In The Legend Of Sleepy Hollow, Brom Bones (Abraham Brunt) and Ichabod Crane are rivals for the affections of Katrina Van Tassel, the beauteous eighteen year old daughter of a wealthy Dutch farmer, Baltus Van Tassel.

Because Ichabod Crane is such an impressionable and foolish man, Brom Bones decides to use this fact to his advantage. Since Ichabod is too cowardly to physically duel with Brom Bones for Katrina's hand, Bones plays practical jokes on the hapless Crane. He and his roughrider friends smoke out the singing school (where Crane teaches) by stopping up the chimney. They also break into the school at night to ransack the place. Not content with these actions, Brom Bones teaches his 'scoundrel dog' to whine whenever Ichabod is instructing Katrina in her singing lessons.

Besides these practical jokes, Brom decides that he will frighten the arrogant Ichabod with a ghostly disguise. When both are invited to a 'quilting frolic' at the Van Tassel residence, Ichabod gleefully thinks that he is about to succeed in gaining Katrina's hand in marriage.

However, Brom decides to scare Ichabod with his Headless Horseman disguise. This is a clever ploy, coming on the heels of various ghost stories shared with abandon during the party. Ichabod, superstitious and gullibly impressionable as usual, is spooked as he travels home in the dark. He fears the worse when he glimpses what he thinks is a gigantic-sized horseman. What's more, the horseman appears to be headless; instead of his head sitting on his shoulders, it is sitting on the 'pommel of his saddle.'

The Headless Horseman mercilessly chases Ichabod on horseback. At last, when Ichabod thinks he is nearing the church bridge (which he thinks will assure his safety), a glance back reveals not the disappearance of the Horseman in 'a flash of fire and brimstone,' but an unexpected action on the Horseman's part. The Headless Horseman throws his head at Ichabod, which hits the schoolmaster in the head.

The Horseman drives on, and Ichabod is never heard from again. In due time, Brom Bones triumphantly wins Katrina's hand in marriage.

What two things does Brom do to get back at Ichabod for pursuing Katrina?

Brom and Ichabod both want to marry the lovely and wealthy Katrina. Brom realizes they are rivals and itches to fight it out openly with Ichabod, the winner taking Katrina. Ichabod, skinny and weaker than the tall, broad, muscular Brom, naturally evades that kind of battle. As the narrator puts it, this avoidance of battle ("pacific system") is very irritating ("provoking") to Brom:

There was something extremely provoking in this obstinately pacific system; it left Brom no alternative but to draw upon the funds of rustic waggery in his disposition, and to play off boorish practical jokes upon his rival.

Brom, therefore, gets together with his "gang" and they play the following "practical jokes" on Ichabod Crane:

They stop up the chimney and smoke out his singing school.

They break into his school at night and ransack it (turn it "topsy-turvy").

Brom teases ("ridicules") Crane in front of Katrina and teaches his dog to whine when he sees Crane.

Finally, Brom fakes up the "headless horsemen" and terrifies Crane into running away and not coming back.

Brom is popular, robust, and the "hero" of the piece, but he comes across as a bully. We wonder how Katrina will fare with him as a husband.

Brom Bones basically resorted to playing pranks on Ichabod in hopes of making him look foolish so he could win Katrina back.  Brom broke into the school house and messed everything up, he stopped up the school house chimney, and he trained his dog to croon and then introduced it to neighbors as Ichabod.

In "The Legend of Sleepy Hollow," how does Brom Bones retaliate against Ichabod?

Brom Bones plays pranks on Ichabod Crane, but he also resorts to using Ichabod Crane's impressionable and superstitious nature against him.

At the end of the story, we learn that Brom Bones marries Katrina. The text tells us that, whenever Brom Bones hears the story of how Ichabod Crane disappeared, he always laughs about the pumpkin. Here, the author hints that Brom Bones impersonated the Headless Horseman in order to defeat his rival, Ichabod Crane.

According to the townsfolk, Ichabod Crane chanced upon a mysterious horseman while returning home from the Van Tassel's harvest party one night. To Ichabod, the horseman was of "large dimensions, and mounted on a black horse of powerful frame." Because of his superstitious nature, Ichabod became frightened by the fearful apparition. He tried to hoodwink the horseman, but the latter kept up with him.

Eventually, Ichabod noticed that the horseman was headless; the latter held his head at the front (or pommel) of his saddle. Upon seeing this, Ichabod kicked his horse so that the animal kept up a fierce gallop. As for the headless horseman, he seemed fearless and had little trouble keeping up with Ichabod.

Soon, Ichabod spotted the church bridge and imagined that if he could reach it, the headless horseman and his black steed would vanish in a flash of fire and brimstone. However, instead of vanishing, the horseman threw his head at Ichabod, which unseated the poor schoolteacher.

According to the story, Ichabod was never seen or heard from again after his unfortunate adventure with the headless horseman. The townsfolk, however, maintain that a shattered pumpkin was later found next to Ichabod's hat, near the bridge. So, it would appear that Brom Bones had the last laugh: Ichabod was never hit with a human head, but rather a pumpkin. This incident is the last of the pranks Brom Bones played on Ichabod.

In "The Legend of Sleepy Hollow," Brom Bones plays tricks on Ichabod Crane in order to pay Ichabod for trying to steal Katrina.  He stuffs the chimney of the schoolroom so that it redirects the smoke throughout the classroom, and Brom and his friends break into the schoolhouse, turning everything topsy-turvy.  He procures a whining, howling dog as an antidote to Ichabods's singing of the psalms, as well.