Ichabod prides himself on being a “rational man,” and when he first hears the story of the Headless Horseman, he dismisses it as the product of superstition. His employer in New York sends him upstate to solve the mystery of Sleepy Hollow due to his relentless attempts to modernize and reinvent the local system of government. Ichabod shows up prepared to analyze and deduct, with a bag full of instruments of his own design. When confronted with the reality that the Horseman exists and is, indeed, Headless, he enters an intense, brief period of internalization where he is forced to adjust his former conclusions and pursue a new course of action. A man “ahead of his time,” Ichabod is already exploring ideas of modernization and urging the police force to “catch up to the times” (“In a short time, we will be in the nineteenth century!”); he is performing autopsies and believes one can derive the reason for death and “clues” from a more careful analytical observation of the pertinent details. Ichabod sneers at the idea of the Horseman at first, but with repeated exposure to local superstitions, becomes more trusting of their truths; he also tries out, abandons, and sometimes entirely reverses his suspicions, conclusions, and theories – sometimes he is precise and right in his conclusion (he manages to draw the connecting threads together, and figure out someone controls the horseman in exchange for their head; he knows it has something to do with a town secret, etc) and sometimes he is wrong (in suspecting Katrina was behind all the evils in town, and that her ‘curse’ was meant to harm him). Ichabod’s inferior Fe shows in his mental collapse beneath this new information, as well as his general politeness that sometimes misses the mark (Lady Van Tassel says he has tried very hard not to notice her hand, nor ask her about it, “when in fact, to do so would be polite”)… and in his clumsy understanding of love.

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Analytical and detached, Ichabod has not only become an expert in his field, he invented his field! He dared to think outside the box and come up with new solutions to problems. He does not care to be caught off guard, and becomes anxious and unable to believe his eyes when he encounters the supernatural. Ichabod does not want to become emotionally involved with Katrina and resists his feelings for her, choosing instead to remain on the sidelines (she says she had a mind to give him her heart). Deeply analytical and logical, once he realizes the Horseman is real, he sets about figuring out how to stop it. But the deeper he falls into the supernatural problems within Sleepy Hollow, the more anxious and paranoid he becomes… fearful of curses, suspicious that the woman he loves may be a witch with nefarious intentions, and worried that he might perish while investigating the case.