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Whitlock was educated at Itchen Grammar School and the University of Southampton. He volunteered for the British Army upon graduation, and soon joined the Hampshires. Part of the British Expeditionary Force, he was one of those evacuated on the last day at Dunkirk, escaping aboard a fishing trawler. At the end of 1940, he volunteered for the Airborne forces. Assigned to the British 1st Airborne Division, he landed near Nijmegen during Operation Market Garden and was one of the relatively few British airborne troops to escape death or capture during the operation. An excellent linguist, he remained in the Army for an extra year, acting as a German translator during the occupation.