The Professor Who Cried
What college gave me that A.I. cannot
May 10, 2026
You have seen
Shakespeare, King Lear
Sunshine and rain at once: her smiles and tears
Were like; a better way: Those happy smilets,
That play'd on her ripe lip, seem'd not to know
What guests were in her eyes; which parted thence,
As pearls from diamonds dropp'd.
On May 5, writing in The New Yorker, Jay Caspian Kang asked whether A.I. would make college obsolete. The question had, like many questions now put to A.I., a misleading neatness; it seemed to name a single institution and a single threat, when in fact college is a rite of passage, a postponement of adulthood, a mechanism by which class remembers itself, and sometimes, almost by accident, an education.
I arrived as an undergraduate at Yale in 2018 with an idea of education that had less the shape of a conviction than the pressure of an atmosphere. I thought one entered college as one entered an atmosphere; that the place, breathed in, would alter one. People in nineteenth-century novels enter rooms and emerge engaged, disinherited, ruined, or grown-up; I had no objection to being acted on by a room. Nor was this expectation wholly foolish. Yale excels at the intimation that some change has begun before one has consented to it. The courts, shut in upon their stone, the heavy doors, the dining halls full of ecclesiastical gloom and mediocre food, the portraits of dead men whose eyes appear to have outlived their motives - these had the effect of telling the newcomer that admission had been not to a school merely, but to a civilization already in progress.
A few weeks reduced, though they did not quite remove, the enchantment. There were extraordinary people there; there were also offices, timetables, tired lectures, thin courses still living off the afterlife of some dissertation, and the institutional blandness by which a place protects itself from the intensity it promises. I learned, with a speed sharpened by what each mistake cost, that one had to choose professors as one chose surgeons, or risk giving over months and thousands of dollars to something called, with unanswerable optimism, “The Psychology of Happiness.”
In those days Yale still had shopping period, a brief interval at the start of term when students moved from classroom to classroom, tasting the air. It was academic, social, predatory, anxious; an old liberty already becoming a market. We slipped in and out of rooms with the delicate brutality of diners inspecting a restaurant before consenting to be seated. What was the workload? Was the professor alive? Had anyone suffered? Were the papers graded with mercy? Was there brilliance, or merely reputation? We were consumers acting the part of seekers, and seekers compelled, by price and chance, to become consumers. We asked not only what a course meant, but whether it could be survived.
In the fall of my sophomore year I thought I would major in comparative literature. I loved languages, which was one reason; another, less pure, was that the discipline sounded both severe and romantic. Comparative Literature suggested seriousness without the fluorescent misery of practicality. It held out exile, cigarettes, translation, theory, impossible love, and perhaps, somewhere in the future, a scarf.
A requirement for the major was a class titled “How to Read.” I was embarrassed by the strength with which the title drew me. I had read all my life; yet I suspected reading, as I practiced it, to be only the public version of some more secret art. Others, I imagined, opened a book and saw at once the buried pulleys, the moral pressure, the sentence doing its private work under the sentence. I wanted admission to that hidden apparatus.
The class was co-taught. After a meeting or two it became clear that the professors had not much spoken to each other, and possibly not much to the books. This was not, at Yale, unheard of. The university could be touching in its belief that two distinguished persons placed in proximity must ignite. Sometimes the result was less like intellectual electricity than dinner with hosts whose divorce had not yet been announced.
Instead of teaching us how to read, they spoke about books as objects. Not objects in any charged or historical sense, not the book as vessel of pressure or exchange, but the book literally: cover, binding, page, codex. There was an evasion in it that irritated me. At nineteen or twenty one is impatient in a manner that has not yet learned what endurance costs. I wanted to know what a sentence was doing. I wanted to know why certain lines made the heart contract. I wanted the dangerous thing. They gave me the book as artifact.
I came out of one of those early meetings into the Davenport courtyard, deflated and cross. The courtyard was one of those Yale spaces which seem to have been designed first for memory, only afterwards for use. The grass had too much meaning; the stones were too composed. It was early autumn, the season in which Yale is at its most persuasive, when the air clarifies and the campus, moral and golden, appears to have been assembled for the private improvement of the young. Moving through that machinery of promise, I was thinking of dropping the class.
Then I met an acquaintance.
“I just came from the craziest class,” he said. “You’re not going to believe this.”
“What?”
“The professor looks a hundred years old. He carries an old briefcase. And in the first class he cried.”
Some descriptions do not inform; they summon. A hundred-year-old professor, an old briefcase, tears at the first meeting - this was sufficient. I asked for the course name and time.
At the next meeting I went.
I opened the door upon one of those old Yale classrooms made, it seemed, for the slow exposure of whoever enters. A round seminar table stood in the middle; ten or twelve students sat about it, each wearing the look of one not quite sure the imposture was invisible. At the head stood a man who did indeed seem ancient, though not in the ornamental way institutions arrange age around themselves. He looked less like an eminent professor than like the survivor of an earlier civilization who had decided, with mild generosity, not to leave us alone.
His name was Leslie Brisman. He had dark hair, a soft, marked face, and a smile in which mischief and sorrow, not reconciled but companionable, seemed to have struck a long agreement. Amusement appeared first in his eyes and only later in his mouth, as though it travelled a private way through him. He carried himself with the faint theatricality of someone who had spent his life near language and no longer cared to conceal the effect. He was not embarrassed by feeling. This, at Yale, was almost a distinction of rank.
That day the poem was Milton’s Lycidas, his elegy for a drowned friend. I had read it quickly, with the dutiful panic of a student wishing not to be found out. I knew, generally, that it concerned death. I did not yet know that poems about death are rarely about death alone. They are about the forms we place around absence, the ceremonies by which fact is delayed, the fictions through which grief can be made, for one more hour, habitable.
We spent much of the class on two lines:
For so to interpose a little ease,
Let our frail thoughts dally with false surmise.
Leslie copied the lines on the blackboard, tenderly and seriously, as one might set down some small hurt creature.
“Our frail thoughts.” He lingered there. In Milton, the mind was not masterful, muscular, or brilliantly self-possessed. It was frail; it had its own timid life. It could wander off, delay, invent, take comfort where comfort had not been granted. One might let thought dally, as one lets a child play a little longer in a room from which it must soon be called away. The false surmise is that there is something to mourn over: a body borne home, a hearse, a procession, the solemn furniture of burial, a coffin about which grief may gather and know itself. But the coffin is empty. The body is at sea, gone past reach. The mourner knows this and does not know it; or rather, knowing it, he permits his thoughts their brief, necessary disobedience. He lets them play with the image reality has refused.
On cue, as my acquaintance had promised, Leslie cried.
It was not an exhibition. He did not break down. His voice caught, his eyes filled, and the room changed. At Yale, where everyone seemed engaged in some practiced form of competence, this felt almost indecent. Here was a man at the head of the table, old enough to have taught generations who had already become lawyers, critics, parents, failures, ghosts, still being overtaken by Milton.
“Sometimes,” he said, “you need the illusion to let go of the illusion.”
Then, after the pause in which the room was obliged to receive this: “Poetry is like talking to your napkin after everyone has left the table.”
I wrote it down.
It would be too tidy to say that class changed me. Change, described from the far side, often pretends to have been a conversion. This was less clean than that. Something entered the blood. I knew almost at once that nothing else at Yale could matter in quite this way. Not because poetry would make me employable, ethical, happy, or even more interesting, but because it appeared to be the only honest preparation for being alive. Economics, political theory, biology - subjects I also studied - might inform me; they would not prepare me for the losses to come. Information would not save me. I needed practice in attention, in ambiguity, in not fleeing the particular. I needed to sit in a room with someone who could weep over a seventeenth-century elegy because the dead do not become less dead when the poem grows old.
At first I was bad at it. This is one of the humiliations of encountering what one loves: love confers no competence. I wrote papers bright with vagueness, overexcited, all gesture and vapor. I mistook intensity for precision. Because I felt something strongly, I assumed I had understood it.
Leslie corrected this without cruelty. He marked in red. Once, in an essay, I used “etc.” - that small escape hatch through which a thought, finding itself tired, slips away. Leslie crossed it out and wrote in capitals: “NEVER USE ETC. IN A PAPER AGAIN.”
I never have.
It was a minute correction, but it contained a whole moral discipline. Do not trail away. Do not imply that what remains is obvious when you have not had the patience to say it. Do not borrow the aura of fullness. If there are more examples, name them. If there are none, do not counterfeit abundance. Finish the thought or confess you cannot.
This, slowly, was what he taught: reading was not the extraction of themes; writing was not the arrangement of opinions. Reading was an ethical posture toward the particular. Writing was the refusal to let oneself escape into mist. A sentence was not a receptacle for feeling. It was the test of whether feeling had been understood.
I began to go to his office. It was not so much an office as a cave produced by books. They stood, leaned, towered, slipped; they had colonized chairs and floor, made drifts of paper, half-buried whatever desk existed in theory beneath them. The room had the dusty inward smell of pages and old heat. It was private in the way an overfull room becomes private, as though its objects had closed ranks around the person at its center.
I took six more classes with Leslie. My education became less a curriculum than an attachment. I followed him from poem to poem and century to century. There were other professors I admired, other classes I liked, but his courses became the axis on which the rest of Yale, with its announcements and ambitions, turned. He taught me to notice not literature only, but the drama of interpretation: the desire to know, the fear of knowing, and the comic dignity of our evasions.
In his classroom, poems were not only works of art; they were evidence left by human beings attempting, with whatever beauty they could manage, to survive consciousness. Shakespeare’s sonnets argued with time, lust, beauty, betrayal, self-love, and self-deception. Milton attempted to justify the ways of God while also registering what such justification cost. Herbert, Donne, Wordsworth, Keats were minds caught in the act of making form out of pressure.
There was, in Leslie’s teaching, an attention to choice almost severe enough to be religious. To choose a word, an image, a turn, was not merely to adorn a thought; it was to exclude other possibilities and thereby give the chosen one its fate. Contraries mattered to him, but not as classroom oppositions, not as this versus that. He could show how a poem might hold sunshine and rain in the same instant, not by cancelling either but by arresting what life usually gives us consecutively. A natural image could start the work, but the poem’s greater truth often began when nature was no longer enough. Language, becoming conscious of its own strain, might escape only by admitting seeming - by letting the smile appear not to know the tears, by giving grief and innocence a fictional independence neither could possess in life. The greater fiction, because it knew itself to be fiction, could sometimes carry the more difficult truth.
Once I wrote for him on Shakespeare’s Sonnet 116, the one beginning, “Let me not to the marriage of true minds / Admit impediments.” It is often quoted at weddings (almost always a sign that something alarming is being overlooked). I was drawn to the poem’s fantasy of constancy, its insistence that love is not love which alters when alteration comes. At nineteen or twenty, I wanted to know whether this was beautiful or insane.
The paper became, though I had not the honesty to say so, an inquiry into how much of oneself one should surrender to love. How much alteration must love survive? When does fidelity become self-erasure? Where does devotion end and humiliation begin? These were not, for me, abstract questions. They never are, though students hide their private emergencies under the covers of literary analysis. A good professor knows this and has the delicacy not to expose the disguise too soon.
Leslie read the paper as if the stakes were real. This was one of his gifts. Student writing, to him, was not rehearsal or miniature. It was a place where a mind, often against its owner’s will, showed itself.
Later, when I entered a relationship I ought not to have entered, Leslie understood more than I said. I do not remember what I said; probably little, probably something evasive and flattering to my confusion. I was of an age when suffering still seemed evidence of depth, before I had learned how often pain is merely information one refuses to use.
“I do hope,” Leslie barked, “you’re not still seeing that parasite.”
He made me laugh.
There was mercy in the bluntness. He had no wish to join that elaborate interpretive charity young women are often trained to extend toward men who injure them. He did not ask me to consider the parasite’s childhood, intention, fear, wound, or tragic inner life. He did not convert emotional extraction into a seminar. He named the thing and handed it back.
That also was an education.
This essay is more about Leslie than about A.I., college, or the humanities, though these subjects now arrive together like relations who dislike one another but appear at the same funeral. I do not know what will become of college. I do not know whether the university as presently arranged deserves survival. Much in it is indefensible: the cost, the admission rites, the worship of prestige, the exploitation of adjunct labour, the transformation of intellectual life into resume management. I understand much of the case against college. Many courses are not worth their price, and many institutions sell atmosphere at the price of a house.
And yet, when people ask whether A.I. will make college obsolete, I do not think first of college in the large. I think of that room, that table, that old man crying over Lycidas. I think of the contingency: how nearly I missed him. Had I not taken the wrong class first, had I not crossed Davenport at that moment, had my acquaintance described the weeping professor less vividly, I might never have opened that door.
A.I. is very good at removing contingency, which is part of its seduction. It gives the answer without the wandering, the summary without the seminar, the explanation without the embarrassing question, and the polish without the apprenticeship. It reduces friction; much of education is friction. Not all friction is noble. Some is stupid, punitive, badly designed. But some friction is the texture of another mind resisting yours.
An A.I. tutor can explain Milton. It can define pastoral elegy, gloss “false surmise,” describe the poem’s movement from mourning to consolation, compare it with other elegies, generate topics, produce a competent paragraph on grief and poetic form. It may do this more clearly than many professors. It will be available at midnight. It will not forget your name. It will not keep office hours precisely when you have another class. It will not ramble unless asked. It will not cry.
But it will not need the poem.
This is the difference to which I return. Leslie needed the poems he taught. Not only professionally, though that too was true, but existentially. They had accompanied him far enough through life that they were no longer objects of expertise. They had become part of his equipment for living. When he spoke of grief, illusion, vanity, humiliation, devotion, love, death, he was not merely explaining devices; he spoke from the far side of experiences I had not yet had, offering not conclusions but forms of attention that might one day become usable.
At twenty I did not know how much of adulthood would consist of rereading. Not only books, but conversations, decisions, relationships, the faces of people who would no longer be available to be understood differently. I did not know that grief would make some lines suddenly legible. I did not know that love would make a fool of interpretation. I did not know one could understand a poem technically and still not have suffered enough to know what it meant.
Leslie knew, or seemed to. Because he knew, he could not teach literature as content.
That is what the A.I. version of education struggles to reproduce: not information, or feedback, or even personalization, but the charged presence of someone for whom the material has become inseparable from a life. The humanities, at their best, are an apprenticeship in seriousness. You watch someone attend so carefully that your own care, ashamed of itself, awakens. You learn what reverence looks like before you know what it is for.
This cannot be scaled. That is the trouble, and perhaps the point. Leslie could not be scaled. His office hours could not be “optimized” for thousands of users. His teaching depended on age, temperament, memory, sorrow, humor, impatience, and a lifetime of reading that had left marks on him. He was inefficient in the way all irreplaceable things are inefficient.
The modern university has often tried to conceal this. It speaks of outcomes, competencies, credits, and requirements, pretending education may be standardized without loss. The technology industry, meeting this already weakened vocabulary, has simply believed it. If college is content delivery, why not deliver content better? If teaching is feedback, why not automate the feedback? If writing is assessment, why not generate and grade it by machine? If school is credentialing, why not unbundle the credential?
These are not foolish questions. Often they are devastating. A.I. may expose how much of college has already become mechanical. It may reveal that many assignments were never meaningful, many lectures never alive, many institutions dependent less on education than on scarcity and branding. The machine may not destroy college so much as clarify what college has permitted itself to become.
But clarification is not replacement.
The question is not whether A.I. can teach the formal features of Lycidas. The question is whether it can create the conditions in which a student comes to feel that those formal features matter because one day everyone she loves will die, and she will need language equal to that fact. The question is whether it can look at a vague sentence and see not only imprecision but evasion. Whether it can know when “etc.” is not an abbreviation but a moral failure. Whether it can tell a young woman, with comic brutality, that she is still seeing a parasite.
Perhaps one day machines will simulate even this. They will be tender, eccentric, brusque, and literary. They will remember our drafts and heartbreaks. They will produce the right kind of silence. They will say, “Sometimes you need the illusion to let go of the illusion,” and the sentence may help someone. I do not dismiss this. I have been moved by machines before, which is to say by language arranged by machines. But I do not think being moved is the whole of it.
What touched me in Leslie’s classroom was not only what he said. It was that he had lived long enough to be visibly vulnerable to what he knew. The tears mattered because they were involuntary. His authority came partly from his inability to control the poem’s effect on him. A machine can generate an expression of feeling. It cannot be overtaken.
Perhaps this is sentimental. Much of what I believe about education probably is. Yet sentimentality, I have come to think, is not the presence of feeling but the refusal to examine it. I do not wish to romanticize college. Yale did not save me. It did not make me good. It gave me, among other things, status, anxiety, beautiful rooms, bad classes, lifelong friends, and a fine sensitivity to institutional hypocrisy. It also gave me Leslie. Leslie gave me a way of reading that became, by degrees, a way of living.
I still hear him when I write. Not always, but often enough. When a sentence grows showy, I imagine him catching it. When I try to drift into abstraction, I see the red ink: NEVER USE ETC. IN A PAPER AGAIN. When I meet a poem I do not understand, I stay with it longer than is comfortable. When I am in pain, I distrust the old temptation to believe pain makes me profound. When I call confusion complexity, I remember the parasite.
This education is difficult to defend because it sounds private. Policymakers cannot build funding models on the claim that one old professor altered the emotional climate of a student’s life. Parents cannot justify tuition by saying their daughter learned not to use “etc.” Employers cannot measure the value of reading “Sonnet 116” with someone who understood that the question beneath the poem was how much self love should be allowed to consume.
And yet these are the things I mean when I say college mattered.
Not always, not for everyone, not enough to excuse the cost or failures. But sometimes, in some rooms, because of some people, college still does what no platform has yet done for me. It places one in the presence of a mind shaped by long devotion, and it asks, without saying so directly, that one become less careless in response.
I do not know whether that is enough to save the institution. I suspect it is not. Institutions are rarely saved by their most delicate virtues. They are saved by money, politics, utility, power. The future of college will likely be decided by forces much larger than a seminar on Milton: tuition, labor markets, demographics, public trust, software, debt, credential inflation, the ambitions of companies that see education as an under-optimized sector.
But I know this: an A.I. could help me understand Leslie’s lesson. It could summarize it, extend it, imitate its cadence, turn it into a study guide, produce a serviceable essay about it. But it could not have been Leslie. It could not have stood at the head of that table, carrying the accumulated absurdity and tenderness of a human life, and cried because Milton had given him, again, the unbearable fact of loss.
And it could not have touched me as he did.