General Cuddihee enlisted with the Army Air Corps aviation cadets on September 21, 1942, and was commissioned a second lieutenant and awarded his wings on January 7, 1944, upon completion of pilot training. A P-47 Thunderbolt pilot, General Cuddihee flew 12 combat missions in the European Theater of Operations, becoming a prisoner of war from July 29, 1944, to April 29, 1945. He joined the 133rd Fighter Squadron, New Hampshire Air National Guard (NHANG) on December 21, 1948, as a fighter pilot flying P-51 Mustangs. He served on extended active duty with the United States Air Force during the Korean Conflict as an instructor fighter pilot and aircraft maintenance officer, returning to the NHANG in June of 1953. He became the flying squadron operations officer in 1954 when the 133rd converted to the F-94B Starfire. General Cuddihee assumed command of the 133rd Fighter Interceptor Squadron in 1956, a position he held when the unit was assigned F-86 Sabrejet aircraft in 1958. General Cuddihee again served on active duty when the NHANG was activated during the Berlin Crisis, 1961–1962, flying C-97 Stratofreighters for the Military Air Transport Service.

He was appointed Deputy Commander for Operations, 157th Airlift Group, on January 30, 1966, concurrent with the unit’s relocation from Grenier Field in Manchester to Pease Air Force Base. He oversaw the 157th’s conversion to the Military Airlift Command’s C-124 Globemaster in 1968, followed by a conversion to Tactical Air Command’s C-130 Hercules in 1971. General Cuddihee was appointed commander of the 157th Airlift Group on August 2, 1975, when the unit was converting to KC-135 Stratotankers to assume an aerial refueling mission with the Strategic Air Command (SAC). Through his efforts, the 157th Air Refueling Group became a true partner in the Total Force as the first Air National Guard (ANG) unit to stand alert with an active duty SAC unit. A command pilot with more than 20,000 flying hours in more than 20 different types and models of military aircraft, General Cuddihee logged his 20,000th flying hour during a historic refueling mission on December 16, 1977. This mission marked him as the most senior military aviator in the USAF, Air Force Reserve, or ANG at that time. General Cuddihee served as an air technician from June 1, 1953, to March 16, 1979, in positions of aircraft maintenance officer, flying training instructor, operations officer, and Air Commander. He served as 157th Air Refueling Group Commander until July 16, 1978, when he was appointed Assistant Adjutant General Air for New Hampshire. He was promoted to Brigadier General on February 8, 1979, and retired on October 31, 1981, with more than 39 years of service.

During his years as commander of the 157th, General Cuddihee’s presence was so pervasive, and the traits of dedication and excellence were so ingrained within the organization, that the NHANG was synonymous with his name. Brigadier General James E. Cuddihee’s legacy is one of highly-trained and motivated participants in the Total Force. Each year, the 133rd Air Refueling Squadron presents an award to the NHANG crewmember who best exemplifies the spirit and high standards of professionalism he exemplified and inspired. In addition, the 157th Air Refueling Wing is proud to dedicate its Operations facility to this outstanding aviator and leader. From “Granite Wings: A History of the New Hampshire Air National Guard 1947–1998,” Gen. Cuddihee received many honors and awards, including the Air Medal, Purple Heart, and the Legion of Merit with Oak Leaf Cluster for his “leadership, dedication and foresight.” The latter was presented to him by President Reagan.A true citizen soldier, in his hometown of Dublin, Cuddihee served as a selectman for five terms between 1948 and 1984. He enjoyed coaching Dublin’s Little League baseball team for many years. In addition, he was a member of the Masons, the Scottish Rite, the Peterborough Rotary, the Reserve Officers Association, and the American Legion.