Prospector:
Can you think of a reason why your wasteland wanderer might be on the Oklahoma/Arkansas border area?
In my case that could be as easy as Jo Wales said "Go to eastern Oklahoma." Kelly would not be in any hurry to go back to the Maze and probably never wants to see it again right now.
Rusty Harry:
Could either of those characters be at least loosely considered a "peace officer" of some sort?
If you squint maybe? Templars are the closest thing to a centralized agency for public safety in the Wasted West, even moreso than the Law Dogs who don't have a central authority they all report to.
I guess this hinges on whether or not the posse knows Kelly is a Templar already, and honestly I'm not bothering to be secretive about it OOC because even if you don't know you'll find out relatively soon I'd imagine.
Templars are in a weird spot: in the lore, they're supposed to be secretive about it so they can test the worthiness of others. But in actual games 1) you almost never get the chance to actually spy on people and see if they're truly worthy and 2) what actually happens is once the posse figures out you've got
teh healz you're "the Templar" from then on XD
In less words, you just can't get four or five other brainers to keep a secret.