- "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 you!"
- —Simon's last words to the Saviors before confronting Negan[src]
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 before his betrayal and attempt to take control of the Saviors from Negan. He served as the secondary antagonist of the second half of Season 6, and the whole of Season 7 and Season 8.
Simon is shown to be a sadistic, brutal, and articulate man considered even by Negan too violent and "psychotic". 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 and is even shown to take pleasure in the violence employed by the Saviors.
As the second highest ranking member of the Saviors, Simon held a large amount of power surpassed only by Negan himself, and also seemed to be a very 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 spite of being Negan's most loyal follower, it is gradually revealed that the two drastically differ in their views on how to deal with disloyalty and defiance on the part of their subjugated communities. Unlike Negan who chooses to kill a few to save many and get others back in line, 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 not bothered causing harm to children or the 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. It is also confirmed that he had all the male survivors above the age of 10 from the Oceanside slaughtered after they initiated a rebellion against the Saviors, something that even shocked Negan himself.
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 finally 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 demonstrates during this conflict that his ruthlessness and desire for blood has completely overclouded his once adept strategic thinking as 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 and quickly retreats, showing that he also has cowardly tendencies.
Upon Negan's return and him humiliating Simon in front of the rest of the council and learning of Negan's next plan of action, Simon reaches the end of his tether and attempts to lead a coup in order to get rid of Negan for good, showing that all respect he had for his leader is now gone and that he is desperate to take over the Saviors. Ultimately Simon's thirst for blood and desire to exterminate his enemies and take command of the Saviors would lead to his own demise at the hands of his leader and closest ally and the man who once considered him his most loyal and valuable follower.
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. 
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. 
At some point Simon and his men encountered a group of survivors and thus enslaved them and forced them to work under Negan's rule. Eventually the group attempted to fight back but they were overwhelmed and defeated. As punishment for their defiance, Simon had every single male above the age of 10 exterminated; something that Negan did not approve of at all. The surviving female survivors later fled their camp and disappeared to a new location.
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. 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 community unscathed.
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.
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.
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.
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.
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.
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.
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!"
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.
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.
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.
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 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. Jadis agrees and 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. Jadis watches her people getting wiped out in horror as Simon sadistically smiles.
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.
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 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. The Saviors raise their guns in solidarity.
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 dismisses Dwight by saying "Better to beg forgiveness than to ask 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.
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, Gregor, Jared and many of the Satellite Outpost prisoners escape from the Hilltop.
Simon meets with Gregory who tries to convince Simon that what happened with the Hilltop isn't his fault. Simon informs Gregroy that he 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.
After Negan's unexpected return, Simon is forced to fall back into line, but is visibly unhappy with Negan's new plan. Simon apologizes for the disaster at Hilltop and asks for forgiveness. 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. Gary and 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.
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.
Simon initially gets the upper hand before Negan eventually overpowers him. He then strangles Simon to death, all the while furiously berating 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's killing Simon right now. Afterwards, Negan gives one final squeeze that crushes Simon's windpipe, killing him instantly. Everyone watches in silence as Negan simply states "What an asshole."
Following Simon's death, he reanimates as a walker and is chained to the Sanctuary fence.
Following the end of the war, the walkers are cleared from the Sanctuary fence, including Simon and are all presumably put down. By the time Rosita arrives to help rebuild, there is no sign of any of the fence walkers.
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 overpowers him and then strangles him to death. Rather than prevent Simon from reanimating, Negan chains him to the Sanctuary fence with the other walkers.
- Unknown Sanctuary Resident (Zombified, Off-Screen, Assumed)
Following Negan's defeat and the establishment of peace, Simon is presumably put down along with the other fence walkers as the Sanctuary fence is clear of walkers by the time Tara and people from the other communities arrive. It is unknown specifically who put Simon's corpse down.
This list shows the victims Simon has killed:
- Library Survivor (Caused or Direct, Alive)
- 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
- 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.
- 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 Annes' 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, having appeared in 3 seasons and 13 episodes overall.
- Additionally he is the only character to be a 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 his extermination of The Scavengers, it was confirmed by Negan in "Worth" that Simon is The Savior responsible for wiping out all the male Oceanside residents aged 10 and above.
- Simon is the sixth series regular to die while being credited under "Also Starring", the first being Gareth, the second being Bob Stookey, the third being Deanna Monroe, the fourth being Jessie Anderson and the fifth being Spencer Monroe.
- Simon is the third known Savior (after Gordon and Savior 5) to be chained to The Sanctuary's fence.
- Steven Ogg joked on Talking Dead that the zombified Simon may be one of the few "smart walkers" left as he knows where he is and what he wants to do which is that he's at the Sanctuary and kill anything in it's path, though more specifically kill Negan.
- Zombie Simon makes high-pitched hissing, presumably due to his larynx being crushed by Negan.
- Simon is the seventh main character to become a walker, the first being Shane Walsh, the second being Merle Dixon, the third being Hershel Greene, the fourth being Deanna, the fifth being Spencer and the sixth being Sasha Williams.