Henry Failing (1834-1898), one of the first citizens of Portland, Oregon, is known for his political business and civic contributions to the city. He lived during a time when Portland transformed itself from a small settlement to one of the great metropolitan and trade centers in the northwest. He was born in New York City on January 17, 1834, the son of Josiah Failing and Henrietta Ellison Failing. His formal education ended at age 12, when he entered the counting house of L.F. Figanere & Co. as an office boy. His training there as well as at a later firm, Eno, Mahoney & Co., gave him a good background in business and accounting. His later successes can be largely attributed to this early training.

Failing left New York on April 15, 1851 in the company of his father Josiah and younger brother John W. They journeyed to Portland via Panama by ship and mule train, arriving by steamer on June 19, 1851. Henrietta and the rest of the family followed two years later in a clipper ship around the Horn. Later that year father and son opened J. Failing and Co., a wholesale hardware business in Portland, at the corner of Front and Oak Streets. At the time, Portland was a small community of approximately three or four hundred people and only two streets. Following a dispute with New York City merchandise supplier Stevens Company, the Failings turned to John A. Hatt of that city for goods. Hatt merged his business with the Failing brothers in 1859, creating Failing & Hatt. In 1864, Josiah Failing turned the business over to his son, Henry, who continued to run it until 1871, when he consolidated the business with that of Henry W. Corbett, his brother-in-law. That subsequent firm, Corbett, Failing, and Company, continued for 22 years.

Henry Failing had numerous business and civic interests. In 1869, he joined his father Josiah and Henry W. Corbett in purchasing a controlling interest in Portland's First National Bank. He served as president of the bank until his death, and during his tenure it became one of the strongest moneyed concerns in the northwest. Failing was also a principal in the Keystone Mining and Milling Company, the Oregon Iron Company of Oswego, and the Willamette Iron and Steel Works. He served three separate terms as mayor of Portland, and during his first term a city charter was established. Also during his tenure a sorely needed system for street improvement was conceived which brought sewer lines to the city.

Failing found many uses for his talents. Always civic-minded, he was one of the first to serve as a volunteer fireman. When a devastating conflagration destroyed much of the city during his last term as mayor, he encouraged its citizens not to accept donations from other cities, believing that Portland should retain its independence. He and other community members contributed money for the relief of fire victims, many of whom had lost homes or businesses. All claims were paid, and money was left over to create a fund for the future relief of disabled firemen.

Failing had a lifelong interest in education, although he was himself largely self-taught. He served as President of the Board of the University of Oregon as well as trustee and treasurer of Tualatin Academy and Pacific University. Many other institutions and causes benefited from his generosity, such as the construction of Skidmore Fountain in downtown Portland. When the Library Association of Portland was established in 1864, Failing joined its board, beginning a fund raising campaign that allowed the Association to find a permanent home. He ultimately served a term as the Library's president, from 1894 until his death in 1898, and he provided the art work which became the core of the Library's present art collecton.

Henry Failing married Emily Phelps Corbett (1836-1870) on October 21, 1858. They had four daughters, three of whom survived to adulthood. They were Henrietta Ellison Failing (1859-1931) and Mary Forbush Failing (1862-1947), who remained unmarried; and Emily Corbett Failing (1867-1922), who married Henry Coalter Cabell (1858-1930) on February 12, 1894. The fourth daughter, Martha Fox Failing, died in infancy.

The Failing home was located on the block bordered by Fifth and Sixth Avenues, and Taylor and Salmon Streets, across from the Corbett mansion. Constructed during 1873-1874, it was a large and elegant house built in the French "Mansard" style. Three years before its completion, Failing's wife Emily passed away, so his daughter Henrietta was then called to serve as the family hostess. In the years 1879 and 1880 Failing and his three daughters traveled throughout Europe, buying furniture and decorative items for the house.

Henry Failing suffered a heart attack in July of 1898. His health then began to decline rapidly, and he died on November 8 of that year. In honor of his importance, Mayor W. S. Mason ordered flags flown at half mast on all city-owned public buildings, and the closure of all the town's businesses. After Failing's death, his daughters Mary and Henrietta lived on in his mansion until 1922, when it was sold, demolished, and soon replaced by the Public Service Building. Some of the house's furnishings were eventually given to the Pittock Mansion and are displayed in what is now called the Failing Room.