[4] Born in Maryland, Cropper earned a Bachelor of Arts in engineering operations from Iowa State University in 1981.

He is a distinguished graduate of the Naval War College, earning a third Master of Arts in national security and strategic studies.

[5] The PBS television series Carrier was filmed while Cropper commanded the air wing aboard the USS Nimitz, and he appears in several episodes.

Naval Test Pilot School, served as a military assistant in the Office of Secretary of Defense William Cohen, and as the Navy Federal Executive Fellow at the Brookings Institution.

He also led "Strike University" at the Naval Strike and Air Warfare Center, served as chief of staff, U.S. Third Fleet, and headed the Joint Chiefs of Staff Working Group chartered with the development of national level security strategy.