The book begins as Jerry Renault is being beaten at a football tryout. He takes a beating on the field, tackled and smashed over and over, but the coach is impressed by Jerry's will and asks him back the next day. Although he becomes ill after practice, throwing up in the school bathroom, Jerry dreams of making the team.
This chapter begins by introducing Obie, who Cormier describes as bored, disgusted, and tired. Obie mentions that most of all, he is sick and tired of Archie Costello. Obie and Archie sit in the bleachers having a fairly hostile conversation in which Obie tells Archie that he should not be receiving communion in church. Obie hates arguing with Archie, primarily due to Archie's inability to be defeated and his brilliance. Archie is the leader of a gang called The Vigils, and is known for ordering classmates to carry out cruel assignments.
In this scene, Archie is attempting to think of the next ten kids he wants to use for assignments, and Obie is taking notes. Archie has to think of two more people. He chooses a classmate known as "The Goober," who is also trying out for the football team. Lastly, he chooses Jerry. Obie protests—Jerry's mom recently died, and he does not think it appropriate to give Jerry an assignment now. Archie thinks of the perfect assignment for Jerry, and tells Obie to assign Jerry to the chocolates.
Jerry thumbs through a pornographic magazine at a store, wondering why he feels so guilty doing it when most of the boys he knows buy and stash the same kinds of magazines. Once Jerry bought one, spending all of his allowance, but when he got home, he was not sure what to do with the magazine. He finally grew tired of worrying that his mother would find it, and threw it away. The magazine had made Jerry wonder if a girl would ever love him.
Jerry makes his way to the bus stop, and from across the street a man calls out to him, accusing him of staring. Jerry and the anonymous man have a brief back and forth, ending with the man calling Jerry a "square boy." This resonates with Jerry, as he thinks of the people who do not do much with their lives. He looks out the bus window and sees an empty advertising board on which someone has written: "Why?" and someone else has responded: "Why not?"
Archie and Brother Leon have a conversation about the upcoming chocolate sale. Brother Leon tells Archie that the school must sell 20,000 boxes. Leon calls the sale "special," and refers to the massive profit the school could make if each boy sold fifty boxes. Archie is not sure why Brother Leon has called him to talk about the chocolates. Brother Leon is an anomaly at the school—a riveting teacher with a cruel twist. He is sarcastic and power-hungry, often making fun of students in class for no particular reason other than that he can.