Hugh O. Failing was born on May 11, 1822, in Arcadia, New York. He married Lucinda Hopkins on April 8, 1844, and they had at least six children: Myron, born around 1844; Sumner, born around 1850; Allie, born around 1852; Junietta, born around 1857; Nona, born around 1867; and George, born around 1869. He worked as a farmer and carpenter in Arcadia, and by 1860, he owned $300 of personal property.
He enlisted in the Union army on August 27, 1862, and he mustered in as a private in Company A of the 160th New York Infantry. According to his service records, he was 5 feet, 4 inches tall, with black hair and black eyes. The regiment took part in the siege of Port Hudson and the Red River campaign. He was promoted to hospital steward in June 1865, and he mustered out on November 1, 1865.
He moved to Monticello, Iowa, after the war and resumed his work as a carpenter. By 1870, he owned $900 of real estate and $100 of personal property. He moved to Bluff, Nebraska, around 1873, and his wife died on May 25, 1893. He died near Central City, Nebraska, on December 7, 1901.