Ichabod Crane is the anti-hero of this story. Brom Bones is the red-blooded hero who bests Crane and wins the girl.
Crane is a symbol of the backward-looking, effete, European-type traditionalist who falls for silly superstitions. He is primarily friends with women. He wants to marry Katrina not out of love for her but out of lust for her wealth.
In contrast, Brom is portrayed as a true American hero, strong, robust, and open-hearted. His friends are male. He loves Katrina for herself, not for the wealth he can gain from marrying her. He doesn't need her money, because he has the skills and ingenuity to make it on his own. He is not particularly interested in the kind of book learning that enthralls Crane, but nevertheless shows he is smarter in practical ways by frightening and outwitting his rival.
It's significant that Brom doesn't beat Crane physically, though he...
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is obviously the stronger of the two. He beats Crane where it seems the schoolteacher would have the advantage: in the arena of brains. Irving, a writer helping to establish the mythos of a brash new nation, shows that common sense and accurately sizing up an opponent matter more than European-style scholarship and traditions.
In "The Legend of Sleepy Hollow" by Washington Irving, Ichabod Crane is certainly an antihero. He does not possess heroic qualities such as bravery, chivalry, strength, and so on. His physical description is almost grotesque. Irving tells us that he is tall, thin, and has a small head with large ears; in fact, he resembles "some scarecrow eloped from a cornfield."
However, aside from his physical description, he is self-serving and will make a few shillings any way he can “by hook and by crook.” He has a "great hunger" for food, but even more, he has a "great hunger" for possessions. When he goes to the Van Tassel's it is not Katrina with whom he falls in love; it is the house and lands. In fact, "when he entered the house, the conquest of his heart was complete." He desires material possessions for his own personal gain; Katrina is simply a bonus.
Even more, he shows no heroic qualities such as bravery or courage. He is easily chased away from Sleepy Hollow and out of Katrina's life by the headless horsemen. Ichabod Crane is certainly no hero.
This is a tough question to answer, as Ichabod Crane could be considered both a hero and an anti-hero. On the one hand, he's something of a lovable underdog: while Washington Irving describes him as an awkward and humorous individual, this description also becomes endearing, as it's clear that Ichabod tries to act the part of the dashing hero but is unaware of how silly and foolish he looks. Additionally, it's suggested that Ichabod is at least a decent teacher and neighbor, as he seems to treat his students well and also help the other inhabitants of the region with simple chores.
On the other hand, it's also suggested that Ichabod is only interested (or at least mostly interested) in Katrina Van Tassel for her family's money. The Van Tassel family is very obviously one of the richest families in the region, and the impoverished Ichabod seems chiefly concerned with marrying Katrina in order to gain the rights to this wealth and all the tasty food that comes along with it (remember, Ichabod is a formidable eater). With this knowledge, it's hard to view him as entirely heroic, no matter how sympathetic he might at first appear. In that case, I'd have to say that Ichabod is more of an anti-hero than a hero, as his subtle sense of greed counteracts the qualities that could make him sympathetic or heroic.