Much humor is generated in "The Ransom of Red Chief" from unexpected characterization.
One would expect two kidnappers to be characterized as vicious and heartless and for a young boy who is snatched from his family to be characterized as fearful and timid. Yet this isn't the way these characters are developed at all.
Nearly as soon as the kidnappers arrive at their destination where they will hold young Johnny, they begin playing games with him—specifically, a game where they pretend to be "Indians." Bill himself takes an especially active role in the game, seeming to enjoy the world of make-believe that Johnny develops. Yet later, Johnny gets the upper hand on Bill, who awakens to the very real possibility that he is about to be scalped by Johnny, otherwise known as Red Chief in their games of pretend. This kidnapper becomes fairly terrified of this wild child and can't sleep with him around.
Johnny himself puts up a good fight early on. When the kidnappers try to lure him in, Johnny throws a piece of brick at Bill. At the campsite, he doesn't try to escape for home and even tells the kidnappers that he actually prefers this kidnapping to returning there:
I don't have any fun at home. I hate to go to school. I like to camp out. You won't take me back home again, Snake-eye, will you?
Again, this is not the expected character development, and Johnny's precocious personality finally proves too much for the men who have kidnapped him.
In the end comes the greatest comedic twist of the story—the kidnappers are forced to pay Johnny's father to take the child back. Their plans have been completely thwarted by a "boy of ten, with bas-relief freckles, and hair the color of the cover of the magazine you buy at the newsstand when you want to catch a train."