On June 2, 1943, the 99th Pursuit Squadron of the Tuskegee Airmen, flew its first combat mission during World War II, when it strafed the island of Pantelleria off the coast of Italy. 

By the war’s end, the 99th, which became known as the “Red Tails” by the distinctive tail markings on its planes, had flown more than 3,000 missions over Europe. It had taken part in the fighting in North Africa, Sicily, mainland Italy, and the bombing campaigns over the continent.

In 1941, the United States War Department (now the Department of Defense), and the Army Air Corps, which was soon to become the Army Air Forces (USAAF) finally, under considerable pressure, agreed to create the first African American flying unit, the 99th Pursuit Squadron. 

African Americans had been trying unsuccessfully to become pilots since World War I. The military at the time was segregated, for example most of the units that had served in the western U.S. (Buffalo Soldiers), had white officers assigned to them. African Americans had a tough time in even becoming civilian pilots.

In 1940, there were only 124 civilian pilots in the nation. However, the number of qualified applicants for the new unit, despite there being very restrictive requirements in place, gave the program the boost it needed to survive. The 99th Pursuit Squadron was activated — without pilots at that point– on March 22, 1941. 

First Lady Eleanor Roosevelt also breathed life into the program when she visited the Squadron on March 29, 1941. Mrs. Roosevelt flew with chief civilian instructor C. Alfred “Chief” Anderson. Anderson, who had been a qualified civilian pilot since 1929, took the First Lady on a half-hour flight. After landing, the First Lady said, “Well, you can fly all right.”

In June 1941, the squadron was transferred to Tuskegee, Alabama for flight training. Captain Benjamin O. Davis Jr. was the first African American pilot to fly solo in an Army Air Corps aircraft. The class graduated in March of 1942. Davis was given command of the squadron in July of that year and promoted to Lieutenant Colonel.

Davis was a fascinating character. His father, Benjamin O. Davis Sr., had served 41 years before being promoted to the rank of Brigadier General. Davis Jr. was appointed to the U.S. Military Academy at West Point in 1932. During his time there, he was isolated, not given a roommate, and was not spoken to outside of the line of duty. He ate his meals by himself. Yet, rather than that situation forcing him out it steeled his resolve.