At one point during the story, Bill tells Sam that they have been together in many adventures, which include natural disasters such as fires, floods, cyclones, and earthquakes. In addition, they have experienced police raids and have been involved in poker games. He also mentions that they've been in train robberies together. Therefore, they seem to have been involved in gambling and theft in the past.
Bill and Sam are now attempting to commit what Sam refers to as a "a fraudulent town-lot scheme." To get the money necessary to carry out this scheme, they are trying to kidnap Ebenezer Dorset's ten-year-old son, who refers to himself as Red Chief, and to charge a ransom of $2,000. While they want to add fraud and kidnapping to their list of crimes, they are entirely unsuccessful as kidnappers. They wind up having to pay Dorset to take his horribly behaved child back at the end of the story.
We get the impression that Sam and Bill are career criminals although it isn't spelled out as such in the story. When the story opens, our two would-be kidnappers have managed to scrape together about $600 which they're going to put towards a town-lot scam they're planning in Western Illinois. But it's not enough. Sam and Bill figure they're going to need another $2,000 to swing the deal—hence, their ingenious kidnapping plan.
Although the two men prove themselves hopelessly incompetent, they do give the impression that they have prior experience of criminal activity. Sam goes into a lot of detail about the preparations that he and Bill Driscoll made when they first decided to kidnap a little boy in Summit, Alabama. It's instructive that he seems to know just what kind of response they can expect from the local sheriffs. This would appear to indicate that Sam and Bill have encountered law enforcement officials in semi-rural communities before.
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