On 09 Feb 1307 the Battle of Loch Ryan was a victory of local forces, led by Dungal MacDowall, supporter of King Edward I, over a force consisting of 1000 men and eighteen galleys led by Thomas Bruce (age 23) and Alexander Bruce (age 22), brothers of Robert "The Bruce" I King Scotland (age 32), supported by Malcolm McQuillan, Lord of Kintyre, and Sir Reginald Crawford. Only two galleys escaped. Malcolm McQuillan was captured an summarily executed.

Thomas Bruce (age 23), Alexander Bruce (age 22) and Reginald Crawford were hanged (possibly hanged, drawn and quartered) at Carlisle, Cumberland [Map].