Henry Ossian Flipper, engineer, the first Black graduate of West Point, the eldest of five sons of Festus and Isabella Flipper, was born a slave at Thomasville, Georgia, on March 21, 1856. He attended school at the American Missionary Association, and in 1873, as a freshman at Atlanta University, he was appointed to the United States Military Academy. Although Flipper was the fifth Black accepted to West Point, he was the first to graduate. At West Point he was often ostracized and had little social interaction with White cadets beyond official activities. He graduated fiftieth in a class of seventy-six on June 14, 1877, and accepted a commission as a second lieutenant. Flipper described his successful struggle against ostracism and prejudice in The Colored Cadet at West Point (1878). In January 1878 he was assigned to Company A of the Tenth United States Cavalry.
As an officer in the Tenth Cavalry, Flipper served at forts Elliott, Concho, Quitman, and Davis, Texas, and at Fort Sill, Indian Territory. He first reached Texas on his way to Fort Sill, where he supervised the drainage of malarial ponds. Flipper's Ditch is now a national historic landmark. He later constructed a road from Gainesville to Fort Sill after a troop of the Fourth United States Cavalry got drunk and deserted the lieutenant assigned to do the job. Flipper also installed a telegraph line from Fort Elliott to Fort Supply, Indian Territory, scouted on the Llano Estacado, and assisted in the return of Quanah Parker's band from Palo Duro Canyon to the Fort Sill reservation in the winter of 1878–79. During the Victorio campaign of 1880 he fought in two battles at Eagle Springs, Texas. For his service in the field Flipper was made acting assistant quartermaster, post quartermaster, and acting commissary of subsistence at Fort Davis, Jeff Davis County. The positions placed him in charge of the fort's supplies and physical plant.
When Col. William Rufus Shafter became commanding officer of Fort Davis in 1881, he immediately relieved Flipper as quartermaster and planned to relieve him as commissary as soon as he found a replacement. Flipper suspected what he later called a systematic plan of persecution, and is said to have been warned by civilians at the post of a plot by White officers to force him from the army. The following year, when he discovered post funds missing from his quarters, he attempted to conceal the loss until he could find or replace the money. When Shafter learned of the discrepancy, he immediately filed charges against him. A divided court-martial acquitted Flipper of charges of embezzlement but pronounced him guilty of "conduct unbecoming an officer and a gentleman." He was dismissed from the service on June 30, 1882. (Accounts of the court-martial proceedings may be found in the San Antonio Express, November 2-December 14, 1881.) President Chester A. Arthur made a final confirmation of the verdict on June 24, 1882. Flipper maintained his innocence until his death and waged a lifelong battle for reinstatement in the army.
He went to El Paso after his dismissal and remained there until 1883, when he went to work as an assistant engineer for a surveying company composed of former Confederate officers. He assisted the company in surveying public lands in Mexico and helped run a boundary line between the states of Coahuila and Chihuahua in 1883. Between 1883 and 1891 he worked in Chihuahua and Sonora as a surveyor for several other American land companies. In 1887 he opened a civil and mining engineering office in Nogales, Arizona. In 1891 the community of Nogales employed Flipper to prepare the Nogales de Elias land grant case (1893), a dispute over title to the San Juan de las Boquillas y Nogales Mexican land grant in Cochise County, Arizona. Flipper served as the government's only witness, and his testimony resulted in the grant's being declared invalid. The ruling saved the property of hundreds of landowners. Flipper's activity in the community led to his appointment as a special agent for the United States Court of Private Land Claims. In that position he worked on court materials, served as an expert on penmanship, and surveyed land grants in southern Arizona. In 1892, before the Nogales case, he compiled and translated Mining Law of the United States of Mexico and the Law on the Federal Property Tax on Mines. In 1895 the United States government published his translation of Spanish and Mexican Land Laws: New Spain and Mexico. Flipper also briefly edited the Nogales Sunday Herald and published articles in Old Santa Fe, which later became the New Mexico Historical Review. He became a member of the Association of Arizona Civil Engineers, the National Geographic Society, and the Southwest Society of the Archaeological Institute of America. He offered to serve in the Spanish-American War in 1898, but bills in the United States House of Representatives and in the Senate to restore his rank both died in committee. He served in the court of private land claims until 1901.
Beginning in 1901 Flipper spent eleven years in northern Mexico as an engineer and legal assistant to mining companies. He joined the Balvanera Mining Company in 1901 and remained as keeper of the company's property when it folded in 1903. William C. Greene bought the company in 1905, renamed it the Gold-Silver Company, and placed Flipper in the legal department, where he handled land claims and sales and kept mining crews out of trouble with the local authorities. Greene, who had learned earlier of Flipper's research on the Lost Tayopa Mine, sent him to Spain to do more investigation. The story of Flipper and the Lost Tayopa Mine appears in J. Frank Dobie's Apache Gold and Yaqui Silver. In 1908 Albert B. Fall bought out William C. Greene to form the Sierra Mining Company and retained Flipper in the legal department. In 1912 Flipper moved to El Paso, and in 1913 he began supplying information on conditions in revolutionary Mexico to Senator Fall's subcommittee on Mexican internal affairs. Flipper drew national attention when he was reported to be in league with Francisco (Pancho) Villa and denied the rumor in a letter to the Washington Eagle dated May 4, 1916. Flipper published an article, "Early History of El Paso," and also reputedly wrote a pamphlet entitled Did a Negro Discover Arizona and New Mexico?, which concerned itself with Estevanico's role in the Marcos de Niza expedition in 1539. In 1916 Flipper wrote a memoir of his life in the Southwest, which was published posthumously as Negro Frontiersman: The Western Memoirs of Henry O. Flipper (1963).
In 1919 Senator Fall called Flipper to Washington, D.C., as a translator and interpreter for his subcommittee. Upon his appointment as secretary of the interior in 1921, Fall appointed Flipper assistant to the secretary of the interior. In that position Flipper became involved with the Alaskan Engineering Commission. He served in the Department of the Interior until 1923, when he went to work as an engineer for William F. Buckley's Pantepec Petroleum Company in Venezuela. In 1925 the Pantepec Petroleum Company published Flipper's translation of Venezuela's Law on Hydrocarbons and other Combustible Minerals.
Flipper worked in Venezuela until 1930 and retired in 1931. He lived out his life at the Atlanta home of his brother, Joseph S. Flipper, a bishop of the African Methodist Episcopal Church. Henry Flipper died of a heart attack on May 3, 1940. In December 1976, when a bust of him was unveiled at West Point, the Department of the Army granted Flipper an honorable discharge, dated June 30, 1882. Two years later his remains were removed from Atlanta and reinterred at Thomasville, Georgia. President Bill Clinton officially pardoned Flipper on February 19, 1999. An annual West Point award in honor of Flipper is presented to the graduate who best exemplifies "the highest qualities of leadership, self-discipline, and perseverance in the face of unusual difficulties while a cadet."