Holden Caulfield is characterized as a young, impulsive, self-declared loner. He does not fit in anywhere, often not even trying to find a place for himself. He keeps failing in traditional roles: he has been sent away to school, probably because he is a difficult son; he flunks out of school after school, because he refuses to do his work or try; and he is liked by no one and has no real friends, male or female, because he is strange and isolates himself. From the beginning of the story, his lack of acceptance makes him feel alienated; in turn, he is angry, dissatisfied, and frustrated. Holden seeks to place the blame for his misery on outside people and things, which he normally judges as phony. He longs for honesty and integrity, but he seems to be the only authentic person he knows. He longs for connection, but no one understands him. He blames the world, with its phoniness and insensitivity, for bringing him down.

Running away from still another school, Pencey Prep, Holden spends time alone in New York City, where he meets with one defeat after another. He is unable to perform with a prostitute, is beaten up by a pimp, is laughed at and rejected by his date Sally. When he goes home to see Phoebe, the one person he has always felt he could count on, she even questions Holden.

Holden's search for meaning becomes a tragedy as he realizes over and over again that he will never find what he is a looking for. He is an idealist clinging to a vision of a society that he will never find. He is a loner looking for human connection that he will never find.

Holden is a tragic hero, not in the classic sense, but because he is a troubled teenager who cannot seem to do anything right in the eyes of a phony society or find a place where he can fit in. His downfall is not from some tragic flaw in his being or some low moral characteristic. In fact, Salinger portrays him as a sensitive youth that adores his little sister and treasures the baseball mitt of his dead brother. Although he is not religious, and even calls himself an atheist, he tries to pray and cares about the downtrodden and the underdog. He donates ten dollars to two nuns when he sees their shabby suitcases and then feels bad that he did not give them more, even though he is practically broke himself. In a desperate act, he tries personally to eradicate all the graffiti in New York City, so the children will not have to see the obscenities. In fact, when Phoebe questions him about what he wants to become in life, Holden says he wants to be "the catcher in the rye," protecting the children from falling off the cliff into a world of misery and phoniness. It is clear to see that Holden's downfall happens because he is unrealistic about himself and the world.

Holden as an Antihero

Holden can really be best defined as a modern day antihero. He is pictured as a weakling, easily beaten up by Stradlater and Maurice, who leave him bleeding and crying on the floor. He is pictured as a coward, who is afraid to go in a club when he sees two tough guys coming out and afraid to call Jane Gallagher because her parents might answer the phone. He is a failure, who flunks out of school and has no friends. Throughout the novel, Salinger shows Holden to be exposed and vulnerable time and time again. It is truly a pathetic picture, a teenager with no self-confidence and no direction who can find no place for himself in the world. Everything about Holden Caulfield is antiheroic.