The sitter was born in America the youngest son of John S. Winthrop of New London, Connecticut. He was a direct descendant of John Winthrop (c.1587-1649) - one of the leading figures in the foundation of the Massachusetts Bay Colony. Over time, the Winthrops remained loyal to the British Crown and in 1782 Robert joined the Royal Navy. After a successful career he achieved the rank of Vice-Admiral of the Blue in 1830. This portrait was painted in 1805, the year after his marriage to Sarah Farbrace at Dover.