1. Introduction This paper deals with the character development of Holden Caulfield in J.D. Salinger’s The Catcher in the Rye. As the novel is about a teenager experiencing freedom and liberty for the first time, it is a story of initiation. The anti-hero of this novel describes his three-day-long trip to New York, as well as his escape from his school and his memories about his childhood. Because of his grades, Holden is forced to leave his school. He decides to leave earlier as supposed, to flee from the rules of the school’s conventions and therefore from the phoniness of his environment, which seem to be unbearable to him. After several harsh confrontations with the city’s inhabitants, and above all his inability to communicate with them, he later has a nervous breakdown. As a result of his brutal experiences, the initiate refuses to accept adulthood, which in his eyes means to be integrated in a society of insincerity and sex. This is why he sticks uncompromisingly to his idealistic values. Just the love of his little sister Phoebe makes him return back home, adopt a mature world view and forget his loneliness. At first view the novel seems to be simply structured and that even the order of the chapters could be changed. This paper tries to change the reader’s first view. It shall mention and analyze the most important metaphors which structure the book and describe Holden’s actual situation. To help the reader understand Holden’s actions and feelings, his dualistic world view, as well as his characteristics and the reasons for his escape will be described. Because his vision of the catcher in the rye and his sister Phoebe play an important role in the story these points play also an important role in the analysis. In the last chapter Holden’s final development will be studied with the aim to find out whether his initiation was successful or not.