Assigned to the Army Air Corps, he received his pilot wings in 1938 at Kelly Field, San Antonio, Texas, then served two years with the Sixth Pursuit Squadron and 18th Pursuit Group in Hawaii before taking a postgraduate course in aeronautical engineering at the California Institute of Technology.

[2][3] After The US entered World War II in December 1941, Holloway was sent to China to observe Chennault's American Volunteer Group (AVG), the Flying Tigers.

During his China tour, Holloway earned status as a fighter ace, shooting down 13 Japanese planes.

After graduation from the National War College in 1951, he progressed through key staff assignments in both operations and development fields at Headquarters U.S. Air Force.

Later, as director of operational requirements, he played a key role in preparing and evaluating proposals for many aircraft and missiles.