Can AI Write Like Chekhov?

An experiment in literary revision

If you like this post, you might also enjoy reading What Keeps Me Up at Night When I Think About AI.

A few months ago, I decided to do a literary experiment with AI. I knew that neither ChatGPT nor Claude could write an original short story worth reading. When you ask AI to write fiction, it just feels machine-generated, much like the illustration above. This is a good thing. As a novelist, obviously, I don’t want AI to become adept at writing fiction. But could it rewrite a story? I decided to see what AI would do with a piece of original fiction if I asked it to rewrite it in a different, well-known voice.

For this experiment, I selected Anthropic’s Claude, which bills itself as being a kinder, gentler AI. Of course, I take this with a whole shaker of salt, because tech companies have been touting their good intentions for decades, even while engaging in notoriously predatory practices. Based on my own experiments, I knew Claude was at least a little better at voice than ChatGPT—less high school term paper, more nuanced. Sure, it hallucinates just like the others (any high schooler who asks AI to write a term paper will end up with a bunch of phony quotes from nonexistent sources). But I wasn’t asking it to do research. I was asking it to read my story and make it the same, only different.

Since tech is known for large-scale theft of intellectual property, I didn’t want to feed it an unpublished story. I wanted to go with something low-stakes, so I chose a flash fiction I’d written in 2022 about familial complications, featuring an intrusive squirrel—A Practical Removal.

If you’re so inclined, you can read the original flash fiction here.

Although AI was trained on a vast trove of original work without the authors’ or rights-holders’ consent, including copyrighted works by writers who are still very much living today, for my exercise, I chose to ask Claude to rewrite the story in the style of a writer whose work has entered the public domain. Thus armed with my low-takes source material, I fed Claude this prompt:

Rewrite this story in the style of Chekhov.

And then I went down the rabbit hole—or into the squirrel’s den.

What Claude did with my story

As you will see, Claude copied the story’s structure, plot, pacing, and characters, while rewriting each sentence in a slightly different vocabulary, with varying syntax and rhythm, adding Chekhovian flourishes. It also changed the story from first person to third, replacing the unnamed “I” with a third-person protagonist named Anna Petrovna.

Here, then, is the AI-generated Chekhovian version of my story. Below the story, you’ll find my thoughts on what this all means.

The Intruder

In the provincial town of N—, where life moved with the predictable rhythm of a grandfather clock, the Wagrams came to dine one evening in early autumn. They brought with them their plump child and their nervous dog—a curious pair that seemed to mirror the restlessness of their masters. Anna Petrovna, the hostess, had prepared what she considered a suitable meal for guests: chicken legs seasoned in the American style, asparagus that no one would touch, and potatoes mashed until they resembled the fog that settled over the town each morning.

The scratching began during the soup course—a faint, persistent sound from above, like a prisoner marking days on a wall. The dog, a creature of base instincts but pure breeding, detected it first. With a sudden movement that caused Madame Wagram to gasp, it leapt onto a dining chair and fixed its gaze on the ceiling, barking with the urgency of one who sees disaster approaching.

The child, still too young to have learned the artifice of social graces, began throwing her carrots at the dog. Each projectile traced an arc through the air before landing with a soft splash in the butter sauce. Anna Petrovna watched the scene unfold with the detached interest of one who has witnessed too many small disasters to be moved by them.

"Down, baby," said Wagram, a man who believed in the power of short commands.

"Don't talk to her that way," his wife responded automatically, though whether she meant the dog or the child remained unclear. These exchanges between them had the well-worn quality of old furniture, comfortable in their familiarity.

It was then that the son—who had maintained a monk-like silence for seven days—pushed back his chair. "I'm done," he announced, the words falling into the room like stones into a still pond. With mechanical precision, he cleared his place, each movement a silent rebellion against the domestic scene. The toddler watched him with the deep understanding that sometimes comes to the very young, recognizing in his actions the universal desire to escape.

The scratching continued overhead, moving from one end of the ceiling to the other like an unseen pendulum. The dog, now on the table, picked its way between the dishes with surprising delicacy, following the sound. Anna Petrovna's husband rose and lifted the animal away, his movements suggesting both irritation and resignation.

"I think you have a pest," observed Wagram, with the satisfaction of one who has identified someone else's misfortune.

"It isn't a pest," Anna Petrovna replied. "It's just the wind." But even as she spoke, she knew she was lying—not to her guests, but to herself. The wind makes many sounds, but it does not scratch at the ceiling with such purpose.

Days passed, then weeks. The scratching grew fainter, like a melody being played in an adjacent room, until it ceased altogether. Anna Petrovna's husband found countless reasons not to investigate: business trips to distant cities, sporting events with their son, household repairs that suddenly seemed urgent. When he finally ventured into the attic, they discovered the truth they had all suspected: a small corpse, curled as if in sleep.

It was around this time that Anna Petrovna learned of her former fiancé's death, the news reaching her through the modern equivalent of town gossip—social media. She contemplated writing to his mother but found herself unable to select the proper words. What does one say about a man who might have been everything but became nothing? In the end, she wrote simply, "I am thinking of you," words that contained neither truth nor falsehood.

Their son had taken up boxing by then, returning home in the afternoons with sweat-darkened clothes and a hunger that seemed to extend beyond food. The Wagrams had drifted away, as neighbors often do, though their child still appeared occasionally through the small door in the fence, like a character in a fairy tale. The dead squirrel had been removed, joining the countless other small tragedies that fill the spaces between lives.

And so they continued, this unremarkable family in their unremarkable house, bound together not by any great passion or principle, but by the quiet persistence of their affection. It was not much, perhaps, but in a world where even squirrels die alone in attics, it was something.

How I Really Feel About AI and Fiction

Something, indeed. I went into the experiment filled with dread. I came out of it filled with more dread. It’s already hard enough to make a truly original work of fiction, or something we think is original. The concept of fair use within copyright law is quite tricky, with many anti-copyright voices setting a low bar for “transformative" use—works that “add something new, with a further purpose or different character, and do not substitute for the original use of the work.”

Is the AI version of my story transformative? I’ll leave that for you to decide. Not that anyone is knocking down my door for this story. And yet.

What if someone took his own original novel and asked A.I. to rewrite it in the style of a living author—Stephen King, for example, or Kazoo Ishiguro, or Margaret Atwood? Granted, writers are much more than the style of their sentences. But given that AI has been trained on King, Ishiguro, and Atwood, would the author not owe something to them for the use of their style?

Of course, authors inadvertently copy the styles of the writers they admire all the time. This is, after all, how we learn. We read and read and read some more, and some echo of the voices we admire most begin to emerge in our early stories. I cut my teeth on Grace Paley. I learned from her stories how to write dialogue, how to write quick, unpretentious sentences. From Ian McEwan I learned the art of the intellectual page-turner. From Maj Sjowall and Per Wahloo, I learned how to be direct. The squirrel story was influenced by Don Delillo’s White Noise, which my son was reading in his high school English class at the time.

But a writer’s natural literary borrowings, which take time and effort, requiring both an ear and a voice and years of love and practice, are a far cry from the act of feeding a story into an AI mill and having it spit out, second later, a “transformed” thing.

A Deeper Dive into How AI “Transformed” My Story

My original story begins like this:

It never really occurred to us that we might have a squirrel, until that night with the Wagrams.

What happened was, our neighbors the Wagrams came over for dinner with their chubby toddler and their skinny dog. Ten minutes into the meal, there was some bumping and scratching in the ceiling over the dining table. The dog leapt onto one of the dining chairs and started barking at the ceiling. The toddler began throwing her carrots at the dog. I am not a stickler for manners, I adore toddlers, perhaps because I can read their minds and understand that everything they do is simply a rational response to the refusal of the world to allow them to make their own decisions. The carrot-throwing would have been fine except the carrots were mashed and swimming in butter.

In Claude’s version, their chubby toddler and their skinny dog becomes their plump child and their nervous dog. Obviously, all Claude has done in this case is switch out the adjectives. Lazy AI 101.

But then Claude gets busy with the similes.

Ten minutes into the meal, there was some bumping and scratching in the ceiling over the dining table

becomes

The scratching began during the soup course—a faint, persistent sound from above, like a prisoner marking days on a wall.

I rarely use similes, because I find them annoying, and I think they often pull a reader out of the fictional dream, but Chekhov was a fan, and who am I to judge?

The toddler began throwing carrots at the dog…The carrot-throwing would have been fine except the carrots were mashed and swimming in butter.

becomes

The child, still too young to have learned the artifice of social graces, began throwing her carrots at the dog. Each projectile traced an arc through the air before landing with a soft splash in the butter sauce.

I’ll give it to Claude-by-way-of-Chekov: the soft splash in the butter sauce is a nice touch. But the arc through the air is, in my humble opinion, both inaccurate and overwritten; that’s really not how carrots move, especially when launched by a toddler.

Claude even tells me how it went about chaining the story. For example

Where Richmond's dialogue is often explicit and contemporary ("Down, baby" / "Don't talk to her that way"), I made the dialogue more formal and understated, typical of Chekhov's characters who often speak around their feelings rather than expressing them directly. The tensions are implied rather than stated.

Yeah, okay, sure, but…

Does AI get the feeling right?

There is something lacking, I think, in Claude’s translation of the story’s final paragraph. The original ends like this:

We were dealing with death and not letting it define us. We were neighborly but reserved. We were a family of average means and practical intent, pushing forward through all those disastrous days. What we lacked in skill we made up for with the stubborn persistence of our love, and that is a fact.

As I mentioned, I’d been reading DeLillo. This becomes, in Claude’s reimagining,

And so they continued, this unremarkable family in their unremarkable house, bound together not by any great passion or principle, but by the quiet persistence of their affection. It was not much, perhaps, but in a world where even squirrels die alone in attics, it was something.

Claude’s image of squirrels dying alone in attics is indeed arresting, but aside from that, I’ll take the emotion of the original over the cleverness of the rewrite.

The genie that will not be bottled

I would very much like to put this genie back in the bottle. A decade ago, when corporations like Google and Facebook were mining our books to train their language learning models, most of us didn’t know what the genie was up to. By the time we knew, the world was a changed place. It feels so science fictiony, but it’s neither science nor fiction. It’s the world we live in.

The obvious end phrase for “It’s the world we live in” would be “for better or worse,” but I don’t believe there is anything good to come of unleashing AI on the arts. There is no “better.” Lest you brand me a luddite, I’m not entirely opposed to AI, which, used wisely, can have enormous benefits in the field of medicine, and which is capable of improving the human condition in ways we don’t yet fully understand. I just wish it would keep its 1s and 0s out of the arts.

I believe that writers will continue to write original fiction, corporations will continue to mine it, and readers will continue to crave something original and human-made. Just as certain segments of Gen Z seek out record players in a Spotify world, later generations will seek out stories written by humans. The question is how long it will be before it is impossible to tell the human-authored works from the others.