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Religion and wealth are criticised by Irving in this story through the part of the wood that Tom finds where the trees represent various supposedly good and wealthy individuals in New England society, such as Deacon Peabody. Note how the tree that bears the name of Deacon Peabody symbolises the inner hypocrisy and hollowness of his character:
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 below it down. On the bark of the tree was scored the name of Deacon Peabody.
The devil shows to Tom through these trees, all of which bear the names of famous people for one reason or another, that outward piety or religion is not enough to prevent inner decay from ruining one's character. The same is true of wealth, as is demonstrated through the name of Crowninshield that Tom finds on the tree trunk that he is sitting on, and which has obviously been hewn down by an axe. Tom remembers that this man was very wealthy and used to make a "vulgar display of his wealth," yet clearly his wealth was not enough to protect him from death. Irving therefore directly criticises religion at the beginning of this story through the presentation of the tree trunks and their link to well-to-do individuals who have gained status in society either through religion or through their wealth.
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