He frequently told outrageous (and false) stories about his own strength and bravery to his sidekick, the dim-witted Scratchy, and claimed that Tails' second tail was completely useless. One day, two bat warriors, Captain Tooth and Sergeant Claw, overheard Witless's bragging and captured him for their Arena of Doom. Witless was rescued by Tails, who learned to fly for the first time, but when the bats dropped him he fell into a giant puddle of mud. (Tails refused to reveal whether he'd let Witless fall on purpose.) As Tails helped pull Witless out of the mud, the bully apologised and thanked Tails for the rescue.