A full length portrait, facing to the left, in a leather coat and breast plate, red, gold laced breeches thrust into boots. He wears a black full bottomed wig and a sword on a heavy silver and gold embroidered baldric and holds a baton in his left hand. He stands against a backdrop of curtains and in the background is a gauntlet and helmet on a covered table. There is sea and sky beyond.

A son of Elizabeth, Queen of Bohemia and a nephew of Kind Charles I, Prince Rupert fought on land for his uncle throughout the Civil War. He became famous as a cavalry leader and in 1644 was made a Commander-in-Chief. After the war was lost, Rupert retired to the Continent where he took command of the Royalist fleet which was practically destroyed by Blake in 1650. After the Restoration he commanded the van at Lowestoft in 1665. He shared command of the fleet with Albermarle at the Four Days Fight and at the St James Day victory, which gave the English command of the seas in 1666. In the Third Dutch War he took command of the Anglo French fleet after the Duke of York’s retirement early in 1673. He commanded at the two battles off Schoonvelt and at the battle of Texel in the same year.

The portrait was painted in about 1834-45 for the Greenwich Hospital Collection and extended to full length. It is based on the three-quarter length Flagman of 1666 in the Royal Collection mentioned in Pepys Diary of 18 April 1666.