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James V had come to the throne as a boy as a direct result of his father being killed by the English at Flodden in 1513. His first years of office were under a Regent and Council, who held him as a minor under the tutelage of Angus and Douglas, which amounted to little more than imprisonment. His Guardians had ensured that his education was minimal, attempting to ensure that when he reached his majority he would still be dependant on them. After several attempts to escape the Guardians he at last succeeded in the summer of 1528 arriving disguised in Stirling.

The Country rose in his support and after a brief campaign Douglas was defeated and Angus escaped to England. In 1530 James having set up his own Council in Edinburgh, was annoyed that the disorganised state of the Borders represented a weakness in the governance of his kingdom and avowed his intention to reduce them to order, no doubt remembering that Douglas originated in the Borders. Before this could be achieved he had to remove those powerful Border lords whose influence might thwart his plans, so he commanded the imprisonment of the Earl of Bothwell, Lord Home, Lord Maxwell, Scott of Buccleuch, Ker of Ferniehirst, and other powerful Border chiefs and proceeded into Eskdale and Teviotdale with a force of 8,000 men to do justice on the Reivers. Cockburn of Henderson and Scott of Tushielaw, two notorious offenders were said to be hanged before the gates of their own castles, but the fate of Johnie Armstrong, of Gilnockie, near Langholm, produced a much deeper impression, although not unmingled with some commiseration, on the Reivers.

Johnie was undisputed "King of the Borders" and it was said that "....from the Scottis bordour to Newcastell of England, thair was not ane of quhatsoevir estate bot payed to this John Armestrange ane tribut [blakmeale] to be frae of his cumber ......and albeit that he was ane lous leivand man, .....he was als guid ane chieftane as evir was upon the borderis...." James invited Johnie to hunt with him at Carlenrig, but Johnie and his men turned up to the meet so splendidly dressed and equipped that the young King took offence. At first Johnie tried to talk his way out of trouble, offering half his "blakmeale" takings, but when he realised the futility of trying to bribe James, he then famously insulted the King, by saying proudly: "I am but a fool to seek grace at a graceless face!"; Johnie and his men were promptly "....all hangit apoun growand trees....". It is recorded that all Johnie’s estates were awarded to the imprisoned Lord Maxwell after this incident, rather suggesting that the whole thing had been a plot from the start, with Maxwell apparently shown to have nothing to do with it.

James V may have believed that his authority was well stamped on the Borders by this raid into the Reivers heartland, but he underestimated Johnie’s place in the scheme of the Borders: Johnie may have been one of the worst brigands to ride "....a heilk moon...." , but he was an Armstrong which was one the largest and most powerful families on the Borders. Reivers could feud amongst themselves, even to the death, but they had a habit of allying together against outsiders.