O. Henry's "The Ransom of Red Chief" is a comic story of ironic reversals. Irony is the difference between what is expected and what really happens. O. Henry artfully uses irony to turn the tables on Sam and Bill, a pair of would-be kidnappers who discover that plans don't always run smoothly and nothing can be taken for granted.

Foreshadowing of the complications begins with the first line:

It looked like a good thing: but wait till I tell you.

In this brief statement, "but" indicates that the way this "good thing" looked had no bearing on what would actually transpire.

One complication is the kidnapping of the boy. One would expect that when enticed by a bag of candy and a ride in the buggy, the boy would readily join the men. He does not. The fact that he was throwing rocks at a kitten should have been a clear indication that this was not a calm or complacent child:

One evening after sundown, we drove in a buggy past old Dorset's house. The kid was in the street, throwing rocks at a kitten on the opposite fence.

Hey, little boy!" says Bill, "would you like to have a bag of candy and a nice ride?"

The boy catches Bill neatly in the eye with a piece of brick.

Another complication arises by the boy's reaction to being taken. One might assume he would be frightened, begging to go home. Quite the opposite is true: he thinks it is a fine adventure, has beaten Bill up "playing Indian," and talks incessantly; these are men who are in no way accustomed to the antics of a young boy, let alone this young boy. He takes his role as "a pesky redskin" very seriously, letting out a war cry so often that Bill's nerves begin to unravel.

That boy had Bill terrorised from the start.

Before the night is out, the narrator (Sam) asks "Red Chief" (as the boy calls himself) if he wants to go home, and the youngster is emphatic that he has "never had such fun"—because being at home and going to school bore him.

Another complication is that "Red Chief" is more dangerous than the kidnappers. The men are actually quite nice to the boy. Bill is supposed to watch him, but is more like a playmate. However, the boy is violent. When Sam wakes the next day, it is to the sound of Bill screaming—and Sam is greatly distressed to hear a grown man make such noises...

They weren't yells, or howls, or shouts, or whoops, or yawps, such as you'd expect from a manly set of vocal organs - they were simply indecent, terrifying, humiliating screams, such as women emit when they see ghosts or caterpillars.

Red Chief is attempting to scalp Bill—they had not anticipated that the boy would be any kind of threat.

Perhaps the most important complication—and the funniest one—is the father's response to Bill and Sam's ransom demand: Dorset (the father) says that for two hundred and fifty dollars, he will take the boy off their hands; but it should be done after dark, for the neighbors will not take kindly to anyone returning the boy to the town. Sam cannot resist the look of appeal that Bill gives him. They return the boy off as agreed, and against his will:

"How long can you hold him?" asks Bill.

"I'm not as strong as I used to be," says old Dorset, "but I think I can promise you ten minutes."

"Enough," says Bill. "In ten minutes I shall cross the Central, Southern and Middle Western States, and be legging it trippingly for the Canadian border."

One might expect these men would never consider the crime of kidnapping again.