William, 8th Earl of Douglas, set out for London in 1451 to foment a rebellion against the Scottish Crown. After the murder of William, his brother James, 9th Earl of Douglas, attempted to avenge his death by armed opposition to King James II. Betrayed by almost all his allies, but not the Bells, the 9th Earl lost at Arkinholme on 1 May 1455. The Earl escaped to France, but his possessions went to the victors and the Bell Family, forfeited Kirkconnel to the Maxwells.
In 1484, the forfeited 9th Earl of Dougas returned to Scotland with a small Army of 500 men. He rested at Bell’s Castle on the eve of the Battle of Kirtle. Not all of the Douglas family supported this invasion of Scotland. The 4th Lord of Drumlanrig, William Douglas, was killed on 22 July 1484 at the Battle of Kirtle, fighting for the Crown against his cousin, 9th Earl of Douglas.
Also killed at this Battle of Kirtle was Sir Simon Carruthers, the oldest brother of Archibald Carruthers, 7th Lord and 2nd Baron Mouswald. Sir Simon was Warden of the West March at the time of his death. Sir Simon's daughters married into the Kennedy and Jarding families. Although not definitively recorded, it was suggested by A. Stanley Carruthers in his book Records of the Carruthers Family, that Archibald Carruthers, 2nd Baron Mouswald, was also killed at the Battle of Kirtle, since he also died in 1484.
An interesting side note, Archibald's son, Sir Simon, 8th Lord and 3rd Baron Mouswald, married the daughter of Douglas of Drumlanrig, before this Sir Simon was murdered in 1504. The reason for the murder, by Thomas Bell of the Broom and Thomas Bell of Currie, is not known. But it has been suggested that it might have been connected with the acquisition of the Pennersaughs estate that Sir Simon had bought in 1499. Pennersaughs is adjacent to the property of Middlebie, owned by the Bells to which the murdering Bells were related.