Chapter 1. Holden Caulfield tells us his story.He refuses to talk about his early life, mentioning only that his brother D. B. is a Hollywood writer. He then begins to tell the story, beginning with his departure from Pencey Prep. Holden's career at Pencey Prep has been marred by his refusal to apply himself, and after failing four of his five subjects, he has been forbidden to return to the school after the fall term. The Saturday before Christmas vacation begins, Holden stands on Thomsen Hill overlooking the football field. Holden has no interest in the game and hadn't planned to watch it at all. He is the manager of the school's fencing team and is supposed to be in New York for a meet, but he lost the team's equipment on the subway, forcing everyone to return early. Holden is full of contempt for the prep school, but he looks for a way to "say goodbye" to it. He fondly remembers throwing a football with friends even after it grew dark outside. Holden walks away from the game to go say goodbye to Mr. Spencer, a former history teacher who is very old and ill with the flu. He sprints to Spencer's house, but since he is a heavy smoker, he has to stop to catch his breath at the main gate. At the door, Spencer's wife greets Holden warmly, and he goes in to see his teacher.

Chapter 2. Holden greets Mr. Spencer and his wife in a manner that suggests he is close to them. He is put off by his teacher's rather decrepit condition but seems otherwise to respect him. In his sickroom, Spencer tries to lecture Holden about his academic failures. He confirms Pencey's headmaster's assertion that "Life is a game" and tells Holden that he must learn to play by the rules. Although Spencer clearly feels affection for Holden, he bluntly reminds the boy that he flunked him and even forces him to listen to the terrible essay he handed in about the ancient Egyptians. Finally, Spencer tries to convince Holden to think about his future. Not wanting to be lectured, Holden interrupts Spencer and leaves, returning to his dorm room before dinner.

Chapter 3. Holden lives in Ossenburger Hall, which is named after a wealthy Pencey graduate who made a fortune in the discount funeral home business. In his room, Holden sits and reads Isak Dinesen's Out of Africa while wearing his new hunting hat. He is interrupted by Ackley, a pimply student who lives next door. According to Holden, Ackley is a supremely irritating classmate who constantly barges into the room, exhibits disgusting personal habits and poor hygiene, and always acts as if he's doing others a favor by spending time with them. Ackley does not seem to have many friends. He prevents Holden from reading by puttering around the room and pestering him with annoying questions. Ackley further aggravates Holden by cutting his fingernails on the floor, despite Holden's repeated requests that he stop. He refuses to take Holden's hints that he ought to leave. When Holden's handsome and popular roommate, Stradlater, enters, Ackley, who hates Stradlater, quickly returns to his own room. Stradlater mentions that he has a date waiting for him but wants to shave.

Chapter 4. Holden goes to the bathroom with Stradlater and talks to him while he shaves. He decides that while Ackley is an obvious slob, Stradlater is a "secret slob." The two joke around, then Stradlater asks Holden to write an English composition for him because his date won't leave him with time to do it on his own. Holden asks about the date and learns that Stradlater is taking out a girl Holden knows, Jane Gallagher. (Stradlater carelessly calls her "Jean.") Holden clearly has strong feelings for Jane and remembers her vividly. He tells Stradlater that when she played checkers, she used to keep all of her kings in the back row because she liked the way they looked there. Stradlater is uninterested. Holden is displeased that Stradlater, one of the few sexually experienced boys at Pencey, is taking Jane on a date. He wants to say hello to her while she waits for Stradlater, but decides he isn't in the mood. Before he leaves for his date, Stradlater borrows Holden's houndstooth jacket. After Stradlater leaves, Holden is tormented by thoughts of Jane and Stradlater. Ackley barges in again and sits in Holden's room, squeezing pimples until dinnertime.

Chapter 5. After a dry and unappetizing steak dinner in the dining hall gets into a snowball fight with some of the other Pencey boys. He and his friend Mal Brossard decide to take a bus into Agerstown to see a movie and Holden convinces Mal to let Ackley go with them. As it turns out, Ackley and Brossard have already seen the film, so the trio simply eats some burgers, plays a little pinball, and heads back to Pencey. After the excursion, Mal goes off to look for a bridge game, and Ackley sits on Holden's bed squeezing pimples and concocting stories about a girl he claims to have had sex with the summer before. Holden finally gets him to leave by beginning to work on the English assignment for Stradlater. Holden writes about a baseball glove that his brother Allie used to copy poems onto in green ink.Several years before, Allie died of leukemia. Though he was two years younger than Holden, Holden says that Allie was the most intelligent member of his family. He also says that Allie was an incredibly nice, innocent child. Holden clearly still feels Allie's loss strongly. He gives a brief description of Allie, mentioning his bright red hair. He also recounts that the night Allie died, he slept in the garage and broke all the windows with his bare hands. After he finishes the composition for Stradlater, he stares out the window and listens to Ackley snore in the next room.

Chapter 6. Home from his date, Stradlater barges into the room. He reads Holden's composition and becomes visibly annoyed, asserting that it has nothing to do with the assignment and that it's no wonder Holden is being expelled. Holden tears the composition up and throws it away angrily. Afterward, he smokes a cigarette in the room just to annoy Stradlater. The tension between the two increases when Holden asks Stradlater about his date with Jane. When Stradlater nonchalantly refuses to tell Holden any of the details, Holden attacks him, but Stradlater pins him to the floor and tries to get him to calm down. Holden relentlessly insults Stradlater, driving him crazy until he punches Holden and causes his nose to bleed. Stradlater then becomes worried that he has hurt Holden and will get into trouble. Holden insults him some more, and Stradlater finally leaves the room. Holden gets up and goes into Ackley's room, his face covered in blood.

Chapter 7. Holden talks for a while with Ackley and then tries to fall asleep in the bed belonging to Ackley's roommate, who is away for the weekend. But he cannot stop imagining Jane fooling around with Stradlater, and he has trouble falling asleep. He wakes Ackley and talks with him some more. Ackley is annoyed by the conversation, and Holden is annoyed by Ackley's "phoniness," so he leaves. Outside, in the dorm's hallway, he decides that he will leave for New York that night instead of waiting until Wednesday. After passing a few days there in secret, he will wait until his parents have digested the news of his expulsion before he returns to their apartment. He packs his bags, puts on his hunting hat, and begins to cry. As he heads into the hallway, he yells "Sleep tight, ya morons!" to the boys on his floor before stepping outside, almost falling, to leave Pencey forever.

Chapter 8. Holden walks the entire way to the train station and catches a late train to New York. At Trenton, an attractive older woman gets on and sits next to him. She turns out to be the mother of his classmate, Ernest Morrow. He dislikes Ernest immensely but tells extravagant lies about him to his mother, claiming that he is the most popular boy on campus and would have been elected class president if he'd let the other boys nominate him. Holden tells her his own name is Rudolph Schmidt, which is actually the school janitor's name. When she asks why he is leaving Pencey early, Holden claims to be returning to New York for a brain tumor operation.

Chapter 9. At Penn Station, Holden wants to call someone but cannot think of anyone to call—his brother, D. B., is in Hollywood; his sister, is young and probably asleep; he doesn't feel like calling Jane Gallagher; or Sally Hayes, who has a mother who hates him. So, Holden takes a cab to the Edmont Hotel. He tries to make conversation with the driver, asking him where the ducks in the Central Park lagoon go in the winter, but the driver is uninterested. In his room at the Edmont, he looks out across the hotel courtyard into the lighted windows on the other side and discovers a variety of bizarre acts taking place. Holden begins to feel aroused, so he calls Faith Cavendish, a promiscuous girl recommended to him by a boy he met at a party and tries to make a date with her. She refuses, claiming she needs her beauty sleep. She offers to meet him the next day, but he doesn't want to wait that long, and he hangs up without arranging to meet her.

Chapter 10. Still feeling restless, changes his shirt and goes downstairs to the Lavender Room, the Edmont's nightclub. Before he leaves his room, he thinks again about calling his little sister. Referring to her as "old Phoebe," he gives a description of her character that is remarkably similar to the description he gave of Allie in Chapter 5. Like Allie, she has red hair and is unusually intelligent for her age. He recalls the time he and Phoebe went to see Hitchcock's The Steps. He notes Phoebe's humor and cleverness and mentions that she writes never-ending fictional stories that feature a character named "Hazle" Weatherfield. According to Holden, Phoebe's one flaw is that she is perhaps too emotional. In the Lavender Room, Holden takes a table and tries to order a cocktail. He explains that due to his height and his gray hair, he is often able to order alcohol, but, in this case, the waiter refuses. He flirts and dances with three women who are visiting from Seattle. They seem amused but uninterested in this obviously young man who tries to appear older and debonair. After tolerating him for a while, they begin to laugh at him; they also depress him by being obsessed with movie stars. When Holden lies to one of them about having just seen Gary Cooper, she tells the other two that she caught a glimpse of Gary Cooper as well. Holden pays for their drinks, then leaves the Lavender Room.

Chapter 11. As he walks out to the lobby, Holden reminisces about Jane. Their families' summer homes in Maine were next door to one another, and he met her after his mother confronted her mother about a Doberman pinscher that frequently relieved itself on the Caulfields' lawn. Holden and Jane became close—Jane was the only person to whom Holden ever showed Allie's baseball glove. One day, Jane's alcoholic stepfather came out to the porch where Holden and Jane were playing checkers and asked Jane for cigarettes; Jane refused to answer him, and, when he left, she began to cry. Holden held her, kissing her face and comforting her. Apart from that incident, their physical relationship was mild, but they used to hold hands constantly. When you held Jane's hand, Holden reminisces, "all you knew was, you were happy. You really were." Holden then feels suddenly upset, and he returns to his room. He is still wide awake, so he heads downstairs and grabs a taxi.

Chapter 12. Holden takes a cab to a Greenwich Village nightclub called Ernie's, a spot he used to frequent with D. B. His cab driver is named Horwitz, and Holden takes a liking to him. But when Holden tries to ask him about the ducks in the Central Park lagoon, Horwitz unexpectedly becomes angry. At Ernie's, Holden listens to Ernie play the piano but is unimpressed. He takes a table, drinks Scotch, and soda, and listens to the conversations around him, which he finds depressing and phony. He encounters an obnoxious girl named Lillian Simmons, whom D. B. used to date, and is forced to leave the nightclub to get away from her.

Chapter 13. Feeling like a coward for leaving Ernie's, walks the forty-one blocks from the nightclub back to the hotel. Along the way, he thinks about his gloves, which were stolen at Pencey. He imagines an elaborate confrontation with the unknown thief, but he acknowledges that he is a coward at heart, afraid of violence and confrontation. When he reaches the Edmont, he takes the elevator up to his room. The elevator operator offers to send him a prostitute for five dollars, and Holden, depressed and flustered, accepts. While waiting in his room, he again thinks about his cowardice, because he feels that his lack of aggression has prevented him from ever sleeping with a woman. Women, Holden believes, want a man who asserts power and control. As he broods, the prostitute, Sunny, arrives. She is a cynical young girl with a high voice. Holden becomes flustered, especially so when she removes her dress. She sits on his lap and tries to seduce him, but he is extremely nervous and tells her he is unable to have sex because he is recovering from an operation on his "clavichord." He finally pays her the five dollars he owes and asks her to leave. She claims that the price is ten, but he refuses to pay her more, and she leaves in a huff.