A three-quarter-length portrait seated to right in commander's undress uniform, 1921 pattern and wearing his cap. His decoration ribbons are displayed prominently on his left. He sits with his hands clasped in his lap and faces straight ahead out of the picture space.

Captain Bennington joined the Navy as a rating. His ability soon won him a commission and he became an acting sub-lieutenant in 1933, serving in HMS 'Victory'. His distinguished career in submarines began in 1935, when he joined HMS 'Porpoise' and in 1936, he was advanced to lieutenant. He was promoted to lieutenant commander in command of the 'Porpoise' in 1942, by which time he had already gained his first DSC. Between 1942 and the end of the Second World War, his patrols against enemy shipping in the Middle and Far East became legendary, and they earned him the distinction of becoming one of the most highly decorated officers in the history of the Navy. Shortly after the war, he was promoted to captain at the unusually young age of 35. He was the only submariner to win two DSOs and three DSCs, and this distinction has been carefully observed in the portrait.

The artist was closely associated with the Euston Road School from 1937 and achieved eminence through portraiture during the Second World War. After serving three years with the Royal Artillery, he was appointed an official war artist in 1943. This painting was received from the War Artists' Advisory Committee.