Principal Skinner challenges superintendent Gary Chalmers to take over Bart's education after one of Bart's pranks leads to a school fundraiser debacle. Chalmers takes an unconventional approach to teaching American history which sparks a fascination in President Teddy Roosevelt.
Encouraged by Bart's educational renaissance, Chalmers takes Bart and his band of "Rough Riders" on an overnight excursion to Springfield Forest, but after a minor accident, the school administration fires Chalmers for taking the boys on an unauthorized field trip.
Determined to get Chalmers' job back, Bart and the boys hold the school hostage until the administration reinstates Chalmers, and they stand up for the teacher who made a meaningful impact.
