Introduction

There is a number that gives this collection its name, and like all great numbers, it carries an argument inside it. At the dawn of the twentieth century, a society columnist named Ward McAllister had famously declared that there were “only about four hundred people in New York” who truly mattered — those who could be comfortably accommodated in Mrs. Astor’s ballroom, the gilded elite whose names anchored the social registers and whose doings filled the newspaper columns. It was a snobbery so confident that it had become a kind of folk wisdom. To the writer who took the pen name O. Henry, this was not merely an offensive idea; it was a failure of imagination, a willful blindness to the teeming, breathing, struggling reality of the metropolis. His answer was both a rebuttal and a manifesto. There were not four hundred people who mattered in New York. There were four million. And every single one of them had a story worth telling.

That conviction is the beating heart of the collection you now hold. These are sketches — the author’s own modest word for them — that turn their attention away from the powerful and the celebrated and toward the people who actually filled the streets, the boarding houses, the department stores, the cheap restaurants, and the cold-water flats of America’s largest and most restless city. They are shop girls and clerks, waiters and policemen, struggling artists and out-of-work actors, immigrants and drifters, lonely widows and ambitious young men freshly arrived from the provinces with their entire fortunes sewn into the linings of their coats. They are, in short, the ordinary people, and O. Henry insisted that there was nothing ordinary about them at all. To read these pages is to be handed a magnifying glass and invited to look closely at lives that the rest of the world hurried past without a second glance.

To fully appreciate what makes these stories so warm, so wry, and so quietly humane, it helps to know something of the extraordinary life of the man who wrote them. He was born William Sydney Porter in Greensboro, North Carolina, in 1862 — the year that appears at the head of this volume’s title — and his path to becoming one of the most beloved short-story writers in the English language was anything but straight. He was a pharmacist’s apprentice, a ranch hand in Texas, a draftsman, a bank teller, and a newspaperman before he was ever a celebrated author. He had an eye trained by all of these occupations, an ear tuned to the speech of working people, and a deep, instinctive sympathy for those who lived precariously, one paycheck or one stroke of luck away from disaster.

That sympathy was not theoretical. It was earned. In one of the most dramatic turns of any American literary biography, Porter was accused of embezzling funds from the First National Bank in Austin, Texas, where he had worked as a teller. The circumstances were murky — the bank’s bookkeeping practices were notoriously loose, and many have argued that he was, at worst, careless rather than criminal — but rather than face trial, he fled to Honduras. It was there, incidentally, that he coined the phrase “banana republic,” a term that has long outlived its origin. He returned to the United States when he learned that his wife was dying, was duly arrested, convicted, and sentenced to prison. He served roughly three years in the Ohio Penitentiary.

It was in that grim place that William Sydney Porter became O. Henry. He began publishing stories under various pseudonyms while incarcerated, partly to support his daughter and partly, one suspects, because storytelling was the one form of freedom available to a confined man. The pen name stuck, and when he emerged from prison he made his way to New York City, the place he would come to call “Bagdad-on-the-Subway,” and he poured himself into the work that would make him famous. He wrote at a furious pace, sometimes producing a story a week for the newspapers, and the city became his great subject. He walked its streets at all hours, struck up conversations with strangers, ate in its restaurants, and absorbed its rhythms until they became second nature.

This biography matters because it explains the particular quality of his gaze. O. Henry did not look down on his characters from a comfortable height. He had known what it was to lose everything, to be ashamed, to start over, to live on the margins and to depend on small kindnesses. When he writes about a young woman counting her pennies to afford a Christmas gift, or a tramp who would rather go to jail than face the indignities of charity, or two friends whose loyalty is tested by ambition, he writes from the inside. The famous warmth of his fiction is not sentimentality applied from the outside like a coat of varnish; it is the genuine fellow-feeling of a man who understood failure and hardship intimately and who chose, again and again, to find the dignity and the humor in them.

This collection was first published in 1906, and it represents O. Henry at the height of his powers, fully in command of the form he had essentially perfected for the American audience. He would write hundreds of stories before his death in 1910 at the age of just forty-seven — a life cut tragically short by illness and the toll of hard living — but this particular gathering remains among the most cherished and frequently anthologized of all his works. If you have ever encountered an O. Henry story in a classroom or an anthology, there is an excellent chance it came from these pages.

A word, first, about the nature of this volume and the choices that shaped it. This is described as a modern translation, adapted for the contemporary reader, and that phrase deserves a moment of explanation so that you know exactly what kind of experience awaits you. O. Henry wrote more than a century ago, in a prose style rich with the slang, the topical references, the brand names, and the conversational idioms of turn-of-the-century New York. Much of this is delightful, and much of it remains perfectly clear. But some of it has inevitably faded with time — references to vanished products and forgotten public figures, colloquialisms that have dropped out of use, sentence constructions that can feel ornate or roundabout to a reader raised on cleaner modern syntax. The purpose of a careful adaptation is not to rewrite the author or to flatten his distinctive voice, but to remove the small frictions that can stand between a contemporary reader and the genuine pleasure of the storytelling — to dust off the windows, as it were, so that the view is as bright and clear as it was for readers in 1906.

What has been preserved, and what no adaptation could ever wish to lose, is the thing that makes O. Henry O. Henry: his unmistakable wit, his affection for his characters, his eye for the telling detail, and above all his genius for the surprise ending. It is impossible to discuss this author without mentioning the famous “twist,” and you should come to these stories knowing that they were built, with the precision of a watchmaker, to deliver a final turn that recasts everything that came before. A story will lead you gently down a familiar path, lulling you into certain assumptions, and then, in its closing lines, it will pivot — sometimes toward irony, sometimes toward tenderness, sometimes toward a quiet ache, and sometimes toward a laugh that catches in your throat. These endings are not mere tricks, though lesser imitators have made them seem so. In O. Henry’s hands, the twist is a way of revealing the hidden truth of a situation, the irony beneath the surface of ordinary life, the way that fate and coincidence and human nature conspire to produce outcomes that are both unexpected and, in retrospect, perfectly inevitable.

I will say no more about specific stories, because to do so would be to rob you of the very pleasures these tales were designed to give. The collection’s most celebrated piece — a story about a young married couple of slender means and the lengths to which love will drive them at Christmas — has become so woven into the fabric of our culture that you may already know its outline even if you have never read it. But knowing the outline and experiencing the story are two very different things, and even readers who think they know what is coming will find themselves moved by the actual encounter with O. Henry’s prose. The same is true of the dozens of other sketches gathered here. Some are romantic, some are comic, some are mysterious, some are touched with melancholy. What unites them is the city itself and the author’s tireless curiosity about the people who inhabit it.

You will notice, as you read, certain recurring preoccupations. O. Henry was endlessly fascinated by the gulf between appearance and reality — between the front a person presents to the world and the truth they conceal behind it. A shabby boarder may harbor secret nobility; a polished swindler may turn out to be capable of unexpected feeling; a young woman pretending to be wealthy and a young man pretending the same may circle each other in a comedy of mutual deception. The city, with its anonymity and its constant churn of strangers, was the perfect stage for these games of disguise and revelation. In a small town, everyone knows who you really are. In New York, you can be anyone you choose to be, at least for an evening — and O. Henry delighted in showing us both the freedom and the loneliness of that condition.

He was equally fascinated by chance. His New York is a place where lives intersect at random, where a chance meeting on a park bench or a misdelivered letter or an overheard conversation can change everything. This is not laziness on the author’s part; it is a worldview. O. Henry believed, or at least wrote as though he believed, that the great city was a vast machine of coincidence, throwing its four million inhabitants together in endlessly surprising combinations. There is something almost mystical in the way his characters stumble into one another, and part of the pleasure of reading him is the sense that anything might happen, that the next paragraph might bring a reunion, a recognition, a sudden reversal of fortune.

And then there is the money. It would be impossible to read this collection without noticing how often the plots turn on dollars and cents, on the precise cost of a meal or a hat or a week’s rent, on the difference between having a little and having nothing at all. O. Henry wrote about money the way only someone who had known its absence could — with exactness, with humor, and with a clear-eyed understanding of how it shapes the choices available to ordinary people. His characters are forever counting, scrimping, saving, gambling, and occasionally splurging in glorious defiance of their circumstances. This attention to the economics of everyday life gives the stories a grounded, lived-in quality. These are not abstractions; they are people who have to figure out how to get through the week, and we recognize them because we, too, have had to do the arithmetic of survival.

Yet for all his attention to hardship, O. Henry was never grim. This is perhaps the most important thing to understand before you begin. He chose, deliberately and consistently, to find the light in dark situations, the generosity in poverty, the laughter in disappointment. His is fundamentally a comic and compassionate vision of life, even when his stories end in sorrow. He extends to his characters a kind of grace, refusing to judge them harshly, finding in even the most foolish or misguided of them something worthy of our sympathy. The shop girls who dream of marrying rich men, the men who scheme and fail, the lovers who sacrifice foolishly — O. Henry loves them all, and his love is infectious. By the time you have read your way through this collection, you will find that you love them too.

Let me offer a few thoughts on how best to approach these stories, drawn from long acquaintance with the pleasures they offer. First, resist the temptation to rush. The modern reader is accustomed to consuming fiction at speed, but O. Henry’s sketches reward a slower, more attentive pace. They are short — most can be read in fifteen or twenty minutes — but they are densely packed, and much of their pleasure lies in the small touches: a perfectly chosen adjective, a sly aside from the narrator, a phrase that captures a whole personality in a few words. The author had a journalist’s economy and a poet’s precision, and if you read too quickly you will miss the very things that make him a master. Read one or two stories at a sitting, savor them, and let the endings land before you move on. These are not stories to be binged; they are stories to be relished.