In 1907, America hummed with the optimism of Teddy Roosevelt's "Big Stick" diplomacy and the growing Boy Scout movement. Amidst this, O. Henry wrote one of his most well-known short stories. "The Ransom of Red Chief" takes readers to this era while twisting the popular image of rugged adventure. Two bumbling conmen attempt a child abduction, only to be tormented by their prize—a hyperactive, knife-wielding, rock-throwing boy who turns their scheme into a comedic nightmare.

The story begins with Sam, the narrator, speaking directly to the reader. He says that he and Bill decided to try their hand at kidnapping while in Summit, Alabama. With obvious foreshadowing, he hints that this is a bad idea.

The two criminals feel very confident when making their plans. They conclude that the town's remoteness and small police force mean their scheme to kidnap Johnny, "the only child of a prominent citizen named Ebenezer Dorset" should be a success. They are eager for it to succeed as they need the ransom to pay for another criminal enterprise they have in the works.

Using a cave as their base of operations, the narrator and his accomplice head into town. There, they find their intended victim throwing rocks at a kitten. They try to tempt him into their buggy with a promise of candy, but Johnny responds by throwing a rock directly at Bill's face. After a brief struggle, the kidnappers get the boy into their buggy and back to the cave.

Johhny seems very confident in his new surroundings. He calls himself "Red Chief, the terror of the plains" and enjoys including his kidnappers in his game of make-believe. He tells Sam that he prefers camping in the cave to being home or going to school and doesn't want them to take him back.

Yes, sir, that boy seemed to be having the time of his life. The fun of camping out in a cave made him forget that he was a captive. He immediately christened me Snake-eye, the Spy, and announced that, when his braves returned from the warpath, I was to be broiled at the stake at the rising of the sun.

That night, Johnny keeps the conmen up for hours as he keeps watch for the imaginary "stealthy approach of the outlaw band." When he is able to sleep, Sam dreams he has "been kidnapped and chained to a tree by a ferocious pirate with red hair." In his sleep, as in waking life, the captive and the kidnapper have exchanged roles.

The next morning, Sam awakes to Bill's screams. Still in the persona of Red Chief, Johnny is attempting to scalp Bill with a knife. Sam is able to de-escalate the situation but remains too nervous to take his eyes off Johnny. Bill doubts that Johnny's parents want him back, but Sam remains confident. Johnny spends the rest of the day thoroughly enjoying himself as he violently torments his captors.

Bill is losing his nerve. He even wants to lower the ransom out of fear that the boy's parents won't pay too high a price and he will be stuck with Johnny.

"I ain't attempting," says he, "to decry the celebrated moral aspect of parental affection, but we're dealing with humans, and it ain't human for anybody to give up two thousand dollars for that forty-pound chunk of freckled wildcat. I'm willing to take a chance at fifteen hundred dollars. You can charge the difference up to me."

They draft a ransom note to be sent to Ebenezar, the child's father. In it, they lay out precise instructions for the exchange and a demand for fifteen hundred dollars. Indicating their sorry state, they sign the letter "Two Desperate Men." Sam sends the letter from the post office in a neighboring town, where he also hears word that people in Summit are talking about the kidnapping.

Sam finds the camp deserted when he returns. After waiting for a bit, Bill comes back. Johnny has thoroughly broken Bill's spirit by riding him like a horse, feeding him sand, and asking endless inane questions. Bill tells Sam that he sent the boy home and no longer thinks the ransom is worth such ill-treatment. To Bill's horror, Johnny silently follows him back to the camp.

That evening, they receive a response from Ebenezer. The boy's father clearly understands that he holds more power in this situation than the kidnappers. Instead of paying the ransom, Ebenezer promises to take Johnny back if Bill and Sam pay him two hundred fifty dollars. Sam is about to object, but Bill is desperate enough to be rid of Johnny that he eagerly accepts the deal.

They take Johnny home the next day and pay his father the reverse ransom of two hundred fifty dollars. The child is upset to lose his new companions, and Ebenezer must physically restrain him. Bill doesn't miss a moment to run away as fast as he can, with Sam catching up to him "a good half mile out of Summit."