Holden Caulfield is portrayed as an exceptionally intelligent, observant, sensitive, and articulate but still immature, naïve adolescent. His description of Mr. Antolini shows both his perceptivity and naiveté. In Chapter 22 he writes:
I wanted to phone up this guy that was my English teacher at Elkton Hills, Mr. Antolini. He lived in New York now. He quit Elkton Hills. He took this job teaching English at N.Y.U.
Holden doesn’t realize the implications of what he has written. Later, the reader will guess that Antolini probably didn’t “quit” Elkton Hills but was asked to leave because he was showing the same interest in boys he subsequently shows in Holden at his apartment. Holden says, “He lived in New York now.” This implies that he was a resident teacher. A boys boarding school would be an attractive place for a man like Antolini to live.
The job he “took teaching English at N.Y.U.” was most likely part-time and untenured. But having married a wealthy woman, he might only want N.Y.U. as a sort of aegis or facade, just as his relationship with an older woman was evidently a mariage de convenance as well as a meal ticket. Being married disguised the fact that he was gay, and his elderly wife bought a pleasant companion, escort, and conversationalist, if not a red-hot lover.
When Antolini answers the door:
He had on his bathrobe and slippers, and he had a highball in one hand. He was a pretty sophisticated guy, and he was a pretty heavy drinker.
Antolini continues drinking heavily throughout their conversation and right up until the time he makes up the couch for Holden to sleep on. Holden misses most of the implications in Antolini’s questions and remarks, which become more and more suggestive. With his heavy drinking, Antolini seems to be working up the courage to take advantage of the opportunity presented by the arrival of his young guest. Here are a few of Antolini’s questions which should have given Holden a warning:
“How’re all your women?”
“They’re okay.” I was being a lousy conversationalist, but I didn’t feel like it.
“How’s Sally?” He knew old Sally Hayes. I introduced him once.
“She’s all right. I had a date with her this afternoon.” Boy, it seemed like twenty years ago! “We don’t have too much in common any more.”
“Helluva pretty girl. What about that other girl? The one you told me about, in Maine?”
“Oh—Jane Gallagher. She’s all right. I’m probably gonna give her a buzz tomorrow.”
Antolini evidently gives up trying to get Holden to talk about his sex life. He says:
“All right. Good night, handsome.”
By now Antolini must be very drunk. Holden should have taken that compliment as a warning—but he sees and doesn’t see. He is a good example of a faux naïf narrator. He mentions that:
I didn’t have any pajamas either and Mr. Antolini forgot to lend me some. So I just went back in the living room and turned off this little lamp next to the couch, and then I got in bed with just my shorts on.
Mr. Antolini didn’t forget. He was thinking about seducing Holden all the time they were discussing academics and “life” and philosophy. Antolini wanted Holden to be virtually naked. The entire novel is about how a sheltered young man from an upper-class home learns many lessons about the real world, and this experience with Antolini will be the most significant. The man Holden respects and trusts turns out to be a secret, sinister menace.