In prison, Porter wrote fourteen stories and began using O. Henry as a pen name. (He had other aliases, but after 1903 he signed everything “O. Henry.”) He was released, with time off for good behavior, in 1901, and moved first to Pittsburgh, where his daughter was living, and then, in 1902, to New York City, a place he had never visited, but where his prospects as a writer were better because he would be closer to his editors.
In New York, he began producing at an astonishing rate. He contracted to write a story a week for the Sunday World, and he continued to write for magazines. In 1904 alone, he published sixty-six stories. He began bringing out collections, notably, in 1906, “The Four Million,” which contains some of his most famous work: “The Gift of the Magi,” “The Cop and the Anthem,” “An Unfinished Story,” and “The Furnished Room.”
Porter’s daughter remained in Pittsburgh, and although he wrote to her regularly and affectionately, they rarely saw each other. His life style made living with a dependent impossible. He kept irregular hours, and his biographer Richard O’Connor says that he was a “womanizer.” As Porter had done since his Austin days, he spent his evenings talking to people he met in restaurants and bars.
Financially, he led the hand-to-mouth existence of most full-time writers, even very successful ones. You can’t live off pieces you’ve already been paid for. You always have to be producing a new piece, and you’re always afraid that it won’t be as good as your last piece. Despite his rate of production, Porter found writing stressful and had trouble with deadlines. And he was frank about the fact that he wrote for the income. When he started getting paid more for his stories, he wrote fewer of them.
Not that he saved up the money. He was never prudent. He gave a lot away, and there is some evidence that he was blackmailed by a woman who knew his secret. Even after he had become famous and his work was in constant demand, he was perpetually pleading with his editors to advance him funds against his next story. He received no royalties from a hit Broadway play based on a character in one of his stories (Jimmy Valentine). A series of popular Hollywood movies were based on another character he had created, the Cisco Kid, but they were made after he died. He tried his hand at a musical, and he contracted to write a novel, but those projects went nowhere. He was a short-story writer. That was what he was good at.
In 1907, he married a woman he had known from his childhood in Greensboro, but his health had been deteriorating, largely because of the drinking. Suffering from cirrhosis of the liver, diabetes, and a dilated heart, he died in 1910. He was forty-seven. He was begging his editor for a fresh advance right up to the end.