Sam, the narrator of the story, writes the letter to Red Chief's father. At his partner Bill's request, Sam reduces the ransom demand from $2,000 to $1,500. Bill is having a lot of trouble with Red Chief and wants to get rid of the wild kid as soon as possible. Sam's letter to the boy's father reads as follows:
Ebenezer Dorset, Esq.:
We have your boy concealed in a place far from Summit. It is useless for you or the most skilful detectives to attempt to find him. Absolutely, the only terms on which you can have him restored to you are these: We demand fifteen hundred dollars in large bills for his return; the money to be left at midnight to-night at the same spot and in the same box as your reply--as hereinafter described. If you agree to these terms, send your answer in writing by a solitary messenger to-night at half-past eight o'clock. After crossing Owl Creek, on the road to Poplar Cove, there are three large trees about a hundred yards apart, close to the fence of the wheat field on the right-hand side. At the bottom of the fence-post, opposite the third tree, will be found a small pasteboard box.
The messenger will place the answer in this box and return immediately to Summit.
If you attempt any treachery or fail to comply with our demand as stated, you will never see your boy again.
If you pay the money as demanded, he will be returned to you safe and well within three hours. These terms are final, and if you do not accede to them no further communication will be attempted.
TWO DESPERATE MEN.
Sam walks over to a place called Poplar Cove to mail his letter at the combination general store and post office. He expects it to be picked up in about an hour and delivered to Summit that same day. Sam sits around the store talking with the locals. The talk is that Ebenezer Dorset's son has been lost or stolen and everybody in Summit is upset about it. That pleases Sam, but what he doesn't realize is that everybody is upset because they're afraid the kid will come back. Unwittingly, Sam and Bill have captured the wildest kid in the whole region. Sam is away from Bill and Red Chief much of the time and doesn't realize what Bill is going through as a babysitter. Red Chief was wild enough when he was at home, but now that he is going through the greatest adventure of his young life he is really turning into a savage. Bill is genuinely afraid of him.
Eventually the two kidnappers receive a communication from Ebenezer Dorset telling them that he refuses to pay the ransom request but making a counter-offer. He will take his son off their hands if they pay him two hundred and fifty dollars. Obviously Mr. Dorset knows his son very well and can imagine what a hard time the two "desperate men" are having with him. They are becoming desperate men in a different sense than Sam originally intended in his note. It doesn't take Bill and Sam long to agree to pay the boy's father the money just to get rid of him. They have a problem getting Red Chief to go home. He was having the time of his life.
When the kid found out we were going to leave him at home he started up a howl like a calliope and fastened himself as tight as a leech to Bill's leg. His father peeled him away gradually, like a porous plaster.
We can see that Sam's letter to Red Chief's father doesn't really have any teeth in it. These men know they can't kill the boy if his father fails to comply with their demands. O. Henry doesn't want to suggest that there might be a murder in his story or even that the victim might suffer any physical abuse. That would detract from the comical tone of the whole story. Red Chief is never in any danger. It is Sam and Bill who are in the real danger. They don't dare to fall asleep at night. One of them might wake up and find Red Chief sitting on his chest ready to scalp him or cut his throat with the case-knife they used for slicing bacon.