Henry Ossian Flipper was born in Thomasville, Georgia, on March 21, 1856, into slavery and spent his formative years in Georgia. His father, a shoemaker and carriage trimmer, worked for years to keep his family united. The Flipper family lived in a community with approximately 65 other enslaved people, most of the men working as mechanics in a new manufactory venture near Atlanta. In 1864 as William Sherman’s army advanced on Atlanta, the Flipper family was forced to relocate to Macon, Georgia. The following year with the Union victory and collapse of the slavery system, the Flipper family chose to return to Atlanta, settling up a home for themselves in one of the still-standing buildings.
Following the Civil War, he attended the American Missionary Association Schools in his home state, which provided educational opportunities for freed slaves. His academic success eventually led him to Atlanta University (now Clark Atlanta University) in 1869, an all-Black institution also founded by the association. In 1873, Flipper petitioned Congressman from the Fifth District, James C. Freeman of Georgia for an appointment to the United States Military Academy at West Point. Henry's dedication to education and his exemplary performance paved the way for Freeman's acknowledgement of the request and eventually his recommendation. In due time, official correspondence made its way to the Flipper residence. Henry had been accepted for cadetship at the U.S. Military Academy.
As a member of Congress representing Georgia during Reconstruction, Freeman was aware of the importance of providing educational and professional opportunities to African Americans in the wake of the Civil War. Recognizing Henry’s academic promise and character, Freeman nominated him for admission to the United States Military Academy in 1873. Freeman’s decision to support Henry’s nomination was likely influenced by a broader goal of promoting racial progress and representation within the military, a critical institution in the United States. By nominating him, Freeman not only helped break racial barriers at West Point but also contributed to advancing the civil rights and societal position of African Americans in the post-war era. In 1873 Flipper was appointed to the U.S. Military Academy. He was only the sixth African American admitted to the academy and faced significant challenges.
During his first year, he roomed with James Webster Smith, the first Black cadet at West Point, who had written to Flipper before his arrival to prepare him for the hostility he would encounter. Smith was later dismissed unfairly from West Point, the reason was for poor grades in physics. In addition to the academic program being very rigorous, the environment was also stressful. All of the other Black cadets in attendance eventually dropped out or were dismissed leaving Flipper isolated from his peers. White West Point cadets and professors were openly and passive-aggressively hostile towards the Black cadets. The White cadets at the military academy socially ostracized Flipper. He received the silent treatment from his classmates, who refused to interact with him, and experienced total social isolation. He described his time as devoid of social engagement, writing, “There was no society for me to enjoy—no friends, male or female, for me to visit".
Despite all of this, he found occasional camaraderie with the barber and commissary clerk. Nevertheless, he persevered. He excelled academically, especially in engineering, law, French, and Spanish. On June 14, 1877, he graduated, becoming the first African American to complete his studies at West Point. General William T. Sherman personally handed him his diploma, marking his remarkable achievement. Flipper took in the moment in a personal way, finding a small victory among his fellow cadets. The New York Times reported the event, noting that Henry had endured “four years of as hard work and unflinching courage as any young man can be called upon to go through". Graduating 50th out of 64 in the Class of 1877, Flipper was commissioned a second lieutenant and assigned to the 10th Cavalry Regiment with the Buffalo Soldiers. He made history as the first non-White officer to lead the Buffalo Soldiers of the 10th Cavalry.
These African American regiments were tasked with enforcing United States policy in the western frontier, where they contended with both the challenges of the terrain and hostility from settlers and other soldiers. Captain Nicholas M. Nolan, the White commander of the 10th Cavalry, was assigned to teach Flipper how to be a cavalry officer. Captain Nolan was censured by several White officers for allowing Flipper into his quarters for dinner, where his daughter Kate was present. Nolan defended his action by stating that Flipper was an "officer and a gentleman" just like any other officer present. Flipper was not immediately assigned to a cavalry troop. Instead, he was given engineering tasks. From 1878 until 1880 Lieutenant Flipper served on frontier duty in various installations in the southwest, including Fort Sill, Oklahoma. His duties included scouting, as well as serving as post engineer surveyor and construction supervisor, post adjutant, acting assistant and post quartermaster, and commissary officer.
Henry served as an engineer, supervising the construction of a road from Fort Sill to Gainesville, Texas, and the installation of telegraph lines from Fort Elliott to Fort Supply. His most significant engineering accomplishment was designing and constructing an irrigation system at Fort Sill to drain stagnant water, which was causing malaria outbreaks. Malaria plagued the troops at the fort, and Flipper suffered a severe attack. A White engineering officer, trained at Germany’s Heidlberg University, had tried but failed to devise a drainage system to eliminate pools of stagnant water. Lieutenant Flipper was assigned the project. Known as “Flipper’s Ditch,” this project effectively prevented malaria, and the ditch was designated a National Landmark in 1977, standing as a testament to his skills.
He was a celebrity in his day. On April 7, 1878, he wrote to the New York Times to dispel a rumor that he had been offered a position as Professor of Military Science at a college in Texas. Apparently, he was exasperated by the numerous letters from fans congratulating him on his appointment. As an officer over Buffalo Soldiers in the 10th Cavalry, Flipper served at Forts Elliott, Quitman, Sill, and Davis. While stationed at Fort Sill, Flipper proved adroit in dealing with reservation Indians. He was assigned ongoing responsibility for inspecting and receiving cattle for issue to them at the Wichita Indian Agency. He served in the military escort that removed Chief Quanah Parker and his band of Comanche and Kiowa from the Texas Panhandle to the reservation near Fort Sill during the winter of 1878–79
Captain Nolan guided Flipper during the first part of the Apache Wars in early 1879. When Troop G’s commander left for detached duty, Flipper was entrusted to serve as acting troop captain for four months. Until November 1879, Flipper commanded this unit by himself while his captain was on leave for four months. He received high praise for his work. He saw extensive field service scouting in hostile Indian country on the Llano Estacado. In 1880, Henry’s regiment was transferred to Fort Concho, Texas, where he served as a scout and messenger for Colonel Benjamin H. Grierson during the Victorio Campaign. The Apache leader, Victorio, resisted reservation life by leading raids across the southwestern U.S. and Mexico. The ninth and tenth Buffalo Soldiers Cavalry Regiments were given the mission to apprehend Victorio and his group and escort them back to their reservation. After the United States Army had several fierce battles and skirmishes with Victorio throughout New Mexico, Victorio returned to Mexico, where Mexican soldiers killed him in 1880.
In late 1880, Henry was transferred to Fort Davis, Texas, where he served as the quartermaster and acting commissary officer. In July 1881, Flipper found a shortage of over $2,000.00 in the quartermaster’s safe. Realizing this could be used against him by officers intent on forcing him out of the army, he attempted to hide the discrepancy, which was later discovered, and then lied about it when confronted. Colonel William R. Shafter, Fort Davis’ commanding officer, suspected him of embezzling and allegedly deserting when he was seen in town with saddle bags. News quickly spread about the missing money. Soldiers and people from the community quickly raised the money to replace what was missing within four days. Shafter accepted the money. This incident led to him being court-martialed on charges of embezzlement and “conduct unbecoming of an officer and a gentleman”. Henry’s court-martial trial took place on September 17, 1881.
While the prosecution presented no evidence of embezzlement, they found Flipper innocent of the main charge of taking money. However, Henry was convicted of the second charge due to alleged negligence and was found guilty of "conduct unbecoming an officer and gentleman." He was sentenced to be "dismissed from the service of the United States." This was a very harsh sentence. His conviction led to his dishonorable discharge on June 30, 1882. Despite recommendations from the Judge Advocate General and Secretary of the Army to reverse the conviction, he was ultimately dishonorably discharged following the sentence’s approval by President Chester A. Arthur, highlighting the racial prejudice in the military justice system. In later writings, Henry suggested that his interactions with Mollie Dwyer, a White woman, sparked hostility from officers, which may have influenced the trial’s outcome.
During president Grover Cleveland’s presidency, Flipper sought relief, but Cleveland declined to overturn or reinstate him. For the rest of his life he fought to restore his good name. As a civilian, Henry Flipper went on to distinguish himself in a variety of governmental and private engineering positions. He held several important government and private engineering positions. First working as an engineer, he also surveyed land and worked as a special agent for the U.S. government on southwestern land claims. Fluent in Spanish, he translated texts on Mexican tax, mining, and land laws. He worked in Mexico from 1901 to 1912 as a mining engineer. After serving as an adviser to Senator Albert Fall on Mexican politics, he became his assistant in Washington, D.C when Senator Fall became Secretary of the Interior in 1921. In 1923, he went to work as an engineer for William F. Buckley's Pantepec Petroleum Company in Venezuela.
Flipper also became an accomplished author and wrote several books for the Department of Justice and personal recollections about his experiences. His first publication was an autobiography, "The Colored Cadet at West Point". The other works included "Spanish and Mexican Land Laws: New Spain and Mexico for the Department of Justice" in 1893. His expertise also led him to work for the U.S. Department of the Interior in Alaska and Washington. During his lifetime, Flipper petitioned Congress for “that justice which every American has the right to ask” and a reexamination of his court-martial and dismissal. In 1898, a bill was introduced to Congress that would have restored his rank and instated him in the Army, but the legislative attempt failed.
Throughout the balance of his life, Henry Flipper maintained that he was innocent of the charges that resulted in his court-martial and dismissal from the Army and made numerous attempts to have his conviction reversed. Henry Flipper retired to Atlanta, GA in 1933 and died nine years later on May 3, 1940. Finally, in 1976, with the recognition of his mistreatment, his discharge status was updated to reflect good conduct, by the Department of the Army, and he was issued an Honorable Discharge dated June 30, 1882. In 1999, President Bill Clinton formally pardoned Henry, acknowledging the injustice and finally restoring his honor. A statue of Flipper stands at West Point and he is celebrated through various honors, including the annual Henry O. Flipper Award at West Point. It is given to graduating cadets at the academy. This award recognizes cadets who show "leadership, self-discipline, and perseverance in the face of unusual difficulties." His life symbolizes the resilience of African Americans in the military, breaking barriers and inspiring future generations to continue the pursuit of justice and equality.