It was just a sunny afternoon flight in a yellow Piper Cub. For pilot Charles Alfred “Chief” Anderson, the flight itself was ordinary. His passenger in the backseat, though, was anything but.
Anderson, a Black man, was taking first lady Eleanor Roosevelt for an airplane ride. In 1940s America, it was unthinkable. That 40-minute hop would become known as “The Flight That Changed History.”
Born in 1907 in Bryn Mawr, Pennsylvania, Anderson was captivated by airplanes from a young age. Yet aviation in the 1920s was not exactly welcoming to Black Americans. For example, aspiring pilot Bessie Coleman had been forced to move to France in order to have a chance to learn how to fly. In Anderson’s case, he was able to join aviation ground schools, but finding someone willing to actually teach him to fly was near impossible.
Yet, Anderson persevered. At the age of 22, he would purchase his own plane, a Monocoupe. Local flight instructor Russell Thaw agreed to teach Anderson in exchange for the use of his plane to visit Thaw’s mother in Atlantic City, New Jersey. This agreement led to Anderson achieving his private pilot’s certificate in 1929. Anderson continued to pursue his ratings, and in 1932, he became the first Black American to receive an air transport pilot’s license.
In 1933, Anderson would meet Dr. Albert E. Forsythe. A pilot himself, Forsythe shared a common goal with Anderson—breaking down the barriers to aviation for Black Americans. They set out to prove that the skies weren’t off-limits—that people of color like them could fly. The pair began pursuing attention-grabbing feats, like completing a flight from Atlantic City to Los Angeles and back. It was the first transcontinental round-trip flight by Black pilots.
The duo continued their escapades with a flight to the West Indies, via many of the islands in the Caribbean. For this tour, they bought a new Monocoupe in St. Louis. While at the factory, they met famed aviator Charles Lindbergh, who was also buying a plane. Lindbergh, who wasn’t exactly known for his inclusive attitude, attempted to dissuade the pair in their endeavors.
Fortunately, Anderson and Forsythe didn’t listen, and their Pan American tour went off without a hitch, garnering much attention in the press.
By 1938, Anderson was a notable and highly respected pilot in the Black community. He was initially recruited to teach for the Civilian Pilot Training Program (CPTP) out of Howard Institute, and later transferred to the CPTP Program at the Tuskegee Institute. It was during his time at the college in Alabama that he earned the nickname “Chief.”
Anderson’s famous flight with Eleanor Roosevelt took place on April 11, 1941. Upon landing, it’s said that Roosevelt exclaimed, “Well, I see you can fly, all right!” It could be said that this flight was the beginning of the famed Tuskegee Airmen, as the flight with Anderson caused Roosevelt to lobby hard in favor of allowing Black Americans into the Army Air Corps during World War II.
Anderson was selected to be the chief instructor for the 99th Pursuit Squadron. The 99th had the honor of being the first all-Black fighter squadron and would later be merged with two others to become the 332nd, known as the “Red Tails” because of the distinctive paint jobs on their aircraft. The Red Tails flew over 1,300 combat missions during WWII, shot down 260 enemy planes, and earned over 150 Distinguished Flying Crosses.
Post-WWII, Anderson continued to be an instructor. For 22 years, he taught intensive ground and flight schools for teenage cadets during the summer. Anderson was also a founding member of the Negro Airmen International (NAI) organization.
He died in Tuskegee, Alabama, in 1996 at the age of 89. In 2013, Anderson was enshrined in the National Aviation Hall of Fame, and in 2014, was chosen to represent the Tuskegee Airman on a postage stamp in the Distinguished Americans Series.
