06/17/2026
❤️🖤💛💚”Did You Know?” Charles Bailey - Tuskegee Airman
Charles Bailey was born in 1918 or 1919 in Punta Gorda, Florida. At the time, Punta Gorda only offered elementary and middle school education for African Americans. The city did not allow African Americans to attend its high school. Therefore, when the time came for him to attend high school, he and his family (mom, dad and nine siblings) moved to Ocala, Florida so he could attend Howard Academy where he excelled in academics and football. After high school, he attended Bethune-Cookman College where he played football on a full-scholarship for two years. Bailey was interested in becoming a pilot but Bethune did not have an aviation program. While in college, he had the attentive ear of Bethune-Cookman’s founder, Mary McCleod Bethune, who arranged for him to transfer to Tuskegee Institute to enroll in Tuskegee’s stellar aviation program.
He enlisted in the US Army Air Corps in 1942. On April 29, 1943, he earned his silver 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 in North Africa. Charles 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. He flew 133 missions over Europe and North Africa. He overcame several obstacles when he took to the air during World War II.
After the war, Bailey returned to Bethune Cookman College to complete his final two years and receive a degree in elementary education.
He married his hometown sweetheart in 1946 and had two children.
He later graduated from the Cincinnati College of Embalming. He and his family moved to DeLand, Florida where he taught school for decades. After retiring from teaching, he opened the Charles P. Bailey funeral home in DeLand.
Lieutenant Charles P. Bailey died in 2001 at age 82.
Fun Fact: Charles Bailey was the first Floridian to become a member of the Tuskegee Airmen.
Fun Fact: Bailey and his six male siblings have been called the “Fighting Bailey Brothers”, as the men, along with their two sisters, all served in the U.S. military during World War II, the Korean War and/or the Vietnam War.
Fun Fact: Bailey flew a beloved P-40 Warhawk “Josephine” aircraft named after his mother and a P-51 aircraft named “My Buddy” in honor of his father.
Fun Fact: During an aerial mission over the Mediterranean, Bailey was physically struck near his heart by shrapnel, fortunately, a Bible Bailey kept in his flight jacket pocket deflected the blow, protecting Bailey.
Fun Fact: Bailey was the youngest of his nine siblings.
❤️🖤💛💚
Visit the Marion County Black History Museum at Howard Academy Community Center to learn about additional Marion County Black History!
In honor of July 4th and our upcoming America250: Black Edition event on July 9th at 6:00p we will highlight African American Freedom Fighters from Marion County.
