The death of his nephew William, Lord of Douglas, and brother Sir Archibald at Halidon Hill left Hugh ‘The Dull’ Douglas the succession of the patrimony of Douglas. However, Scotland at this time was going through the paroxysms of the Second War of Independence, and Edward III and Edward Balliol controlled much of the south of the country. Balliol, having paid homage for his kingdom to Edward, had also ceded to the Crown of England, in perpetuity, the Forests of Selkirk, Ettrick and Jedburgh, and the shires of Roxburgh, Peebles, Dumfries, Linlithgow, Edinburgh and Haddington – in essence, all the territories in which the Lord of Douglas held property. Edward had re-appointed Douglasdale to Robert de Clifford, 3rd Baron de Clifford, grandson of Robert de Clifford, 1st Baron de Clifford, who had been granted it by Edward I of England following his dissolution of the Kingdom of Scots in 1296. Clifford never got to enjoy his new properties, by way of stout resistance from the men of Douglas led by William Douglas of Lothian.
Hugh the Dull had probably escaped to France to the court of David II at Château Gaillard in 1337. Here it was that his young nephews William Douglas, 1st Earl of Douglas and Archibald Douglas, 3rd Earl of Douglas had sought refuge. Certainly by that date, Edward III had appointed Andrew de Ormiston as prebend of Hugh’s parish of Roxburgh.
The second son of William the Hardy, Lord of Douglas, William Wallace’s companion in arms, and Eleanor Ferrers. Hugh’s elder brother was Sir James Douglas, a hero of the Wars of Independence, and his younger was Sir Archibald Douglas, Guardian of the realm, and Scots commander at the Battle of Halidon Hill.By 1337, William Douglas of Lothian, using the same guerrilla tactics employed by Hugh’s brother James, had carved out a power base in the Borders and had styled himself Lord of Liddesdale. It is assumed that the Lord of Douglas, no warrior, had given executive control of the Douglas territories in the south to him. In 1342, Liddesdale, hankering after formal power, coerced the Lord of Douglas into resigning the majority of the rest of the Douglas territories over to him with all administrative powers pertaining. Hugh of Douglas resigned his lordship in favour of his nephew William, still in France, making him Ward of Liddesdale.
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