Louis Auchincloss, the novelist, lived to a great age. When he died, in 2010 at 92, he was a New York institution, a link to the vanished world of Edith Wharton novels, and in his last decades he endured the fate of a male Brooke Astor, a zoological curiosity in modern New York, a creature as out of place, in the America of his time, as a prairie bison.

But for all his archaism of manner and antediluvian sureness of taste, Auchincloss in old age was neither a quaint nor a complacent figure, and in his last books he was nakedly candid about the primal sins of the Wasp ascendancy to which he belonged. Like his hero Saint-Simon (the memoirist of the Sun King’s Versailles), he was determined to tell the truth about his class, even if it meant spilling the beans.

When Auchincloss published his classic prep-school novel The Rector of Justin, in 1964, he was in the doghouse as far as many of his old schoolfellows at Groton, the Massachusetts boarding school, were concerned. “I was very much criticized,” he said. In fictionalizing the life of Groton’s founder, Endicott Peabody—high priest of one of Wasp-dom’s more curious cults—he dared to hint that there had been problems at the school.

Familiar with the unforgiving nature of the WASP Cosa Nostra, Auchincloss prudently attempted a smoke screen. Francis Prescott, the headmaster in the novel, is not straight Peabody but a mélange of Peabody and Learned Hand, the judge whom Auchincloss called “the greatest human being that it has ever been my privilege to know.”

To no avail. During the course of the novel, the urbane Hand and the earnest Peabody struggle for Prescott’s soul. Peabody wins. When Prescott laments that his school, Justin Martyr, is little more than a factory of “snobbishness and materialism,” it is the authentic note of Peabody, who in his old age confessed his failures of vision at Groton to Malcolm Strachan, an intense young instructor in the school’s English department.

Strachan, who was Auchincloss’s mentor at Groton, aspired to write a book that would capture the pathos of Peabody, who as a young man founded a school intended to envelop its students in a transformative culture of love and pastoral care, but who lived to be an old man who saw his creation as yet another well-oiled machine to keep kids in line and set them up for Wall Street.

When, in 1960, Strachan died, the book unwritten, Auchincloss resolved to write it himself, or rather what he called “my idea of it.”

Justin Martyr, the fictional Groton in The Rector of Justin, is in its early days a “Garden of Eden,” as its magnetic young headmaster romps with his boys and miraculously heals the “sick soul” of the most wounded child. But there is a snake in the garden. What sort of snake? The reader learns only that during a “hard” period in Francis Prescott’s headmastership, paradisial Justin Martyr became a fallen “disciplinary factory.”

A similar mystery surrounds the actual Groton’s metamorphosis from a school guided, after its founding, in 1884, by what one graduate called the “controlling principle … of love” into a preppy gulag that such WASPs as Averell Harriman (’09), Dean Acheson (’11), and Joseph Alsop (’28) found almost too painful to talk about.

Endicott Peabody intended for Groton to envelop its students in a transformative culture of love and pastoral care. He lived to see his creation as yet another well-oiled machine to keep kids in line and set them up for Wall Street.

In 2003 Auchincloss called me to say he would blurb a book I was bringing out. We fell to gossiping about historically WASP institutions. He was connected to a thousand of them; I to only two, Groton and Davis Polk & Wardwell, the firm in which Auchincloss’s father, Howland, had been a partner, and in which I for a time practiced law.

Turning to Groton, Auchincloss said that Malcolm Strachan told him of a conversation in which Peabody, who was then near death, spoke of one of his earliest students, Warwick Potter.

Warwick Potter came to Groton when it opened, in 1884: a youth of immense charm, a preppy Endymion. Described by the secretary of his Harvard class as the possessor of “a very attractive and winning personality,” he won the heart of one of his Harvard professors, the philosopher George Santayana. When Warwick died, at 22—beautiful young man struck down by jealous god—Santayana expressed his grief in the sonnet sequence “To W. P.”

A trifle effeminate, perhaps, young Warwick—“ladylike,” Santayana implies. His nicknames at Groton were “the Biddy,” a word for a female servant, and “Miss Ryan,” a name the boys would have associated with working-class girls. In an age when well-to-do WASP males could not so much as kiss girls of their own class unless they were betrothed to them, they instead dallied with young women from low-rent districts. At Groton, there was Warwick.

The crisis came when Peabody learned that a sixth former, as seniors were called, was heard to say, “Miss Ryan’s my fag.”

The Many Sides of Fagdom

Had the Groton boys been caught practicing voodoo in the chapel, Peabody could hardly have been more rattled. Pretty-boy Warwick a “fag,” an underclassman slaving for an older boy as at Eton and Harrow? Was it possible?

Though he had been educated in England, Cotty, as his friends called Peabody, had a horror of anything that might promote what he euphemistically described as “sentimentality.” Fagging, in an age of hysteria about same-sex orientation, was especially suspect, for cruel though it was, it had its sentimental side.

In his 1870 novella Venus in Furs, Leopold von Sacher-Masoch showed that compulsion could be sensuous, and anyone who had been at Eton knew that the fancies of fag and fagmaster sometimes turned to thoughts of love. As Auchincloss’s Prescott says, “I did not think a hundred examples of David and Jonathan were worth one of sodomy!”

But there was also the humiliation and predation. Cyril Connolly remembered being told to “report any boy at once who tried to get into our bed” before going up to Eton. Sadism prevailed in a school that has more recently educated our own Windsor princelings, William and Harry. Connolly’s fagmaster at Eton would make him “stand on a mantelpiece and dance while he brandished a red-hot poker between my feet and said: ‘What is your name?’ ‘Connolly.’ ‘No—what is your real name? Go on. Say it.’ ‘Ugly.’”

Yet the relation between fag and fagmaster was not inherently sexual. If it had been, it could not have been a staple of Victorian literature from Tom Brown’s School Days to Raffles: The Amateur Cracksman. But the bullying that occasionally turned into love could also lead to degradation, and in later life English statesmen and guardsmen blanched at the recollection of indignities suffered in Eton’s Long Chamber.

The crisis came when Peabody learned that a sixth former, as seniors were called, was heard to say, “Miss Ryan’s my fag.”

Shortly after Warwick Potter was supposedly made a fag at Groton, a more brutal regime took root in the school: a system of institutional sadism that the artist George Biddle (Groton ’04) saw as intended to forestall the more insidious, closeted sadism (or affection) of fagging.

As at Prescott’s Justin Martyr, friendship between older boys and younger ones was discouraged at Groton. Walks in the woods were suspect—they might tempt boys, Auchincloss wrote, to “wax sentimental about nature and perhaps each other.” Franklin Roosevelt himself, four years ahead of Biddle at Groton, was out of line when, as he and Biddle “walked together back to the schoolhouse,” the “gray-eyed, cool, self-possessed, intelligent” future president gave Biddle “the warmest, most understanding and friendly smile.”

On another occasion when Biddle consorted with an upperclassman, the prefects took action: his “clothes were ripped off” and he was thrown out the window. Other offenders of the school’s code were “pumped.” After evening prayers the victim, trembling, Biddle says, like a condemned heretic before the Grand Inquisitor, was hustled down to the cellar, held under a running spigot, and “forcibly drowned for eight or ten seconds.”

The Writer’s Dilemma

Auchincloss said that he thought seriously of taking up the problem of prep-school predation in The Rector of Justin. The difficulty, he told me, was that he could not have treated the question at all realistically in the early 1960s, the ambiguous period of Philip Larkin’s “Annus Mirabilis,” when the bans on the unexpurgated Lady Chatterley’s Lover had been lifted but the real 60s and its full-frontal candor had not yet begun.

Four decades later it was different. Some months after we spoke, Auchincloss published The Scarlet Letters, in which he re-creates in realistic, not to say full-frontal, detail an incident in which Rodman Jessup, a 14-year-old at St. Jude’s, a fictional Episcopal all-boys school, is grabbed in the shower by fellow students: they “tickled his testicles and tweaked his penis until he ejaculated …”

In his 2007 novel, The Headmaster’s Dilemma, Auchincloss depicts a homosexual rape at Averhill, another fictional prep school, as 15-year-old Elihu Castor is assaulted by “Bossy” Caldwell: “When orgasm came he breathed in a horrible ecstasy” and “obeyed his partner’s hissed instructions …”

It’s not D. H. Lawrence, but for Auchincloss it was personal. In his memoir A Voice from Old New York (published in 2010, after his death), he said that he himself was preyed on at Groton. He was called “Louise,” “Rebecca,” and “Becky” by bully boys, and was “subject to a sexual violation that would have created a major scandal today.”

Waugh and Lampedusa mourn their fallen toffs. Auchincloss surveys his own decaying class with a cooler eye: his WASPs are a rather hard-nosed group, with a keen sense of their own interests and appetites. If you had been assaulted by a gang of WASPs in rutting, you would likely be as unsentimental.

Louis’s trade (in addition to drawing wills in the Wall Street firm of Hawkins Delafield & Wood) was writing up preppies, but his passion was invested in the gorgeous cynicism of the court of Louis XIV—he was averse to easy moralizing. The New England schools that molded the WASP elite were, he saw, sexually morbid, on account of both the predation and the methods employed to discourage it. But even at its worst, in the days of sexual hysteria, the prep school was, he was convinced, a superior instrument for opening the mind than anything inspired by John Dewey’s quackery.

“The older I get,” Auchincloss makes Francis Prescott say in The Rector of Justin, “the more I realize that the only thing a teacher has to go on is that rare spark in a boy’s eye. And when you’ve seen that … you’re an ass if you worry where it comes from.... An equation, a Keats ode, a Gothic Cathedral, a Mozart aria, the explosion of gases in a laboratory” are “related—and divine.”

The schools in which this vision flourished were, Auchincloss concedes, off-puttingly posh and erotically unhealthy. But their techniques of stimulating the brain—poetry and art had a surprisingly large place in Cotty Peabody’s Groton—were as liberating as their traditions of pastoral mentorship. All institutions are corrupt; only a few, Auchincloss says, have the power to transform.

Michael Knox Beran is the author of several books, including The Last Patrician: Bobby Kennedy and the End of American Aristocracy and, most recently, WASPs: The Splendors and Miseries of an American Aristocracy