There’s a thing I call the Headmaster’s Trilogy which I give to new heads at Hyde:
- John McPhee’s The Headmaster
- The Rector of Justin by Louis Auchincloss
- The Headmaster’s Papers by Richard Hawley
(The Rector book is out of print and hard to find.)
If I were going to add a 4th, Josiah Bunting’s All Loves Excelling shifts the canon away from the “all boys club” of the above three, focusing on a girl spending a postgraduate year at a boarding school. Powerful.
Interesting, but years ago (and I forget where) there was a symposium at some conference that focused on these three books and asked the question, “Why does boarding school literature have such sad endings?”
No question, aside from McPhee’s book, the other three have gut-wrenching endings. (People still come up to Hawley and curse him out for his ending!) I won’t spoil it for you!…
The Auchincloss book always grabbed me. It’s a novel supposedly based on the life of Endicott Peabody of Groton. In the end, he realizes that the old school grads coming back to honor him at the end of his life are not thanking him for teaching them the virtues on the school shield, but are thanking him (and presumably Groton) for handing them the keys and passport to the good life of privilege. He attempts to remind them that it’s about the virtue… not the good life. They agree out of politeness, but he sees that they missed it and he is now an old man who can no longer reach them. That scene has always haunted (and motivated!) me.