Bill Driscoll of "The Ransom of Red Chief" is a con-man who, along with his partner Sam, decides to kidnap the son of a prominent citizen of the small town of Summit, Alabama. With Sam, Bill assumes that the residents to such a "deleterious and self-satisfied class of peasantry" will be easy prey. However, when they approach the freckled son of the town's banker, the child throws a piece of brick into Bill's face. This action is the beginning of Bill's role reversal into terrorized victim.
From this point on in O. Henry's humorous tale, Bill is terrorized by the boy who calls himself "Red Chief, the terror of the plains." He "never closed an eye again in sleep as long as that boy was with us." At one point Red Chief attempts to scalp Bill after tying him. After this incident, Bill's anxiety increases to the point where he begs Sam to not leave him alone with the boy; he begs Sam to reduce the amount of the ransom so that the father will assuredly take the boy back.
With his characteristic ironic twist upon the stories that he writes O. Henry has Bill and Sam are reduced from con-men to "desperate men" who pay Dorset to reclaim his son. After the father takes the boy, Bill apprehensively asks how long he can hold him so that he can flee:
"In ten minues I shall cross the Central, Southern and Middle Western States, and be legging it trippingly for the Canadian border."