Air Chief Marshal Sir John Cheshire joined the Royal Air Force in 1961 as a cadet at the RAF College, Cranwell. On graduation as a pilot, he flew Hastings transport aircraft with No24 Squadron at RAF Colerne, and then C130s with No48 Squadron in Singapore. He then returned to Cranwell as an instructor, before serving at HQ 38 Group where he was responsible for tactical air support for the United Kingdom Special Forces. In 1974 he attended the Canadian Forces Staff College and then returned to flying duties at Lyneham on C130 aircraft. Initially, he served as Flight Commander Operations on No30 Squadron and then as Commander of the Special Forces Flight. This was followed by a tour in the Air Plans Directorate of the Ministry of Defence in London.
From 1980-1982 Air Chief Marshal Sir John Cheshire served as the last RAF Commander of the Air Wing in Brunei where he flew Bell, Sikorsky and Bolkow helicopters as well as the HS 748 of the Sultan's Royal Flight. He then returned to the United Kingdom as the Station Commander of RAF Lyneham. In 1985, after a short tour as Group Captain Contingency Plans at HQ United Kingdom Air Forces, High Wycombe, he commenced Russian language studies prior to being appointed as the UK Defence and Air Attache to the Soviet Union in 1987. He returned from Moscow at the end of 1990 and was appointed as the Deputy Commandant of the RAF Staff College, Bracknell. In 1992, he was appointed as Assistant Chief of Staff Policy and Requirements, at the Supreme Headquarters Allied Powers Europe. In 1995 he was appointed as United Kingdom Military Representative at Headquarters NATO, from where he moved to his present appointment, Commander-in-Chief, Allied Forces Northwestern Europe, on 11 March 1997.
Air Chief Marshal Sir John Cheshire's interests include squash, game shooting, golf and collection of antiques. He is married to Sam and they have a married daughter and son, who is a serving Army Officer.