Before I begin this series, let me first say that these picks are not in any particular order. Second, these picks are opinion based, and I mean no disrespect to any of the choices. Again, I am fascinated with the character Holden Caulfield.
My first choice is John Cheever. Cheever was expelled from his academy in 1928 for the charge of smoking on campus. He spent portions of his life detailing the horrors of prep school life, but later settled just telling stories about preppies. Cheever is a classic example of Holden Caulfield in my humble opinion.