David Wanklyn Lieutenant Commander Malcolm David Wanklyn ( 28 June 1911 – 14 April 1942 ) was the Allies ' most successful submariner in the Second World War in terms of tonnage sunk , and received the Victoria Cross , the highest and most prestigious award for gallantry in the face of the enemy that can be awarded to British and Commonwealth forces . Early life . He was born in Kolkata , India to William Lumb Wanklyn and Marjorie Wanklyn ; he was married to Elspeth . Military career . Wanklyn joined the Royal Navy in 1925 , trained at Dartmouth Naval College , and was assigned as a midshipman in 1930 to the battleship HMS " Marlborough " , part of the Third Battle Squadron ; and the following year to the battlecruiser . After attending promotion courses in 1932 he joined the navy ' s submarine arm . From August 1933 he served in the submarine HMS " Oberon " which was part of the Mediterranean Fleet , but in October 1934 transferred to HMS " L56 " based with the rest of the 6th Submarine Flotilla at Portsmouth . In 1936 he was promoted to First Lieutenant ( i . e . second in command ) of the boat . In January 1937 he moved to HMS " Shark " . He became second in command of HMS " Otway " , part of the 5th Submarine Flotilla in August 1939 but was shortly afterwards promoted to be commander of HMS " H32 " . He was given command of HMS " Upholder " , which was then under construction , in August 1940 . As a 29 year - old Lieutenant - Commander in the Royal Navy during the Second World War , he was awarded the VC for his " utmost courage " on 24 May 1941 south of Sicily . Commanding HM Submarine " Upholder " on her seventh patrol , an Italian troopship ( the 18 , 000 ton former liner " Conte Rosso " ) , which was with a strongly protected convoy , was torpedoed while the submarine ' s listening equipment was broken and periscope use was not reliable . The troopship sank , " Upholder " escaped after evading 37 depth charges . Death . By the end of 1941 Lieutenant - Commander Wanklyn had sunk nearly 140 , 000 tons of enemy shipping , including a destroyer and troopships , tankers , supply and store ships . Wanklyn was killed along with his crew when " Upholder " was lost on her 25th patrol , becoming overdue on 14 April 1942 . The most likely explanation is that she fell victim to depth charge s dropped by the Italian torpedo boat " Pegaso " north east of Tripoli on 14 April 1942 although no debris was seen on the surface . The attack was 100 miles away from Wanklyn ' s patrol area ; it is thought that he may have changed position to find more targets . It is also possible that the submarine was sunk by a mine on 11 April 1942 near Tripoli , when a submarine was reported as approaching a minefield . More recent research carried out by Italian naval specialist Francesco Mattesini points to a German aerial patrol supporting the same convoy , composed of two Dornier Do - 17 s and two Messerschmidt Bf - 110 s , which attacked an underwater contact with bombs two hours before the " Pegaso " incident . The author also asserts that the seaplane crew was unsure if the target they pintpointed to " Pegaso " was a submarine or a school of dolphins . Mattesini , however , admits the possibility that " Pegaso " could have finished off the submarine previously damaged by the German aircraft . Wanklyn was the Allies ' most successful submariner in terms of tonnage sunk .