Sir William Douglas, Lord of Liddesdale (circa. 1300-k.1353) was also known as the Knight of Liddesdale and rather dubiously the Flower of Chivalry. He was a Scottish nobleman and soldier during the Second War of Scottish Independence.

Douglas' father, James Douglas of Lothian, a minor landowner in the Lothians was a second cousin of the Good Sir James Douglas, a hero of the First War of Scottish Independence. At some point circa. 1323, Douglas succeeded to his small desmesnes. Circa. 1327 he became godfather to his third cousin Archibald, son of Sir Archibald Douglas, and nephew of the "Good Sir James". Douglas was to hold minor positions of state and is not much heard of until 1332.

Robert the Bruce died in 1329 and also "The Good Sir James" on Crusade in 1330, Bruce's son David II was an infant. Edward III of England had just attained his majority and was known to resent his father, Edward II's disgrace at the hands of the Scots, and his own supposed humiliation when forced to sign the Treaty of Northampton in 1328, at just sixteen years old.

A party known as the Disinherited (senior Anglo-Scottish Nobles on the losing side after Bannockburn) successfully lured Edward Baliol, son of former King John of Scotland from France in 1331, with the aim of restoring him to the throne and their privileges. Throughout the winter and spring of 1332 the Disinherited led by a veteran campaigner Henry de Beaumont and Baliol, with tacit support, but outward neutrality from Edward III, were gathering supplies and men for the invasion of Scotland. The last of the old guard Thomas Randolph, 1st Earl of Moray, Bruce's nephew died in July and the leadership crisis in Scotland made it ripe for the picking. Exposing loopholes in the Treaty of Northampton, which forbade any military incursions across the Border, Baliol's forces set sail from the Yorkshire coast and landed at Kinghorn in Fife, and marched to meet the forces of David Bruce. The Battle of Dupplin Moor, was a decisive defeat for the defenders and Baliol was crowned King of Scots on the 24th of September. Baliol had little support in his new kingdom, except in his ancestral lands in Galloway. Baliol and his army marched across the Lowlands, and was being slowly eroded by guerilla tactics learnt only twenty years previously. Baliol was ambushed at the Battle of Annan on the 16th December 1332. Baliol's brother Henry is said to have died in the skirmish, and it is the first time that William Douglas is recorded in battle, and Baliol himself had to flee south ignominiously.

In 1333, Edward dropped all pretence of neutrality, repudiated the Treaty of Northampton, and attacked Scottish Berwick-upon-Tweed, Douglas' kinsman Sir Archibald Douglas, now Guardian of Scotland, rushed to meet the English host and battle commenced at Halidon Hill. A crushing defeat for the Scots, Sir Archibald was killed, William, the young Lord of Douglas also. Hordes of valuable hostages taken. Young King David II, Douglas' Godson William Douglas and his brother John Douglas escaped to France. However, Edward chose to restore Baliol to Scotland and retreated south. The supporters of King David elected two new guardians of the realm, John Randolph, 3rd Earl of Moray, Bruce's great-nephew and Robert Stewart, High Steward of Scotland and Bruce's grandson. In 1335 Edward decide to take matters into his own hands again and entered Scotland with a force large enough to occupy the whole south of the country, taking Edinburgh castle and heavily rebuilding and refortifying it.

William Douglas had been captured earlier in 1333 and he escaped the carnage that had wiped out or captured the leading men of the nation at Halidon Hill. Upon his release in 1334, he started raiding Galloway under the command of John Randolph, 3rd Earl of Moray, capturing Guy II, Count of Namur at the Battle of Boroughmuir. After Randolph's capture and without his support Douglas started building his own power base. Douglas returned to his lands in Lothian and as he had a pitiful amount of tenantry to draw upon, he organised a company of men that would follow him based on his martial prowess. "The armed bands led by Douglas, his contemporary Alexander Ramsay and others lived 'in poverty' and 'like shadows', fighting a guerilla war against the English....Ramsay based his followers in a network of caves at Hawthorndean in Midlothian, while Douglas, operated from lairs in the [Ettrick] Forest or the Pentland Hills, was wounded twice and risked capture ambushing larger English forces. But these leaders engaging in small-scale warfare were the only active opponents of the English in the South." Later historians and chroniclers would put a gloss on Douglas and his guerillas as "schools of Knighthood", earning him the epithet Flower of Chivalry.

As mentioned previously Douglas did not have a large tenantry base to work with himself, so the majority of the men that led his companies were bound by kinship, and their adherents. In his native Lothian, Douglas' clear leadership won over local gentry and their followings, but throughout the rest of the south it was Douglas' military successes that won him great support. He became known as the "Flail of the English and Wall of the Scots". Douglas was starting to be viewed in much the same way as his illustrious cousin "The Good Sir James" had been a generation before.

In September 1335, the rump of the Bruce party, gathered at Dumbarton Castle and re-elected as Guardian of the realm, Sir Andrew Murray, son of William Wallace's lieutenant and his namesake. A month later Murray's forces met with the English pro-Baliol forces under David de Strathbogie at Culblean, in Aberdeenshire. Murray's army divided into two with Douglas' leading the forward unit. When he saw Strathbogie arrayed for battle Douglas halted, as if hesitating in the face of the enemy's preparedness. This had the desired effect and Strathbogie led his men in a downhill charge; but their ranks began to break on reaching a burn, and Douglas ordered a counter-charge. Sir Andrew with the rearguard immediately launched an assault on the enemy's exposed flank. The charge was so fierce that the bushes in the way were all born down. Pinned down in front and attacked from the side, Strathbogie's army broke. Unable to escape, and refusing to surrender, Strathbogie stood with his back to an oak tree and was killed in a last stand with a small group of followers, including Walter and Thomas Comyn. The battle of Culblean, though by no means the largest confrontation in the conflict was pivotal in the fortunes of the followers of David Bruce, and heavily demoralised the forces of Baliol.

In the later 1330s Douglas continued to consolidate his powerbase in Southern Scotland using the Great Forest of Ettrick as cover to mount increasingly punishing raids upon the English, as had "The Good Sir James" before him. The English still held Roxburgh Castle, and the ever hard pressed Borderers, who were 'encouraged' under duress to 'return to the Kings's faith', regarded the Lothian-based Douglas as yet another warlord rather than a Freedom-fighter, imposing his will by raid and enforced leadership.

Earlier Sir Archibald Douglas had laid waste to Galloway, Edward Baliol's patrimony and had seized Liddesdale to prevent access to and from England. Archibald claimed the Lordship thereof by Force Majeure, rather than by legal means. William Douglas did the same, seizing control of Liddesdale in 1337 and capturing the following year,Hermitage Castle the key fortress in Liddesdale and over much of the Border country. Hermitage had been a royal castle under the Bruce, having been forfeited by Sir William de Soulis in 1320. It was captured during the Baliol invasion and granted to the Englishman Sir Ralph de Neville.

Such was Douglas' burgeoning experience and ability, that he was able to recapture the heavily defended Castle of Edinburgh, in English hands since the invasion of 1335. A repeat of Thomas Randolph, 1st Earl of Moray's daring recapture in 1314 where they scaled the Castle-rock was impossible as a result of Edward's new fortifications. Douglas had to come up a new strategy. In fact he went for a very old one, that of the Trojan Horse. The garrison of the castle in constant need of supplies and fodder for their beasts and horses, used various local merchants for that purpose. Douglas and his lieutenants dressed as merchants, and acquired some hay wains, in which they concealed their warriors. On gaining entry to the castle the final wagon stopped to bar the gates from closing. Douglas' men poured from the wagons and through the open gates came the citizenry of Edinburgh to slaughter the English defenders, throwing many off the Castle-rock.

Control of Edinburgh gave Douglas the power and influence to control all of Southern Scotland from Dumfries to the Merse. However, his legal position was tenuous and had to be maintained by force. While his predecessor "The Good Sir James", had been tied by bonds of personal friendship and loyalty to The Bruce, there were no such links between the exiled David II and the remaining Guardian, Robert Stewart. William received no support militarily and no preference in the issuing of charters of land from Robert. To ensure that his efforts to secure his pre-eminence were not in vain, Douglas decided to visit King David in France in an attempt to forge a friendship between them.

In 1339, Douglas visited the King at Château Gaillard on the Seine, 50 miles North-West of Paris. Douglas returned from France with a party of French Knights and Crossbowmen and the promise of Royal favour in return for helping arrange and prepare the way for the King's return to Scotland.

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*The History of the House and Race of Douglas and Angus, Hume of Godscroft. Mortimer and MacLeod, Aberdeen 1820 *The Black Douglases, Michael Brown. Tuckwell Press, East Linton. 1998

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