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O. Henry, born William Sydney Porter on September 11, 1862, in Greensboro, North Carolina, began his writing career while imprisoned for embezzlement, necessitating the use of a pseudonym to hide his identity. His impact on American literary tradition is so great that one of the most prestigious literary prizes, the O. Henry Award, is named for him, and it recognizes excellence in short story writing. He was born during the American Civil War and lost his mother to tuberculosis at age three. As a child, he was educated at his Aunt Lina’s private school, and then as a teenager and adult he became a licensed pharmacist and found a love for New York City and celebrating the daily life of ordinary people and social outcasts. Such an appreciation for his own time and city is found in many of his short stories, which are typically set in New York at the turn of the 20th century, and feature Everyman figures, such as policemen and the unhoused in stories like “The Cop and the Anthem,” or ordinary couples making well-intentioned mistakes in “The Gift of the Magi.” O. Henry eventually was on the run from the law to avoid being tried for embezzlement, abandoning his wife and child. He was caught when he returned to his dying wife and he was sentenced to prison. It was during his time in prison that he found his love for writing, and there, he began working under the pseudonym O. Henry to avoid anyone finding out about his conviction and background. References to run-ins with the law are present throughout his works, and he often creates sympathy for criminal protagonists, such as in “A Retrieved Reformation,” featuring a bank robber who falls in love. “After Twenty Years” has a similar sympathetic protagonist, who is only caught in the end because of his loyalty to loved ones.
His writing career was cut short by his early death in 1910, but his impact on literature and popular culture was instant. During his writing career, he was compared to French naturalist Guy de Maupassant, an impactful writer whose work focused on the victories and struggles of ordinary people in their daily lives. O. Henry brought this form of writing to American literature.
Many of O. Henry’s works are set within New York City. His work celebrates mundane and quotidian New York life, and the physical context of the city becomes its own character and external force, pressing the characters to function and react to its realities. For instance, Bob makes it clear that his criminal lifestyle has caused him to frequently move throughout the West in order to avoid capture, and yet he visits New York City to meet an old friend because he feels safe within the anonymous chaos of the big city. By 1905, when “After Twenty Years” was written, the New York City Subway system was completed. The city’s population grew to 3.4 million, making it easy for inhabitants and visitors to move throughout the city anonymously. As the city’s population grew, so did crime, and thus the need for organized crime prevention and a police force, a force that Bob in “After Twenty Years” greatly underestimated: the New York City police department knew Bob was coming before he had even gotten there. The very city that Bob sought for its anonymity winds up being much more connected than he anticipated, to his downfall.
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By O. Henry