Near the beginning of the novel, Tom is punished by Aunt Polly by being forced to whitewash the fence in front of his house on a Saturday morning. With a thirty-by-nine-yard fence in front of him, Tom is feeling miserable. An adventuresome, fun-loving boy, Tom would much rather be out playing on a beautiful day off from school. He almost manages to bribe Jim into trading places with him, painting while he goes to the pump to fetch water, but Aunt Polly interferes. Then Tom has an idea of how he can trick his friends into doing the odious work for him.

Ben Rogers, a robust, energetic, red-blooded boy like Tom, a boy Tom has feared would ridicule him, comes into view, eating an apple and pretending to be a steamboat. He is Tom's first victim. Tom convinces him that whitewashing a fence is an enviable activity. Tom tells Ben that it's not everyday he gets to paint a fence and not a task just anybody can do.

Soon, Ben is asking if he can paint too. Tom withholds, and Ben soon offers him the rest of his apple for the privilege of doing the chore. Tom repeats this trick with other boys and soon enough earns a nice haul of goods in exchange for letting others do an odious job for him. This establishes Tom early on as a bold, quick-thinking trickster figure who can turn adversity into gain.