Born in Greensboro, North Carolina, Porter worked at his uncle's pharmacy after finishing school and became a licensed pharmacist at age 19. In March 1882, he moved to Texas, where he initially lived on a ranch, and later settled in Austin, where he met his first wife, Athol Estes Roach. While working as a drafter for the Texas General Land Office, Porter began developing characters for his short stories. He later worked for the First National Bank of Austin, where he wrote The Rolling Stone weekly in newspapers.

After moving to Houston in 1895, he was charged with embezzlement stemming from an audit of the bank and fled to Honduras before trial. During his stay in Honduras, he began writing Cabbages and Kings, which originated the term "banana republic". Porter surrendered to U.S. authorities when he learned his wife was dying from tuberculosis, and he cared for her until her death in July 1897. He began his five-year prison sentence in March 1898 at the Ohio Penitentiary, where he served as a night druggist. Porter wrote 14 stories from prison under various pseudonyms, one being O. Henry.


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Released from prison early for good behavior, Porter moved to Pittsburgh to be with his daughter Margaret before relocating to New York City, where he wrote 381 short stories. He married once more to Sarah (Sallie) Lindsey Coleman before she left him in 1909. Porter died on June 5, 1910, after years of deteriorating health. Porter's legacy includes the O. Henry Award, an annual prize awarded to outstanding short stories.

Porter graduated from his aunt Evelina Maria Porter's elementary school in 1876. He then enrolled at the Lindsey Street High School. His aunt continued to tutor him until he was 15. In 1879, he started working in his uncle's drugstore in Greensboro, and on August 30, 1881, at the age of 19, Porter was licensed as a pharmacist. At the drugstore, he also showed his natural artistic talents by sketching the townsfolk.

Porter traveled along with James K. Hall to Texas in March 1882, hoping that a change of air would help alleviate a persistent cough he had developed. He took up residence on the sheep ranch of Richard Hall, James Hall's son, in La Salle County and helped out as a shepherd, ranch hand, cook, and baby-sitter. While on the ranch, he learned bits of Spanish and German from the mix of indigenous and immigrant ranch hands. He also spent time reading classic works of literature.

Porter's health did improve. He traveled with Richard to Austin, Texas, in 1884, where he decided to remain and was welcomed into the home of Richard's friends, Joseph Harrell, and his wife. Porter resided with the Harrells for three years. He went to work briefly for the Morley Brothers Drug Company as a pharmacist. Porter then moved on to work for the Harrell Cigar Store located in the Driskill Hotel. He also began writing as a sideline and wrote many of his early stories in the Harrell house.

As a young bachelor, Porter led an active social life in Austin. He was known for his wit, story-telling, and musical talents. He played both the guitar and mandolin. He sang in the choir at St. David's Episcopal Church and became a member of the "Hill City Quartette", a group of young men who sang at gatherings and serenaded young women of the town.

Porter met and began courting Athol Estes, 17 years old and from a wealthy family. Historians believe Porter met Athol at the laying of the cornerstone of the Texas State Capitol on March 2, 1885. Her mother objected to the match because Athol was ill, suffering from tuberculosis. On July 1, 1887, Porter eloped with Athol and they were married in the parlor of the home of the Reverend R. K. Smoot, pastor of the Central Presbyterian Church, where the Estes family attended church. The couple continued to participate in musical and theater groups, and Athol encouraged her husband to pursue his writing. Athol gave birth to a son in 1888, who died hours after birth, and then a daughter Margaret Worth Porter in September 1889.

Porter's friend Richard Hall became Texas Land Commissioner and offered Porter a job. Porter started as a draftsman at the Texas General Land Office (GLO) on January 12, 1887, at a salary of $100 a month, drawing maps from surveys and field notes. The salary was enough to support his family, but he continued his contributions to magazines and newspapers. In the GLO building, he began developing characters and plots for such stories as "Georgia's Ruling" (1900), and "Buried Treasure" (1908). The castle-like building he worked in was woven into some of his tales such as "Bexar Scrip No. 2692" (1894). His job at the GLO was a political appointment by Hall. Hall ran for governor in the election of 1890 but lost. Porter resigned on January 21, 1891, the day after the new governor, Jim Hogg, was sworn in.

The same year, Porter began working at the First National Bank of Austin as a teller and bookkeeper at the same salary he had made at the GLO. The bank was operated informally, and Porter was apparently careless in keeping his books and may have embezzled funds. In 1894, he was accused by the bank of embezzlement and lost his job but was not indicted at the time.

He then worked full-time on his humorous weekly called The Rolling Stone, which he started while working at the bank. The Rolling Stone featured satire on life, people, and politics and included Porter's short stories and sketches. Although eventually reaching a top circulation of 1,500, The Rolling Stone failed in April 1895 because the paper never provided an adequate income. However, his writing and drawings had caught the attention of the editor at the Houston Post.

Porter and his family moved to Houston in 1895, where he started writing for the Post. His salary was only $25 a month, but it rose steadily as his popularity increased. Porter gathered ideas for his column by loitering in hotel lobbies and observing and talking to people there. This was a technique he used throughout his writing career.

While he was in Houston, federal auditors audited the First National Bank of Austin and found the embezzlement shortages that led to his firing. A federal indictment followed, and he was arrested on charges of embezzlement.

After his arrest, Porter's father-in-law posted his bail. He was due to stand trial on July 7, 1896, but the day before, as he was changing trains to get to the courthouse, he got scared. He fled, first to New Orleans and later to Honduras, with which the United States had no extradition treaty at that time. Porter lived in Honduras for six months, until January 1897. There he became friends with Al Jennings, a notorious train robber, who later wrote a book about their friendship.[3] He holed up in a Trujillo hotel, where he wrote Cabbages and Kings, which notably coined the term "banana republic".[4] Porter had sent Athol and Margaret back to Austin to live with Athol's parents. Unfortunately, Athol became too ill to meet Porter in Honduras as he had planned. When he learned that his wife was dying, Porter returned to Austin in February 1897 and surrendered to the court, pending trial. Athol Estes Porter died from tuberculosis (then known as consumption) on July 25, 1897.

Porter had little to say in his own defense at his trial and was found guilty on February 17, 1898, of embezzling $854.08. He was sentenced to five years in prison and imprisoned on March 25, 1898, at the Ohio Penitentiary in Columbus, Ohio. Porter was a licensed pharmacist and was able to work in the prison hospital as the night druggist. He was given his own room in the hospital wing, and there is no record that he actually spent time in the cell block of the prison. He had 14 stories published under various pseudonyms while he was in prison but was becoming best known as "O. Henry", a pseudonym that first appeared over the story "Whistling Dick's Christmas Stocking" in the December 1899 issue of McClure's Magazine. A friend of his in New Orleans would forward his stories to publishers so that they had no idea that the writer was imprisoned.

Porter was released on July 24, 1901, for good behavior after serving three years. He reunited with his daughter Margaret, now age 11, in Pittsburgh, Pennsylvania, where Athol's parents had moved after Porter's conviction.

Porter's most prolific writing period started in 1902, when he moved to New York City to be near his publishers. While there, he wrote 381 short stories. He wrote a story a week for over a year for the New York World Sunday Magazine. His wit, characterization, and plot twists were adored by his readers but often panned by critics.

Porter married again in 1907 to childhood sweetheart Sarah (Sallie) Lindsey Coleman, whom he met again after revisiting his native state of North Carolina. Coleman was herself a writer and wrote a romanticized and fictionalized version of their correspondence and courtship in her novella Wind of Destiny.[5]

Porter was a heavy drinker, and by 1908, his markedly deteriorating health affected his writing. In 1909, Sarah left him, and he died on June 5, 1910, of cirrhosis of the liver, complications of diabetes, and an enlarged heart. According to one account, he died of cerebral hemorrhage.[6]

After funeral services in New York City, he was buried in the Riverside Cemetery in Asheville, North Carolina.[7] His daughter Margaret Worth Porter had a short writing career from 1913 to 1916. She married cartoonist Oscar Cesare of New York in 1916; they were divorced four years later. She died of tuberculosis in 1927 and was buried next to her father.

According to the cemetery, as of 2023, people have been leaving $1.87 in change (the amount of Della's savings at the beginning of "The Gift of the Magi") on Porter's grave for at least 30 years. The cemetery says the money is given to area libraries.[8]

Most of Porter's stories are set in his own time, the early 20th century. He had an obvious affection for New York City, which he called "Bagdad-on-the-Subway",[9] and many of his stories are set there, while others are set in small towns or in other cities. They frequently feature working class characters, such as policemen and waitresses, as well as criminals and social outcasts. In his day he was called the American answer to French naturalist Guy de Maupassant, whose work was similarly concerned with the struggles of common people and often had twist endings. 152ee80cbc

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