Why does the boy prefer staying with Sam and Bill to going home in "The Ransom of Red Chief"?
In O. Henry's story "The Ransom of Red Chief," the kidnapped boy is having the time of his life. He has never camped out before, so he enjoys the hideout that Sam and Bill have up on the mountain. When Sam asks him whether he wants to go home, he says, "What for?" He explains that he doesn't like going to school and that he doesn't have any fun at home. While he is being held for ransom, however, Bill is his constant playmate. Despite how rough he is with Bill, Bill must keep him quiet and happy until they can arrange for the ransom. Red Chief proclaims that he has never had so much fun in all his life.
At one point, Bill boxes his ears, but the boy gets back at him by hitting him in the head with a rock. Bill then has to serve as Red Chief's "hoss" for the day while Red Chief becomes the Black Scout. Bill can't take it anymore and sends the boy home, but he comes back to their camp. When they finally take him back to his father's home, the boy clings to Bill's leg and doesn't want to return. One can speculate that even though the boy seems to be strong-willed, he probably doesn't get away with quite as much mischief at home. He has taken advantage of the two men to get his own way for the entire time they have had him in their custody. For a "rowdy" boy like Red Chief, getting his own way seems to be his favorite way to live.
Of course, one could also speculate that the boy was wise enough to realize that the more obnoxious he made himself, the sooner he would return to his own home, which may indeed have been his motive the whole time. Since the story is told from Sam's point of view, we only know what Sam has told us. It's possible the boy and his father had a very happy reunion after the two petty criminals sprinted away.