It’s never easy to be “the new boy in town,” especially a small one like Sleepy Hollow–which probably felt even smaller before Washington Irving put it on the map with his classic short story, “The Legend of Sleepy Hollow.” And yet, this is what Ichabod Crane must be as he comes to town to fulfill an instructing position at the schoolhouse. It doesn’t take him very long to hear about a supposedly mythical being called the Headless Horseman, a.k.a. the Galloping Hessian of the Hollow. While Ichabod might have thought he could evade its lore by virtue of being an outsider, “It is remarkable that this visionary propensity is not confined to native inhabitants of this little retired Dutch valley, but is unconsciously imbibed by everyone who resides there for a time.”

So it is for Ichabod. As Irving describes Ichabod as a “worthy wight” (or does he secretly mean white?), we get the distinct sense that Sleepy Hollow is about to make his fortune even worse–even though it doesn’t seem possible based on the physical description, “His head was small, and flat at top, with huge ears, large green glassy eyes, and a long snipe nose, so that it looked like a weathercock perched upon his spindle neck, to tell which way the wind blew.”

That he exhibits what now (and should have then) come across as pedophiliac tendencies in consorting with his pupils doesn’t do much to make him very likable as a character. Sure, he has that “erudite” edge with regard to his game with the townswomen, but “when school hours were over, Ichabod was even the companion and playmate of the larger boys; and on holiday afternoons would convoy some of the smaller ones home, who happened to have pretty sisters, or good housewives for mothers, noted for the comforts of the cupboard. Indeed it behooved him to keep on good terms with his pupils.” Mhmmm, surely. Since we all know it wasn’t the “pretty sisters” he was after based on the barrage of misogynistic descriptions and sentiments forthcoming from this point in the narrative. Clearly, Ichabod hates women, even if it’s indicated through the narrating mouthpiece of Irving.

Moreover, his pompousness doesn’t exactly seem warranted when taking into consideration that of course he’s going to seem learned amid a population of farmers. Accordingly, “he was… esteemed by the women as a man of great erudition, for he had read several books quite through, and was a perfect master of Cotton Mather’s History of New England Witchcraft.” Big deal, so he read a book that showcases yet another prime example of his sexism.

As though to further condescend to the intelligence of the easily impressed women of Sleepy Hollow, Ichabod would enjoy “gathering grapes for [them] from the wild vines that overran the surrounding trees; reciting for their amusement all the epitaphs on the tombstones” on Sundays in the churchyard. Gee, Ichabod how kind to regale the ladies at the expense of the dead. But even that still can’t manage to get him laid, least of all by the object of his ultimate unattainable affection, Katrina Van Tassel. As the portrait of his coming to know Katrina goes, “He would have passed a pleasant life of it if his path had not been crossed by a being that causes more perplexity to mortal man than ghosts, goblins, and the whole race of witches put together, and that was–a woman.” But maybe if the mortal man wasn’t so controlled by a single appendage nowhere near his brain, it wouldn’t be so difficult to understand the so-called “whimsies” of a woman. To compound the chauvinist sketch of how Ichabod perceives her, Irving writes, “She was a blooming lass of fresh eighteen, plump as a partridge, ripe and melting and rosy-cheeked as one of her father’s peaches, and universally famed, not merely for her beauty, but her vast expectations.” Is she a fuckin’ prized hen up for competition in the state fair or a goddamn human being? Evidently the former since her expectations are constantly ignored based on the prospective suitor offerings of the town alone.

Yet oh, it doesn’t stop there, for no sexist account of a woman is complete without the accusation of sluttery. And lo and behold, Irving then goes on to say, “She was withal a little of a coquette, as might be perceived in her dress.” So she was probably showing a little cleavage with a hem that came above the ankles. Obviously, this meant Ichabod would be done for thanks to “a soft and foolish heart toward the sex; and it is not to be wondered at that so tempting a morsel soon found favor in his eyes, more especially after he had visited her in her paternal mansion.” So tempting a morsel. A woman described as food, how egalitarian.

Worst of all, it quickly becomes transparent that Ichabod’s interest isn’t in the person of Katrina, so much as the wealth she can provide. While surveying the property she lives on, “…his heart yearned after the damsel who was to inherit these domains, and his imagination expanded with the idea how they might be readily turned into cash, and the money invested in immense tracts of wild land, and shingle palaces in the wilderness. ” So no, the chauvinist cochon doesn’t even have the benefit of genuinely loving Katrina for who she is going in his favor.

Further, what would a dated in its sexism story be without a touch of light racism thrown in too? As Ichabod sits in his classroom sulking in the thoughts of his competition with Katrina’s only other viable suitor, Brom Bones, “…a kind of buzzing stillness reigned. It was suddenly interrupted by the appearance of a Negro, mounted on the back of a ragged colt. He came clattering up to the school door with an invitation to Ichabod to attend a merrymaking to be held that evening at Mynheer Van Tassel’s.” Then, at the party, we have the needless delineation, “The musician was an old gray-headed Negro, who had been the itinerant orchestra of the neighborhood for more than half a century. His instrument was as old and battered as himself.”

Elsewhere, the bigoted male voice takes form in specifying the appearance of “buxom lasses, almost as antiquated in dress as their mothers, excepting where a straw hat, a fine ribbon, or perhaps a white frock gave symptoms of city innovation.”

Though Ichabod tries his best to appear regal and worthy at the party that evening, his assumption that staying on behind after the Van Tassels’ guests leave will award him with the final approval of Katrina to be her one and only proves false. When she doesn’t take the bait, the inward sentiment, “Oh, these women! these women! Was Katrina’s encouragement of the poor pedagogue all a mere trick to secure her conquest of his rival!” confirms both Irving and Ichabod’s culminating true feelings about what they view as the less fair sex. These women after all are merely con artists and strategists predicating all decisions on the man who can give them the most attractive child.

Yet perhaps had Ichabod not been such a pussy and come right out and asked Katrina if she was interested in him instead of just bolting from the party like a little bitch boy, he wouldn’t have had to tango with the Headless Horseman himself (rumored by some to be simply Brom Bones dressed in an elaborate costume). Whether Ichabod died at the hands of the legend or ended up in New York City as it was later reported by one townsperson, the bottom line is, his comeuppance was karmically fair based on such an overt level of female discrimination in the face of simultaneously fearing them. One supposes that old maxim is accurate: we hate what we fear.