Under the leadership of Archibald "The Grim", 3rd Earl of Douglas, the illegitimate son of Sir James "The Good", the Douglases gained the Lordship of Galloway and, through marriage to Joanna Murray, the family possessions of the Murrays of Bothwell. Archibald's daughter, Mary, married the Duke of Rothsay, Prince of Scotland while his son and heir, also Archibald, wedded Princess Margaret, eldest daughter of Robert III . Archibald was also responsible for the construction of Threave Castle, a long time Black Douglas Stronghold. In 1384, Archibald defeated the English garrison at Lochmaben Castle and in so doing removed the last of the English Army in Annandale. He died at Threave Castle in 1400.Carrying on the military tradition of his fore fathers, Archibald "The Tyneman", 4th Earl of Douglas, Duke of Touraine fought against King Henry IV of England at Shrewsbury. Archibald, bent on the extermination of the King, hunted the field ruthlessly for the Monarch. King Henry, for his own security, had dressed a number of his noblemen in the royal attire. Three of these impostors met their fates at the blade of Douglas. Douglas was captured and mercifully released by the victor.source:http://charm.www5.50megs.com/drysdale/drysdale.htmladded:07jan2006
Hij had een relatie met Joanna Moray Countess of Strathearn of Moray.
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