Top 25 Walking Dead Villains of all time

4. Simon

Introduction: Simon warned Rick early on, before his official meeting with Negan, “to be kind to the people in that RV because it could be the last time he sees them.” Simon would later attempt to take Negan’s throne amidst the resulting anarchy of Rick’s war.

Biggest moment of Villainy: Simon had all of the Scavengers killed despite Negan’s orders, leaving Jadis entirely deserted. He would later plan to do the same to the Hilltop, telling a questioning Dwight, “Better to beg forgiveness than to ask permission.”

Everybody Hurts Sometimes: While Simon never cowers or shows weakness at any point past superficial language (“Very happy to have you back boss man!”), it is sad to see him being strangled to death by Negan in their one-on-one fight for control of Sanctuary. A loss of an excellent character.

The Good Side: Simon is not fully loyal to Negan and actually looks to help Dwight get his redemption against Negan by giving him the opportunity to take him out. He is, however, betrayed by Dwight, and fans never got to see what his version of Sanctuary would have looked like. Simon is less about seeing people as a resource for productivity than Negan, and more about taking out the opposition to send a message.

Simon was not above working with others to his own benefit so long as he was coming out the winner of any deal.

First Appearance: “Last Day on Earth” (season 6, episode 16)

Last Appearance: Living – “Worth” (season 8, episode 15), As a Walker – “Wrath” (season 8, episode 16)

Cause of Death: Simon is strangled by Negan in a one-on-one hand-to-hand combat in front of all of Sanctuary.

Memorable Quote: “Okay friend! Plenty of ways to get to where you’re going. What if it’s the last day on earth for you? Or someone you love. What if that’s true?” (Ominously To Rick after he says his group is leaving on the road)

Next: 3. Shane Walsh