His father, John Lyman Whitehead Sr, was a 1916 Yale graduate who served as the Business Manager and Treasurer at the now-defunct Saint Paul's College.

[3] African American aviation units were concentrated in the 477th Composite Group,[4] which moved to Lockbourne Army Air Base in Ohio on 13 March 1946.

[4] Whitehead briefly left the Air Force in January 1947 to enter West Virginia State College, where he earned a Bachelor of Science degree in 1948.

After graduation he returned to duty with the 332nd Fighter Group,[2] but it was disbanded on 1 July 1949,[3] in the wake of President Harry S. Truman's Executive Order 9981 integrating the armed forces.

[2] In June 1949, Whitehead was posted to Williams Air Force Base in Arizona, where he became the first African American jet pilot instructor.

[2][5] In the 1960s he flew combat missions in the Vietnam War, and served at Edwards Air Force Base in California as a squadron and deputy group commander.