He married Athol Estes in 1887. To provide for his family he sold his stories to supplement his income. His wife gave birth to two children, a son who died in infancy, and a daughter named Margaret.
In 1891 Porter was a teller in the First National Bank of Austin. in 1894, He came under scrutiny as the banks only bonded employee because an audit revealed that funds were missing. A grand jury indicted him on four counts of embezzlement totaling $5,000. Interestingly enough, he jumped bail and fled to South America. But he came back due to his wife’s tuberculosis. In 1898, he was found guilty and was sentenced to 5 years in prison. When he came out, he assumed the name O. Henry.
One of the things that characterized O. Henry’s writing was money ruling world. Many feel that this love/hate relationship with money was due to the fact that O. Henry spent his money as quickly as he wrote his stories. His fame and income increased as exponentially as his person demons took hold. O. Henry spent his latter years fighting alcoholism. He did remarry, but they mutually agreed to split two years later. He tried theater, but ended up almost financial ruined. He died in a hospital from kidney failure on June 5, 1910 with 23 cents in his pockets.