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- Welcome to Bullworth
- This Is Your School
- The Setup
- Save Algie
- A Little Help
- Defend Bucky
- That Bitch
- The Candidate
- The Big Prank
- Help Gary
- Russell in the Hole
The chapter starts with Jimmy being dropped off by his mom and new stepdad outside the gates of Bullworth Academy. He is greeted by Miss Danvers and is told to go to the main office and speak to Dr. Crabblesnitch. On the way, Jimmy is confronted by three of the Bullies, Trent, Ethan and Davis. He meets Dr. Crabblesnitch, is again harassed by the Bullies on his way to the Boys' Dorm. Outside the dorm, he's ambushed by the Bullies. After beating Wade Martin in a fight, Jimmy gloats, when Russell Northrop barges out of the dorm and attacks him. Jimmy is saved by Mr. Hattrick, but Hattrick says nothing to Russell, instead getting on Jimmy's case for not being in the school uniform.
Gary then takes Jimmy on a tour of the school. Jimmy is convinced by Gary to retrieve some chocolates for Eunice, and he ends up kissing her. Gary then shows him the four cliques, the Nerds, Preppies, Greasers, and Jocks.
Jimmy's first months in Bullworth consist mainly of fighting off the Bullies and making friends with the Nerds. He acts as a bodyguard for Algie. He's attacked by Davis with a slingshot after Davis sees him talking with Dr. Crabblesnitch and accuses him of being a teacher's pet and a narc. He saves the nerd Bucky from the Bullies, helps Beatrice retrieve some stolen lab notes from the jock girl Mandy, and is hired by the Nerd leader Earnest to protect him during the speeches in the class presidential elections. Through this he develops a tenuous friendship with Gary and Petey. Gary continually talks about how he's always thinking and how he intends to take over the school.
Shortly after Halloween, Gary convinces Jimmy to accompany him into the school basement. They end up at The Hole, a concrete fighting pit in the sewers below school. Here, Gary turns on Jimmy and tricks him into a fight with the Bully leader Russell. Jimmy beats Russell, thereby pacifying the Bullies, but Gary gets away.