Lt. Charles P. Bailey Sr. always loved to fly but as Jim Crow grounded black Americans, the dream looked grounded too till he met Mary McLeod Bethune, founder of Bethune-Cookman College in Daytona Beach, which he attended on a football scholarship.
Bethune had the ear of Eleanor Roosevelt, the first lady and so it was that Bailey was transferred to Tuskegee. Alabama’s Tuskegee Institute being the school founded by Booker T. Washington in 1881 to teach blacks trades, introducing aviation in 1939.
Bailey graduated as a Tuskegee Airman in 1943 and by that feat became the first black aviator from Florida to become a Tuskegee Airman. He was also one of Punta Gorda, Florida’s “Fighting Bailey Brothers,” made up of seven sons and two daughters who distinguished themselves in World War II and the Korea War as well as in their respective lives as civilians.
Bailey was part of the 99th Fighter Squadron, originally formed as the Army Air Force’s first African American fighter squadron, then known as the 99th Pursuit Squadron. He is credited with shooting down two Focke-Wulf-190 German fighter planes in “Josephine,” a P-40 Warhawk named after his mother, and later in “My Buddy,” a P-51 dedicated to his father. The Germans referred to his all-black 99th Fighter Squadron as the “Black Birdmen.”
“At 1425 hours (2:25 p.m.) on the afternoon of Jan. 27, 1944 Lt. Bailey caught an FW-190 headed in the general direction of Rome with a 45-degree deflection shot (from his P-40). The pilot was seen to bail out,” according to a 99th Squadron Mission Report.
“Bailey earned an Air Medal with four oak-leaf clusters, awarded for valor in aerial combat. In May 1945, he added the Distinguished Flying Cross. In 15,553 sorties and 1,578 combat missions, the Tuskegee Airmen downed more than 1,000 enemy aircraft without losing a single fighter.” The black airmen received 150 Distinguished Flying Crosses, Legions of Merit and Red Stars of Yugoslavia.
But being a Fighter Pilot was risky business as Bailey soon found out. Once, while flying over the Mediterranean Sea, he was hit with shrapnel. The bible he carried over his heart in his flight suit pocket absorbed the blast saving him. Others were not so lucky. During World War II, 66 Tuskegee pilots were killed in action with 32 becoming prisoners of war.
On April 29, 1943, he earned his wings and gold second lieutenant’s bars upon graduation. Bailey was one of the first members of the 99th Fighter Squadron and part of only 450 black pilots who saw action during World War II.
Bailey flew 133 combat missions over enemy territory. Together with his squadron, they saw action in Sicily, Naples-Foggia, Anzio, Rome-Anzio, Normandy, Northern France, Southern France, North Apennines, Rhineland, Central Europe, the Po Valley and the EAME Theatre in Germany.
After the war, Bailey returned to Bethune-Cookman to complete his final two years and received a degree in elementary education. He 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.
The family relocated to DeLand, Florida where Charles Sr. taught in schools for decades. When he retired from teaching he opened the Charles P. Bailey Funeral Home in DeLand.
In 2007, a dedication ceremony was held at the DeLand Naval Air Station Museum. His memorial bust and history can be viewed at 910 Biscayne Boulevard at the DeLand Airport. A terminal at Punta Gorda’s airport is named after him and the rest of the Fighting Bailey family. Lt. Charles P. Bailey, Sr. passed in 2001.