In "The Ransom of Red Chief" by O. Henry, two men, Bill and Sam, decide to kidnap a little boy in the town of Summit. They choose Summit for several reasons. First of all, it is a small town populated mostly by farmers, workers and tenants. Bill and Sam think these people will be pretty harmless and will not give them a lot of trouble. They figure anyone who loses his/her child to kidnapping will be more than willing to pay to get that child back. 

"Philoprogenitiveness, says we, is strong in semi-rural communities; therefore, and for other reasons, a kidnapping project ought to do better there than in the radius of newspapers that send reporters out in plain clothes to stir up talk about such things." (Henry 1)

Philoprogenitiveness is defined as the love for one's children, and the men believed that due to this, their plan would go well. They also felt that in a small town, the worst that could happen was that the police or some "lackadaisical bloodhounds" might come after them. Bill and Sam thought they had the perfect plan.

In "The Ransom of Red Chief," why do Bill and Sam choose Summit for their scheme?

At the beginning of the story, Sam, who is the narrator, gives several reasons why he and Bill choose Summit for their kidnapping scheme. As Sam says in the text:

There was a town down there, as flat as a flannel-cake, and called Summit, of course. It contained inhabitants of as undeleterious and self-satisfied a class of peasantry as ever clustered around a Maypole. 

The word "undeleterious" means harmless, and Sam refers to the inhabitants of Summit as "peasantry." Here, O. Henry's language reveals Sam and Bill's attitude toward the citizens of Summit. Sam and Bill think that it will be easy to pull off the kidnapping because the people of Summit are simple, rural folk who won't put up a fight, so to speak. Another quotation from the beginning of the story demonstrates the same attitude:

Philoprogenitiveness, says we, is strong in semi-rural communities; therefore and for other reasons, a kidnapping project ought to do better there than in the radius of newspapers that send reporters out in plain clothes to stir up talk about such things. We knew that Summit couldn't get after us with anything stronger than constables and maybe some lackadaisical bloodhounds and a diatribe or two in the Weekly Farmers' Budget. So, it looked good.

"Philoprogenitiveness" means to have a love for children or to produce many offspring. Sam characterizes a rural town like Summit as a place where people love children and have close-knit families; therefore, citizens of Summit would be outraged by a kidnapping and pay any amount of money necessary to get their children back. Furthermore, Sam figures that, because Summit is such a small town, he and Bill won't face any real trouble or challenges to their scheme. As Sam puts it, a few constables and a rant in the newspaper won't put a damper on their plan to get $2000. Of course, the situational irony of the story is that Sam and Bill mischaracterize Summit; their incorrect assumptions about the town are partly what lead to their downfall. Sam and Bill end up kidnapping Red Chief, a boy who is so mischievous and uncontrollable that Red Chief's own father seems to want the boy off of his hands (as do the inhabitants of Summit).

In The Ransom of Red Chief, why do the kidnappers choose the town of Summit?

Bill and Sam are con-artists who need $2,000 more to start a bigger con up north in Illinois. At the opening of the story, they are in Summit, Alabama, a flat and small community with no real access to the outside world. Their reasons for deciding to do a kidnapping and ransom in a small town is due to the following reasons: "Philoprogenitiveness," which is the deep love of parents' for their children; the fact that the town doesn't have a large newspaper for reporting their doings; and, the hope that "Summit couldn't get after us with anything stronger than constables and, maybe, some lackadaisical bloodhounds" if they were chased.

First, Bill and Sam are hoping that the parents of some unlucky kid will love him so much that they will most likely pay anything to get him back. These men are working under the assumption that people who live in small towns are ignorant, uneducated and easy targets, too.

Next, the kidnappers want to handle this project with as little publicity as possible. Since there is no big newspaper around to call the public's attention to the matter, they won't be recognized later for the scheme anywhere else in the country. Big newspapers would publicize the kidnapping and possibly publish their pictures in the paper if the men were discovered. This way, a small town would not be large enough to cause them any mischief during or after the scheme. Sam elaborates by saying the following:

" . . . a kidnapping project ought to do better there than in the radius of newspapers that send reporters out in plain clothes to stir up talk about such things."

Finally, if everything that could go wrong does go wrong, then they feel like they could outwit or outrun any local police or dogs who might be sent after them. Therefore, within the first three paragraphs of the story, the expectations of the kidnappers are outlined. This gives O. Henry the foundation upon which to shoot each expectation down by way of ironic twist during the story.