Krupp go back to the Cretaceous period, followed by Tinkletrousers. Book 10 has Tinkletrousers travel back in time to fix the timeline, making the 9th book not matter. Krupp was fired as principal when Harold and George were kindergartners, and Captain Underpants never existed.
Due to some time shenanigans from Tippy Tinkletrousers (the new name of Professor Poopypants from Book 4), Mr. In Book 8, alternate universe versions of Harold, George, and Captain Underpants (all evil) are brought to the regular universe, and cause massive havoc, and by the end of the book, although the evil versions are sent back, the non-evil versions are all sent to jail for their crimes. Eventually it gets fixed, and he gains his powers back. When they switch back, Melvin has stolen Captain Underpants' powers, but Captain Underpants does heroics without his powers. In Book 6 and 7, Krupp switches bodies with Melvin Sneedly using a device Melvin created. Book 5, Wrath of the Wicked Wedgie Woman, Krupp is revealed to be Jewish. In the third book, Captain Underpants and the Invasion of the Incredibly Naughty Cafeteria Ladies from Outer Space (and the Subsequent Assault of the Equally Evil Lunchroom Zombie Nerds, Captain Underpants gains superpowers from Extra-Strength Super Power Juice, which the boys found on the main antagonist of the book's spaceship. Captain Underpants is also incredibly dumb, which doesn't help out during adventures. Where Krupp is mean and abusive, Captain Underpants is kind and always trying to help people. Captain Underpants is the opposite of Krupp. Krupp becomes Captain Underpants whenever someones snaps their fingers, and turns back when water is dumped or spilled on him. Then they decide to use the ring to convince Krupp that he is Captain Underpants, which turns out badly for them. After getting caught on camera committing their pranks, and forced to basically become Krupp's slaves, George and Harold get a hypno-ring that they use to get out of trouble. George and Harold also create comics, and create their most popular comic, Captain Underpants. Two students that especially get on Krupp's bad side are fourth grade students George Beard and Harold Hutchins, the school's pranksters. Krupp, along with the other teachers, are cruel to the students around them.
Benjamin Krupp is the principal at Jerome Horwitz Elementary School in Piqua Ohio.
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