This skilled fighter has been overshadowed in time by his heroic leader but the deeds of Douglas offer a powerful thread in the story of 14th Century Scotland and the unbridled violence of the Wars of Independence.
Born in 1286 into a family loyal to the Scottish Crown, his grandfather was killed alongside William Wallace and his father murdered in an English jail for his support of the hero.
After returning to Scotland aged 18 after time in Paris, Douglas witnessed the seizure of his family land by Edward I.
After supposedly meeting Bruce near Moffat following the murder of rival Red Comyn in 1306, the scene was set for Douglas’s lifelong fighting career alongside Scotland’s new king.
The next year on Palm Sunday, Douglas attacked the English garrison at his family seat of Douglas Castle in Dumfries and Galloway.
Most of the English soldiers had left the castle to attend mass when the Scots attacked, entering the church to the war-cry ‘Douglas!’ ‘Douglas!’.
The massacre later became known as ‘the Douglas Larder’ given the English soldiers who survived the attack were taken to the castle’s cellar where they were beheaded.
Their heads were mounted on a stack of broken wine casks and set aflame, according to accounts. The castle itself was set on fire.
Douglas’ ability to pounce and trounce a larger army earned him a feared reputation with the English troops.
In February 1314, Black Douglas moved to capture Roxburgh Castle in the Borders with his men ordered to cloak themselves in cow hide and crawl on their hands and knees towards the castle after dark.
The guards fell for the rouse and the Scots used hooks and rope ladders to scale the walls.
After fighting alongside Bruce at Bannockburn, Douglas was given free reign to fight under his own flag and cut a bloody swathe across the English border – burning crops and villages, and terrorising the local population.
Folk songs were recited by mothers to reassure there young they were safe from everything - and that not even the wicked Black Douglas could harm them.
Hush ye, hush ye, little pet ye,
Hush ye, hush ye, do not fret ye,
The Black Douglas shall not get ye.
The death of Robert the Bruce in June 1329 led to a powerful pilgrimage of Douglas and a handpicked group of high-status followers to Jerusalem to take their leader’s heart on a crusade to the Church of the Holy Sepulchre in Jerusalem.
Douglas carried the embalmed heart of Bruce in a cask around his neck as the men set sail on the mission with a promise that it would be returned to Melrose Abbey to its final resting place.
The men, who were joined by more supporters in Flanders, incorporated a stop in Spain after hearing of a crusade by Alfonso XI of Castile against Muslims of Granada.
Douglas and his men joined Alfonso’s army after arriving in Seville and were to soon come into contact with the Moors near Teba, a castle on the frontier of Andalucia.
The battle came to a swift, satisfactory conclusion for Alfonso but, not being fully aware of the mode of warfare, Douglas found himself deserted by his men.
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, they found Douglas dead, hewed with “five deep wounds” but with the cask unharmed.
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.
His skeleton was interred in St Bride Kirk in his home village of Douglas.