History Main / EvilPrincipal

* ''Anime/RevolutionaryGirlUtena'': Though technically one step above this as the "acting" Chairman of the School Board, BigBad End of the World/[[spoiler:Akio Ohtori]] thoroughly qualifies. In a grotesque twist, he hides this status beneath a [[VillainWithGoodPublicity public persona]] of being its [[PuttingThePalInPrincipal theoretical opposite]], presenting himself as a CoolTeacher and ReasonableAuthorityFigure who's OneOfTheKids and occasionally HotForStudent. (And yes, that latter one carries the SurprisinglyRealisticOutcome [[RapeAsDrama in all the worst ways]].)

* ''Webcomic/NineteenNinteySomething'': Principal Mulroney is one of the few characters who got worse in the comic's reboot, going from an apathetic DeanBitterman to an utter asshole willing to intentionally flunk a student in order for her to be available for him to steal her ideas for school improvement for another year.

* ''VideoGame/{{Kindergarten}}'':

* ''VideoGame/SenranKagura'''s anime and manga adaptations turn [[spoiler:Dogen]] from a mere investor to the Headmaster of [[ThugDojo Hebijo Clandestine Girls' Academy]], which he uses to carry out his criminal operations and try to TakeOverTheWorld. He manipulates troubled girls into joining, instills a TrainingFromHell regimen to beat the kindness out of his students and turn them into his minions, and displays a willingness to kill them if they defy his orders or if he no longer needs them.

* The Principal of ''VideoGame/{{Kindergarten}}'' serves as the BigBad of the game, having taken away Billy for his experiments and giving drugs to anybody who tries to look into it. He also has no qualms [[WouldHurtAChild shooting the kids]].
* At first glance, the Principal in ''VideoGame/Kindergarten2'' appears a lot nicer than the principal from the first game, but the way her daughter acts makes it clear that something is off. [[spoiler:This is ultimately because she made her daughter into a cyborg forced to obey her, and she has three students down below for experiments with plans to take over every school in the world. She will also kill her daughter if she starts to disobey her.]]
* Principal Kobayakawa from ''VideoGame/Persona5'' displays apathy to students' troubles under a [[FauxAffablyEvil mask of politeness]], as he turns a blind eye on Kamoshida's sexual abuses because the teacher's athletic achievements are giving the school some [[SlaveToPR good reputation]]. He's also a low-ranking member of TheConspiracy, and when the order came to investigate the Phantom Thieves, he requests his honor student Makoto to do it for him, pressing and then blackmailing her to uncover a group known for its secrecy, even as she gets in trouble with the {{Yakuza}}. It's worth noting when [[spoiler:he's [[YouHaveFailedMe offed by his superiors for incompetence]], none of the students show any pity]].
* ''VideoGame/SevenMysteries'': In the original version, [[spoiler:The Headmaster flat-out organizes the murder of his students if they get too close to the dark secrets of the school, and blackmails Sang and Thuy into being his muscle]]. In the remake, [[spoiler:he's more of a pawn of the Demon who doesn't want to help out but is forced to]].

** ''Literature/HarryPotterAndTheOrderOfThePhoenix'': Dolores Umbridge [[TyrantTakesTheHelm takes charge]], uses her blood-quill on at least two students, and allows Filch to whip students.

* ''Anime/RevolutionaryGirlUtena'': Though technically one step above this as the "acting" Chairman of the School Board, BigBad Akio Ohtori thoroughly qualifies. In a grotesque twist, he hides this status beneath a [[VillainWithGoodPublicity public persona]] of being its [[PuttingThePalInPrincipal theoretical opposite]], presenting himself as a CoolTeacher ReasonableAuthorityFigure who's OneOfTheKids and occasionally HotForStudent. (And yes, that latter one carries the SurprisinglyRealisticOutcome [[RapeAsDrama in all the worst ways]].)