This portrait is by the greatest American painter of the eighteenth-century, John Singleton Copley. Together with its companion work, 'Anne Irving, Mrs Duncan Stewart', it would have been painted in Boston where Copley worked until he emigrated to London in 1774. Duncan Stewart came from a famous Highland family which supported Prince Charles Edward Stuart during the Jacobite Rising of 1745. He lived in Connecticut where he held the post of Collector of Customs. During the American War of Independence he took the loyalist side. Eventually, the family estate of Ardsheal in Argyll, confiscated after the 1745 Rising, was restored to him and he returned to Scotland.