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The Man Who Invented Manhattan

May 2024
19min read

Fewer than half of O. Henry’s short stories actually take place in New York, but we still see the city through his eyes

For most of this century, and often against the starkest evidence, New York City has persisted in seeing itself as “Baghdad on the Subway,” an Arabian Nights swirl of color, motion, tough characters with soft hearts, soft characters with sturdy hearts, tinsel, tears, and laughter. This is largely O. Henry’s doing. It was his stories, his portrait of the city in the decade ending in 1910—its shopgirls named Delia, Delia, or Dulcie, its derelicts and cops, its struggling, forever loyal couples, its ambitious artists and showgirls, its neighborhood streets and parks, its boarding houses and furnished rooms, its “sports” and “swells"—that gave New York much of the jaunty, plucky, raffish image it wears to this day.

O. Henry’s stories of this New York go on forever. By 1920 nearly five million copies of his books had been sold in the United States. There have been dozens of radio and stage dramatizations and motion-picture versions of his stories. The Four Million, the most famous of his anthologies, has been succeeded by volume after volume of collected stories. Even his early newspaper pieces were collected, as late as 1939, and he has been translated widely into other languages.

He was not a serious chronicler of the iron city like his contemporaries Stephen Crane, Theodore Dreiser, and Edith Wharton; his arch style and intimate manner are more akin to the Broadway columnists of the day and the Tin Pan Alley lyricists who are his real descendants. But despite everything he avoided and glossed over about New York, everything he gilded and cartooned, he was a peerless manufacturer of sentiment who knew how to make his readers as happy as his characters. He had that pleasing touch. It pleased writers as different as Ernest Hemingway, Sinclair Lewis, Vachel Lindsay, James M. Cain. It still pleases the reading public, if not the professors.

Efficient short stories, commercial or not, are playlets, little one act dramas. O. Henry’s, written to fill a newspaper column or two, are tinier than most. They are read in a flash. That is the way he wrote them. But they represent an enduring legend that O. Henry did the most to create. Even in New York, the “terrible town,” as that New Yorker Henry James called it on his return from England in 1905, when O. Henry’s star was at its brightest, most people are good at heart. They are cheerfully jealous of the “swells” but do not expect to join them. They make so little money that there is a lot of belt tightening, but they do not expect advancement in this life. What they do expect, what they most earnestly hope for—is romance, a big date on Saturday night, perhaps even a carriage ride or a boat trip down to Coney Island.


Marriage, not the big money, is what O. Henry’s people lived for. And marriage in O. Henry is generally ideal, a state of self-sacrificing bliss, as in his most famous tale, “The Gift of the Magi.” Anyone with the slightest sentimentality about Old New York gets a kick out of that ancient world as O. Henry drew it—icemen, organ grinders, brass cuspidors, powder puffs with rice powder, “mashers,” “confidential clerks,” “typewriters” (meaning typists), cops (always Irish), with walrus mustaches, talking in dialect.

What a lovely world that was. Someone gets knocked out in traffic and wakes up in the gutter to be greeted by a surgeon asking, “How do you feel, old man?” It was a world of scotch with hot water, cigar stores with a light always burning above the counter, boarding houses on Eighth Avenue for “theatrical people.” A cabby gets so drunk he forgets he was just married—in the Little Church Around the Corner—to the young girl he is driving about.

Delightful as these touches are, no one reads O. Henry just for the period history. You cannot reconstitute an authentic New York from these comforting characters, a whole city’s worth of people who find happiness in virtue. But O. Henry had a direct interest in such a quest.

In the spring of 1902 a stocky blond Southerner who would one day describe himself as looking like “a healthy butcher” arrived in New York. He had come via Pittsburgh, leaving his motherless daughter with her grandparents, to pursue what he had barely begun, a career as a writer. He had already published a few stories and was to write nearly three hundred in his short lifetime. Some early ones had been signed Olivier Henry; before long this became O. Henry. The author’s real name was William Sydney Porter, and he had a good reason for a pseudonym. He had just gotten out of jail.

The stocky young Southerner’s real name was William Sydney Porter, and he had a good reason to use a pseudonym. He had just gotten out of jail.

The man who was to live in literature as a chronicler of “Baghdad on the Subway” (sometimes “on the Hudson") was born in Greensboro, North Carolina, in the middle of the Civil War. He came of respectable stock: the grandfather on his mother’s side was the editor of the Greensboro Patriot; the father was a doctor and inventor. After his wife succumbed to tuberculosis (O. Henry was only three when his mother died, and tuberculosis was to stalk him for the rest of his life, taking his first wife and eventually his only daughter), Dr. Porter distracted himself with alcohol and inventions—a perpetual-motion machine, a steam-driven horseless carriage, a device for picking cotton. He grew vague, neglecting his medical practice and his young sons.

For rearing, the young Will was turned over to his father’s unmarried sister, Evalina, who ran the household and operated a small private school and who was a strong believer in oldfashioned Southern storytelling and reading aloud. O. Henry received the last of his formal education from her when he was fifteen.

Perpetual-motion machines are not likely to be large contributors to the family income, and Will helped by working in his uncle’s pharmacy. Suspected of carrying the family “weakness in the chest,” he was sent at twenty to Texas, to the son of another Greensboro doctor, a sheep rancher who had use for an extra hand. On the eve of Theodore Roosevelt’s “strenuous life,” the rugged outdoors were seen as a cure for any weakness.

Porter spent the next fifteen years in Texas, the setting for about forty of his early stories, first in the rough and tumble of the sheep ranch, then briefly once again in the profession he detested, pharmacy. He worked for two years as a bookkeeper for a real estate firm, four years as an assistant draftsman in the General Land Office. While at the land office he fell in love with a seventeen-year-old high school student, Athol Estes, whom he courted in part by helping her with her homework. Two years later they eloped and were married on July 5, 1887.

In 1891 he took the position that was to be his undoing, as paying and receiving teller with the Bank of Austin at a salary of one hundred dollars a month. Even by the freewheeling standards of the place and the time, the Bank of Austin was carelessly run. It had pushed one of Porter’s predecessors into early retirement, another into a suicide attempt. The bank operated on an honor system turned sloppy. Funds could be and were withdrawn and replaced as though they were kept in the bread box. For Porter it was a dangerous environment. He was a grasshopper, not an ant, when it came to money, and financial improvidence was to chase him all his life. Even in the decade of his greatest success, when the money flowed in regularly, he stayed on the edge, forced by what he called lupus americanus at the door to wheedle editors into giving him small advances. Never one to keep a careful eye on expenditures, he let money go as it would; generous to a fault, he was the wrong man to be expected to prove bank books at the end of a working day. Nor could he resist an informal loan to himself when he needed it. He would certainly have meant to pay it back.


In the meantime William Porter was on the way to becoming O. Henry. He had always liked telling stories. Aunt Lina’s campfire had given him practice, and later he liked to open up over drinks among friends. He was a good talker and gained a reputation for being witty. Soon after his marriage he started writing down his stories as a means to extra income. The large number of papers and magazines of the time made it relatively easy to get published. In any case he was successful on the spot, publishing small pieces in the Detroit Free Press and in Truth, a New York magazine. Naturally, he thought he could do more. In 1894, still a bank employee, he borrowed $250 on a note signed by two friends, bought a printing press, and started a humorous weekly, The Rolling Stone. He served as editor, principal writer, and staff cartoonist. While the magazine was still in its infancy, Porter’s bank suddenly came under pressure to tighten up its procedures, to make an example of some instance of laxity. The careless, good-natured Porter was fired and threatened with prosecution.

Porter may have used the bank’s funds to help finance the magazine. People thought so. At first he had its success to console him for his troubles with the bank. The Rolling Stone’s combination of a smart-alecky tone and the heavy-handed ethnic humor of the day pushed sales to more than a thousand copies a week. Encouraged, Porter tried to expand out of Austin into other Texas cities. They proved less receptive, and after a few months circulation faltered. If he did use the bank’s money to keep it going, it was a useless embezzlement because The Rolling Stone died in 1895 on its first anniversary.

Porter was now thrown onto the generosity of his parents-in-law and found them models of liberal-handedness. They would support him with occasional gifts disguised as loans for the rest of his life. Eventually, Porter was offered a job as a society reporter with the Houston Post. He sharpened up his writing and quickly rose to columnist at a salary of twenty dollars a week, sometimes supplemented by his winnings at poker or by what he earned with pieces for the Cleveland Plain Dealer and other newspapers.

This ended in July 1896, when an order was finally handed down for his arrest on embezzlement charges. Whether Porter was guilty or not, he did himself in by fleeing to Honduras. Knowing that he would have to face trial, he came back less than a year later because his twenty-nine-year-old wife was about to die. The authorities did their best for him, looking the other way and postponing action until after her death, protecting her from seeing her husband a convict.

In March 1898 Porter was sentenced to five years in the Ohio Penitentiary in Columbus. As prison sentences go, his was relatively easy. His background in pharmacy now came to his rescue, earning him a job and a bed in the prison hospital, rather than a cell, and sparing him much of the debasement of prison life. After his nightly rounds checking on patients, Porter had time to write. By 1898 he was sending out stories. Ten of his best known were composed in prison. Three of them, signed O. Henry, were published while he was an inmate. (Porter would never satisfy anyone’s curiosity about his pen name. When he was asked, his answer was usually that “O. Henry” looked good in print and was easy to say.)

Released from jail on July 24, 1901, after three years and three months, with time off for good behavior, and dressed not in the cheap suit issued to exiting inmates but in a stylish one bought with money he made from his published stories—Porter was always a careful dresser, a bit of a dandy—he headed for Pittsburgh. His daughter, Margaret, now twelve and hardly knowing the father who had been so long “away on business,” had been taken there by her grandparents to be far from scandal and gossip.


Pittsburgh and Porter were a bad match; he loathed it. In a letter to a prison friend he described the city that would someday head the list for livability as inhabited by people who were “the most ignorant, ill-bred, contemptible, boorish, degraded, insulting, sordid, vile, foul-mouthed, indecent, profane, drunken, dirty, mean, depraved curs.” He stayed as long as he could, for Margaret’s sake, but was soon looking for a way out. Writing, at which he had already managed a modest success, seemed to be his future, especially if he could get to New York to be close to a particular coterie of editors.

There was some encouragement. Gilman Hall, an editor at Ainslee’s Magazine, had found his work promising and urged him to come to New York to discuss it. Hall had published Porter’s story “Money Maze” while he was still in prison and had also bought “Rouge and Noir” and “The Flag Paramount,” paying him seventy-five dollars for each. In their first experience of what was to become Porter’s pattern with the magazine, Ainslee’s found itself solicited for one hundred dollars against future work, Porter writing that he preferred to settle in, not merely visit, the city. The editors had to send another hundred dollars before he even stepped on the train. As so often with Porter, the first hundred had quietly disappeared. (Some of it may have passed across a bar; like his father, Porter was a heavy drinker.) So, burdened with his secret and more than his usual reticence, he arrived in 1902 in the city that ever after would be seen, and even see itself, partly through his eyes.

O. Henry boasted that he could find material anywhere and produced one story on the basis of no more than a restaurant menu, just to show he could do it.

New York in those years was a city in which early automobiles—the PopeHartford, the Pope-Toledo, the Thomas Flyer—were beginning to take over the streets. You could go for a drink to McGurk’s Tavern or to the racy Haymarket at Sixth Avenue and Thirtieth Street, or to one of the dance halls the Cairo, the Tivoli, the Bohemia. Thugs like One-Lung Curran and his Gophers and the Stovepipe Gang made Hell’s Kitchen dangerous. Prizefighters like Freckled Fritz could be cheered at ringside; Jim Jeffries, the heavyweight champion, still undefeated when he retired (for the first time) in 1905, was drawn by Charles Dana Gibson. There were no lasting American plays as yet, but theater on Broadway was hot. The metropolis was the great new, modern thing, especially for a boy from Greensboro, an ex-convict who had found the perfect place in which to be someone else.

So inextricable is O. Henry from the sentiment about Manhattan that he helped to create that it comes as a surprise that only (forty of his stories were set in the city and that he lived and wrote in New York for only eight years. Most of his early tales were written for Ainslee’s; one issue included three, under three different pseudonyms. By July 1903 he was writing a weekly piece for the popular and lively New York World’s Sunday edition. At the same time, Munsey’s Magazine had first refusal on all his magazine pieces, to be paid for at the magnificent rate of ten cents a word.

Porter boasted that he could find material anywhere and produced at least one story, “Springtime àla Carte,” about a typist of menu cards, on the basis of no more than a restaurant bill of fare, just to show that he could do it. When the pressure was on for the weekly story for the Sunday World—very often that meant that an editor was sitting on the couch in Porter’s room, waiting for him to finish a piece for which he had long since had an advance—Porter needed to look no farther than the headlines of the World for inspiration:




His favorite haunts were mostly downtown—Gramercy Park, Madison Square Park and the Flatiron Building, lower Fifth Avenue with its shops and restaurants, Herald Square, the Village, the boarding houses and razzmatazz of Hell’s Kitchen and the theater district, Pete’s Tavern on Irving Place, whose fine long bar and tile ceiling survived Prohibition intact and which still looks remarkably close to the way it did when Porter drank there. New York in the early 1900s had its share of the grit and grimness of today’s city, and crime, corruption, scandal, disease, homelessness, and prostitution were part of the city’s daily life then as now. But in O. Henry it is essentially a visitor’s city, a New York in which most people, at least, seem to be seeing it all for the first time. It was picturesque, something gently to love and gently to mock at the same time, what the poet Wallace Stevens as a young newspaper reporter rejoiced in as “the electric town that I adore.” Did O. Henry adore it? There is an unmistakable Southerner’s condescension in his style. It could be witty, it could be sly, but it would always smack of the intelligent didact, the lover of fancy words and echoes of classic Shakespearean quotations. Still, his stories are charged throughout with inexhaustible good feeling. There is no real urban menace; there are just snapshots of the “Imagine that!” kind. The only real disturbances in O. Henry come from lovers missing each other by death’s intrusion. Just occasionally, even marriage becomes restrictive, mildly boring. (O. Henry’s second marriage was not happy.) His strong narrative sense was whipped up by the demands of his Sunday-supplement audience for stories that, even if they did not always end happily, had the supreme merit of always being resolved. That was the one thing Wharton, Dreiser, and Crane found most uncharacteristic of American lives.


But even if O. Henry was essentially an outsider, he had a certain authority that derived from his tone, the diction that could perform such high-wire somersaults for him, and the energetic forward momentum of his plots that worked things out in just half a newspaper page.

It is for his sympathetic portraits of “little” people, mostly women, that O. Henry is best known—for his shopgirls, typists, laundry workers, women living with the barest of decencies in furnished rooms on $6.00 a week.

What did $6.00 a week mean in the decade ending in 1910? O. Henry’s primary outlet, the New York World, sold for one cent in New York and Jersey City, two cents elsewhere, five cents on Sunday. Stetson hats could be purchased at Saks for around $3.00. Fourteen-inch ostrich plumes, regularly $2.98, were on sale at Bloomingdale’s for $1.29; men’s suits for $12.88. Five rooms with bath could be rented at 404 East Fifty-second Street for $22.00 a month. Girls were sought to pack cigarettes, to label bottles, to work on mangles, and (“over sixteen only”) to be generally useful in a laundry, for $5.00 a week.

One of O. Henry’s girls dines on veal chops and fritters for twenty-five cents and leaves a lavish tip of ten cents. Coffee was two cents. The rich could buy a top-of-the-line thirty to thirty-five-horsepower Bosch Magneto automobile for three thousand dollars, and New York arrivistes could maintain fine apartments, dress well, dine out frequently, hire servants, and generally show off for less than twenty thousand dollars a year.

In O. Henry’s story “One Thousand Dollars,” the “calm … forty, and sequestered,” ironic clubman named Old Bryson lists what a thousand dollars might buy: “One man may buy a happy home with it and laugh at Rockefeller. Another could send his wife South with it and save her life. A thousand dollars would buy pure milk for one hundred babies during June, July, and August and save fifty of their lives. You could count upon a half hour’s diversion with it at faro in one of the fortified art galleries. It would furnish an education for an ambitious boy. I am told that a genuine Corot was secured for that amount in an auction room yesterday. You could move to a New Hampshire town and live respectably two years on it. You could rent Madison Square Garden for one evening with it… .”

What has always been most touching in O. Henry stories is the gallantry with which his ordinary workers and couples struggle to maintain dignity and make ends meet. In “A Service of Love,” Joe Larrabee, an aspiring painter, and his wife, a hopeful singer, rejoice over thirty-three dollars. “Thirtythree dollars! We never had so much to spend before. We’ll have oysters tonight,” says Delia, the wife. “And filet mignon with champignons,” adds her husband. “Where is the olive fork?”

In his ironic drawl O. Henry conveyed his concern for strugglers in a battle with fate and circumstance not of their own making; when he feels engaged, he can be eloquent. In “An Unfinished Story” Dulcie, who sells “Hamburg edging”—a kind with lace—in a department store for a salary of six dollars a week and lives in the third-floorback of a West Side brownstone, has a date with a “swell.” She has fifty cents left over from her week’s wages and decides to use it for a bit of glamour.

“Dulcie stopped in a store where goods were cheap and bought an imitation lace collar with her fifty cents. That money was to have been spent otherwise—fifteen cents for supper, ten cents for breakfast, ten cents for lunch. Another dime was to be added to her small store of savings; and five cents was to be squandered for licorice drops… . The licorice was an extravagance—almost a carouse—but what is life without pleasures?”

This is the story that ends with O. Henry’s famous cri de coeur. He imagines himself at the Last Judgment:

”… I dreamed that I was standing near a crowd of prosperous-looking angels, and a policeman took me by the wing and asked if I belonged with them.


” ‘Who are they?’ I asked."

“’Why,’ said he, ‘they are the men who hired working-girls, and paid ‘em five or six dollars a week to live on. Are you one of the bunch?’"

"‘Not on your immortality,’ said I. ’I’m only a fellow that set fire to an orphan asylum, and murdered a blind man for his pennies.’”

When the tone works less well, it spins along like filler, words at wholesale to occupy the relentless demands of a weekly magazine, and it can become irritatingly artificial. But when O. Henry is fully at the throttle, he pulls it all together into something of small but genuine sublimity. In his most cherished and anthologized story, “The Gift of the Magi,” written at the specific request of the Sunday World for a Christmas story that was “faintly religious,” O. Henry’s affectionate compassion pushes what is otherwise a slight piece of treacle into a little masterpiece on the transforming power of domestic love. Delia and Jim, a young couple, live in one of O. Henry’s six-dollar-a-week furnished flats. Christmas is coming, and there is no money.

O. Henry made his readers feel that he had shown them to themselves exactly in the form that they would have chosen; he still defines New York to itself.

“One dollar and eighty-seven cents. That was all. And sixty cents of it was in pennies. Pennies saved one and two at a time by bulldozing the grocer and the vegetable man and the butcher until one’s cheeks burned with the silent imputation of parsimony that such close dealing implied. Three times Della counted it. One dollar and eightyseven cents. And the next day would be Christmas.”

Between them they have two treasures: Jim’s gold watch, which had been his father’s and grandfather’s, and Della’s beautiful dark hair that reaches to her knees. In order to buy Jim a Christmas present, Delia sells her hair for twenty dollars, spending the proceeds on a “platinum fob chain simple and chaste in design … worthy of the watch.” Jim comes home for dinner and stares at Delia’s cropped head.

“‘Jim darling,’” Delia says, “‘don’t look at me that way. I had my hair cut off and sold it because I couldn’t have lived through Christmas without giving you a present.’"

” ‘Don’t make any mistake, Dell … about me. I don’t think there’s anything in the way of a haircut or shave or a shampoo that could make me like my girl any less. But if you’ll unwrap that package you may see why you had me going awhile at first.’”

Jim has bought Delia a magnificent set of combs for her hair. Then he says, in one of O. Henry’s loveliest, most controlled passages: “‘Dell … let’s put our Christmas presents away and keep ‘em a while. They’re too nice to use just at present. I sold the watch to get the money to buy you combs. And now suppose you put the chops on.’"

“The magi, as you know, were wise men—wonderfully wise men—who brought gifts to the Babe in the manger. They invented the art of giving Christmas presents. Being wise, their gifts were no doubt wise ones, possibly bearing the privilege of exchange in case of duplication. And here I have lamely related to you the uneventful chronicle of two foolish children in a flat who most unwisely sacrificed for each other the greatest treasures of their house. But in a last word to the wise of these days let it be said that of all who give gifts these two were the wisest. Of all who give and receive gifts, such as they are wisest. Everywhere they are wisest. They are the magi.”

O. Henry was consistently visual, an able cartoonist sensitive to the look of the city, inside and out. Part of the continuing pleasure in reading him lies in the visual details, which his pinch of sardonic distance gave the quality of a Dutch interior seen through a scrim. In ‘The Furnished Room” he shows us: “A polychromatic rug like some brilliantflowered, rectangular, tropical islet lay surrounded by a billowy sea of soiled matting. Upon the gay-papered wall were those pictures that pursue the homeless one from house to house: The Huguenot Lovers, The First Quarrel, The Wedding Breakfast, Psyche at the Fountain. The mantel’s chastely severe outline was ingloriously veiled behind some pert drapery drawn rakishly askew like the sashes of the Amazonian ballet. Upon it was some desolate flotsam cast aside by the room’s marooned when a lucky sail had borne them to a fresh port—a trifling vase or two, pictures of actresses, a medicine bottle, some stray cards out of a deck.”

When he is in the streets of what, echoing Melville, he calls “this great water-girt city,” O. Henry gives us its “formidable, pitiless, restless, fierce angles … waiting in the dark… .” In “Squaring the Circle” a mountain man from Kentucky arrives in Manhattan and is made vertiginous by its pitiless rush forward. “He looked four ways, and saw the world hurled from its orbit and reduced by spirit level and tape to an edged and cornered plane. All life moved on tracks, in grooves, according to system, within boundaries, by rote… . People streamed by in straight rows; the horrible din and crash stupefied him.”


Most often O. Henry gives us types, sometimes mere types (as many a greater artist has done): the respectable women corseted and plumed, or modest and discreet; the “floozies,” fallen women who come to see the error of their ways before the story ends. His men are sentimentalized husbands or beaux or their rough-and-tumble counterparts—brawlers and bullies, sports and swells. There are romantic, often maudlin attachments, but no suggestion of sex, except, ever so faintly, among the fallen sorts. When true love enters the picture, O. Henry’s New York can be all valentines. That this is a false impression of reality is attested by the many ads of the period for cures for “blood poisoning in all its stages” by quacks with comforting names like Old Doctor Grindie and Old Doctor Grey. Porter himself, who lived most of his New York years as a bachelor and was called by his friends in the reticent vocabulary of the time a “full-blooded man,” frequented prostitutes and sometimes found women by placing personal ads.

Nothing combines O. Henry’s mixture of charm, irony, and sentimentality better than his story “The Cop and the Anthem,” with its vagrant hero, Soapy. “On his bench in Madison Square Soapy moved uneasily. When wild geese honk high of nights, and when women without sealskin coats grow kind to their husbands, and when Soapy moves uneasily on his bench in the park, you may know that winter is near at hand.” Winter is coming: Soapy wants to spend it in a warm jail. He tries everything he can think of to get arrested. The cop—an O. Henry cop with a brogue who says “Lave them be"—cannot be induced to oblige. Finally, when Soapy has decided to mend his ways, to go straight and get a job, he is arrested for vagrancy. The O. Henry ending in its purest form. These are the endings we crave, openly or secretly, before ambiguity becomes an acquired taste. The artist has released us, has knitted up all the raveled threads, and has sent us on our way, content. Of course it’s not realistic. Instead, it’s satisfying.

With stories like Soapy’s as well as in the ones that strike a deeper chord, O. Henry made his readers feel that he had shown them to themselves exactly in the form they would have chosen. Who can resist that heart of gold, that diamond in the rough, even now? O. Henry still defines New York to itself, still offers us the eternal fairy tale of urban life-as-possibility. The silken lure of New York remains “If you can make it here, you can make it anywhere,” and New Yorkers pride themselves on their combination of thick skin, soft heart, and extraordinary resiliency. They still cling to that O. Henryesque optimism that there is a future in which it is possible to have confidence.

Not so for William Sydney Porter. He died in 1910, of what appears to have been complications of overweight and drinking. He was forty-seven years old.

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