What could Bill and Sam have done to make their plan more likely to succeed in "The Ransom of Red Chief" by O. Henry?
The most obvious thing Bill and Sam could have done in "The Ransom of Red Chief" by O. Henry to make their plan much more effective was to choose another boy. Of course they only chose nine-year-old Johnny because he was the son of Ebenezer Dorset, someone they were certain had the means to pay them, and it certainly seemed like a wise decision at the time. Their choice, however, turned out to be disastrous. To avoid making such a horrible choice in the future, they should review what went wrong this time.
First, the two kidnappers failed to do their due diligence (their homework) by scouting out their potential victim and his family before kidnapping him. They knew the family was rich, but if they had spent any time at all watching the boy and his family, the men would undoubtedly have observed signs of potential trouble ahead. Ebenezer Dorset reveals as much in his reply to the ransom letter:
Gentlemen: I received your letter to-day by post, in regard to the ransom you ask for the return of my son. I think you are a little high in your demands, and I hereby make you a counter-proposition, which I am inclined to believe you will accept. You bring Johnny home and pay me two hundred and fifty dollars in cash, and I agree to take him off your hands. You had better come at night, for the neighbours believe he is lost, and I couldn't be responsible for what they would do to anybody they saw bringing him back.
So we know that Johnny has been a terror both to his own family as well as the neighbors, something the men undoubtedly would have noticed if they had spent any time observing the boy in his own environment.
Second, once they had the boy, Bill let him have too much control. In the short time it took "Old Hank, the Trapper" to drop Bill and the boy off at camp and then return the wagon, Bill had already become Red Chief's (Johnny's) captive simply to appease the boy and keep from getting any more bruises. Of course Bill is not cruel by nature, so he would not have treated the boy badly; however, he certainly could have taken control of the situation rather than let the boy determine how things were going to go in camp.
Finally, Sam could have come back to camp and set things right, but he, too, falls victim to Johnny's overwhelming personality and wishes. Both men act as if Johnny were a grown man whose orders must be followed rather than an annoying (and admittedly somewhat violent) nine-year-old boy. Sam seems to be the stronger and perhaps more intelligent of the two men, so when he, too, succumbs to the boy's demands, neither man stands a chance.
In short, everything that goes wrong with this kidnapping which ends up costing them two hundred and fifty dollars (and many bumps and bruises) is their fault. They could have prevented this mock tragedy by doing a little investigation and then by asserting themselves as the adults that they are rather than submitting themselves to the will of a child.