Charles P. Bailey Sr., born in 1919 in Punta Gorda, Florida, emerged as a trailblazing figure, becoming the first Black native of his state to soar among the illustrious Tuskegee Airmen. As the youngest of nine siblings—seven brothers and two sisters—he was part of an extraordinary family legacy known as the “Fighting Bailey Brothers,” whose collective service spanned World War II and the Korean War, with his sisters also contributing to the nation’s efforts. Raised in a close-knit family, Bailey’s early years were marked by determination and ambition. Before World War II, he graduated from Howard Academy, an all-Black school in Ocala, and pursued higher education at Bethune-Cookman College in Daytona Beach for two years. Driven by a sense of duty, he enlisted in the Army Air Corps, setting the stage for his historic contributions.
On April 29, 1943, Bailey’s perseverance culminated in a defining moment when he earned his pilot’s wings and the rank of second lieutenant upon graduating from aviation cadet training at the Tuskegee Institute. Shortly thereafter, he joined the 99th Pursuit Squadron, which deployed to North Africa. Initially tasked with non-combat missions, the squadron soon entered the crucible of war, and Bailey distinguished himself as one of only 450 Tuskegee Airmen to engage in combat. Piloting a P-40 Warhawk named “Josephine” in honor of his mother and a P-51 Mustang dubbed “My Buddy” after his father, he downed enemy aircraft and flew an astonishing 133 missions across Europe and North Africa. His valor earned him the Air Medal and the prestigious Distinguished Flying Cross.
After the war, Bailey returned to Florida, where he completed a degree in elementary education and dedicated himself to shaping young minds. He married Bessie L. Fitch, his hometown sweetheart, and together they raised two sons. The family eventually settled in DeLand, Florida, where Bailey continued his career in education before pursuing a new path. Graduating from the Cincinnati College of Embalming, he founded the Charles P. Bailey Funeral Home, serving his community with compassion and dignity.
Bailey’s legacy endures through the honors bestowed upon him. The city of DeLand recognized his contributions, and a terminal at Punta Gorda’s airport bears the name of the Fighting Bailey family, a testament to their collective sacrifice and service. Charles P. Bailey Sr. passed away in 2001, leaving behind a profound legacy as a pioneering aviator, devoted educator, and pillar of his community.