Ebenezer Dorset's son because Dorset is the wealthiest man in the region. It is evident Sam and Bill have no prior experience with kidnapping. The two men must be bachelors who know nothing about controlling little boys; the ten-year-old who calls himself Red Chief has the worst characteristics of the worst little boys, as Sam and Bill discover soon after kidnapping him.

As Sam says at the beginning of his story,

It looked like a good thing: but wait till I tell you. We were down South, in Alabama—Bill Driscoll and myself—when this kidnapping idea struck us. It was, as Bill afterward expressed it, “during a moment of temporary mental apparition”; but we didn’t find that out till later.

Sam thinks kidnapping is a good idea, but Bill afterward called it "a moment of temporary mental apparition," or "aberration." Both men use bigger words than they understand in an attempt to make an impression on the yokels they deal with in their profession. In this respect, Sam and Bill are like the King and the Duke in Mark Twain's novel Huckleberry Finn. Sam and Bill do not anticipate running into a yokel who is smarter than they are. This kind of story was popular in America in the horse-and-buggy days. Readers enjoyed reading about how "city slickers" were outwitted by apparently ignorant and unintelligent country folk. 

The kidnapping scheme was the result of desperation, ignorance, bad planning, and inexperience. The resolution illustrates O. Henry's theme: Crime does not pay. The reader can understand how Bill and Sam gradually realize that they have gotten themselves into a mess and how painful it must have been to part with $250 of their meager capital. Sam and Bill still have to travel all the way to Southern Illinois if they are going to work their "fraudulent town-lot scheme," and they will still need over two thousand dollars when they get there.

Bill and Sam have combined cash assets of $600 and reckon that they need about $2000 more to fund a "fraudulent town-lot scheme in Western Illinois." A couple of small-time criminals, they are looking to pick up some easy money to fund their next con. They reason that a kidnapping in a "semi-rural" location offers reduced risk: there isn't a large or well-organized police force to investigate, and there isn't the kind of newspaper that would send out investigative reporters to stir up the public interest.

Ebenezer Dorset is a prominent citizen and mortgage officer, and so Bill and Sam target his only son as their victim. They note that he is a "forecloser," and they may reason that he is an appropriate target since bank officers who handle foreclosures are often thought of as unsympathetic. They believe that Dorset would be able to pay them the $2000 they plan to ask for ransom.

In O. Henry's short story, "The Ransom of Red Chief," two men named Bill and Sam kidnap a little boy from his father, Ebenezer Dorset. Bill and Sam, together, had about six hundred dollars, but they needed another $2000.00 for a money making plan they had concocted. They decided that a man like Mr. Dorset would gladly pay to get his son back. Mr. Dorset was considered a well-to-do citizen in the town of Summit, where he was a mortgage broker. Bill and Sam thought it would be easy to get a man like that to turn over some money. Of course, nothing is ever as easy as it looks, and Bill and Sam, in the end, had to pay old Mr. Dorset to take back his mischievous little boy!

The boy didn't think he had any reason to need to "escape." In his imagination, he was Red Chief, the Indian who was in charge of the two captives, Old Hank and Snake-eye. Obviously he couldn't abandon his prisoners by leaving his hideout cave until they had both been properly punished - Old Hank was "to be scalped at daybreak" and Snake-eye would "be broiled at the stake at the rising of the sun."

Given the tremendous adventure of it all, given his nine-year-old enthusiasm and non-stop energy, given the fact that he had never had the opportunity to go camping with two men who did whatever they could to go along with his ideas - why would he want to leave?

These two small-time criminals had a stake of six hundred dollars and needed two thousand dollars more to set up a new fraudulent scheme in Illinois, which sounded like a scheme to sell land they didn't really own to people, take their money, and then run.  They thought a kidnapping would be a quick and easy way of raising this money and settled on Summit as a good place, since it did not have much in the way of law enforcement: just some constables and maybe a few "lackadaisical bloodhounds."  They chose the son of a prominent man in Summit, Ebenezer Dorset, because he worked for a bank, was an upstanding citizen, and was the most likely to be able to afford to pay this ransom.  Little did they know that by the time they were done with their kidnapping scheme, they would be begging Ebenezer to take back his mischievous child.