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William Sydney Porter (O. Henry)

Updated on August 23, 2017

The Man Behind the Stories

O. Henry is famous for writing short stories with a twist ending, such as The Gift of the Magi, The Last Leaf, and The Ransom of Red Chief. I found his real life even more fascinating than his stories! The internet allowed me to read letters to, from, and about him, hear his voice in a radio interview, and see a picture of him and his family. I hope you will enjoy learning about this great author with a "beautiful soul" and help me solve some of the mysteries I came across.

To know more about his stories, visit my lens O. Henry Short Story of the Month.

Interesting Facts


William Sidney Porter (later spelled Sydney) was born in Greensboro, N.C., on September 11, 1862. Although it has nothing to do with the terrorist attack, his birth date certainly caught my eye... He loved New York and many of his stories are set in the City.


Born in Greensboro, NC, he then moved to a Texas ranch. After being accused of embezzlement by the bank he worked for, he absconded to New Orleans, LA, and then to Honduras. He came back to Austin, TX, to face trial and take care of his wife, Athol, who was terminally ill. He was sentenced to five years in jail at the federal penitentiary in Columbus, OH. Released after three years for good conduct, he joined his daughter Margaret and in-laws in Pittsburgh, PA. He was offered a contract with New York World newspaper, and moved to New York, NY. He lived a short time in Long Island, NY with his second wife, Sara Coleman.


In jail, Will Porter worked as a pharmacist. He also started writing under the pseudonym of O. Henry. He sent his stories to a friend in New Orleans, who sent them in turn to magazines in New York. Nobody knew these wonderful stories came from a prisoner! Although he went through a tough time - losing his wife to tuberculosis and being sent to jail shortly after - his stories are far from being dark and depressing. In fact, they are light, humorous, surprising, uplifting.


Will was working as a teller at the First National Bank of Austin when an examiner came and found discrepancies in his books, although there has been much debate about his actual guilt. The bank was clearly mismanaged, and from what I read, my conclusion is that he just happened to be at the wrong place, at the wrong time.

Below is a quote from an article I found online, on :

The patrons used to enter, go behind the counter, take out one hundred or two hundred dollars and say a week later, "Porter, I took out $200 last week. See if I left a memorandum of it. I meant to."

Was he guilty, or not? He was sent to jail not only for embezzlement, but also for absconding instead of facing trial. He had very little to say for his defense, still mourning the loss of his wife Athol, who died a few months before his trial.


Young Will Porter used to carry an unabridged dictionary and read it as a book. He would look up words he didn't know, and was fascinated by words. His vocabulary skills are sometimes compared to Shakespeare's. Yet, he never attended college and left school at fifteen years old to work for his uncle's drugstore...

His stories are filled with witty expressions, seldom used words, and allusions to other pieces of fiction, such as Shakespeare, greek mythology, Arabian Nights, contemporary "dime novels" (cheap paperback novels of the late 1800's), and Kipling, among others.

He uses dialects in such a way we can almost hear his characters talk. His choice of words and metaphors surprise and delight. In Texas, he learned French, German, and Spanish well enough to use some foreign vocabulary when a story calls for it.


O. Henry was sometimes called the "American De Maupassant." His stories end with a twist of fate, or a revelation of who his characters really are, or an unexpected turn that surprises and delights, draws tears or laughters - or both - from his readers. Yet, his stories are about ordinary people, in ordinary situations. He tells the story of a hobo, or a grafter, or even a shop girl, in their every day life.


His stories reflect universal values, such as unconditional love, self sacrifice, honor, and compassion. They often have a touch of spirituality, without being religious in nature. They are also nonjudgemental, often portraying characters that are usually ignored in our society, in a respectful way.

About Rejections...

From O. Henry's only interview, New York Times, April 4th 1909.

The following quote is from the only autobiographical interview O. Henry ever granted. It was featured in the New York Times April 4th, 1909. A copy of this article is part of the Greensboro Public Library's O. Henry Collection.

"I sent stories to newspapers, weeklies, and magazines all over the country. Rejections? Lordy, I should say I did have rejections, but I never took them to heart. I just stuck new stamps on the stories and sent them out again. And in their journeying to and fro all the stories finally landed in offices where they found a welcome. I can say that I never wrote anything that, sooner or later, hasn't been accepted.

"As for rejections, take 'The Emancipation of Billy,' as good a story as I ever wrote--it was rejected no less than thirteen times. But, like all the rest, it finally landed."

O. Henry's Family - Learn about O. Henry's immediate family.


Athol was only seventeen when she eloped and married O. Henry in 1887. Her parents were concerned about her frail health, and doubted O. Henry could provide for her financially. They accepted him in the family after the fact, and were a great support throughout O. Henry's life.

In 1888, she gave birth to a son, who died a few hours after birth.

In 1889, she gave birth to Margaret.

On July 25th, 1897, Athol died after a seven-year battle with tuberculosis.

Athol is said to have been the inspiration for Della, in The Gift of the Magi.


In 1907, O. Henry married his childhood sweetheart. She was an aspiring writer, and O. Henry helped her get in contact with New York publishers.

They lived together in Long Island for a year, but O. Henry had to be in the midst of NYC action in order to write. He moved back to New York to continue his writing career, while Sara moved to Asheville, N.C., her hometown.

In 1916, Sara wrote a novel called Winds of Destiny, based on the letters she had received from O. Henry.


Margaret Worth Porter was O. Henry's only child. She was born on 9/30/1889, in Austin, Texas.

She was only seven when her mother died of tuberculosis. Less than a year later, her father was sent to jail and she was taken care of by her maternal grandparents. She was told he was travelling for business. She only found out he had been in jail after his death. They eventually moved from Austin, TX to Pittsburgh, PA.

During the three years he was in jail, O. Henry wrote to his daughter frequently, and she wrote back to him. Some of their letters can be found online.

Margaret was nearly twelve when her father was released from jail and came back to live with them in Pittsburgh, PA, on July 24, 1901.

Less than a year later, O. Henry was offered a contract to write one story per week for the New York World and he moved to NYC.

O. Henry resented the fact that he never had a chance to attend college. He made sure he gave the opportunity to his daughter, by regularly sending money to pay for her college.

Margaret attended Princeton University. She had a short writing career, from 1913 to 1916.

In July, 1916, she married the famous NYC cartoonist, Oscar Cesare. They divorced four years later, and she eventually moved to California and married A. J. Sartin in 1927. She died of tuberculosis three days after her wedding.



  • 1904: Cabbages and Kings (attempt to construct a novel by linking separate short stories, and adding some)
  • 1906: The Four Million (stories set in New York City)
  • 1907: The Trimmed Lamp
  • 1907: Heart of the West (stories set in Texas)
  • 1908: The Voice of the City (stories set in New York City)
  • 1908: The Gentle Grafter
  • 1909: Roads of Destiny
  • 1909: Options
  • 1910: Strictly Business
  • 1910: Whirligigs
  • Post Humously:
  • 1910: Let Me Feel Your Pulse
  • 1911: Sixes and Sevens
  • 1912: Rolling Stones (also the name of his humorous weekly newspaper he ran for one year)
  • 1917: Waifs and Strays
  • 1920: O. Henryana
  • 1923: Postscripts
  • 1936: O. Henry Encore
  • 1986: O. Henry's Texas Tales


  • The Pimienta Pancakes (my personal favorite, for his hilarious choice of words)
  • Whistling Dick's Christmas Stocking (one of his first stories published under the name of O. Henry)
  • The Last Leaf (a moving story about a dying sister)
  • The Green Door (talk about "twist of fate!")
  • The Gift of the Magi (probably his most popular story - perfect for the Holidays)
  • Let Me Feel Your Pulse (his last story, a reflection of his own situation)
  • The Ransom of Red Chief (very funny and witty, one of his most popular stories)
  • The Ransom of Mack (nothing to do with Red Chief)
  • Shoes (story set in Central America - Ships is the continuity)
  • Ships (read Shoes first!)
  • Witches Loaves (touching, surprising, what else can I say?)
  • A Retrieved Reformation (my second favorite)
  • The Cop and the Anthem (a hobo tries to get put to jail for winter, to stay warm...)


  • O. Henry Biography, by C. Alphonso Smith (1916)
  • Through the Shadows with O. Henry, by Al Jennings (1921) Al Jennings was a train robber who befriended O. Henry in Honduras. They were later reunited in jail, and saw each other again in New York.
  • Winds of Destiny, by Sara Lindsay Coleman (1916) Sara was O. Henry's second wife. The story she wrote is fictive, although she weaved it around authentic letters she received from O. Henry while courting.

Short Story Collections

Many of his stories can be read online, but I recommend you get them in print. You may want to read them again, and again, and again...


O. Henry's Full House - Short movies based on some of his stories, one of them starring Marilyn Monroe.

Guilty or Not Guilty?

O. Henry was accused of embezzlement and sent to Ohio Penitentiary. I believe he was innocent. Based on what I've read so far, the bank he was working for was clearly mismanaged. His only mistake was absconding to New Orleans instead of facing trial.

Was O. Henry guilty of embezzlement, or was he just a victim of circumstances?

Let me know what O. Henry story is your favorite.

Help me improve this lens! I am open to constructive criticism.


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