The Headmaster's Dilemma

The Headmaster's Dilemma

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by Louis Auchincloss

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In The Headmaster’s Dilemma, Louis Auchincloss revisits the prep school world of his most famous novel. That book, The Rector of Justin, published in 1964, took the form of a fictional biography, giving the reader the full life story of a much beloved and revered, if also feared, headmaster of an exclusive New England prep school. In The Headmaster’s


In The Headmaster’s Dilemma, Louis Auchincloss revisits the prep school world of his most famous novel. That book, The Rector of Justin, published in 1964, took the form of a fictional biography, giving the reader the full life story of a much beloved and revered, if also feared, headmaster of an exclusive New England prep school. In The Headmaster’s Dilemma, we see up close what happens when a school’s ideals and founding principles collide with the exigencies of change.

The Headmaster’s Dilemma is the story of Michael Sayre, the handsome, avant-garde headmaster of Averhill, the great New England prep school as he is faced with a school administrator’s worst nightmare: a lawsuit brought by fervent parents in response to an incident involving their son and an upperclassman. To make matters worse, Michael is losing support from both the board of trustees—led by the conniving Donald Spencer—and senior faculty members. With the help of his supportive wife, Michael attempts to right these wrongs, while keeping Averhill’s best interests in mind.

Editorial Reviews

Library Journal

This is an effortlessly masterful novel from a legend in American letters who has spent his career chronicling the morally complex lives of New York's wealthy leisure class. Like his 1964 novel, The Rector of Justin, it's set at an elite prep school in the Northeast, and at its heart is an ugly incident involving a sexual assault in a boys' dormitory. This event ignites a dangerous conflict between two old rivals working at the school-the progressive headmaster, Michael Sayre, and the ambitious, vindictive chair of the Trustees, Donald Spencer. Spencer, who has sustained a long and quarrelsome history with Sayre, attempts to use the fallout from this incident to force the headmaster to resign. The characters here are all superbly drawn, from the unscrupulous Spencer to the tragically vulnerable young man who is assaulted. Auchincloss fearlessly examines the adolescent culture of bullying and sexual predation at this prestigious school. He also depicts the moral, political, and legal challenges faced by the valiant headmaster with extraordinary sympathy and insight. Recommended for all libraries. [See Prepub Alert, LJ5/15/07.]
—Patrick Sullivan

Kirkus Reviews
Auchincloss's latest (The Friend of Women, 2007, etc.) concerns a scandal set in an exclusive New England prep school being buffeted by the winds of change in the mid-1970s. Michael Sayre is a young lion of Northeast society, handsome, cultured and witty to a fault, though too sturdy and responsible to be looked down upon as a fop. Seemingly perfect for his new position as headmaster at Averhill-a tradition-steeped factory churning out the future masters of the universe-Michael has hardly finished modernizing the place (co-ed student body, open-minded curriculum, less emphasis on dead languages) when a scandal drops into his lap. An accusation is made of sexual impropriety between two male students, one a bullying upperclassman, the other a fey mother's boy-neither of them well-acquainted with the truth. It's normally the sort of thing to sweep under the rug, but Michael has an enemy on the board in the form of resentful old classmate Donald Spencer, eager to shake his adversary's confidence. Some of the passages rise to heated melodrama, complete with epic declamations and wily drawing-room maneuverings, but the author handles the material with characteristic agility. Genteel combat among the gimlet-eyed gatekeepers of the upper-crust, their hold on society's reins slowly slipping.

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Houghton Mifflin Harcourt
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Michael Sayre thought afterward that it had all started on an early spring afternoon in 1975 when he and Ione and Donald Spencer were sitting in the small rose garden behind the headmaster’s house having coffee after Sunday lunch. They had not eaten in the big school dining room at the main table because Donald Spencer, chairman of the trustees, had only limited time for what he had termed an important visit and had requested a meeting alone with the headmaster and his wife.
The residence that rose above them was a charming old New England manor house, and the great boarding school of which it was the center, to match it, had been tastefully conceived as a colonial village of sober and regular white house fronts grouped about a shimmering oblong lawn studded with elms and dominated at one end by the chapel, a chaste meeting house with a tall spire. As the institution had grown and expanded through the decades, other and larger buildings had been added and playing fields lain out, but these had been sufficiently distanced from the original village atmosphere of plain living and high thinking evoked by the school founder in the 1880s. Averhill, for all its four hundred students and great modern reputation, was still considered by many of its alumni and parents as a stalwart fortress against the creeping vulgarity of the day.
And so Michael liked to think of it. He had been headmaster for three years now, appointed as a result of the successful efforts of younger members of the board to convince the others that a leader was needed to make some adaptations to the exigencies of change in educational thinking. And he had already achieved some of these: girls had just been admitted; the limits of the courses widened. He had come to Averhill with a considerable reputation as a liberal; he had been the admired editor of a popular radical newspaper and a nationally known protester of the war in Vietnam, and although some of the more conservative of the school trustees had gagged at his appointment, the general feeling was that if change had to come it had better come through one of their own. Michael himself was a graduate of the school where he had had a brilliant record, and he was supposed to have a deep concern for the original ideals of the institution. It also didn’t hurt that he was possessed of striking good looks and had a beautiful, charming wife.
Yet what did all this avail to alleviate the disgust that he felt at what Donald Spencer was now proposing? And the worst of it was that not a single item in the chairman’s grandiose scheme was in the least objectionable. It was the case of the whole being greater than the sum of its parts. Much greater.
What Spencer was offering was simply a major addition to the school plant, the cost of which would be provided by his own fortune and those of his wealthy partners and friends. There would be a huge new gymnasium with every conceivable modern appliance, a hockey rink, a nine- hole golf course, a ski run, a swimming pool, new tennis and squash courts, and a small theatre for movies and amateur dramatics. All of these structures would be outside the present campus, but they would double its area and to some extent dwarf the existing buildings.
Spencer saw no objection to this.
“People coming to the school for the first time would not be put off by its note of old-fashioned quaintness. They would recognize at once that they were visiting a thoroughly up-to-date institution with every modern improvement. They would see right away that they were dealing with a school that could rival Andover and Exeter in every sport that can be played!” An acute observer might have deduced from the different appearances of the headmaster and his chairman the difference in their points of view. They were the same age, forty, and had been formmates at Averhill. Michael was tall, well made, and muscularly coordinated, with a serene pale countenance, a high noble brow, wide-apart calmly gazing blue eyes, and thick long auburn hair. Women were apt to call him beautiful. Spencer was short and plump, with an egg-shaped balding head and suspicious yellow-green eyes. The two were generally supposed to have been on friendly terms, even as schoolboys, and their families had enjoyed cordial relations, yet both had always known, without admitting it to each other or to anyone else, that a mutual dislike and mistrust lay fatally between them.
Donald had expressed no opposition when a unanimous vote of the trustees had invited Michael to take up his present position. He had voiced his objections privately to some of the older board members, but when he had seen that the battle was lost he had gone along with their desire to appear wholly agreed to the alumni. It was his habit, anyway, to conceal dissent so long as dissent served no purpose of his own. He haddddd other ways of implementing his designs. As a boy at Averhill he had proved a rare example of the power of shrewdness over muscle. A poor athlete himself and with unprepossessing looks, he had yet known how to burrow his way into the confidence of the form leaders both by flattering their prowess on the playing field and at the same time letting it be slyly known that his gimlet eye had uncovered their vulnerable spots. He was also skilled at uniting a crowd against a selected opponent by the adroit use of prejudice, thus gaining for himself the reputation of a cleansing authority. The boys had respected him and feared his bitter and wounding tongue.
He had done well enough at Averhill and later at Harvard, but there was always an air about him that he was waiting, biding his time. His real success came after he joined the staff of his father’s great Wall Street bank and rapidly achieved a position and a fortune that made the distinguished paternal career seem small in comparison. He took over the mergers and acquisitions department and eventually carved it into a separate company that became famous for its toughness and ruthlessness even in that tough and ruthless field. If the evertriumphant Donald shed a tear over the destruction of fine old businesses or the widespread loss of jobs, he must have shed it very privately.
It was the envy in Donald’s yellow-green eyes, an envy never expressed by his politic lips, that had first alerted Michael, even as a schoolboy, to the awareness that there were aspects of his own personality that might arouse this feeling in others. He had learned that modesty and even humility were the proper companions of self-respect from his father, the eminent and beloved professor of philosophy at Columbia, and had never regarded his own natural gifts as particularly special or given to him for any purpose other than to make the world a tiny bit better. It was hardly his fault that the kind of social success that he so effortlessly attained was precisely the kind that Donald so signally lacked and desperately wanted. Boys, and girls, too, loved Michael. They put up with Donald. One was the innermost of the “ins”; the other would always be on the circumference. Donald’s hostility had waxed with years. The alumni and older faculty members of the school might respect or even revere their famous (or infamous?) chairman for his huge gifts to Averhill, but most of the students (despite their often conservative Republican parents) and virtually all the younger teachers applauded the courageous liberalism of the popular headmaster. Donald knew it was said that he had to buy the approval of his peers; on Michael this approval seemed to rain down from heaven.
“When are you planning to submit this project to the board, Donald?” Michael asked, placing a blueprint on the coffee table before them.
“Just as soon as you okay it. You don’t expect any opposition from that quarter, do you?” “You mean, do I think they’ll look this gift horse in the mouth? Never. They’ll be dazzled.” A pause followed that Donald interrupted in a somewhat sharper tone. “What about you, Mike? You’re with me, are you not?” Michael was silent, but after some moments he nodded slowly, very slowly, several times. Donald looked at Ione, as if she might give him the answer.
“When Michael nods that way, Donald, it doesn’t mean he’s agreeing with you. It means he’s thinking.” “I’m thinking of what this means to the school, Donald. Not just in terms of improved athletic facilities. But in what it may do to the image of Averhill.” “What can it do but improve it?” “Aren’t you a little begging the question? You know, of course, that in these days the choice of a boarding school has largely passed out of the hands of parents. It’s the kids who now make the decisions. Every spring they take off on what they call the school tour, and the poor parents must drive them patiently all over New England to inspect St. Paul’s, or Taft, or Hotchkiss, or Choate, or whatever. The day when a Groton grad registered his son on birth for admission to the school he then had to attend is long past.” “It’s passed for some,” Donald retorted, a sneer in his tone. “It hasn’t passed for me. When my son Sam asked me when we were to take the ‘school tour,’ I said, ‘Right now, if you like.’ At my bidding and to his astonishment we put on our hats and coats and walked up Park Avenue to Eightyeighth Street where I pointed to a building. ‘But, Dad, that’s the Robert Wagner High School!’ he protested. ‘Precisely,’ I told him, ‘and that’s where you’re going if you don’t go to Averhill.’ And hasn’t he done well here?” “Very well indeed. But there aren’t many fathers as forceful as you, Don. Ask any of his formmates who made the decision to come to Averhill.” “Well, what’s that to me so long as they made the right choice?” “Because students don’t always make it. It’s not their fault. How can they have the right criteria at thirteen or fourteen to tell a first-rate school from a second- or even a third-rate one? Naturally, they’re going to be impressed by appearances: big gyms, shiny classrooms, well-mown lawns, everything spic and span. What do they know of the quality of teaching or the preparation for a serious mission in life? Those things don’t show. Of course, they’ll be dazzled by your proposed additions.” “Well, I’ll be damned if I see anything wrong with that!
Who cares why they come so long as they come? And I’ll tell you something else, my friend. The grander the plant, the easier your future fundraising. The rich like to put their money where other rich have put theirs.” “You mean charity tends to go where it is least needed?” “That’s a cynical way of putting it. I’d rather say that charity prefers success to failure. It helps those who help themselves. We’re competing for kids in an area where the kids make the decision. Obviously we have to give them what they want.” “Which means, I take it,” Michael commented in a graver tone, “that we have to offer the rich students all the luxuries they have at home. Which costs more and more, so that tuition must rise to pay for each new embellishment. Won’t we reach a point where we will have to confine our student body to the Forbes list of America’s wealthiest?” “You have your scholarships.” “Yes, but not that many. And there are plenty of parents already who hesitate to send their children to schools where they will rub shoulders with kids whose families have yachts and private jets and who are constantly talking about them.” “Maybe that will whet their ambition to get ahead in a commercial society. Is that such a bad thing? You talk about the Forbes list as if it were a catalogue of America’s most wanted. But those men are the leaders of our society. It should be our privilege to educate their offspring!” “You might have more of a point, my dear Donald, if your tycoons could bequeath their brains as well as their money to their progeny. But that, except in your own admirable case, is not often the situation.” “Oh, I know your passion to fill Averhill with the smartest students. But have you ever stopped to think that they’re just the ones who don’t need Averhill? Getting between a really bright kid and a library or laboratory is like getting between a hippo and the water. They educate themselves! The glory of the private school is something we can’t boast about. It’s what we can do with the dumbbells.” Michael chose not to reply to this. It was a point that had much troubled him. The real danger of men like Donald was not when they were wrong but when they were right. However, the latter’s next remark put him clearly in the wrong.
“And while we’re on that subject, Mike, I might observe that I view with some concern the distinct increase of Jewish and Oriental boys in the school since you took over. It’s all very well to have some, but there comes a point where you’re changing the fundamental character of the institution.” “How many is some?” “Oh, you can’t reduce these things to an exact number. You have to use your discretion, of course.” “And if I have none?” Michael sighed. “We’ve come a long way from Socrates who needed nothing but a courtyard and a few questions. I don’t suppose he worried about the ethnic origin of those he taught.” “Don’t you believe it!” Donald exclaimed with a rude chuckle. “He’d have kicked out a Persian!” Ione now entered the discussion by asking Donald about the possibility of creating an art gallery for the school where they could mount visiting shows or even start a permanent collection of their own. It was a favorite project of hers, and Donald showed a mild interest in it. Anything interested him, Michael reflected sourly, if it contained the opportunity of putting his name on it in capital letters. He let them talk, dropping out of the conversation, and letting his eyes drift over the playing fields to the blue-black line of the awakening forest.
He was wondering, as he so often found himself doing, if he had been right in taking his present job. It was not a throbbing worry; he was too used to it for that. It was a soft, constant, sometimes even oddly relaxing worry. He had no idea of making a break with his commitment. He had undertaken a task, and he would certainly stick to it. But he was quite able now to contemplate the possibility that he might fail. As the voices of his wife and his chairman jangled in his ear, he could almost fancy her as Eve and him as the serpent in the garden.
But the idea was ridiculous. He had to get away from Donald. Impatiently he arose.
“I’ll study these plans tonight, Don, and I’ll call you the first thing on Monday. I just can’t discuss it further today — I’m sorry. Please forgive me, but I’ve got to go for a stroll.” As he strode quickly across the empty playing fields toward the blessedly solitary woods, he tried to be fair in his mind to the chairman of the board. After all, even allowing for his egotism, wasn’t there some element of generosity in the throwing of his millions at the school? That many philanthropists sought personal glory from their bounty did not mean that nobler motives were total strangers to them. And shouldn’t one pity Donald for the obvious fact that his wealth had failed to make him happy? How could it when he had always had it? And wasn’t his wife an alcoholic? Didn’t people say that she regretted having married him for his money? And hadn’t he suffered at school from a cruel nickname derived from the fact that he had been endowed, at least in his early teens, with a smaller than usual penis?
At this last thought Michael pulled himself up to shudder in disgust at the ways of the world. Did history have to be made out of the resentments of physically underprivileged great men? Had millions had to die because Napoleon was stubby and Kaiser Wilhelm had a withered arm and Cardinal Richelieu hemorrhoids? Had hundreds of Americans been thrown out of work and fine old businesses wrecked because of the late development of Donald Spencer’s private parts? With a weary sigh he turned his steps back toward the school.
Who was he, after all, to think he could change the world? What would it gain him to stand between Donald and the rip tide of his millions? Did he think for a minute that the board would back him? Did he not know that they would tear down the chairman’s pants and place their lips devoutly on his fat exposed rear end?
As he approached the headmaster’s house he saw that Donald had left and that Ione was sitting alone at the coffee table idly examining a blueprint. The temperature had dropped and she had put on a striking red sweater that went well with her gold necklace and large gold bracelets. He recalled that she had said that only gold could be worn with sweaters. Her tan hair was also gold-tinted, but the hardness suggested by the shining metal was softened by her beauty. Michael reflected as always that he could get through anything with her behind him.
“You look exhausted, my love,” she said as he came up. “You should really have a drink or a vitamin pill before any meeting with dear Donald.” He slumped into the chair beside her. “Oh, he’ll have his vulgar sports plaza, I’ve faced that. There’s no fighting his big bucks.” “Yes, but you can moderate them. I’ve been going over the plans. They can be cut down. The new buildings can be scattered. The whole thing can be spread out and muted.” “But he’d never stand for it, darling. He’s got his great architect. The whole thing’s a must. It’s what he calls a work of art. You can’t fiddle with works of art.” “The board may not see it that way.” “Ione, you’re dreaming! They’ll gobble it up.” “You have friends on the board. More than you think.” “But not enough for a battle like this.” She suddenly stood up, as if to make a great point. “And you have the ace of trumps up your sleeve! You can threaten to resign!” He too jumped up, but in astonishment. “And if they accept my resignation?” “Then we’ll go! There are plenty of other places that will want you. Do you think, my darling, that I haven’t known how often you’ve been wondering if Averhill is really the right place for you? Or if any New England boarding school is the right place for you?” He gazed at her in admiration. “Darling, what’s got into you?” Copyright © 2007 by Louis Auchincloss. Reprinted by permission of Houghton Mifflin Company.

Meet the Author

Louis Auchincloss was honored in the year 2000 as a “Living Landmark” by the New York Landmarks Conservancy. During his long career he wrote more than sixty books, including the story collection Manhattan Monologues and the novel The Rector of Justin. The former president of the Academy of Arts and Letters, he resided in New York City until his death in January 2010.

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The Headmaster's Dilemma 5 out of 5 based on 0 ratings. 1 reviews.
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