As Tom Walker is taking a shortcut home through the dark, dreary swamp, he stops to rest at an old fort, which has a bad reputation of being a place where Indians once held incantations and made sacrifices. When Tom Walker discovers a skull in the soil, he gives it a kick and is immediately reprimanded by Old Scratch. Tom is surprised by the devil, who is carrying an ax over his shoulder and has been chopping down the surrounding trees, which have the names of prominent men in the colony carved into the bark. The trees in the swamp with the names carved into the bark represent the men's souls. Tom also notices that some of the trees have more scores in them than others, which represents the various sins of particular community members. Old Scratch has just finished chopping down Crowninshield's tree and tells Tom that he will have plenty of firewood for the winter. Later on, Tom discovers that the wealthy Crowninshield has recently died, which reveals that the devil took his soul by chopping down his tree.

When Tom Walker encounters him, the Devil is busy cutting down trees. He tells Tom Walker that he will have a good harvest of firewood for winter.

As Tom surveys his surroundings, he realizes that the Devil has scored the names of important men onto certain trees. The trees are all tall and magnificent in build. However, Tom notices that one of the trees appear to be "fair and flourishing without, but rotten at the core." This tree has Deacon Peabody's name on it, and Tom marks that the tree is almost ready to fall.

In fact, the trunk Tom has been seated on bears the name of Crowninshield, a wealthy man who lived an ostentatious (showy) life, purportedly acquired through buccaneering (piracy). When Tom confronts the Devil about his right to cut down the trees, the Devil answers that the land belonged to him long before any settlers set foot on it. He imagines himself a judge, the "great patron and prompter of slave dealers, and the grand master of the Salem witches."