Knickerbocker says that he first heard this story at a Corporation meeting among burghers in the “ancient city” of Manhattoes (i.e. Manhattan), told by a shabby old man (the storyteller). Most of the attendees enjoyed the tale, but one other elderly gentleman seems doubtful and not amused, as if wary of the tale.
By introducing yet another framing device to the story, in which Knickerbocker himself got the story from another storyteller, Irving simulates the historian’s job of sifting through archives and witness testimonials. The elderly gentleman provides a counterpoint to this emphasis on fact.
He asks the storyteller what the moral of the story is. The storyteller answers that every situation in life has its advantages, as long as you keep in mind the following joke. Someone who races goblin troopers will probably have a rough ride. Therefore, if a country schoolteacher fails to win the heart of a Dutch heiress, he is certain to achieve success in politics.
This logical syllogism has spawned countless interpretations over the centuries. There’s certainly some kind of relationship meant to be drawn between Ichabod’s doomed courtship, his dreamy, imaginative temperament, and his later success—but it’s also possible Irving is just playing with the reader as well.
The wary gentleman seems even more confused by this logical syllogism, as the storyteller looks back at him triumphantly, before the gentleman claims that he still has doubts about the tale. The storyteller responds that he doesn’t believe half of the story himself.
Throughout “Sleepy Hollow,” claims about the story’s veracity have competed with hints that it’s no more than an imaginative tale. Here, Irving seems to wink at the reader, implying that the tension will remain unresolved.