Salinger's The Catcher in the Rye takes place largely in a boarding school by the name of Pencey Prep and New York City where the main character, Holden, subconsciously searches for a "wise old man figure" to help him through his troubles. Holden is a young man of age seventeen. He has been placed in multiple boarding schools after the death of his younger brother, Allie. Holden is experiencing slight trauma after being dismissed from the latest school, Pencey Prep. Three men stand out as possibilities to play this invaluable part of "wise old man" in Holden's confused life, Holden's father, Mr. Caulfield, Holden's history teacher at Pencey Prep, Mr. Spencer, and finally, Holden's beloved English teacher from Elkton Hills, Mr. Antolini. Each of them try to play this part yet fall short and end up scarring Holden because of their own emotional trauma, lack of quality advice and a slight mishap because of a drink too many, respectively. Salinger vividly illustrates how Holden is pushed into deeper emotional trauma because of his father's, Spencer's and Antolini's failure to become positive mentors in Holden's life.
Holden's father, Caulfield, was not a substantial part of Holden's life during his son's search for meaning, let alone a positive influence. After the death of Allie, Caulfield seems to push Holden almost out of his life and sends him away to a series of preparatory boarding schools. Holden is sent to Elkton Hills, Whooton Prep and now Pencey Prep soon after the death of his brother Allie to leukemia. This action taken by Caulfield shows how he lacks the strength to handle the responsibility and pressures of raising a son after the loss of the other. Another example of Caulfield's inability to cope with the loss of a son is how he drinks and smokes often to relieve stress and frequently leaves the bottles and cigarette butts lying about the house. This habit of Caulfield's seemingly induced Holden to start drinking and smoking himself and erroneously taught Holden that this habit was appropriate.