On this day in 1898 William S. Porter -- the drug store clerk, cowboy, fugitive, bank teller, cartoonist and future "O. Henry" -- began a five-year prison sentence for embezzlement. Porter had published several stories prior to his prison term, but the fourteen written behind bars represented a new style and quality, and began his rise to popularity. Porter hoped a pseudonym would keep the disgrace of his conviction from his young daughter, who was told that he was away on business. Why Porter settled on "O. Henry" is variously explained: as a drug store clerk in his teens, Porter would have known of the famous French pharmacist, Etienne-Ossian Henry, whose name appeared in the drug dispensary guide as O. Henry; he took the name from one of his prison guards, Orrin Henry; while courting a young lady he called a stray cat over with "Oh Henry!" and then later wrote about the incident, signing the unpublished piece, "O. Henry"; as ranch hand in his early twenties, he knew the cowboy song "Root, Hog, or Die," and found it apt: "... Along came my true lover about twelve o'clock / Saying Henry, O Henry, what sentence have you got?"
Porter may or may not have been guilty of taking $5,000 while working as a bank teller, but he certainly appeared so when he fled to Honduras. He turned himself in when he heard that his wife was dying -- she was his model for the wife in "The Gift of the Magi," one devoted to him throughout his many misadventures -- and received a five-year sentence, from which he was released after three for good behavior. Prison allowed him not only the time to write but association with many characters who had stories to tell, and it did not seem to cramp his style: he was so popular and well-connected in the prison hierarchy that he and bank robber Al Jennings were able to run a secret Sunday dinner club, with roast beef, wine and place-cards. Porter was a man who liked to sprinkle a little perfume on his handkerchief, and for his release in 1901 he somehow finagled a good suit, a new derby and pigskin gloves.
Within two years he was established in New York City, writing a story a week for the New York World and living in the nomadic, alcoholic style that would kill him within seven years, aged forty-seven. There were some 300 stories in all, many drawn from Porter's wandering about New York, the city he called "Baghdad-on-the-Subway," and where he said he found "at every corner handkerchiefs drop, fingers beckon, eyes besiege, and the lost, the lonely, the rapturous, the mysterious, the perilous, changing clues of adventure are slipped into our fingers."