In the 14th century one of the most important events in Scottish history took place in Dumfries. When Alexander III died in 1286 and his young grand-daughter Margaret, the Maid of Norway, died soon after, Scotland was left without a ruler. The Scots nobles looked to Edward I of England to choose the next King. He wanted to bring Scotland under his control so first he insisted that the claimants recognise him as overlord and then he appointed John Balliol, the son of Lady Devorgilla, as his puppet King. He, like his chief rival Robert Bruce from Annandale, was descended from David I.

When he demanded that Scotland supply men and money for an English war against the French, the Scottish barons instead made an alliance with France in 1295. Edward marched into Scotland with a huge army and defeated Balliol at Dunbar. He installed English nobles in the Scottish castles and the Earl of Surrey was made governor of Scotland. A rebellion led by William Wallace of Elderslie, near Paisley, broke out. Together with Andrew of Moray they succeeded in recapturing Scotland. Edward, however, returned in 1298 with another army and defeated them at Falkirk. Wallace escaped and was not captured until 1305 when he was sent to London and executed.

Scotland looked as if it was to be simply an English province. Robert Bruce again came to the fore. His chief rival to the throne was John Comyn, Lord of Badenoch. Known as "Red" Comyn he was the nephew of John Balliol. At first they tried to come to an agreement but on Thursday 10th February 1306 they met in the church of the Greyfriars in Dumfries. An argument developed and Bruce stabbed Comyn. He dashed outside to his colleagues and said "I doubt I have slain Comyn". One of then, Sir Roger de Kirkpatrick, replied "You doubt? Then I'll mak siccar (make sure)" and dashed inside the church and stabbed Comyn again, killing him. That afternoon Bruce recaptured the castle at Castledykes from its English garrison and began the fight that eventually led him to the Scottish throne.

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