lands and took much booty from Darlington and other nearby towns and villages. Sir James 'The Good' Douglas' son William succeeded to the title as Lord of Douglas but may not have completed his title to the estates, possibly because he might have been underage. He died at Halidon Hill with his uncle, Sir Archibald Douglas. James' younger brother, Hugh the Dull, Lord of Douglas, a canon serving the See of Glasgow and held a prebendary at Roxburgh became Lord Douglas in 1342; Hugh of Douglas resigned his title to his nephew, the youngest surviving son of the Regent Archibald, William Lord of Douglas who was to become the first Earl. The First Earl's legitimate son James Douglas, 2nd Earl of Douglas succeeded him. His illegitimate son by Margaret Stewart, 4th Countess of Angus was George Douglas, 1st Earl of Angus, who was the progenitor of the Earls of Angus also known as the "Red Douglases". The prestige of the family was greatly increased when James Douglas's great nephew, James Douglas, 2nd Earl of Douglas married Isabel, a daughter of King Robert II of Scotland. In 1388 at the Battle of Otterburn he was instrumental to the Scots' victory but was killed during the fighting. Leaving no legitimate heir, his titles passed to the illegitimate son of his great-uncle. 15th century Wars with England Archibald Douglas, 3rd Earl of Douglas did much to consolidate the family's power and influence. He successfully defended Edinburgh Castle against Henry IV of England in 1400 but died the following year. His son, Archibald Douglas, 4th Earl of Douglas, married the daughter of Robert III of Scotland. The fourth Earl fought against King Henry IV of England at the Battle of Shrewsbury in 1403, where he was taken prisoner. In 1406, with the death of the king, the 4th Earl of Douglas became one of the council of regents to rule Scotland during the childhood of James I of Scotland. In 1412, the 4th Earl had visited Paris, when he entered into a personal alliance with John the Fearless, Duke of Burgundy, and in 1423, he commanded a contingent of 10,000 Scots sent to the aid of Charles VII of France against the English. He was made lieutenant-general in Joan of Arc's French army, and received the title Duke of Touraine, with remainder to his heirs-male, on 19 April 1424. The newly created French duke