Nothing about the plan Sam and Bill hatch goes as expected in "The Ransom of Red Chief" by O. Henry. They picked a rather sleepy little town where nothing really happens, and they targeted the banker's son because they assumed the banker would be willing and able to pay. It seems so reasonable, but things just do not go well for the hapless kidnappers from the very beginning. The men should have known they were in for trouble when they find their intended victim in the street throwing rocks at a kitten. Not an auspicious beginning.
The boy, Johnny, quickly turns the tables on his captor, Bill, and transforms himself into "Red Chief, the terror of the plains." Both of the men find themselves terrorized by a little boy, and they do not seem to find any way around it. They have to keep him until he is sufficiently missed and they can make arrangements for the ransom.
In order to do that, Sam has to leave Bill with Red Chief for the day. In a rather ironic role reversal, he tells Johnny that he must be nice to Bill because he is going to be Bill's "playmate for the day."
"Now, you come in and make friends with him and say you are sorry for hurting him, or home you go, at once."
This is the worst day for Bill, as he has to be Red Chief's horse. It is a grueling day, and this is how Bill describes it to Sam:
"I was rode," says Bill, "the ninety miles to the stockade, not barring an inch. Then, when the settlers was rescued, I was given oats. Sand ain't a palatable substitute. And then, for an hour I had to try to explain to him why there was nothin' in holes, how a road can run both ways and what makes the grass green. I tell you, Sam, a human can only stand so much. I takes him by the neck of his clothes and drags him down the mountain. On the way he kicks my legs black-and-blue from the knees down; and I've got to have two or three bites on my thumb and hand cauterized."
This is the end for Bill, and after this day he wants to send the boy back; in fact, things are so bad that he is willing to pay Johnny's father to take him back--something Johnny's father suggests, as well, knowing Johnny like he does. Whatever it takes to rid himself of Red Chief is good for Bill, and Sam soon agrees.
This is certainly a kidnapping-gone-wrong, and Bill bears the brunt of Red Chief's terrorizing.