- "Yes... Tell me I don't gotta go down the line, tell me Maggie!!"
- —Simon to Maggie[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 high-ranking member of the Saviors, serving as Negan's right-hand man and serves as the secondary antagonist of the second half of Season 6, Season 7 and Season 8.
Simon is shown to be a brutal, cunning and highly intelligent man. He has been shown to be extremely loyal to Negan, never questioning his orders. Like Negan, Simon is not beyond using fear and intimidation to achieve his ends and is shown to be very capable of cold blooded murder and also doesn't appear to be 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. He is shown to not be bothered by causing harm to children and adolescents 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 is shown to even more bloodthirsty than Negan to a degree as seen in "The Big Scary U" in which he suggests they exterminate everyone at the Hilltop to send a message to the other communities, though Negan angrily shuts him down; claiming people are a resource.
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.
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 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 commnuity 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 new news to him, 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. Dr. Carson correctly guesses that his brother, Emmett Carson, the Sanctuary’s former doctor, was killed. In exchange for taking Dr. Carson, 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 Dr. 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. "People are a resource," Negan insists. "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 King 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, Regina shoots one of the workers and at that moment, 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 coming out of a truck, he asks 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. 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. When Maggie asks how he and the Saviors got out, Simon says that Eugene is the one who figured out how to escape the Sanctuary.
He then tells Maggie she can either cooperate with him or kill her in front of her all her people. 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.
This list shows the victims Simon has killed:
- Library Survivor (Caused, Alive)
- Dean (Indirectly Caused)
- Numerous counts of zombies and unnamed people
- "Simon. You got a pen?"
- —Negan to Simon.[src]
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 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.
- "Your name's Simon."
- —Rick to Simon[src]
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 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.
- "Because from now on... I'm your Negan."
- —Simon to Gregory[src]
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.
Simon And Eugene havent spoken directly to each other but it seems he adores him for figuring out a way to lead the walkers out of The Sanctuary.
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.
Simon and Regina have not spoken directly to each other but as top Savior Lieutenants, it can be assumed that they have a steady relationship.
- "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"
- 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 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 is currently the longest living secondary antagonist on The Walking Dead.
- Additionally he is the only character to be a secondary antagonist for more than half a season.