Why the Culture of the So-Called Great Books is Hostile to Trans People

For a long time, I didn’t enjoy literary Twitter because so much of the content was about mediocre (and ephemeral) contemporary writers, but I figured I just wasn’t following the right people. So I pared down my list and sought out publications, newsletters, and individuals who are interested in classic literature: the so-called Great Books that’ve defined our history and culture and thought (I’m writing a book for Princeton Press about the Great Books movement).

The result of this search has been fantastic. I now routinely wake up to articles about Mary Wollstonecraft or George Orwell or some new translation of a 19th-century Vietnamese epic. It’s everything I could’ve wanted.

Except for, you know, the transphobia.

Because the same people and the same outlets that cook up great meals about old literature tend, with terrible regularity, to include a sprinkling of transphobia in their recipes. For instance, recent newsletters I’ve received have included one writer musing on her suspicion of nonbinary people and another writer applauding the NYT for holding firm against fanatical activists who don’t want anyone to hear anything negative about transgenderism, no matter how true it might be.

I anonymized the quotes because I don’t think these views mean someone should get canceled or fired. In some cases, there’s even a nugget of a debatable point. But the view is always delivered with smug certainty that the reader of the newsletter or publication almost certainly agrees that the transgender fanatics have gone way too far these days. Which is to say, the community of people who love the Great Books is rife with suspicion of trans people, and seems much more preoccupied with trans issues than the general public.

This is also apparent at the level of the publication: the forums for writing about the Great Books tend often to be forums for transphobic writing.

For example, take Compact, where Nick Land recently wrote a defense of the canon (comparing it to Biblical scripture), but which also publishes almost weekly dismissive articles about “The Gender Ideology.” The National Review runs a Great Books podcast. Commentary, another conservative journal, routinely covers the Great Books. Or take Tablet, which published my own explication of the techniques of Classical Chinese fiction, but which ran last year an article on how the Pritzker siblings were brainwashing kids into believing in “Synthetic Sexual Identities.” The New Criterion and Spectator also regularly cover classic literature and almost every issue will contain some sneering reference to male rapists in women’s prisons or the concept of “men who menstruate.” At this point, it would be simpler to list the high-culture critical magazines that aren’t avowedly transphobic (The New York Review of Books, The London Review of Books, The Times Literary Supplement and The LA Review of Books constitute the entirety of the list, so far as I know.)

The forums for writing about the Great Books tend often to be forums for transphobic writing.

And none of the latter has an explicitly pro-trans bent to match the anti-trans bent of all the outlets mentioned above. In fact, it would be impossible to name any corresponding left-wing publications with an interest in the Great Books. Even the very-academic New Left Review rarely covers a writer older than Marx.

The references to trans people and trans identities in these publications tend to be very much of the “facts don’t care about your feelings” variety. To these people, trans women clearly are not women. As one newsletter writer put it describing the controversy over a book called The Men, “for transgender fanatics, who believe that people without Y chromosomes can also be men, the book’s title is an outrage.” The kind of gender-critical person who’s steeped in the Great Books is quick to assert that only fanaticism, not reason, can explain modern “gender ideology.”

Their objection to transgenderism might have originated from visceral disgust or religious conviction, but ultimately they also believe that science and logic make the truth of their own position self-evident. These are people who tend to pride themselves on their reasoning abilities. Often, like Ben Shapiro (who insists on misgendering even trans women who have flawless female gender presentations), they litter their books and essays with references to Plato or Aristotle or St. Augustine (transphobes love St. Augustine).


There’s no essential reason why an interest in old books or ancient culture ought to be associated with transphobia, as gender minorities have existed at most times and places, including in classical civilization: in ancient Rome the cult of Cybele was administered by emasculated female-identified priestesses. Certainly gender changes are not at all uncommon in the Great Books, featuring in Ovid, Virginia Woolf, and The Mahabharata, amongst others.

The boring argument, of course, is that in many minds the Great Books represent tradition and the superiority of Western culture, so people who love the Great Books tend to be politically conservative, and politically conservative people tend to be transphobes. It’s the same as how, in my experience, when someone turns against Covid precautions or vaccines, they shortly thereafter also become gender-critical. It’s not an essential connection, it’s just a cultural one. You fall in with a new group of people and adopt their beliefs.

But since much of the argument in favor of the Great Books is that they “open peoples minds” and “teach them to think,” I think it’s worth exploring the ways in which that isn’t true. Because I do think there are systematic biases in the Great Books that actually encourage transphobia.

I use “Great Books” as shorthand to refer to a list of about a hundred authors, mostly from before the 20th century, who constitute, in the opinion of a small group of intellectuals and editors, the foundational texts of modern civilization. Various great books lists exist: the most famous is Mortimer Adler’s Great Books of the Western World, which forms the basis for curricula at U. Chicago, Columbia, and St. John’s College. Another example would be Harvard President Charles Eliot’s Five Foot Shelf. A much-more expansive form would be Harold Bloom’s Western Canon. And a version that I favor, incorporating selections from East as well as West, was Clifton Fadiman’s New Lifetime Reading Plan.

Great Books proponents push for older books because they perceive that older books tend to be more influential and more solidly grounded in terms of critical stature.

But all Great Books lists tend to consist primarily of pre-20th century works. A majority of the books in existence have been published since 1900, but in the view of Great Books proponents, contemporary literature is for fun, not for study. Great Books proponents push for older books because they perceive that older books tend to be more influential and more solidly grounded in terms of critical stature. A strong version of this is Nick Land’s opinion that the literary canon is like the biblical canon in that once a book is added to “the canon” it can never be removed.

Great Books lists vary in how they weigh a book’s intellectual influence versus its purely aesthetic merits. Aristotle will appear in every Great Books list, but in aesthetic terms most of his extant works are turgid and ugly. But philosophical works must usually also be works of beauty in order to achieve inclusion. This is why Hume appears on Great Books lists, but not Leibniz. One was a foundational empiricist, the other was a foundational rationalist, but Hume is a beautifully readable writer.

The problem is that, starting with the ascendance of Kant, it became quite rare for a philosophical work to also have any aesthetic merit. You no longer see the lucid prose and clear argumentation of a Hume or Voltaire or Rousseau. Because of their immense, overweening influence, Kant and Hegel are sometimes included in Great Books lists (though it’s hard to imagine anyone besides PhDs in philosophy actually reads them). Subsequently, on the Continental side, only Nietzsche is typically included in Great Books lists. On the Anglo-American side, William James and J.S. Mill make these lists, but none of the great logicians (not even Frege or Wittgenstein) tend to appear.

The relevance here is that Great Books lists almost never include the writings in the Continental philosophical tradition that form the foundation of much of our modern understanding of transgender identity. You will never see a Great Books list that contains Husserl, Levi-Strauss, Derrida, or any other modernist or postmodernist thinker.

A recent post in Quillette made this connection explicit, saying that English departments have died because they don’t teach the canon and instead assign abstruse works of Continental theory. Thus, while a Great Books proponent will be well-versed in Enlightenment-era and pre-Enlightenment thought, they tend to dismiss later philosophical thought, which they often associate with “postmodernism.” As a result, Great Books proponents tend to be rationalists.


Rationalism is the tendency, often attributed to Descartes, to think that one can derive fundamental truths about the world simply from the operation of pure reason. Rationalism has many things to recommend to it—for one thing it seems at times to provide a path to moral and metaphysical truth.

But since rationalists are searching for absolute truth, they tend to be very uncomfortable with things they are unable to see or measure. Note, it’s important not to confuse rationalism here with empiricism. Empiricism is the idea that knowledge must come observing and measuring the world, as given to us by the senses. Empiricists have no trouble with the idea of transgender people, because they understand the obvious: we are here, we exist, we have always existed.

Rationalists, on the other hand, are looking for something beyond the observable world. They want to be reassured that the world contains some deeper order. If an empiricist sees a table with three legs, they think, hmm sometimes tables have three legs. If a rationalist sees a table with three legs, they say, that’s not a table, because tables need to have four legs.

What rationalists dislike about the subjective world of inner states is that other peoples’ inner states are not accessible to them.

Rationalists are looking for what Kant called the thing in itself. They believe there is a true world that undergirds the apparent world, and that when the apparent world seems wrong or askew, it’s because it has deviated from the principles of the true world.

What rationalists dislike about the subjective world of inner states is that other peoples’ inner states are not accessible to them. You cannot ever know another person from the inside. The person can tell you, but they might always be lying or misrepresenting their own experience.

Again, to an empiricist this is no problem, because an empiricist understands that all knowledge is just an approximation. But a rationalist wants something deeper—something absolutely certain. That’s one reason rationalists are comforted by the Great Books—the great age and universal acclaim these books have received gives the rationalist assurance that the books are good in themselves—and that their goodness isn’t merely socially constructed and arbitrary.


Rationalism is great. I’m a rationalist a lot of the time. If you want to be sure about anything in the world besides your own experience, your choices are, essentially, rationalism or religion. But the problem with rationalism is that the method often leads to absurdities, and if you stick rigorously to your rationalist system, you’ll make arguments that fly clearly in the face of reality. In other words, you look like the transphobe living in a world that’s FULL of men with XX chromosomes who claims that the idea of an XX male is a delusion being propagated by “transgender fanatics.”

To make this argument, the rationalist must ignore the fact that many people with two X chromosomes identify as men, are visually indistinguishable from men (at least when clothed), and operate in society as men. The existence of such men is an empirically observable fact.

Transphobes act like they’re stating a scientific fact (the existence of men with two X chromosomes is impossible), when really they’re making a normative argument (we shouldn’t say someone with two X chromosomes is a man).

Rationalists begin with an intuition about how the universe works, but if their intuition proves to not match the exterior reality, they insist the exterior reality is false.

Like the Marxists who thought that the “inevitable” victory of the proletariat just needed a helping hand, rationalism is fundamentally anti-scientific, precisely because it’s not falsifiable. Rationalists begin with an intuition about how the universe works, but if their intuition proves to not match the exterior reality, they insist the exterior reality is false.

The certainty rationalists experience is intoxicating, but it comes at the cost of a terrifying insecurity, because ultimately there is nothing backing your visions of the proper functioning of the universe.


And this is exactly why most of the 20th century was a process of philosophers and intellectuals weaning themselves off the intoxicant of rationalism and looking for sources of certainty that were a little more secure and a little less grandiose.

If you move further down the philosophical road, you come to phenomenology, which begins to offer solutions to many of the problems that obsess the rationalist. Edmund Husserl, a late 19th-century German philosopher, put forward the proposition that a person can know their own experience with absolute certainty, and thus, our search for absolute truth should begin by exploring our own consciousness.

For instance, like the rationalist, the trans person also has an intuition about the proper operation of the universe: we sense that something is off-kilter in how we’re being gendered—but our intuition cannot be falsified, precisely because it refers to interior states that we know with absolute certainty. Paradoxically, the trans person has exactly the sort of certainty about gender that the rationalist craves but is forever denied.

Rationalists are angry that their pre-given world includes the existence of a phenomenon—people with XX chromosomes who claim to be men—that conflicts with their known world.

Thus, where rationalism strips personal experience (as being outside the realm of pure reason) from the search for meaning, phenomenology and its offspring tend to make personal experience a central part of their method.

Husserl was the first to distinguish between the “known world”—the world as we know it through science—and the “pre-given world,” which is the world as we know it through our personal experience. And it’s only through these concepts that we can begin to untangle the muddle the rationalist has made of their own thinking about trans people.

Rationalists are angry that their pre-given world includes the existence of a phenomenon—people with XX chromosomes who claim to be men—that conflicts with their known world. And they want the pre-given world to be hammered into place so it fits with their known world. But that’s simply not how life works. Rationalists are unable to honestly think about and debate the existence of trans people because they are ideologically committed to the idea that it’s possible to fully know and explain the pre-given world.

Trans people, on the other hand, already know the pre-given world and the known world conflict. This is literally our entire life story! We are informed from an early age that men are XYs and women are XXs, and men have poles and women have poles. And we try for many years to make our own feelings conform to those received notions. But eventually, the dissonance becomes impossible, and we conclude it is not the concrete fact of our existence that is wrong–what is wrong instead are the ideas that have kept us from recognizing the truth of our experience.

For my own part, I knew with certainty that I wanted my sex and gender to be different. And that is a fact that is equally as real—is as empirically valid—as the fact that most people born with XY chromosomes are content with the body and social role of a man. The latter fact can do nothing to discount the former one. It’s not the job of trans people to fit our experiences to a scientific framework, it’s the job of the framework to fit us.


On the other hand, I face a problem when the rationalist says, “It is an empirical fact that I do not see you as a woman.”

Because I fully believe that, at least in the case of a non-passing trans woman like myself, the rationalist is telling the truth. But what the rationalist doesn’t recognize is that my framework (“trans women are women”) is capable of explaining his experiences, whereas his framework neither explains my experiences nor, crucially, his own!

To a rationalist, a trans woman cannot be a woman, because a woman is defined by her genitalia and reproductive anatomy (i.e. by her female sex). And it’s true that I do not possess female reproductive anatomy or genitalia, and that most people can accurately deduce that fact from looking at me. But I don’t dispute the fact that, to most people, I don’t appear to be a woman.

Indeed, I experience this same conundrum when I look in the mirror. I do not see a woman. I see a man. Thus far, the rationalist and I are in perfect agreement.

The transphobic rationalist privileges their own lack of dysphoria, saying that it is natural for a person to not feel that their gender is at odds with their appearance.

But what they do not perceive is that there is an internal gender-sense that also exists, and that this gender-sense becomes most apparent when a person’s gender is at odds with their external appearance, a condition called gender dysphoria.

The transphobic rationalist privileges their own lack of dysphoria, saying that it is natural for a person to not feel that their gender is at odds with their appearance. They may even say that gender does not exist (or, rather, that it is perfectly correlated with sex).

But there is no reason why their lack of dysphoria should be regarded as natural, merely because it is the more common condition. Indeed, there is strong evidence that they do in fact experience dysphoria—they merely direct that dysphoria outwards, at trans people, rather than at themselves.


The crazy-making thing about the transphobic rationalist is that their experience of my gender (“this person is clearly not a woman”) is is not an argument against me—it’s an argument in favor! Because if they look at me and see someone who is obviously or clearly a man, then they are experiencing a pre-given, non-scientific instinct about gender! They are saying, I have an instinct about gender identity, and this person doesn’t accord with that instinct. And the clarity they experience is exactly the same clarity I experience when looking in the mirror—I am clearly not a woman. It’s an assessment that feels unshakeable and not mediated by language or culture. It feels like there is something mismatched between my appearance and my gender identity.

If they were more honest, the transphobe would dig into the roots of their experience and realize, some trans women look like men to me, and some look like women.

Except because the transphobes are so philosophically limited, they instead turn away from the truth, and they say, “I am not gendering a person. I am sexing them (i.e. determining their biological sex, rather than their gender).” And the tendency is to believe them, precisely because we tend to believe people when they describe their inner experience.

But if they were more honest, the transphobe would dig into the roots of their experience and realize, some trans women look like men to me, and some look like women, and the difference between them isn’t in their chromosomes or their genitals, it’s in their external gender presentation. In fact, the enduring appeal of trans porn is rooted in this precise dichotomy. A trans woman still looks like a woman even if you can see her penis. You might know intellectually that she has certain chromosomes and perhaps used to look like a man, but looking at her still gets straight men aroused.

But, rather than resort to introspection, transphobes tend to insist that they can always tell when someone is trans. Because if there’s even one case where they look at a person and think woman and discover that they have XY chromosomes, then their whole framework collapses.

The problem is that, because they are rationalists, these transphobes want to perceive some deeper truth beneath the way they gender a person. What they want is for manhood and womanhood to be rooted in some teleology: some sense of the purpose of the different sexes. Then they could say, a trans woman can’t be a woman because she doesn’t have the anatomy that allows a woman to carry out her function (gestating and birthing a child).

Unfortunately, the way we gender a person simply doesn’t work, in truth, the way it would need to work for their argument to hold water. When we are instinctively gendering a person, we do not use their chromosomes or their genitalia—facets associated with their reproductive system—instead we use certain easily manipulated aspects of their external appearance (voice, body shape, gender presentation) that can easily be at odds with their reproductive organs. Those are the facts, and, unfortunately, they clash very deeply with the transphobe’s feelings.

For this reason, one of the most amusing clips on YouTube is one of Ben Shapiro slipping up and using “she” to refer to Laverne Cox and then struggling to correct himself and use “he” even though it obviously doesn’t come naturally—Shapiro is gendering Cox, in his mind, as a woman, but he’s forced, because of his politics, to lie and say that he sees Cox as a man.

If Shapiro didn’t know trans people existed, he would instinctively gender Cox correctly (in fact, it’s common knowledge amongst trans people that the more conservative a state, the easier it is to pass, precisely because people don’t imagine you might be trans). A rationalist’s transphobia is not a part of the pre-given world.

These transphobes ignore the truth of their own experience, which is that they have a natural instinct that people who claim to be a certain gender ought to look and act in a certain way.

Meanwhile, trans people have exactly the same instinct, except we experience it about ourselves. We claim to be a certain gender, but our appearance doesn’t match, so we feel upset, and we act to bring our appearance in line with our gender. Transphobes are literally experiencing gender dysphoria when they look at us, and they are using the experience to claim that gender dysphoria doesn’t exist.

And when those transphobes love the Great Books, they are often also overtly self-congratulatory about their “skepticism” and their ability to “resist dogma” without recognizing that their own commitment to dogma has led them to embrace conclusions that are absurd. Moreover, because their intellectual prowess is at the core of their identity, the idea they might be wrong is deeply unsettling. Which, paradoxically, makes them dig in and turn hating trans people into the core of their identity.

But at least they have good taste in books.