“The Ransom of Red Chief” derives from the tall tale so familiar in American humor. Ordinarily, the tall tale answers a question: “How big was the ox?” “How slow was the horse?” In this story, the question is, “How bad was the ten-year-old boy?” Thus, the tall tale simply exaggerates reality; in this case, the reality is the average ten-year-old boy, and the exaggeration is Johnny Dorset.

The narrative technique of the story is also reminiscent of the tall-tale tradition. Sam, the leading con man, speaks in the first person, as if relating his story to an audience: “Wait till I tell you,” “Yes, sir, that boy seemed to be having the time of his life.” He is given to malapropisms, such as “philoprogenitoveness,” and to literary words, such as “sylvan” and “dastardly,” which suggest that he is overreaching his real capacities, as he does in the story. However, both Sam and Bill can use the language of frontier America, too, comparing Johnny to a “welter-weight cinnamon bear” or a “two-legged skyrocket” when they choose to exaggerate, saying that Johnny has “somewhat got on my nerves,” in a comic understatement.

Nor is the story without its scenes of comic pathos, all related by Sam, as when Bill apologizes for releasing Johnny, then turns to find the boy behind him and seems for a time to be losing his sanity. It is Sam who describes Bill’s pleas, which finally result in a “getaway” from the kidnapped boy and in paying the “ransom” to his father.

Because the story is written in the comic tradition, it lacks the sentimentality that has dated some of O. Henry’s other stories. Fusing as it does the elements of classical comedy and those of the American tall tale, “The Ransom of Red Chief” is one of the writer’s most successful productions.