In a military career spanning 35 years, Charles G. Chick" Cleveland made numerous contributions to tactical fighter operations, military education, and top-echelon planning. Graduating from the Military Academy in 1949, he chose to become an aviator and earned his pilot wings at Williams AFB, Arizona. He was first assigned to the 31st Strategic Fighter Wing at Turner AFB, Georgia flying F-84s. Cleveland was introduced to combat in 1952 and served as a flight commander flying F-86s with the 334th Fighter-Interceptor Squadron at Kimpo Air Base, South Korea. In Korea, he shot down four MiG-15s and is credited with two probably destroyed and four damaged.
Shortly after returning from Korea, he transferred from Turner AFB to the 27th Fighter-Bomber Wing at Bergstrom AFB, Texas, where he was the project officer for the unit's conversion to the F-101. On 12 December 1957, during Operation FIRE WALL, Cleveland flew the F-101 at an average speed of 1212.6 mph, 5 mph faster than the official record set by Major Adrian Drew on 19 December 1957. In February 1959, he was reassigned to Royal Air Force Station Woodbridge, England, where he served as a flight commander and Operations Officer in the 78th Tactical Fighter Squadron, and then as Commander, 92nd Tactical Fighter Squadron. On 10 August 1962, while at Woodbridge, Cleveland became the first pilot to achieve the 1000-flying-hour mark in the F-101. His Air Force career next took him to Wright-Patterson AFB, Ohio as an F-111 project officer.
He then went to Vietnam, where he served as the Executive Assistant to General Westmoreland, Commander, US Military Assistance Command. After Vietnam, he attended the Royal Air Force College of Air Warfare and was then assigned to Headquarters 3rd Air Force. In April 1970, he became the Vice Commander, 20th Tactical Fighter Wing, Royal Air Force Station Upper Heyford, England. A year later, he assumed command of the 3535th Navigator Training Wing at Mather AFB, California and initiated training for the concept of a pilot/navigator team in two-seat fighter aircraft. Following tours at Air Training Command (ATC) headquarters and the Pentagon, he returned to Randolph AFB as Vice Commander, ATC. Lieutenant General Cleveland's capstone military assignment was Commander, Air University, Maxwell AFB, Alabama from July 1981 to August 1984. He retired with over 4500 flying hours and 145 combat missions in Korea and South Vietnam. After his retirement, he was Executive Director for the United Way in Montgomery, Alabama and served as the Commissioner, Department of Human Resources for the state of Alabama.
On 5 August 1952, Lieutenant Charles G. Cleveland and his wingman, flying F-86s, sighted two MiG-15s at 7000 feet, near the Yalu River. Lieutenant Cleveland met his adversary in a left-to-left pass and opened fire when he maneuvered to the MiG's "6." Taking heavy hits in the fuselage, the MiG pilot made a fatal error by reversing and starting a right climbing turn. Cleveland "saddled up and put several more rounds in to the MiG. When the engine section exploded at 11,000 feet, the pilot wisely ejected. This marked the first of four confirmed MiG-15 kills Cleveland would score over North Korea.