The First Fifty Years:
A Review of Headmaster’s Thoughts at York Prep
Ronald P. “Ronnie” Stewart, the headmaster of York Preparatory Academy, cheerfully proclaims himself a “curmudgeon” and a “cranky old man” near the outset of Headmaster’s Thoughts, his curated collection of columns previously published in his school’s website over the past fifteen years. Fortunately, he happens to prove himself a rather witty and insightful old-timer with a wide range of interests. While his references may occasionally befuddle the younger reader—not many folks under sixty-five will recall Congressman Wilbur Mills or his scrap with stripper Fanne Fox—Stewart displays a distinctive gift for using humor and gentle irony in nudging the reader toward embracing his view of the world.
Stewart is certainly a man with a set of core principles. In one of his essays, he argues that the keys to success in life are being one’s own best friend and having a passion for something outside oneself. For Stewart, that passion is clearly education. One senses the values of the storied headmasters of yesteryear in his spirit; he does no fundraising and teaches several classes personally, including one on ethics to graduating seniors, to keep himself in the fray. Maybe it helps to ground Stewart that he is English-born and Oxford-educated, but while he now enjoys fox hunting, he was once a “milk man’s boy” in a poor family and grew up in the gray decade of post-war London. He returns to his childhood repeatedly—to explain his lack of appreciation for fine foods, his belief in the importance of best friends, the lessons he learned from being evacuated during the Blitz—and yet the book is surprisingly forward-looking, a testament to the future and not the past.
The two seminal events in Stewart’s early life were his role as a barrister in defending Charlie Kray (the eldest of the Kray brothers, notorious British mobsters) and his marriage to Jayme, a fellow summer camp counselor in Maine. The former experience made him question the ethics of advocating for clients he knew to be guilty of horrific crimes and to eventually leave the practice of law; his marriage to Jayme, a teacher, led them to found York Prep in 1969. She still serves as Director of College Guidance. Several of Stewart’s essays focus on their team dynamic—and he goes so far as to say that he doubts either of them could have run a school without the other. “About life,” writes Stewart, “I used to say that I was passionately moderate and moderately passionate”; he rightly points on that this is an oxymoron.
As is unsurprising in an essay collection that originated as a series of internet postings for his school community, Headmaster’s Thoughts contains numerous gems of wisdom on schooling and the parent-child relationship. He writes, for instance, “My first observation is that most parents overestimate their ability to affect who their child is, and, by extension, the way their child learns.” And for a man who references Phaedrus and the British Test Act of 1871, he is nonetheless able to see that character is of far greater value than book learning. In one of his most perspicacious observations, he notes that “[t]o be particularly bright is as much a learning difference as to have dyslexia, and it can be a lonely learning difference.” (As an ethics teacher, he also grapples with a handful of interesting moral quandaries—such as a student who asks whether he should inform his father that the father’s new girlfriend has attempted to seduce him.)
Lest one conclude that Headmaster’s Thoughts is a heavy read, the essays are a blend of humor and commonsense in the spirit of S. J. Perelman or James Thurber. In writing a clever piece about back surgery, Stewart observes: “I finally turned to a famous back surgeon (they are all famous) … .” What follows could as easily pass for a Jean Carroll stand-up routine. Yes, Stewart is funny, a crafty trick for having us swallow his medicine.
At several moments in Headmaster’s Thoughts, Stewart muses on questions of retirement, and once, when a parent asks him what will happen to the school if he dies, reflects specifically on his own mortality. He makes it clear that he has no intention of embracing either any time soon. That gives readers hope that there will be a Headmaster’s Thoughts II; let us just hope we do not have to wait another five decades. #