The DEI self-destruct sequence that’s been triggered at formerly elite prep schools (like Andover and Chicago’s Latin and Francis Parker) may provide a hint
It’s a mystery that is more vexing than who dispatched Tupac or Biggie. More baffling than who put the rocks at Stonehenge. And even more stupefying than the rumor that Kamala Harris left an ice-cold carafe of Sancerre untouched last Monday at 11:00 am before a rally with Meagan Thee Stallion (again, that’s just speculation).
The enigma I can’t seem to solve is: Who killed the preppy?
Some may identify correlated — but I promise you, not causal — linkages between the demise of J. Crew, Obama building a compound on Martha’s Vineyard, and the debut of “twerk” and “ableist” in the Oxford English Dictionary in 2015 and 2021, respectively (or OED for you incorrigible Yalies).
Trust me, these are just TikTok theorists. When I started investigating the beginning of the end for the one group responsible for keeping the ethos of the American dream alive (and turning yours truly who was born on the wrong side of the tracks into at least a marginal success), I genuinely believed that dissecting the death of the preppy would require AP-level math to pinpoint the combination of factors and conditions that offed the modern-day Holden Caulfield, seemingly almost overnight.
But in a moment, it all came to me, like a strong G&T hitting hard after de-rigging a Herreshoff 12½ following a later afternoon sail around the harbor.
After all, it was like yesterday when three-row station wagons (diesel, preferred), the kind with a rear-facing third seat that would go for 500,000 miles, paraded the streets of places like Kenilworth, Westport, and Bryn Mawr. These were the weathered chariots in which mummy transported her threadbare offspring — whether Protestant, Jewish, or Catholic, preppies came out of the womb that way, back in the day — on their way back from squash lessons, or, when summering, from the yacht club, where the next generation learned proper sailing on a monohull (because "real sailors" laugh in the face of stability and speed).
Yet almost overnight, these well-mannered birthing parents traded in their understated ways for brat, bling, and BLM, swapping core Judeo-Christian and Renaissance ideals for the church of crass materialism, two-spirit kink, and faux outrage (wait, that sounds like the checklist required to get baptized in the Episcopalian church these days!)
Caymans and Kendi
That dented Volvo or old Mercedes diesel that mummy drove? Replaced by Porsche Caymans (or for preppy moms on a budget, a lesser BMW X3 or, horror of horrors, an Escalade). Tennis or squash matches? Try again. In a world of vibes and massaged seats, who wants to chase a ball around a court when you can play in miniature with paddle tennis or, even worse, pickleball? And don’t get me started on the changing of the sailing guard with the rise of the devil’s boat: catamarans.
It was at this very moment that the preppy downtrend began to take shape. Sure, the trading out of class and manners for ostentatious displays of wealth and fake racquet sports among the DEI class may have started preppy immolation. But it was the swapping of a millennium of traditional philosophy for the overnight embrace of woke (i.e., critical theory) that ultimately struck the prep death blow.
Indeed, we can trace the permanent burial of the preppy to moms (and their increasingly chunky and often blue-haired daughters) who all at once fell hook, line, and Kendi for every social justice fad that presented an opportunity to virtue signal, perhaps, in part, to make amends for their newfound love of ostentatious displays of wealth.
But what about the preppy dad and sons, you ask? Many stood by as bystanders.
And I think I know why.
To wit, I propose that the failure of preppy men to stand up and defend their honor was a plot line straight out of Greek literature, or Lysistrata, to be specific. Flash forward over 2,000 years to the beginning of the fall of another empire, and Aristophanes’ play featuring women denying sex to force men to stop fighting a war has become the rallying cry of woke ladies who lunch.
You know, moms who can’t stop apologizing for the Birkin-bag privilege their husband’s 80-hour work week affords (not that prep schools that their children attend even teach Greek anymore, having quietly swapped out the budget for bow-tied classical studies teachers for DEI administrative half-wits).
Close your eyes, and you can almost hear the cries from Winnetka to Bethesda: “I’ll give you some action tonight, but only if you become an anti-racist, commit to overthrowing capitalism, fire a Jew, and hire a plus-size DEI executive at your firm to run HR, dear (but you can’t run a plagiarism checker on them/their’s PhD in Afro-nationalistic Palestinian gender critical theory as "it’ might not pass the test.”)
Indeed, seemingly — but not surprisingly — at the same time as “equity” was swapped for law and order in places like Chicago, New York, and San Francisco, preppy moms threatened inverse Borat (no hitting that!) unless hubby came along for the DEI ride.
But did the preppy die just because of cucked men?
Not quite. It’s not that simple, you see. My theory is that even though the final blow (or lack thereof) happened just as fast as George Soros was able to buy up dozens of district attorneys in a single election cycle to rain down hellfire on major cities — so he could then buy up commercial real estate cheap after the body counts piled up — the end was a long time coming.
To channel Hemingway: “How did you go bankrupt? Gradually, then suddenly.”
Who is this preppy?
My dear readers, if you are more familiar with Family Guy than Ferris Bueller, I’m guessing you’re probably completely lost at this point in the essay. And you’re probably asking: what is this preppy species? It sounds like some alien fossil or something (or, as prep schools might teach these days, an “undocumented” fossil).
But no, my friends, the preppy was real. He was, as the late Christopher Hitchens might have described him (thanks ChatGPT), a “custodian of a fading aristocracy, maintaining their heritage through rituals of exclusivity and an inherited disdain for the unwashed masses."
I only partially share the LLM Hitchens’ perspective. I think the preppy was representative of something good. No, something extraordinary. Back when it was fashionable to conform to the elements that would enable the American dream for so many — before it was replaced by the aggrievement games — such as being understated and keeping your head down (while working hard), the prep ethos provided an on-ramp, heck even a rulebook, to getting ahead — for everyone.
In fact, in 1990, Lisa Birnbach published a book that would top the best-seller list for over 30 weeks: The Official Preppy Handbook. While written entirely as a lampooning satire of prep culture, it ended up, ironically, becoming a sort of unofficial guide to being a preppy: How to dress, how to act, where to summer, what to say (and what to keep to yourself, including your feelings), and, of course, how to make things look effortless, especially that gentleman’s “B” in Calculus.
At times of seriousness (much of the book is pure cheek), Birnbach really did capture the preppy ethos. To wit: “Being preppy is not about being flashy or ostentatious. It’s about embracing a lifestyle that values subtlety, quality, and tradition … Preppies have an unspoken code that governs their behavior and lifestyle. This code includes a deep respect for heritage and tradition, a focus on education and intellectual pursuits, and an appreciation for the finer things in life that are never to be flaunted. They know that true style is about grace and ease, not about being trendy or conspicuous.”
As Birnbach observes, preppy values were instilled not just through birthright but grooming in schools (back when grooming centered on manners and mannerisms, not hormone therapy and chest binders). This was an era when the most significant rebellion was sneaking a bottle of whiskey (or coed) into your room (or dorm), not hashtagging your way through a BLM protest, or screaming “From the River to the Sea” in Harvard Yard.
No, the prep ethos was the polar opposite. And it offered a manual for upward mobility for everyone (I’m a case in point), stressing humility and hard work, concepts now lost in the cacophony of performative DEI activism and anti-capitalist rhetoric funded by Daddy's Amex black card — all the while as prep school culture has come to prize outrage over accomplishment, immolating everything prep education once stood for.
From the classics to cultural appropriation
Schools like the once preppy epicenter, Phillips Andover, which used to focus on merit and rigorous debate (before the "Interdisciplinary Studies Department" decided to "embed race, class, gender, and sexual orientation into the curriculum"), now have students mastering the art of self-censorship according to a recent study. Conservatives are doing it at a rate of 94.7 percent, while 70.8 percent of libertarians are keeping their mouths shut.
But at Andover, according to the same report. only about a third of liberals and socialists feel the need to zip it. I guess when 91.1 percent of students support BLM and over 80 percent back affirmative action (data from the same survey), the safest debate on campus these days is whether it is best to shout down your opponent for their whiteness or simply label them a Zionist colonizer (perhaps not so ironically, the town of North Andover approved a permit to fly a Palestinian flag in its square after October 7th).
Meanwhile, The Latin School of Chicago — now operated by a unionized faculty because what prep school doesn’t need the DMV experience to complement equitable brainwashing — has taken cues from Andover and other indeed former "elite" institutions. The school is less interested in producing the next Teddy Roosevelt or Elon Musk and more focused on molding tomorrow's Hamas sympathizers, gender studies professors and climate jihadists. Debate? Forget it. Free speech is so passé — unless you're shouting about how capitalism is the root of all evil while secretly texting your hedge fund dad (or governor) for another Venmo payment.
The kicker? If a white student dares to say they’re not attracted to black girls — because, gasp, personal preferences — it’s now grounds for expulsion at places like Latin (yes, this happened). All the while, over at Francis Parker School a few blocks north in Lincoln Park, they’ve moved beyond your average sex-ed class.
After all, who needs the basics when you can pass around butt plugs and taste different flavors of lube during in-school activities (yes, this also happened — it also happened at the Shipley School, in Bryn Mawr, Pennsylvania). And rumor is they even gave the gentleman behind the taste test a slight pay bump the following year, despite having to hire a crisis PR firm after the “butt plug Dean” was caught on video bragging about the kink. You’ve gotta love a world where the people teaching your kids about orifice accessories make six figures while sneering at the concept of sex for, well, reproduction.
The tragic comedy of it all? These once-great institutions, where prep culture and values were reinforced for generations as students learned the value of citizenship, hard work, and the power of the individual to change the world, have devolved into $50-$75K-a-year woke daycares hellbent on tearing down everything they used to stand for.
Prep schools like Latin now train the next generation to despise everything remotely good, useful, or productive about the world, teaching kids to march in lockstep to everything the New York Times tells them they should believe.
And the irony: Many parents continue to pay out the nose for this nonsense despite the fact these schools are no longer elite, and their college records (for non-minorities, athletes, and legacies) have become worse than many public and parochial schools. But shhh, don’t tell anyone that!
So why does this all matter unless we’re just writing an inscription on the prep tombstone?
Because I believe we can link the keying in of the self-destruct code at places like Andover and Latin with the election of equity-spouting, bumbling, elected half-wits like Kim Foxx and Brandon Johnson (after all, someone not only voted for these jokers but funded their campaigns).
Not to mention Alvin Bragg, the mastermind behind the absurd legal theories in Manhattan that led to the politically motivated prosecution of Donald Trump (perhaps it's no surprise that Bragg is a proud graduate of The Trinity School in NYC). Clearly, nothing says “I’m fit to lead,” like a diploma from a prep school that’s traded Aristotle for DEI outrage.
But how? And, more important, why?
As we’ll discover, the death of the preppy is anything but a cold case — and not the kind involving Rolling Rock or Yuengling, which I will admit to secretly enjoying before Penn football games back in the day when the women’s swim team was, actually, the women’s swim team.
So sit back, pour yourself two fingers of your favorite poison (we’ll pretend it’s a Speyside single malt, not oat milk), and join me as we unravel the mystery of who killed the preppy. Spoiler alert: It just might be the same forces attempting to sabotage the very soul of this great nation.
And most important, if we can pinpoint the root cause and extirpate the mental malware behind it, maybe, just maybe, perhaps we can get things back on track just in time to mix this evening’s cocktails.
Merit shaken, not intersectionality served for me, please.
J.D. Busch, who works in tech and finance during the day, writes about the decline of elite society at night, and is nearly finished with his first book, “Who Killed the Preppy,” from which part of this essay is excerpted.
