Spoilers for The Walking Dead 8x05.
"Simon's my right hand man," Negan tells Rick in 7x01. "Having one of those is important. I mean, what do you have left without him? A whole lot of work."
Simon is Negan's second in command and with Negan indisposed and assumed dead — he was trapped in a trailer with Alexandria's Father Gabriel, cut off from the rest of the Sanctuary by a flood of walkers — the erratic Simon became de facto leader of the Saviors. But is Negan's right hand man as loyal as he purports to be?
Simon already has egg on his face from his dealings with the cowardly Gregory, the "in name only" leader of the Hilltop colony who has been supplanted as the real leader by a pissed off and pregnant Maggie: Simon and Gregory got into some shady dealings last season, with Simon eventually bringing Gregory to the Sanctuary and trotting him out when Rick Grimes rolled up to the Sanctuary's door step with the assembled forces of the alliance in 8x01.
Gregory issued an ultimatum to the Hilltop members in Rick's posse: stand down and go home, or be tossed out of the Hilltop on your ass. "The Hilltop stands with Negan and the Saviors," Gregory said, only to look stupid — and piss off Simon — when no one accepted the offer.
In a flashback to 8x01 — moments before Rick showed up to issue his ultimatum to Negan — Gregory assures Negan and his lieutenants the Hilltop is his. "I let a fox into my hen house," he says of Maggie. "She and her people took advantage of my generous nature. I see that now, and I will fix it."
"We go in with the right stage picture," Simon says, "a thick and veiny show of force surrounding Gregory when he lays down the law, I think things go back to copasetic. If they don’t, we take a flier on the place and kill everyone there. Unfortunate play, but the other communities will get the message and we achieve equiliburiam. Plan A. Plan B—"
Negan explodes. Slams Lucille on the table in-between words. "People are a resource! Money on the table. People are the foundation of what we are building here! Who the hell do you think you’re talking to? Are you confused about who we are? Are you confused about who is in charge?" Negan pushes. "Are we backsliding, Simon? Please… tell me we’re not backsliding."
"We are not backsliding," Simon says. "This is a pronounced event in a fragile moment."
Negan could already be throwing some side eyes at Simon — first there's the rebellion in Alexandria in 7x16, which got an army of Gregory's people "straight up my ass," Negan says, then the Hilltop refuses to stand down — all of which makes Simon looks bad.
"I’m Negan. And as I understand it, everyone in this room is," Simon reaffirms during a crisis meeting while Negan is indisposed. As Gavin points out, there's a rat in the Saviors — someone in the room.
"Someone in here made everything out there happen," he says, as Simon gets in Dwight's face. "We're gonna find the subhuman who did this to us, and we’re going to kill him very slowly in front of everyone here over the course of a few days," Simon threatens, his eyes now burned into Eugene, the clear front runner for the infiltrator.
After Negan's escape from the trailer, he heads upstairs just in time to thwart a mutiny against Simon and the Saviors — but Simon is far from being on easy street. “We have some serious business to attend to… like talking to my right hand man," Negan says, ominously. "You see, we gotta figure out how all this coulda happened like it happened." Negan knows something is up. He just doesn't know what.
As we know, Dwight is the traitor in the Saviors' ranks while Eugene is a Negan loyalist, but Simon's intentions are about to be tested.
The Walking Dead airs Sundays at 9/8c on AMC.