Charles P. Bailey

Charles Phillip Bailey Sr. (November 25, 1918 – April 1, 2001) was a U.S. Army Air Force officer and one of the Tuskegee Airmen's most decorated combat fighter pilots. He was Florida's first African American fighter pilot. He flew 133 missions over Europe and North Africa, and was credited with shooting down two enemy aircraft.

For his heroics during World War II, the U.S. Army Air Corps awarded Bailey four Air Medals and the Distinguished Flying Cross.

Early life Bailey was born on November 25, 1918, in Punta Gorda, Florida. Known to his family and friends as "Phillip", Bailey was the son of Archie Bailey and Josephine Bailey.

After graduation, Bailey attended the historically black university Bethune-Cookman in Daytona Beach, Florida, where he played football on a full scholarship. Bethune arranged for Bailey to transfer to Tuskegee Institute to enroll in Tuskegee's stellar aviation program. On April 29, 1943, Bailey graduated as a member of the Single Engine Section Cadet Class SE-43-D, receiving his silver wings and commission as a 2nd Lieutenant.

In Fall 1943, the U.S. Army Air Corps assigned Bailey to the 99th Fighter Squadron as a replacement pilot in North Africa's Casablanca. He flew 133 combat missions throughout Central Europe, Germany, Sicily, Italy, France, and the Rhineland.

Flying his beloved P-40 Warhawk “Josephine" aircraft named after his mother, Bailey shot down two Focke-Wulf Fw 190 German fighters. Bailey also flew a P-51 aircraft named “My Buddy" in honor of his father.

Post-Military Bailey reenrolled at Bethune-Cookman College, graduating with a bachelor's degree in Elementary Education.

In 1995, doctors diagnosed Bailey with Alzheimer's disease. In 2000, Bailey went missing after wandering from his home in Deland, Florida. Initially, a search team was unable to locate him. When one of the search crew members shouted "Do you know anything about the Tuskegee Airmen?” a hungry, dehydrated Bailey suddenly responded "Yes.”

Family 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.

Maurice M. Bailey (1906–1990): The eldest brother and Florida A&M University graduate served as a sergeant with the “Red Ball Express,” a predominantly African American outfit that supplied frontline white troops with munitions, food and fuel in World War II's European Theater. Also a veteran of the Korean War, Maurice was interred at Arlington National Cemetery. Paul Bailey (1922–1987): As a U.S. Army Private First Class, Paul was a chaplain's assistant assigned to the Western Pacific's Company D, 2805th Engineering Battalion. After World War II, Paul graduated from Bethune-Cookman College and the Boston Conservatory of Music with degrees in music. Berlin J. Bailey (1912–1997): As a U.S. Navy E-4 and electrician's mate 3rd class, Berlin served in World War II's Pacific Theater in the 3rd Construction Battalion which was front and center at Guadalcanal, one of World War II's fiercest battles in the South Pacific.

In 1946, Bailey married Bessie L. Fitch Bailey (June 25, 1915 - December 6, 2008), a Punta Gorda, Florida native and Bailey's classmate at Bethune-Cookman University who served 25 years as Executive Secretary for Richard V. Moore, former Bethune-Cookman University President. Bessie previously served as educator Mary McLeod Bethune's personal secretary for 20 years at the National Council of Negro Women Headquarters in Washington, D.C. Commissioned by Jim and Beverly Outlaw, the bust was made by artist Ralph Batten.

Commendations

BadgePilot Badge 1st RowDistinguished Flying Cross Air Medal with four bronze oak leaf clusters Presidential Unit Citation 2nd RowAmerican Campaign MedalEuropean–African–Middle Eastern Campaign Medal with one bronze oak leaf clusterWorld War II Victory Medal

Death Bailey died on October 14, 2001, in DeLand, Florida. He was interred at Greenwood Cemetery in Daytona Beach, Florida.