Superintendent Chalmers is talked into educating Bart about Theodore Roosevelt, which turns out successful. Bart invites the bullies to his education, and they all like it; however, when Nelson's arms are fractured in a field trip to find Teddy Roosevelt's spectacles, Chalmers gets fired. The boys then take over the school, with all the kids in it, and agree to release it if Chalmers gets his job back.
The episode starts with Homer, Marge, Bart and Lisa going to the Springfield Elementary School auction. Bart poses as an English widow named Edith Knickertwist on the phone. 'She' bids thousands of dollars for each item meaning the school would have raised $116,000 had it not been a prank. Skinner gets angry with Superintendent Chalmers (mainly over a matter of being lop-shouldered) and says he should try teaching Bart.
Chalmers is nervous about this as he can, but last time he was teaching, teenagers danced on him. Later, Superintendent Chalmers reveals his hero as former President Theodore Roosevelt. Bart learns about Teddy Roosevelt and gets Milhouse, Jimbo, Dolph and Nelson. After Nelson gets hurt in an accident at a field trip, Superintendent Chalmers ends up getting fired. Once again it is up to Bart to help get his job back, by getting all the teachers out of the school and locking the doors and windows to protest. The teachers are happy to leave but realize they are unable to get their paychecks and become angry. Skinner wants Willie to smash the door with a tractor but Bart and the bullies threaten to break the photocopier. Bart instructs the bullies to gather everyone in the gym and Milhouse to take a nap. Meanwhile, the police and FOX News have been called. After talking with Bart, Chief Wiggum slams down his gun hitting the School Boardman. Chalmers is reinstated and has his title increased to super-in-duper-intendent. Afterwards, Milhouse acts like he is heavily drunk after not taking his nap.