The first Douglas to stride across the stage of Scottish history was Sir William Douglas who fought and died for William Wallace. His son, Sir James Douglas was a supporter and lifelong friend of Robert the Bruce. "Good Sir James" died taking Bruce's heart on a crusade to the Holy Land. The 2nd Earl of Douglas died at the Battle of Otterburn in 1388 as his army defeated an English force led by Prince Henry "Hotspur". In 1402 the 4th Earl was defeated by the same Henry Hotspur at the Battle of Homildon Hill.
William Douglas, 10th Earl of Angus died at Paris 3d March 1611, in the 57th year of his age, and was buried in the church of St. Germain de Prez, where a magnificent monument was erected to his memory