In O. Henry's short story "The Ransom of Red Chief," it doesn't take Bill and Sam too long at all to realize that their prospective kidnapping scheme may just backfire on them. The two need some money to carry out yet another scheme, so they decide they will kidnap Ebenezer Dorset's young son and hold him for a two-thousand-dollar ransom.

Right away, the men realize that their task might not be as easy as they have expected, for their "victim" hits Bill in the eye with a piece of brick as they try to kidnap the youngster. The boy, who calls himself Red Chief and has bright red hair to match his name, puts up quite a fight, but he soon decides that he likes camping out and doesn't want to go home.

The first night with Red Chief is not at all enjoyable, for Red Chief talks non-stop all evening and then keeps Bill and Sam up for three hours with his games. They are realizing more and more that they might have made a big mistake. Bill is even more sure of that the next day when Red Chief decides to scalp Bill (and nearly does), puts a hot potato down Bill's back, and hits Bill in the head with a rock from his slingshot.

The next day is worse yet, as Bill must play horse for Red Chief (complete with "oats," actually sand, for a meal). When Sam returns from sending the ransom letter (with a reduced ransom demand), Bill informs him that he has sent the boy home, not realizing that the boy is actually right behind him. Bill now knows for sure that their kidnapping attempt has been a major mistake and that it has backfired on them in a major way, and he just wants the whole experience over with.

In "The Ransom of Red Chief," how does the kidnapping backfire on the kidnappers?

Bill Driscoll and the narrator, Sam, plan to kidnap the only son of a prominent resident of Summit, called Ebenezer Dorset. Summit is a laid-back town, down south, and the two men figure that they can easily get away with the kidnapping in that part of the world.

However, they soon determine that they have bitten off more than they can chew. The little boy absolutely loves being held captive by the two men. He likes being away from home and likes the idea of camping on the mountaintop. The two men soon realize that the little boy is just something else: he is extremely mischievous and hyperactive. He talks incessantly and does not tire of playing. At the beginning of his stay at the hideout, the boy decides that he is Red Chief and that Sam is Snake-eye the spy and Bill is his captive, Old Hank, in a game of Cowboys and Indians. He then proceeds to torture Bill mercilessly: he tries to scalp Bill at dawn; he throws a big stone at him using a sling; and finally, he works him hard, as his horse, in a game of Black Scout. Thus, it is no surprise that Bill is soon fed up with the boy’s antics. He convinces Sam to reduce the ransom from two thousand to fifteen hundred dollars to ensure that the boy’s father does not have second thoughts about picking up the little rascal.

The kidnapping goes awry when they receive a letter from Mr. Dorset, telling them that he is willing to take the boy off their hands if they are willing to pay him $250, as the boy is not missed at home. The kidnappers, tired of the boy’s pranks, agree to Mr. Dorset’s terms; they take the boy back home, pay up the $250, and leave Summit without achieving what they had set out to do. Instead of making money from Mr. Dorset, they pay him for kidnapping his son.