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. 

Davis became only the fourth African American to graduate from West Point — the first three had done so in the 1870s and 1880s. At the time of his commissioning, the Army had only two African American officers, Davis, and his father. 

At the time of its initial deployment in April 1943, the 99th was redesignated as the 99th Fighter Squadron and it was flying Curtiss P-40 fighters from its base in North Africa. Its first combat mission, the bombing and strafing of Pantelleria, was part of Operation Corkscrew. The squadron would go on to support the invasion of Sicily. Captain Charles Hall was the first officer from the 99th to shoot down an enemy aircraft.

In September 1943 senior officers in the Army asked that the 99th be pulled from front line duty due to poor combat performance. Davis went to a news conference at the Pentagon to defend the unit. The unit was allowed to continue flying and Davis formed the 332nd Fighter Group, an all-black fighter unit. 

Any doubts about the 99th’s performance were put to rest during the Anzio landings in Italy. In a two-day period over the beachhead at Anzio, the Red Tails shot down 12 German aircraft. 

Once the invasion of Italy had succeeded, the fighter group was moved to Ramatelli airfield on the Adriatic coast. The group transitioned to P-47 Thunderbolts and P-51 Mustangs. It then began escorting the heavy bombers on missions to Czechoslovakia, Austria, Hungary, Poland, and Germany.

The Red Tails created an impressive combat record flying over 3,000 missions and destroying over 300 enemy aircraft. Davis earned a Silver Star and 88 members of the Red Tails earned the Distinguished Flying Cross.