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Tue, 11.25.1919

Charles Bailey, Pilot, and Teacher born

Charles Bailey

*Charles Bailey was born on this date in 1919. He was a Black army pilot, educator, businessman, and WW II hero.  

From DeLand, Florida, he was the son of Archie, and Josephine Bailey raised these children in a small town on the southwest coast of Florida; their hometown offered no schooling for Blacks. He and his brothers and sisters had no option but to attend schools in other communities. The injustices of Jim Crow segregation and deeply rooted racism presented unjust obstacles. Bailey graduated from the all-black Howard Academy in Ocala. There was no black high school in Charlotte County. So, he lived with his family in the Ocala area while attending high school there.

For two years, in the late ’30s, Charles was enrolled at Bethune-Cookman College in Dayton Beach, one of the state's few black institutions of higher learning. While in college, Bailey enlisted in the Army Air Corps. On April 29, 1943, he earned wings and gold second lieutenant’s bars upon graduating from aviation cadet training at Tuskegee Institute in Alabama. Charles was one of the squadron's pilots a month later when the 99th Fighter Squadron shipped out to participate in the Allied Invasion of North Africa. Bailey was one of 1,000 Black men who made up the U.S. Army's 99th Fighter Squadron. Forced by segregation to train at an isolated Army airfield in Alabama, they destroyed 261 enemy aircraft. Bailey flew 133 missions over Europe and North Africa.

He overcame several obstacles when he took to the air during World War II. First, there were Nazi forces, and then there were the racial expectations of failure upon the Tuskegee Airmen fighting American segregation. After the war, he returned to Bethune-Cookman to complete his final two years. He received a degree in elementary education.

Charles married Bessie L. Fitch of Punta Gorda in 1946. They had two children, Charles Bailey Jr. and James A. Bailey. Later, he also graduated from the Cincinnati College of Embalming. Eventually, the family moved to DeLand, FL, where he taught school for decades. Retiring from teaching, he opened the Charles P. Bailey Funeral Home in DeLand. Lt. Charles Bailey, Sr., was the last of the line. He was the last of Punta Gorda, Fla.’s “Fighting Bailey Brothers.”

The last of a family of seven sons and two daughters distinguished themselves in war and life during World War II, Korea, and much of the 20th Century. Charles Bailey was the first Floridian to become a member of the Tuskegee Airmen; he died in July 2001 at 82.

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