This painting is the only known portrait of Sir William Kirkcaldy of Grange completed during his lifetime. Recognised as one of the most influential figures of the time in Scotland, Kirkcaldy led an intriguing life. After implication in the murder of Cardinal Beaton in 1546, Kirkcaldy fled to France only to be captured and imprisoned in 1547. After escaping in 1550 he began service with the French army. It was also at this time that Kirkcaldy became a spy, and, subsequently, exploited his associations with France and Scotland to the advantage of the English crown. His services to the queen did not, however, save him from the gallows following his unsuccessful defence of Edinburgh Castle against the Earl of Morton in 1572. He was tried for treason and executed in 1573.