The Headmaster’s Dilemma is set in a New England boarding school with a relatively new, fairly young headmaster brought in to "modernize" the school. I found the book deeply unsettling – on one level because of the nature of the incident between two students that the headmaster must resolve; but more particularly in trying to understand the actions of the headmaster in dealing with the aftermath. The author has set it up so that the headmaster, the Chair of the Board of Trustees, and the father of one of the students involved were themselves classmates at the same academy and in some respects they are still playing out some of their own old issues from that period. The headmaster has to balance the issues of truth (can it even be found in this situation?); the impact that disclosure might have on the students’ futures, the school’s reputation, his own reputation and future prospects; and, not least, justice. It is a dilemma.
This book is all plot. There was nothing, in my view, exceptional about the writing – unless you include the literary references scattered throughout the text. For the informed reader these may bring a smile; for others, perhaps a “Huh?” Here are two examples: can you identify them?
“He would be Sydney Carton and Rosina the guillotine!”
“His favorite motto was Oscar Wilde’s famous advice on how to deal with temptation…”
What do you think of this as a literary device? Is it playing fair with the reader?
I would have preferred a less convenient resolution so that there could have been a more in-depth exploration of the issues and the choices. That said, this book should definitely be required reading for any parent sending a child off to boarding school.