James ‘the Black’ Douglas: The Most Feared Knight in Scottish History

In my humble and entirely professional opinion, James Douglas could beat William Wallace in a fight. Before you scream ‘heresy!’, let me bolster that admittedly extraordinary claim with equally extraordinary evidence.

James Douglas, Robert Bruce’s indomitable captain during the Wars of Independence, is overshadowed only by Bruce himself as the most compelling of Scotland’s fourteenth century personalities. Douglas is something of a Janus figure in the history of the British Isles. While many Scots came to know him as ‘the Good’ Sir James for his championing of Bruce’s cause, it was his mastery of fear as a tool of war, his personal ferocity in battle, and his brutally effective raiding style that caused people in the north of England, often subject to said raids, to bestow on him his most enduring moniker – ‘the Black’ Douglas. His bogeyman reputation amongst the English was such that, while he was still very much alive and active, mothers in Northumbria and Cumbria supposedly sang to their children:

 Hush ye, hush ye, little pet ye,

Hush ye, hush ye, do not fret ye,

The Black Douglas shall not get ye…

 A chilling folk story has this refrain followed by a calloused hand grasping the mother’s shoulder, and a growling voice uttering, “don’t be too sure of that…”

James Douglas doing his black work at the Douglas Larder. Illustration by Andrew Hillhouse.

James Douglas doing his black work at the Douglas Larder. Illustration by Andrew Hillhouse (andrewhillhouseprints.co.uk)


...and me doing my best Black Douglas impression!

…and me doing my best Black Douglas impression!

Douglas led and partook in many dramatic episodes in the period between joining Bruce in 1306 and his death in 1330, including the crafty and brutal retaking of his ancestral home, Douglas Castle, in the incident know as the ‘Douglas Larder’ in 1307, and the capture of the nigh-impregnable Roxburgh Castle in the Borders by surprise attack in February 1314. Douglas fought at Bannockburn, though he was not a commander of his own schiltron spear formation as depicted in John Barbour’s The Bruce, but rather acted as a sub-commander connected to King Robert’s own force.

In the aftermath of the battle, Douglas pursued the defeated Edward II to Dunbar, with Barbour suggesting he did so with a force outnumbered by the king’s five to one and following so close that the English king’s company dared not even stop to ‘make water’. This and other actions brought James the reputation of being “mair fell [fierce] than was ony [only] devill in hell”. His battle record speaks for itself: according to Barbour, Douglas gained fifty-seven victories to thirteen losses, and those losses were more tactical withdrawals than true routes. 

The final and perhaps most famous episode of all came with the death of King Robert Bruce on June 7th, 1329. Upon his death Bruce assembled his captains and tasked Douglas to bear his heart on crusade to the Church of the Holy Sepulchre in Jerusalem, possibly as posthumous repentance for Bruce’s murder of his rival for the crown, John Comyn, at the High Kirk in Dumfries in 1306 and the suffering he inflicted on his own people with his ‘scorched earth’ tactics. Jerusalem, however, was firmly in the hands of the Mamluk Sultanate, but an alternative cause was readily available in the form of King Alfonso XI of Castile’s crusade against the Moors in Andalusia, Spain. Douglas and a hand-picked group of Scots knights bade their homeland farewell, promising to return Bruce’s heart to Melrose Abbey upon their victory and with Douglas bearing the heart in a cask around his neck.

A battle ensued in the shadow of the Castillo de la Estrella, the ‘Castle of the Stars’, near the village of Teba between Seville and the Moorish power base in Granada. Somewhere a command was misinterpreted, causing the Scots to charge the Moorish lines unaided. Inevitably they were surrounded. His end clearly upon him, the story as recounted by Sir Walter Scott goes that Douglas removed the cask from around his neck, declared aloud “Pass first in fight…as thou wert wont to do, and Douglas will follow thee, or die”, then charged the enemy one last time. 

When the surviving Scots searched the field following the crusader’s victory, they found Douglas dead, hewed with “five deep wounds” and with the cask unharmed underneath his broken body. Douglas’ flesh was boiled from his bones as per the usual custom for long-distance transport of noble remains and his heart was removed, now a companion to that of Bruce, while his skeleton was interred in St Bride Kirk in his home village of Douglas. It is this episode that gives us the term ‘Brave heart’, used by Scott, but never in reference to Wallace – the true Braveheart is Robert Bruce, and his steadfast friend the Black Douglas.

The specifics vary depending on whom you ask. No mention of such last words is made in The Bruce, the main source for later writers, and so it seems that it was, like so much else, a product of Scott’s imagination in Tales of a Grandfather. After all, if ever there was the Romantic equivalent of a ‘Midas touch’, Scott possessed it. What we know is that Douglas fought and died at Teba bearing Bruce’s heart; the specifics, as with all great stories, are perhaps best left to the imagination.

In case you’re still not convinced, it seems Douglas was not only a master of the arts of war but the art of the one-line comeback. During the Andalusian Crusade an English knight approached Douglas when the Scot first arrived at the crusader’s court. By that time Douglas’ reputation had haunted the imaginations of warriors throughout Europe, and none could believe that this master of terror was the man before them – he didn’t even have facial scars, and everyone knows a true knight bears his scars like a badge of honour. The English knight remarked as such, and Douglas – retaining total poise and, I like to imagine, taking a bit out of an apple like a cartoon villain – retorted, “Praise God, I always had strong hands to protect my head.” Basically, anyone who got close enough to give him a scar didn’t survive to tell the tale. 

Another was a snap back at the Pope himself. While laying siege to Berwick, then a part of Scotland but occupied by an English garrison, Douglas received a letter from the Pope. It demanded that he cease shedding the blood of fellow Christians and abandon the siege at once, on pain of excommunication and eternal damnation. Douglas, not one for half measures or heavenly ideals, made his intent clear. His reply was as simple as it was defiant: “I would rather enter Berwick than paradise.”

Much of my time at the National Trust for Scotland's Bannockburn Heritage Centre was spent telling the story of James Douglas and the heroes of the Wars of Independence. Photo by Lenny Warren/Warren Media www.warrenmedia.co.uk

Much of my time at the National Trust for Scotland’s Bannockburn Heritage Centre was spent telling the story of James Douglas and the heroes of the Wars of Independence. Photo by Lenny Warren/Warren Media www.warrenmedia.co.uk

Regardless of whether or not you now agree with the bold claim I began this article with, what is undisputed is that James Douglas is one of the finest soldiers, tacticians and individual warriors that Scotland has ever produced. His name may be eclipsed by those of Wallace and Bruce, but in his own time he stood on the pantheon right alongside those giants of history. Some stake their claim to history through fame and fortune, but James Douglas cared not for these trappings; his was the way of the sword, aimed always at the terror-stricken hearts of his people’s enemies.