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  • Alas, Poor Villain: Since later stories have been interpreting the Horseman as a real entity, Ichabod's unknown fate with it becomes a whole lot darker.
  • Alternate Character Interpretation: There is a strong recent trend to make Ichabod Crane, not merely the protagonist of the story, but actually an heroic character, while Brom Bones is regarded as at best a Jerk Jock — which are both far from Irving's intention to have Bones be the hero and Ichabod a superstitious wimpy moocher.
    • On the other hand, Ichabod seemed more interested in his girlfriend's father's money than his girlfriend, so it's also kinda easy to make him an Asshole Victim.
    • The Horseman: a Scooby-Doo Hoax by Brom Bones used to scare Ichabod away, or a real demonic figure back from the dead to haunt the forest?
      • For that matter, even if it was Brom, did he really just scare Crane off, or use the locals' belief in the Horseman to get away with a much darker manner of disposing of his rival?
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