began in 1902 in New York City

. Henry was always a lover of classic literature, and while pursuing his many ventures, O. Henry had begun writing as a hobby. When he lost his banking position he moved to Houston in 1895 and started writing for the The Post, earning $25 per month (an average salary at this time in American history was probably about $300 a year, less than a dollar a day). O. Henry collected ideas for his column by loitering in hotel lobbies and observing and talking to people there. He relied on this technique to gain creative inspiration throughout his writing career; which is a fun fact to keep in mind while reading an imaginative masterpiece of a story like Transients in Arcadia. The many twists and turns of his own life, including his travels in Latin America and time spent in prison, clearly inspired his stories' twists and wordplay.

O. Henry's prolific writing period began in 1902 in New York City, where he wrote 381 short stories. He wrote one story a week for The New York World Sunday Magazine for over a year. Some of his best and least known work is contained in Cabbages and Kings, his first collection of published stories, set in a central American town, in which sub-plots and larger plots are interwoven in an engaging manner. His second collection of stories, The Four Million, was released in 1906. The stories are set in New York City, and the title is based on the population of the city at that time. The collection contained several short story masterpieces, including The Gift of the Magi, The Cop and the Anthem, and many others. Henry had an obvious affection for New York City, a reverence that rises up through some of these stories