Lancaster was brought up in Portugal as a merchant and soldier, but returned to England in 1587. He thereafter became a trusted employee of the London merchant Thomas Cordell, commanding his merchant ship ‘Edward Bonaventure’ in the fleet against the Armada in 1588. In 1591 he took the same ship on the first English trading voyage to the East Indies, which was disastrous in it’s loss of life and investment, but provided useful information about the Portuguese presence in the area. His second task was an expedition against the Spanish and Portuguese in South America, capturing and plundering Pernambuco. These expeditions led to the formation of the East India Company of which Lancaster became director in 1600. He commanded the four ships, ‘Hector’, ‘Susan’, ‘Ascension’ and ‘Red Dragon’, on the Company’s first expedition in 1601. The ‘Red Dragon’ and ‘Hector’ returned in September 1602 and Lancaster was knighted by James I in 1603.

In the upper left hand corner is a depiction of a ship, possibly intended to represent the ‘Edward Bonaventure’. To the right of this is an inscription giving Lancaster’s age in 1596 and his date of death, and to the right is a Latin verse. The inscriptions were presumably added after his death. His right hand rests on a terrestrial globe, indicating his voyages. This portrait, formerly at Clarendon Park, Salisbury, by the mid-19th century, was purchased at Sotheby sale in London on 8 December 1971.