The morning after the Van Tassel party, Ichabod Crane did not come to breakfast, nor any other meal that day. Townspeople searched for him, but found only his hat floating in the brook and a smashed pumpkin. There was much speculation about what had happened to the missing schoolmaster. The already superstitious citizens of Sleepy Hollow discussed their theories. Most agreed that Ichabod met his end at the hands of the headless horseman. An old farmer heard that Ichabod was still alive, living in another part of the country. No one seemed to know for sure what had truly happened to Ichabod. Brom Bones, who was quick to marry Katrina Van Tassel, seemed to have a knowing look on his face whenever anyone told the tale of Ichabod Crane and the headless horseman. When the part about the smashed pumpkin was mentioned, Brom would burst into laughter. This caused some in the village to suspect that Brom knew more than he let on.
Brom Bones appeared to feel triumphant when Ichabod disappeared. He married the lady that Ichabod was sweet on. If Brom was indeed the "headless horseman" who went after Ichabod, he might also have felt triumphant that he chased his rival away. If this was the case, he was able to achieve victory by chasing away the skittish Ichabod and marrying the woman he admired.