Porter was born in Greensboro, North Carolina, in 1862.  His father was a doctor.  His mother died of tuberculosis when he was a child.  He showed a deep imagination and strong artistic talents as a child.  He loved reading from an early age.  As a teenager, he began working at his uncle’s drugstore as a pharmacist and drew sketches of the customers in his spare time.

In 1882, he moved with a friend to South Texas to attempt to rehabilitate his shaky health.  He worked for a time on a sheep ranch as a ranch hand and a cook.  Two years later, he moved to Austin to work as a pharmacist.  It was in Austin that Porter began writing.  Initially, it was a hobby, but it gradually took up more and more of his time.

In 1887, he married and took up a new job.  Porter worked for four years at the Texas General Land Office drawing maps and took a job as an accountant at an area bank in 1891.  However, three years later, the bank came across several accounting errors, accused him of embezzlement, and fired him.  At that point, he took up writing full time, publishing his own weekly humor magazine, The Rolling Stone.  Though popular, the magazine failed within a year and Porter soon found work with The Houston Post.

Not long after the move to Houston, federal auditors charged him with embezzlement from his former bank job.  He was arrested but released on bail.  He soon fled to New Orleans where he continued to write and took up the pen name of O. Henry after a conversation with a friend.  He then fled to Honduras but returned to the United States when his wife’s health collapsed.  His wife died within weeks of his arrival, and he was again arrested.

The trial was held in Austin, where he was sentenced to five years in prison in 1898.  Ironically, the same courthouse today is owned by the University of Texas and has been rechristened O. Henry Hall.

He was released in 1901 for good behavior.  In 1902, he moved to New York where he landed a job writing weekly stories for The New York World Sunday Magazine.  He would write more than 300 short stories between 1902 and his death, many known for a sudden, surprise twist at the end.

Perhaps his most famous story was "The Gift of the Magi," originally appearing in December 1905.  It is the touching tale of a young couple in turn-of the-century New York who want to get something special for each other for Christmas but have no money.  Unbeknownst to each other, they give up something they prize to buy their gifts.  The wife sells her luxuriant hair to afford a silver chain for her husband’s pocket watch.  The husband, however, had sold his watch to pay for jeweled hair combs for his wife which were so popular at that time.  The story has since been retold many times and dramatized on screen in many forms.

Two other stories included “The Caballero’s Way,” (1907) which introduced The Cisco Kid, a character reproduced by many other authors; and “The Ransom of Red Chief,” which appeared in The Saturday Evening Post in 1907 as the tale of two kidnappers who kidnap a rich, spoiled brat in hopes of ransom but end up paying the father for him to take the incorrigible child back.

His heavy drinking steadily took its toll on him.  It cost him his marriage.  His second wife left him in 1909.  He descended further into the bottle and died in 1910 at age 47.  In spite of his sad end, he was praised in later years.  Schools in Garland and Austin were named for him as well as in his native Greensboro.  In 1918, the prestigious O. Henry Award was established in his memory for outstanding short story writers.