A three-quarter length portrait, to the left, in embossed half armour and red trunk hose. Grenville is shown holding a baton in his right hand. In the left background is a plumed close helmet.

In 1585 he commanded the fleet which his cousin, Sir Walter Raleigh, had organized to colonize Virginia. On the return journey he captured a Spanish ship and pillaged the Azores. He was second in command of the Azores Fleet under Lord Thomas Howard which hoped to capture the Spanish treasure fleet in 1591. The English fleet was nearly caught at the Azores by a much superior Spanish fleet but escaped except for Grenville, who, it is thought from bravado, engaged the Spanish and fought for 15 hours against 15 ships. He then surrendered and died of his wounds. The ‘Revenge’ his flagship, sank shortly afterwards. The painting is inscribed ‘Ano Dni Aetatis suae 29’ ‘Killed in a sea fight near the Azores’. It is a copy of a contemporary original by an unknown artist. The original is lost and there is another version of this portrait in the National Portrait Gallery.