Springfield Elementary School is hosting a fundraiser auction and invites all the families with children in their classes, including the Simpson family. Every item in the auction is sold to an English widow named Edith Knickertwist, who is bidding over the phone. When the auction is over, Bart reveals that he was the real Mrs. Knickertwist and that there is no money for the school. Frustrated over Bart's latest prank and pressured by his supervisor Superintendent Chalmers, Principal Skinner challenges Chalmers to take over Bart's education. Chalmers accepts and immediately gives Bart his own lesson plan, which primarily consists of former U.S. president Theodore Roosevelt. He makes Bart interested in the subject by talking about Roosevelt's heroic and rebellious nature. Classmates Milhouse, Nelson, Jimbo, Kearney and Dolph soon join Bart in his education.
With the success of his lessons, Chalmers plans to take them all on a field trip to Springfield Forest, in which Roosevelt left one of his spectacles. The field trip does not go well, however, as Nelson breaks his arm when he tries to reach for the spectacles. Since it was an unauthorized field trip, Nelson's mother threatens to sue the school for medical expenses, which leads to Chalmers getting fired. In order to save Chalmers' job, Bart and his friends, who now go by the name "The Brotherhood of the Spectacles", take over the school in a hostage situation and stand up for the teacher who made a meaningful impact to them. They lock all of the teachers out of the school and demand that Chalmers get reinstated. A SWAT team prepares to storm the school, before Chalmers walks up to convince Bart to stop. Luckily, Chief Wiggum accidentally drops his gun, knee-capping the school representative State Comptroller Atkins, who thereafter agrees to reinstate Chalmers because they can recover the money lost in the previous lawsuit with a new lawsuit against the police department.