Henry Ossian Flipper: A Trailblazer in Military History

Henry Ossian Flipper’s journey to becoming the first African American to graduate from the United States Military Academy at West Point is a story of resilience and perseverance. His life and career, marked by discrimination and injustice, also highlight his remarkable achievements in engineering, public service, and literature. From his birth into slavery to his eventual pardon by the U.S. government, Henry’s story serves as an inspiring legacy of overcoming adversity in the pursuit of justice and honor.

Early Life and Education

Henry Flipper was born into slavery on March 21, 1856, in Thomasville, Georgia, to Festus and Isabella Flipper. His father, a shoemaker and carriage trimmer, worked for years to keep his family united. When Festus’ enslaver planned to move to Atlanta, he used his savings to successfully petition for the purchase of his wife and son so the family could remain together. After the Civil War, the Flipper family settled in Atlanta, where Festus established a successful shoemaking business.

The Flipper family valued education highly, and Henry attended schools for Black students established by the American Missionary Association, a Christian abolitionist group that provided educational opportunities for freed slaves. His academic success eventually led him to Atlanta University, an all-Black institution also founded by the association. His dedication to education and his exemplary performance paved the way for his acceptance into the United States Military Academy at West Point in 1873, thanks to a nomination by Congressman James Freeman of Georgia.

Congressman James C Freeman

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.

West Point and Military Training

Henry entered West Point on July 1, 1873, officially joining the Corps of Cadets. 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, leaving Flipper isolated from his peers.

Throughout his four years, Henry endured relentless racial discrimination. 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 this, he found occasional camaraderie with the barber and commissary clerk.

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. 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.”

Military Career: Serving in the Western Frontier

Upon graduation, Henry was commissioned as a second lieutenant in the U.S. Army, joining the 10th Cavalry Regiment, or “Buffalo Soldiers,” stationed at Fort Sill in present-day Oklahoma. These African American regiments were tasked with enforcing U.S. policy in the western frontier, where they contended with both the challenges of the terrain and hostility from settlers and other soldiers.

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. Known as “Flipper’s Ditch,” this project effectively prevented malaria, and the ditch was designated a National Historic 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 the 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. 

In 1880, Henry’s regiment was transferred to Fort Concho, Texas, where he served as a scout during the Victorio Campaign, pursuing Apache leader Victorio, who resisted reservation life by leading raids across the southwestern U.S. and Mexico. Henry’s role involved coordinating with Colonel Benjamin H. Grierson, whose troops eventually forced Victorio back to Mexico, where he was killed by Mexican soldiers in 1881.

Court-Martial and Dismissal

In late 1880, Henry was transferred to Fort Davis, Texas, where he served as the quartermaster and acting commissary officer. In July 1881, he discovered that $3,791.07 was missing from the commissary funds. Fearing that he would be blamed, Henry repaid the money with the help of local supporters instead of reporting the loss. Colonel William R. Shafter, Fort Davis’ commanding officer, suspected him of embezzling and allegedly deserting when he was seen in town with saddle bags.

Henry’s court-martial trial took place on September 17, 1881, where he was charged with “embezzling public funds and conduct unbecoming an officer and gentleman.” While the prosecution presented no evidence of embezzlement, Henry was convicted of the second charge due to alleged negligence. 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, President Grover Cleveland upheld it, 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.

Life After the Military

After his discharge, Henry embarked on a successful career as a civil engineer, mining expert, and surveyor in the American Southwest and Mexico. He authored two books, The Colored Cadet at West Point and Black Frontiersman: The Memoirs of Henry O. Flipper, sharing his experiences in the military and on the frontier. His expertise also led him to work for the U.S. Department of the Interior in Alaska and Washington.

Henry died on April 26, 1940 in Atlanta, Georgia at the age of 84 and was buried in Thomasville, Georgia.

Legacy and Posthumous Recognition

In 1976, his descendants and supporters petitioned the Army Board for the Correction of Military Records. After reviewing his case, the board concluded that Henry’s conviction and punishment had been “unduly harsh and unjust.” His discharge status was updated to reflect good conduct, 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.

His story is celebrated through various honors, including the annual Henry O. Flipper Award at West Point, given to cadets who exemplify leadership, integrity, and perseverance. 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.

 

Watch our documentary “In Search of Bass Reeves” for more on Black pioneers of the Old West.