In the swamp, Old Scratch shows Tom a number of trees bearing the names of prominent and prosperous members of the Massachusetts colony. The inward rot concealed within the trunks of those trees serves as a metaphor for the spiritual corruption of the individuals named.
Tom looked in the direction that the stranger pointed, and beheld one of the great trees, fair and flourishing without, but rotten at the core, and saw that it had been nearly hewn through, so that the first high wind was likely to blow it down. On the bark of the tree was scored the name of Deacon Peabody, an eminent man who had waxed wealthy by driving shrewd bargains with the Indians.
The tree appears to be “fair and flourishing,” and likewise, Deacon Peabody is a successful and respectable man in the eyes of the world, an upstanding citizen of the Massachusetts Colony. And yet, much as the tree trunk is revealed to be “rotten at the core,” Peabody’s innermost soul is tainted by the source of his wealth: unfair and uneven business dealings with Native Americans. Irving suggests through this metaphor that the early sources of wealth in America were largely unethical, and though no Native Americans appear in the story directly, their presence haunts the text. Though Deacon Peabody has benefited from economic exploitation during his life, the moral logic of the story demands his punishment, and much as the tree is weakened by its rot and liable to fall, Peabody soon dies.
A “short-cut” that Tom takes through the swamp on his way home one day serves as a metaphor for Tom’s desire to get ahead in life quickly, without doing the necessary work.
One day that Tom Walker had been to a distant part of the neighborhood, he took what he considered a short-cut homeward, through the swamp. Like most short-cuts, it was an ill-chosen route.
To take a simple short-cut seems innocuous, but Tom’s impatient desire to achieve his goals swiftly and easily is characteristic of him, and this trait lands him in deep trouble later on in the story. This early physical “short-cut” serves as a metaphor for all of the other, ethical short-cuts that Tom will take in the story, from his decision to make a deal with Old Scratch to get his hands on Captain Kidd’s treasure, to his decision to invest that treasure in a money lending business. Even his attempts to evade the devil by carrying a Bible around with him might be thought of as a “short-cut,” as Tom refuses to do the hard work of correcting the wrongs he has inflicted on others, and thus reforming himself spiritually. As Irving’s narrator warns the reader, a short-cut is often an “ill-chosen route,” and ultimately all of Tom’s attempts to jump on a “fast track” to wealth only accelerate him towards his doom.