I enjoy reading famous author's lesser-known works for a few reasons, such as the ability to brag about it at cocktail parties; and also, more seriously, because we can see what overlaps there are--what tropes, motifs, or themes seem stable--and also make some guesses about why these pieces are less famous. So, "The Devil and Tom Walker" involves a man who disrupts the community and who gets caught up in a supernatural power, until he is chased/carried off by a man on a horse. Which sure sounds like Ichabod Crane and the Headless Horseman--only here, it's about the miser Tom Walker and the Devil.
This story builds up slowly at first, as pieces fall into place: here's a paragraph on Kidd and his lost treasure, which includes the note that the Devil oversees all treasure burying; here's a paragraph on Tom Walker and his wife, who are both misers, even miserly towards each other, so that "fierce were the conflicts that took place about what ought to have been common property"; then, when Tom Walker wanders into the forest, we get a short history of the Indian fort there; and only then do we finally introduce Tom Walker to the Devil.
Now, if you told this story straight out, you might start with Tom meeting the Devil, trading his soul for gold, and then setting up as a usurer in Boston. (Usurers, we learn, are second only to slavers as the Devil's favorite people; which is a pretty strong critique of slavers in 1824 and reason #1 why this story isn't more famous: how many Southern magazines would reprint this story with that critique of slavery?) So all the stuff about his wife and the buried treasure seems incidental to the main story of a Faustian bargain.
But the history of the treasure is part of Irving's interest in early Americana and history; and it connects up with the questions of how other people get their money: there's buccaneering, usury, and the sort of speculation that causes and crashes bubbles. (And theft if we add in the fact that Walker's wife walks off with the family silver to try to bargain with the Devil.) The only person who really trades fairly is--the Devil. He makes a deal and sticks to it; even his terms for Tom Walker's usury business aren't as strict as the terms that Tom sets for himself:
"You shall open a broker's shop in Boston next month," said the black man.Which is reason #2 why this story probably isn't more famous, while Hawthorne's "man meets devil" story "Young Goodman Brown" is on many high school syllabi: Irving's tone here is pretty comic, giving us a plain-dealing Devil and people who aren't so nice. So, when Walker's wife walks out on him with the family silver and never returns, we hear, "Tom consoled himself for the loss of his property with the loss of his wife...".
"I'll do it to-morrow, if you wish," said Tom Walker.
"You shall lend money at two per cent. a month."
"Egad, I'll charge four!" replied Tom Walker.
"You shall extort bonds, foreclose mortgages, drive the merchant to bankruptcy—"
"I'll drive him to the d——l," cried Tom Walker, eagerly.
And Irving never really lets up on the critique here, noting that Tom builds himself a big house to show off how rich he is, but can't bring himself to spend the money to furnish it. And he shows how Walker's spiritual conversion is really just the translation of spiritual matters into economic matters, where Walker thinks about his soul's double-entry bookkeeping--sins vs. prayers. That the economic and the spiritual don't mix might be reason #3 why more people don't read this story.
Lastly, Irving make one great move in the meeting scene between Tom and the Devil. We might expect that meeting to be rather upsetting to Tom, but Irving hangs a lampshade on it: sure, we'd expect Tom to be scared by this, but he's not. Partly because he's "hard-minded" and partly because his wife has given him plenty of practice in fighting.