Holden Caulfield is portrayed as a cynical, jaded teenager who is extremely judgmental and critical of others. As a traumatized, neurotic adolescent, Holden fears growing up and entering the competitive world of adults. He views adults as complete phonies and believes that most people are insincere frauds who pretend to be somebody they are not in order to preserve their reputations.
In chapter two, Holden demonstrates his judgmental personality by criticizing his former headmaster, Mr. Haas, for attempting to make a good impression on the parents when they visit. Holden says,
One of the biggest reasons I left Elkton Hills was because I was surrounded by phonies. That's all. They were coming in the goddam window. For instance, they had this headmaster, Mr. Haas, that was the phoniest bastard I ever met in my life. Ten times worse than old Thurmer. On Sundays, for instance, old Haas went around shaking hands with everybody's parents when they drove up to school. He'd be charming as hell and all.
In addition to viewing authority figures as phonies, Holden's judgmental personality also extends to his peers. Holden is severely critical of his annoying next-door neighbor, Ackley. Holden describes Ackley by saying,
The whole time he roomed next to me, I never even once saw him brush his teeth. They always looked mossy and awful, and he damn near made you sick if you saw him in the dining room with his mouth full of mashed potatoes and peas or something. Besides that, he had a lot of pimples. Not just on his forehead or his chin, like most guys, but all over his whole face. And not only that, he had a terrible personality. He was also sort of a nasty guy.
Holden also reveals that he is judgmental towards people he doesn't even know. When he takes Sally Hayes on a date to the theater, she runs into someone she knows and Holden immediately begins judging him. Holden says,
Then all of a sudden, she saw some jerk she knew on the other side of the lobby. Some guy in one of those very dark gray flannel suits and one of those checkered vests. Strictly Ivy League. Big deal ... Finally, though, the jerk noticed her and came over and said hello. You should've seen the way they said hello. You'd have thought they hadn't seen each other in twenty years. You'd have thought they'd taken baths in the same bathtub or something when they were little kids. Old buddyroos. It was nauseating.
Holden's assessment of Sally's friend depicts his critical, judgmental personality. Holden is also judgmental towards his brother D.B., who is a talented screenwriter in Hollywood. Holden mentions that he used to enjoy D.B.'s stories but accuses him of being a "prostitute" in Hollywood because he sacrificed his art for money. Holden's judgment also extends to the entertainment industry. He is severely critical of actors and critiques Sir Laurence Olivier's performance in Othello by saying,
He has a terrific voice, and he's a helluva handsome guy, and he's very nice to watch when he's walking or dueling or something, but he wasn't at all the way D.B. said Hamlet was. He was too much like a goddam general, instead of a sad, screwed-up type guy.
Overall, Holden has an extremely negative perspective and is severely critical of others. He often judges people based on their appearances and refuses to exercise sympathy or tolerance.