Headless Horseman

The Headless Horseman is one of Chernabog's elite warriors in the Cabal of Darkness, and is an undead warrior with no head.

Role in Reconnect
Brom Bones tells Ichabod Crane the story of the Headless Horseman, who lost his head long ago during the Revolutionary War. Every Halloween night he rides in Sleepy Hollow looking for a new head. The best way to escape him is to cross the bridge, as the Horseman's dark powers are limited only to the woods. That very night Ichabod rides home alone and keeps imagining that he is being followed. When he finds that it's only cattails bumping on a log, Ichabod and his horse hysterically laugh but suddenly stop as another laugh joins them. They both slowly turn around to find the Headless Horseman about to attack them. He gives chase, laughing all the while. When Ichabod momentarily is trapped on the Horseman's own black steed, he looks down the Horseman's neck to find nothing but evil hollow laughter. Ichabod runs for the bridge and barely manages to make it across. As Ichabod turns around, he screams as the the black horse rears up and the Headless Horseman throws his head (a jack'o'lantern set on fire) right at him. But just as the pumpkin is about to hit Ichabod, Sora manages to use his keyblade to deflect the weapon right back at the Horseman, causing a huge explosion when it hits the evil ghost, which also knocks out Sora and his friends in the process. The very next morning, Sora wakes up to find Ichabod's hat next to a shattered pumpkin, but Ichabod had vanished. Sora hopes the best for the schoolmaster, hoping that somewhere he may still be alive and well reformed of his greedy ways. Thankfully, in the credits sequence, Ichabod is seen still alive and married to a wealthy widow in a distant county.

Later on during the battle of Annuvin, the Horned King summons the Headless Horseman to battle Riku and Leon with a Cauldron Born clone of Shere Khan as its new steed. The Horseman, while stronger than before due to it wearing the chest armor of Xehanort's keyblade armor, meets his end when Gurgi jumps into the Cauldron to negate its evil power, causing the ghostly hessian and the cauldron born to disappear into darkness.