picked de' Conti for his traditional style of oil painting. Prominently inscribed on the top left the painting reads, "The Earl of Douglas surnamed Black Dudley" (referring to James, Lord of Douglas). It is unknown how many renditions de' Conti created, but there is one that resides in the Seattle Art Museum, another once owned by Henry VIII belongs to the Royal Family, and at least one belongs in a private collection. Rise to power Sir William the Hardy is the first of the Douglas Lords on record to take a major part in domestic and international affairs. He partook in Wallace's uprising against English rule in Scotland and died captive in the Tower of London. His son Sir James Douglas, his estates forfeit to the English crown, swore allegiance to Robert the Bruce in 1306 prior to the latter's coronation, and was to share the deprivations and small victories of Bruce during the years leading up to Bannockburn. Afterwards he was appointed Warden of the Western March on the Scottish Border. Following Bruce's death, Sir James Douglas, now known as either "the Black Douglas" to the English, or the "Good Sir James" to the Scots, took the King's heart on crusade, and died fighting the Moors in Spain. Earldom of Douglas The Good Sir James's nephew William, Lord of Douglas was created 1st Earl of Douglas in 1358, and greatly increased Douglas territory by marrying Margaret, Countess of Mar. The creation of the Earldom can be accurately dated to 26 January that year, because of a charter witnessed by Douglas on the 25 January where he is described as "William, Lord of Douglas, Knight", and another of the 27th of the month as the Earl of Douglas. The power of Douglas was further increased by the marriage of the 2nd Earl to Princess Isabel, daughter to Robert II of Scotland. The acme of Douglas territorial power came when Archibald the Grim, Lord of Galloway a bastard son of the Good Sir James inherited the Earldom following the 2nd Earl's death at the Battle of Otterburn. "Black Archibald" as he was also known, was by right of conquest Lord of Galloway; and by right of his wife, the Moray heiress Joanna de Moravia, the Lord of Bothwell and its vast entail. Already one of the largest landowners in the realm, Archibald the Grim was now the greatest Tenant-in-chief of the