The Man Who Invented Manhattan


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.