Brom Bones (Abraham Van Brunt)

Brom Bones's chief rival is Ichabod Crane, the awkward schoolmaster who arrives in Sleepy Hollow and begins courting Katrina Van Tassel. Because openly attacking a schoolteacher would make Brom look like a bully, he wages a psychological campaign instead — clogging chimneys, vandalizing the schoolhouse, and training a dog to disrupt Ichabod's singing lessons — before likely delivering the final blow as the Headless Horseman.

Yes — Brom Bones marries Katrina Van Tassel after Ichabod Crane's disappearance from Sleepy Hollow. Their marriage is the story's closing social resolution, confirming Brom as the victor in the rivalry. Irving hints, however, that Katrina may have deliberately encouraged Ichabod's courtship to provoke Brom's jealousy and force his hand, complicating the idea that Brom's triumph was entirely his own doing.

Irving never explicitly confirms it, but the evidence strongly points to Brom. He rode his black horse Daredevil that night, the pursuer hurled a pumpkin rather than a supernatural projectile, and — most tellingly — Brom is observed to "look exceedingly knowing" every time the pumpkin detail comes up in conversation. Narrator Diedrich Knickerbocker's playful, winking tone frames Brom as the architect of the entire hoax.

Brom refrains from open violence because attacking a slight schoolmaster would be socially disgraceful — he would look like a bully rather than a champion. Irving notes that Brom had "a degree of rough chivalry" that prevented direct assault. Forced out of his comfort zone of physical contests, Brom adapts, turning his energy toward psychological torment and, ultimately, the theatrical spectacle of impersonating the Headless Horseman.

Brom's sly grin whenever the shattered pumpkin is mentioned is Irving's subtlest and most damning character detail. It reveals that beneath the brawling folk hero lies a calculating schemer who converted an entire community's superstitions into a personal weapon. The gesture also shows Brom's self-satisfaction: he won the rivalry, married Katrina, and kept his secret — enjoying private credit for a perfectly executed deception.

Brom courts Katrina as the most eligible heiress in the county, and she eventually becomes his wife — but the dynamic is more layered than straightforward pursuit. Irving suggests Katrina may have coquettishly encouraged Ichabod's attentions specifically to stoke Brom's jealousy and push him toward commitment. If so, Brom's "victory" was partly engineered by Katrina herself, positioning her as a strategic agent rather than a passive prize.

Brom is not framed as a villain — narrator Diedrich Knickerbocker consistently presents him as a roguish folk hero, shaping reader sympathy in his favor. Yet his campaign of harassment drives Ichabod from his livelihood and community, consequences that are genuinely serious despite Irving's comic tone. Brom occupies a morally ambiguous middle ground: a champion of his community whose methods are manipulative and whose "victory" comes at real cost to another person.

Daredevil — described as a "fiery" creature that only Brom can control — functions as a direct extension of Brom's dominance and vitality. Irving places him in sharp contrast to Ichabod's borrowed, broken-down horse Gunpowder, visually encoding the rivalry between the powerful local champion and the hapless outsider before a word of competition is spoken. Brom's mastery of Daredevil underscores his status as the community's undisputed physical hero.