How do they convince Red Chief to willingly go back home?
The two would-be kidnappers get Red Chief to go back to his home with him by telling him a direct lie which they know will be too tempting for him to resist.
We took him home that night. We got him to go by telling him that his father had bought him a gun and we were going to hunt bears the next day.
Then when they get Red Chief home they turn him over to his father. Bill and Sam pay the $250 reverse ransom to Ebenezer Dorset who has agreed to hold the boy for as long as possible while the they make their getaway.
"How long can you hold him?" asks Bill.
"I'm not as strong as I used to be," says old Dorset, "but I think I can promise you ten minutes."
Evidently the boy's own father has just as much trouble handling his son as the two kidnappers had experienced. Both of them are vastly relieved to get this wild kid off their hands even for ten minutes. Both take off at a run and are soon a mile and a half out of Summit. No doubt they will never return to Summit again, and no doubt they will never try kidnapping again.
The moral of the story is "Crime does not pay." O. Henry wrote other stories on the same theme. One of the best known of these is "A Retrieved Reformation." O. Henry may have treated "The Ransom of Red Chief" as a comedy, but he seriously believed in the wisdom of leading a straight life. He had served several years in prison for embezzlement and apparently never got over it. He wrote under a pen name. He was afraid of his past becoming known. He was an alcoholic who was known to drink two quarts of whiskey a day. He died of alcohol-related diseases when he was only in his forties.