Sam's plan to extort money from a wealthy parent doesn't go as planned primarily because the boy Sam and Bill choose to kidnap is a difficult child and the father is unwilling to accept their offer for the boy's return.
Red Chief foils their plan from the beginning because he isn't homesick and isn't afraid of his captors. On the contrary, he terrorizes them, especially Bill, requiring him to be his "hoss" and causing him...
Sam's plan to extort money from a wealthy parent doesn't go as planned primarily because the boy Sam and Bill choose to kidnap is a difficult child and the father is unwilling to accept their offer for the boy's return.
Red Chief foils their plan from the beginning because he isn't homesick and isn't afraid of his captors. On the contrary, he terrorizes them, especially Bill, requiring him to be his "hoss" and causing him pain by biting him and throwing a rock at his head. These behaviors make Bill especially doubt that Mr. Dorset will pay the demanded ransom, so he suggests lowering the amount, which Sam does.
Ebenezer Dorset does not react in accordance with the "philoprogenitiveness" upon which the petty criminals' plan depends. He acts as if he does not want his son back. In fact, rather than paying the required ransom, he gives Sam and Bill a "limited time offer" where he will take his son back if they pay him the low, low sum of $250.
Because Red Chief has terrorized them so much and because his father refuses to pay the ransom, the would-be extortionists find themselves paying a ransom to get rid of the child. Thus everything turns out the opposite of what Sam and Bill initially expected, presented an example of the irony that O. Henry is so well known for.
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