William Dring (1904-90) earned his reputation as a fine draughtsman and portrait painter whilst studying under Henry Tonks at the Slade School of Art between 1922 and 1925. He worked as a teacher of drawing and painting at the Southampton School of Art until 1940 when he was employed by the War Artist Advisory Committee, first as official war artist to the Admiralty and later to the Air Ministry. He made a large number of portrait drawings of individuals and groups, all remarkable for their informality. Dring travelled extensively to complete his commissions. The drawing is always precise and carefully modelled using pastel, a medium in which he specialised, and which allowed him to capture the likeness and spirit of his subjects quickly and under a variety of circumstances.

George David Archibald Gregory (1909-75) joined the Navy in 1930 as Sub-Lieutenant, but was promoted to Lieutenant in 1932. Between 1938 and 1940 he was placed in command of HMS ‘Sturgeon’ in the North Sea. His command of this S-class submarine suffered a shaky start, when they fired three torpedoes against fellow British submarine HMS ‘Swordfish’, which fortunately missed. Soon after, an attack on a German U-Boat, 20 miles off the coast of Denmark, failed. Triumph soon followed however when the ‘Sturgeon’ successfully sank several German, Danish, and Norwegian ships. In 1939, Gregory was awarded a Distinguished Service Order after a successful attack on German armed trawler V-209/ ’Gauleiter Telschow’, 100 nautical miles west of the German islands of Helgoland.

After this initial honour his career went from strength to strength. He was promoted to Lieutenant Commander in October 1940 and a month later was awarded a Bar to his DSO after several more successful missions. As Lieutenant Commander he was placed in command of two more submarines HMS ‘Oberon’ and HMS ‘Traveller’, until his promotion to Commander in 1942. After the war he was stationed as Commander on the British destroyer HMS ‘Constance’, which served in the Far East Division as part of a Flotilla. Gregory rose through the ranks of the Navy until his retirement in 1966, being promoted to Captain in 1951, Rear-Admiral in 1960 and Vice-Admiral in 1963. In recognition of his life-long service he was awarded with a CB in 1962 and became KBE in 1964. Although Dring captured Gregory’s likeness early in his career, we can still see in his eyes and expression a dignity and thoughtfulness which no doubt contributed to his later success.