Holden has been expelled from four schools. At the beginning of The Catcher in the Rye, he is leaving Pencey Preparatory Academy after failing four of his five subjects. He explains that Pencey is his fourth school, making the expulsion part of a repeated pattern rather than an isolated setback.
The earlier schools include Whooton School and Elkton Hills, both of which Holden discusses through memories and complaints. Pencey is the school most fully shown in the novel, and its administrators have already notified Holden's parents that he will not return after the Christmas vacation. Holden travels to New York early so he can avoid facing them immediately.
A frequent source of confusion is the difference between four schools and four failed subjects. Holden fails four subjects at Pencey but has been expelled from four schools in total. Another detail is that he passes English at Pencey, which helps explain why his former English teacher, Mr. Antolini, remains an important figure. His expulsions reflect both academic failure and his alienation from institutions, although the novel leaves some details of the earlier departures vague.