As a young man, he moved to Austin, Texas where he worked as a bank teller. He moved again to Houston, Texas in 1895 and became a newspaper columnist.
In 1896, however, he was called back to Austin, where he was charged with embezzling money from the bank where he had worked. Not wanting to go to prison for his crime, O. Henry fled to Honduras, and stayed there for six months before returning to the United States.
Upon his return, the court tried him and put him in an Ohio prison for three years. While in prison, he began writing short stories and it is there that he took the pen-name O. Henry for his writings.
After his release from prison in 1901, he moved to New York, which is the setting for many of his stories. He is the author of over 250 stories and is most famous for his use of surprise or 'twist' endings. Notice the twists and surprises in the endings to "The Last Leaf", "The Green Door", and perhaps his most famous story, "The Gift of the Magi".
Honors were now coming to O. Henry from everywhere. The poet laureate of England, John Masefield, visited Will and said that Rudyard Kipling, himself successful with the short story, wanted the poet to say hello for him. Willa Cather, then an editor but already writing novels, admired his work. William James, the famous philosopher at Harvard, was recommending O. Henry's books to his students. Mabell Wagnalls of the dictionary publishing family became a dear friend and introduced Will to high society.
At this time, poor health robbed his stamina. Despite the doctors orders, O. Henry could not stop drinking. He complained of constant fatigue. At night he couldn't sleep. He lost his appetite. Only malted milks pleased him. But no matter how ill, he made it his business to pass down familiar streets where old friends, depending on his unfailing charity, waited for him.
During this time two more books were published. Both were 1910 volumes. Strictly Business, praised by historians for its authentic sociology of derelict life, featured "A Municipal Report, " which has appeared in anthologies of short stories more often than any other story written in America. In this tale O. Henry demonstrates perfect management of picturesque dialect and sharp descriptive detail. His figures, Casesar, the black cabby, and Major Caswell, the professional Southern bore, are full of humanity.
