disappearance Simon took Dwight as his Second-in-Command.

Gary
"Nah Gary. I got this."

- Simon to Gary before shooting Neil

Gary and Simon are shown to have a good relationship, as Gary is often seen in scenes with Simon at the Hilltop and lately, in gun battles. Unlike most of his fellow Saviors, Simon refers to Gary by his name and like his relationship with Negan, Simon appears to trust Gary as a personal right hand man, this is shown when he enlists Gary's help on their visit to the Scavengers at the Junkyard. Gary shows no hesitation helping his fellow Saviors massacre the Scavengers on Simon's orders.

Rick Grimes
"Your name's Simon."

- Rick to Simon

Simon and Rick have an uneasy, mostly negative relationship. Initially, Rick does not think much of Simon, and considers him another minor obstacle, but as time goes by, Rick's repeated interactions with him and his men put him more on edge and cause him to become increasingly concerned for the safety and well-being of his group.

Upon meeting for the first time, Rick and his group were en-route to the Hilltop, only to be stopped Simon and a small group of his men. He demands that Rick give up their supplies, however when negotiations could not be made, Rick later informs him that they're leaving - Simon does not object and surprisingly lets them all go, showing that he at least respects his choice to leave. Both Rick and Simon share a somewhat civil discussion about the possibility of their days on Earth being their last. Simon bids them farewell and warns Rick to be "extra nice" to his group, should their days be numbered, to which Rick replies that he do the same for his people, showing that the two hold some respect for each others' views.

Later, Simon is present when Rick and his group encounter a massive roadblock constructed with fallen trees, watching as they witness the logs being set ablaze and the Saviors' captive survivor being hanged from an overpass. Reminding him of their earlier discussion, Simon taunts Rick and advises him to take extra care of his group; this warning causes Rick and the group to become uneasy and increasingly wary, and they drive hastily away.

After several roadblocks and a failed diversion which finds Rick and his group cornered by a large gathering of dozens of Saviors in a small clearing, Simon makes his presence known and taunts the Alexandrians before taking their weapons and making them kneel in a line. At this point, Rick's interactions with the Saviors have caused him to become fearful of them; he finally learns that he had severely underestimated the Saviors and is left almost speechless. Defeated, Rick attempts to negotiate before being cut off by Simon, who tells him that his time for talking is over.

Days later, when Daryl escapes from The Sanctuary, Simon leads a group of Saviors to Alexandria, where he confronts Rick, who plays dumb about Daryl's whereabouts. As the Saviors ransack the community, Simon mocks Rick and the others, and as they leave, he makes a point of reminding him that the next tribute is due soon.

Simon and Rick are later involved in a gunfight between the Saviors and the other communities, in which Simon and Rick shoot at each other, showing now their negative relationship. Despite this and everything he has done, Rick offers Simon a chance to surrender and not be killed in "Mercy", showing that he is more concerned with killing Negan than him. Simon however refuses, choosing to remain loyal to his leader.

Carl Grimes
"This is yours? Yeah. It's yours."

- Simon to Carl about his gun.

Carl and Simon have an uneasy, mostly negative relationship, with the latter often mocking Carl by flicking his sheriff's hat numerous times. After Carl murders two Saviors while trying to infiltrate the Sanctuary, Simon appears to have a hostile attitude towards the boy, implying in a conversation at Alexandria with Rick regarding Daryl that Carl got off for his deed too easily and should have been punished further. The two are later involved in a gunfight between the Saviors and the other communities, in which Simon and Carl shoot at each other.

Gregory
"Because from now on... I'm your Negan."

- Simon to Gregory

Simon first meets Gregory when Simon and a group of Saviors came to take supplies from him. After Rick's people had killed every Savior from one of the outpost, Simon is now responsible for the Hilltop and Gregory, being "his Negan". He tries to convince Simon about him not working with Rick, but Simon doesn't believe him. When Gregory intends to give up Maggie and Sasha to him, Instead, he finds boxes of scotch. Simon says Negan will be pleased and orders a nearby Savior to put the liquor in Negan's truck. He later forced Gregory to kneel before him.

When Simon visits the Hilltop again, Gregory offers him a drink of Gin, but Simon declines saying he enjoys tequila and says that Negan wants one of the Hilltop residents. In exchange for taking Dr. Carson, Simon gives Gregory a crate of aspirin.

Gregory assures him that he’s an ally to Negan. He explains that he needs to hold on to his people’s trust; otherwise, someone less cooperative could take over. He hints that he might eventually need Negan’s help quelling insurgents within the community. Simon gives Gregory a hand-written note that will grant him entry into the Sanctuary should he ever need to seek their help. Their relationship remains neutral afterwards.

In "Mercy", during the Militia's attack on the Sanctuary, Simon is angered that Gregory is unable to make the Hilltop fighters back down and kicks him down the stairs, showing that he no longer trusts him and considers him useless.

Eugene Porter
Simon and Eugene haven't spoken directly to each other, but it seems he adores him for figuring out a way to lead the walkers out of The Sanctuary.

Maggie Rhee
"Tell me I don't gotta go down the line, tell me Maggie!!"

- Simon to Maggie

Simon and Maggie have a enemy relationship. Simon's first major interaction involved holding Jerry as a hostage, and forcing her to submit to him and the Saviors.

Gavin
Simon and Gavin have never spoken directly to each other but it seems there is a respect as both are among Negan's top Lieutenants. Gavin helped save Simon's life when he yelled 'Gun' after a worker pulled a weapon out to shoot him, to which Regina immediately shot the worker. Simon is currently unaware of Gavin's death.

Regina
As top Savior Lieutenants, it can be assumed that they have a steady relationship. In "The Big Scary U", she saved Simon's life, by killing a worker, as he was nearly shot by a revolting worker.

Jadis
"It occurs to me that I've not yet received the full definition of an apology. I fell like I've gotta some transgression acknowledgement, the guns certainly cover restitution. But what I'm not yet feeling... Is the remorse. Say it again!! I don't think you mean that. Light it up, gents. Light it up now!!!"

- Simon to Jadis, before ordering his men to execute the Scavengers.

Like Negan, Simon did not appear to think much of Jadis or the Scavengers despite their betrayal of Rick to aid them. He was angered when Jadis and her people betrayed the Saviors by going to the Sanctuary with Rick to kill them. He openly expressed his want to wipe them all out to Negan, but was stopped in his tracks and ordered to only take one out to make the others fall in line. When Simon arrived at the Junkyard, he came across as charismatic, before demanding an unsuccessful apology and taking all of Jadis' guns, however when Jadis did not appear to show any remorse for her actions, Simon executed her two lieutenants, Brion and Tamiel right in front of her, leading to Jadis punching him in the face and knocking him over. Simon then orders his men to kill all the Scavengers except for Jadis, showcasing just how much hatred Simon had for her.

Appearances
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Season 6

 * "Last Day on Earth"

Season 7

 * "The Day Will Come When You Won't Be"
 * "Go Getters"
 * "Rock in the Road"
 * "The Other Side"
 * "The First Day of the Rest of Your Life"

Season 8
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 * "Mercy"
 * "The Big Scary U"
 * "How It's Gotta Be"
 * "The Lost and the Plunderers"
 * "The Key"
 * "Do Not Send Us Astray"
 * "Worth"

Trivia

 * In the casting call for the game Grand Theft Auto V, Steven Ogg's character was named Simon, later changed to Trevor in the final version.
 * 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", he also appeared slightly impressed with Jadis' metal artwork in the Junkyard.
 * Simon is said to enjoy alcoholic beverages, most notably tequila and supposedly gin; however he later compares it to turpentine, he also dislikes scotch as he personally describes it as "ashtrays and window cleaner".
 * Simon holds the longest lifespan of any secondary antagonist on The Walking Dead. Lasting from Season 6 finale "Last Day on Earth" to "Worth".
 * Additionally he is the only character to be a secondary antagonist for more than two and a half seasons.
 * Simon has killed the second largest amount of living people, having a total of at least 172 victims. Negan has the largest with a total of 200 victims.
 * Following his extermination of the Scavengers, it was heavily theorized (and later confirmed by Negan) that Simon is the Savior responsible for wiping out all the male Oceanside residents aged 10 and above.
 * 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.
 * Simon killing every male at Oceanside was confirmed by Negan in “Worth.”
 * Simon is the fourth original main character in the TV series to die. The first being Merle, the second being Beth, and the third being Sasha.
 * Simon is the second savior (after Gordon) to be chained to The Sanctuary's fence.
 * Simon being strangled to death by Negan is a call back to when The Governor killed Pete Dolgen in “Dead Weight.”
 * Both Simon and Pete took charge of their respective groups after the leaders were dead or presumed dead.
 * Both had a rift developed with the main antagonists with Simon’s rash decisions for Negan and Pete’s bad leadership for The Governor
 * Both were ultimately strangled to death by the leaders or main antagonists of their respective season, as well as being restrained by chains and being left to turn. Chained to the bottom of the river for Pete, and chained to the fence for Simon.
 * Simon is the seventh main character to become a walker, the first being Shane, the second being Merle, the third being Hershel, the fourth being Deanna, the fifth being Spencer and the sixth being Sasha.
 * Simon is the fifth male main characters to become a walker.