"The idea for these guys came from the brains of the writers who wrote this episode, David Leslie Johnson-McGoldrick, and Eddie Guzelian. They were brainstorming, and I believe that they were the ones who were kind of like, 'You know what? It might be fun to have this left turn,'" Kang told EW.
"In an earlier episode we saw a group of wagons going by, and you saw this kind of sign that was painted on the back of a street sign. It's sort of like the apocalypse version of tagging or whatever, saying that 'This is our territory.' The symbol, it's a horizon and then a road going up to meet the horizon at a point. So that was the idea behind that."
That mysterious red symbol surfaced again on a blackmail letter revealing the group to be "pirates" who, in 913, strike a deal with King Ezekiel (Khary Payton) and Carol (Melissa McBride) to act as escorts protecting the roads, allowing travellers safe access to the fair set to assemble the Kingdom, Hilltop, Alexandria, and Oceanside.
"What we were really looking to do was introduce a group that has sort of an unusual MO, and had a really unique perspective on life, and a unique way that our people have to deal with them," Kang said.
"It was a lot of fun, and we were really lucky to get the wonderful actor Angus Sampson to play the role of the lead Highwaymen, so that was a lot of fun for us to work on."
The group emerge in direct response to Carol eliminating Savior Jed (Rhys Coiro) and his band of mangy marauders, who she burned alive in 906, 'Who Are You Now?'
"We thought of them as if a mob moved into this territory that was created by a power vacuum after Carol took out Jed in that group when she so famously set them all on fire earlier in the season," Kang revealed.
"We thought, how interesting if the action that she took there which kind of stamped out one problem from her mind actually created the side problem. And yet, we like the fact that this group is sort of morally ambiguous. Really, are they bad guys, or did they just have their own thing that they're trying to do just as our people do? Certainly our people have done some things that are in the gray area themselves."
The Highwaymen play into the wider themes of the season, which once saw Rick Grimes (Andrew Lincoln) and Michonne (Danai Gurira) attempt to usher in an era of civilized peace following their jailing ousted Savior leader Negan (Jeffrey Dean Morgan).
Those plans — mostly abandoned after Rick's disappearance — are again at risk with the arrival of the walker skin-clad Whisperers, whose barbaric ways are now clashing with the survivors' humanity.
"We wanted to tell this story of how do groups coexist with each other or not? Because there's certainly a very specific story with the Whisperers that's happening," Kang said.
"Then here's a different kind of group, and how do you negotiate what are your borders, or where you go? ... I don't really see the Highwaymen as being good or evil. They're just people who exist in this world, and they're trying to grapple with having neighbors just like our people are."
Instead, the Highwaymen are swayed to act as protectors when Carol diffuses tensions by offering payment in the form of a movie night, made possible by the Kingdom's "side mission" to retrieve a prized projector bulb.
"I also think Carol is so smart because she reads the situation better than anyone really. There are people who are like, 'Well, we're gonna have to kill 'em all.' She's like, 'Well, they wrote a letter,'" Kang continued.
"She's looking around and seeing people — they're basically apocalypse cosplayers. They're in this weird warehouse with mannequins, and they're kind of wearing these uniforms. They obviously like to have a little bit of fun, the guy's acting like he's the Wizard of Oz. So she kind of just takes the gamble, like maybe something that's sort of fun and frivolous will appeal to them, 'cause clearly they, as a group, are having a little bit of fun in the apocalypse."
The Walking Dead airs Sundays at 9/8c on AMC.
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