Douglas, the origin story:
There are two origin stories for the Douglas family.
The first is the Legend of Sholto. This is a myth, but it is a good tale with -possibly- the whispers of truth. It tells of a story of a battle in 767 between Slovathius, king of Scotland, and a pretender: Donald Bane. Bane’s victory was at hand when a warrior turned the tide of victory in Slovathius’ favour. When the King asked the name of this warrior somebody said ‘Sholto du glass’. This was either the warriors’ name already or it was a miscommunication/misidentification because this phrase in Gaelic just means something along the lines of ‘the black -or dark- man over there’. Thereafter the man would be known as Sholto Douglas and he was gifted these lands as thanks for his brave service.
The real history begins with what Historians call ‘the Davidian Revolution’, when David I of Scotland (ruled 1124-1153) invited the knights of Europe and England -often knights with no prospect of inheritance i.e. second sons- to Scotland in order to establish continental and Anglo-Norman feudalism in Scotland. This coincided with David’s establishment of Royal Burghs with Lanark being created in 1140. Given that Douglas is a Gaelic word, this valley was likely inhabited by Gaelic speaking people of Galloway: a Norse/Gaelic semi-independent Kingdom or Lordship which, although recognising the King of Scots as a high king, was a thorn in the side of the Scottish Crown (and would continue to be so for some time thereafter). At that time Douglasdale was a border town between Galloway and the Kingdom of Scotland. It is no wonder, then, that the lands here were assigned to one of those newly arrived knights: Theobold le Fleming. His task would be to maintain the King’s order in the valley and wider region. David’s rule had been hard-won and feudalism was the key to gaining -and then maintaining- stability in unruly territories.
Theobold’s descendants, the Douglasses, would later become Lords of Galloway themselves but in the early days it is very likely that they were vassals of Galloway, owing allegiance both to the Lords of Galloway, and to the Crown of Scotland.
William de Douglas, the first to be styled as Lord of Douglas certainly played a role in the army of Lochlann, Lord of Galloway, in 1181 when he was dispatched by the then King of Scotland (William I, ‘The Lion’) to put down a rebellion of the Meic Uillem in what is now Moray. This gives us a nice connection to the legend of Sholto as that rebellion was led by a powerful magnate by the name of Domnall Ban. As Douglasses were occasionally described as being dark or black in the historical record, and as William I was the first to take the name of ‘de Douglas’ it is possible that the story of Sholto is an evolution of the story of William de Douglas.
Regardless: the name ‘Douglas’ means ‘black water’ in Gaelic and it is most likely that the family took the name after the parish which had already developed here prior to their arrival. The parish, in turn, had taken its’ name from the steam which runs through this valley.
Explaining the epithet ‘Black Douglas’:
The term “the Black Douglasses” was not used contemporaneously in medieval Scotland in the way we understand it today. Instead, it evolved later as a retrospective label to distinguish one branch of the powerful Douglas family from another.
During his lifetime, Sir James Douglas was known to the Scots as “the Good Sir James” for his loyalty and military prowess. However, to the English, he was feared and referred to as “the Black Douglas” or as ‘Douglas Grim’: a name that carried connotations of terror and brutality.
The collective term “Black Douglasses” came into use later, primarily to differentiate between the two major branches of the Douglas family, the Reds and the Blacks. The Black Douglasses, were mostly descended from Sir James’ illegitimate son, Archibald the Grim, (or ‘the Black’ or sometimes ‘Black Archibald’). The Red Douglasses, meanwhile, are descended from the the Good Sir James’ younger brother, Archibald. Tthe first ‘Red Douglas’ was George Douglas, an illegitimate son of Archibald’s own legitimate son, William Douglas, who was the 1st Earl of Douglas.
The label “the Black Douglasses” as a dynastic term was likely not used by the family themselves nor was it used in official records at the time. It is a historiographical construct which was later applied by chroniclers and historians to clarify lineage and political affiliations and to indicate a descent from the Good Sir James via Archibald the Grim (‘the Black Douglas’ and his illegitimate and youngest son, ‘Black Archibald’). The term, therefore, is either a reference to James’ English characterisation (and thus pertaining to ‘dark deeds’) or to Archibald who was described in the historical record as being dark featured. The Black Douglas line was extinguished when James Douglas, the 9th Earl, died in 1491.
Explaining the epithet ‘Red Douglas’:
The term “Red Douglasses” is used to describe what would become the Angus branch of the Douglas family. Similarly to the Black line, this was not contemporaneously used in medieval Scotland. Like the term “Black Douglasses,” it emerged later as a retrospective label to help writers and readers distinguish between the two major branches of the family. The Black and the Red lines were far from the only branches of the Douglas dynasty.
The Angus Douglasses are descended from George Douglas, the illegitimate son of William, 1st Earl of Douglas. George’s father was the son of the Good Sir James’ youngest brother, Archibald. The ‘Reds’ are therefore not directly descended from the Good Sir James; rather they trace their lineage to his father, William le Hardi. This branch held the title of Earls of Angus and played a significant role in Scottish politics from the 15th century onward. The term “Red Douglasses” was likely coined after the fall of the Black Douglasses or, at the earliest, around the time of the battle of Arkinholm where the Angus line sided with the Crown against their kin, the Earls of Douglas (the ‘Blacks’). There is no evidence that the term “Red Douglasses” was used in contemporary medieval documents. It is therefore more likely to be another historiographical construct created by later writers for the purposes of distinguishing the Angus branch from the ‘Black’ branch.
While the decision to use ‘Black’ to describe the dynasty of the Earls of Douglas is easier to understand, the reasoning behind the use of ‘Red’ to denote the Earls of Angus is more obscure. Several theories have been put forward: The crest of the Earldom of angus contained a red lion rampant and a red belt while the crest of the Scottish Crown (whom they supported over their kin) also contained a red lion. Another suggestion is that the description pertains to one of the Red Douglasses physical appearance in contrast to the dark features associated with the Black line: one or more of the earls of angus may simply have been ginger. This would, however, mean that the Reds were being referred to as such at the time and this has yet to be uncovered in the historical record, so the story is possible: but unlikely. Additionally, no other Scottish noble was explicitly referred to as ‘red’ due to having red hair in contemporary sources.
There is one notable piece of evidence, however: Gilbert de Umfraville, an earlier earl of angus (he died in 1308) was referred to as ‘the Red Earl’ at the time. While the Later Douglas Earls of Angus had no connection to Umfraville, the Earldom itself may simply have become associated with the colour from that earlier time. This would simply mean that ‘the Red Douglasses’ is shorthand for ‘pertaining to the Earldom of Angus’. Why Umfraville himself was nicknamed ‘The Red Earl’ is unclear but it is not beyond the realms of possibility that he had distinctive red features; although it is similarly likely -if not more so- that this is a label denoting temperament, martial activity, or allegiance (to the English crown in particular).
Neeretheless, the Douglas branch took over the Earldom of Angus when George, an illegitimate son of William, the 1st Earl of Douglas inherited his maternal grandfather’s titles (his mother was Margaret Stewart, the Countess of Angus; she was also William’s -widowed- sister-in-law). Said grandfather was Thomas Stewart, 2nd Earl of Angus and he was the son of John Stewart, the 1st Earl. This close connection between the Red Douglasses and the house of Stewart goes some way in explaining why the Earls of Angus were more sympathetic to the Stewarts than they were to the Black Douglasses. These Stewarts had gained the title of Earls of Angus from the Bruce kings because the Umfravilles had backed the losing side (England) at Bannockburn and so their Scottish titles had been forfeited.
Theobold le Fleming (1120-1193 )+ Unknown = William 1, Lord of Douglas
Theobold, sometimes styled as Le Fleming or as ‘Flamatico’, arrived in Scotland in the 1100’s. He was born in Lancashire (England) in 1120 and died in Scotland in 1193. He was granted lands in Lanarkshire by the Abbot of Kelso sometime after 1150. There is a likelihood that Theobold was related to the de Moravias (the Morays/Murrays). The two families’ coats of arms are very similar, the de Moravia noble family also arrived during David’s reign and many Douglasses held lands or clerical offices in Moray territory. The latter may be explained by William I’s role in putting down the aforementioned rebellion in that territory and by his marriage to a sister of Freskin (who is known to be the progenitor of the de Moravias). Additionally, the only noble houses to support William Wallace were de Moray, and de Douglas. It is entirely likely that when William I de Douglas married Margaret, Freskin’s sister, he was marrying within his kinship network. Freskin was a Flemish settler who also answered David’s call and later acquired the lands of Moray (and others) some time between 1165-1171. Freskin was the great great grandfather of Andrew de Moray who died of his wounds after his and Wallace’s victory at the battle of Stirling Bridge. The Douglas who threw in his lot with him was the great grandson of Freskin’s sister, Margaret, and so the houses of Douglas and Moray most certainly did have familial ties between the time of William I in the early 1200’s and the Wallace rebellion at the end of that century. What is up for debate is whether this kinship predated the time of William I, with Theobold -possibly- being a relative of Freskin as well. The strength and ease of the relationship, the stark similarity in the family coat of arms, their mutual Flemish origins, and the timings of their arrival all indicate that this is a strong possibility.
William de Douglas (mid-late 12thC.- c.1214) + Margaret, sister of Freksin of Kerdal = Archibald I
William de Douglas died in in 1213 or 1214. He was the first to appear as de Douglas in the historical records. He was a witness to a charter in 1174 so he must have been born long enough before that to already be an adult by then. As well as Archibald, he had several other sons and a daughter with Margaret: Brice or Bricius de Douglas (meaning devotee of St Brigit, otherwise known as St Bride so it is possible this was not his real name although he could have been named as such), Prior of Lesmahagow before becoming Bishop of Moray in 1203 (d.1222); Alexander de Douglas, Canon of Spynie, and Vicar capitual of Elgin; Henry de Douglas, canon of Spynie; Hugh de Douglas, canon of Spynie, Archdeacon of Moray; Freskin de Douglas, parson of Douglas and then Dean of Moray; Margaret de Douglas, married Hervey de Keith Marishcahl of Scotland. Here, again, wer see strong connections between the Douglas family and the Morays and we also begin to see the very early signs of a connection between the Douglas family and St Bride (with the church here being dedicated to the saint in the late 1300’s).
Archibald de Douglas (1190’s-1239) + Margaret, Daughter of Sir John Crawford of Crawford = William de Douglas ‘Longleg’.
Archibald was born shortly before 1198 (we know this was when he was confirmed) and died sometime around 1239. He too spent a lot of time in Moray, as attested by the charters of his brother, Bricius. He was already knighted by 1226 as he is recorded as Lord of Douglas at that time.
William ‘Longleg’ de Douglas (c.1220-c.1274) + Constance Battail of Fawdon (possibly his 2nd wife) = Hugh; William le Hardi; and Willelma de Douglas (a daughter who died in 1302).
Longleg was born around 1220 and died around 1274. He was one of the magnates who bore witnesses to the meeting which established a regency in 1255 (Alexander III of Scotland was only a minor during the first part of his reign from 1249, the regency ended in 1262). He was also lord of Fawdon in Northumberland. David Hume of Godscroft recorded that William went on Crusade in 1270 (the 8th Crusade which targeted Tunisia) but, if a Douglas did go on crusade (accompanying the Scottish force led by David I Strathbogie, Earl of Atholl), then it is possible that it was his son, William le hardi. If it was indeed Longleg, he would have been in his 50’s -or possibly just turning 50- at that point. In 1264 Longleg was attacked at Fawdon by Gilbert de Umfraville, Earl of Angus, over a dispute relating to withheld rents. Longleg was imprisoned and his son, William, was seriously injured. It is possible that Longleg’s oldest son, Hugh, inherited the Douglas estate upon his father’s death but we can’t be certain. However, by the end of the 1270’s we know that the lands had passed to the second son, William.
William Le Hardi Douglas (c.1243-1298) + Elizabeth, daughter of Alexander Stewart, 4th High Steward of Scotland = James (the Good sir James). Elizabeth died in 1288.
Le Hardi + Eleanor de Lovaine = Hugh ‘the Dull’; and Archibald, the progenitor of the Red Douglas line.
Le Hardi was born around 1243 and died in 1298. When he was around 21 years old he was seriously wounded in the aforementioned fight at Fawdon: the records indicate that he survived a decapitation attempt. He married into the powerful Stewart family but his wife died in 1288. By that time he had already been knighted as he appears in the record as a knight in that year. Later that year he besieged Fa’side castle near Tranent from whence he abducted Eleanor de Lovaine, whom he would soon marry. See the Story of Eleanor and le Hardi near the bottom of this page for more information.
James Douglas, the Black Douglas or the Good sir James (before 1288-1330) + 2 unknown mothers = William, Lord of Douglas; and Archibald ‘the Grim’.
James Douglas was born some time before his mother’s death in 1288 and died at the battle of Teba in 1330. In his youth he was sent to France for his safety during the Wars of Scottish independence. Here he served as a squire for William Lamberton, Bishop of St. Andrews with whom he returned to Scotland in 1304. For several years by this point, Douglas lands had been gifted to one of Edward’s commanders, Robert Clifford. When, in 1304, Scottish nobles presented themselves before Edward at the siege of Stirling Castle, Douglas was present. However, when Edward learned of who Douglas was (the son of Le Hardi), he was cast out: being the only nobleman not to be forgiven or have his titles restored by the English king. When Bruce rose in rebellion against Edward, Douglas had little choice but to join him (it was the only way to get his titles back). James operated a guerrilla war in the South of Scotland in the first years of the rebellion. See the Story of the Good Sir James near the bottom of this page for more information.
Sir James was succeeded by his oldest son, William, Lord of Douglas (early 14th C. – 1333). He was killed very soon after at the Battle of Hallidon hill in 1333. His uncle (The Black Douglas’ half-brother) Archibald was the commander at the battle and he was also killed. We do not know when this William was born but we do know that he was the first of the Good Sir James’ sons and that he was an adult by 1331. William’s crest bore the symbol of Bruce’s heart meaning the Douglas family adopted that part of their crest immediately after the events that led to James’ death at Teba.
William was succeeded by his uncle, Hugh the Dull of Douglas who was the second son of Le Hardi and the older brother of the Archibald who had been killed at Hallidon Hill. Hugh had, in accordance with normal practice of the time, been a man of the cloth prior to the death toll at Halidon hill rendering him the next legitimate heir of the Douglas estates.
Hugh ‘the Dull’ Douglas (1294-1346) was the Good Sir Jame’s uncle. Hugh is absent from the historical record between the forfeiture of his father’s lands in 1296 (aged 2) and 1325 where he appears as a canon of Glasgow Cathedral. It is important to note here that Glasgow Cathedral played a significant role in the Wars of Impendence and this appears to be evidence of the Douglas family having a close kinship connection to that institution during those tumultuous years. In the aftermath of Halidon Hill and amid the constant civil strife and English aggression, Hugh probably fled to France in 1337. Here he was accompanied by his nephews, William Douglas, the future 1st Earl of Douglas and son of his younger brother, Archibald, and another Archibald, (the illegitimate son of James) known as ‘the Grim’ who would be the future 3rd Earl. Hugh retired to parish duties in Roxburgh and lived a life of obscurity to the Historical record. All that we know is that he died in 1346 and that, by that time, he had resigned his lordship to his younger brother’s son, William, while he (meaning William) was still young and in France. Hugh, clearly, had no desire for the high politics and violence of the Black Douglas dynasty.
William Douglas, 1st Earl of Douglas. (c.1232-1384) + Margaret of Mar (daughter of the Earl of Mar) = James Douglas, the 2nd Earl of Douglas; and Lady Isabel, countess of Mar.
William Douglas, 1st Earl of Douglas. + his widowed sister-in-law, Margaret Stewart = George Douglas (the first Red Douglas Earl of Angus); and Lady Margaret (who seems to have had a positive relationship with her half-sister, Isobel, receiving lands from her in 1404).
William, the 1st Earl of Douglas was born around 1323 and died in 1384. He was the first to be styled as ‘Earl of Douglas’, reflecting the dynasty’s rise through the ranks of nobility. He was the nephew of the Good Sir James and the son of the Archibald who had died at Hallidon Hill. William’s mother was Beatrice de Lindsay, the daughter of Alexander de Lindsay of Crawford (a nearby parish). From his father’s death he is recorded as being a ward of a kinsman and godfather, another William Douglas (the knight of Liddesdale) who fought his own fearsome guerrilla campaign against the English in the early 1300’s (in fact, it is because of this man that Hugh the Dull even had anything to inherit). William returned to Scotland in 1348 in the aftermath of the disastrous Scottish defeat at Neville’s Cross (which had resulted in Liddesdale being captured). He was one of the negotiators for the release of David II of Scotland (who had also been captured at Neville’s Cross). Liddesdale and William would soon be enemies, however, with the latter killing Liddesdale in 1353. More war with England came in 1355: by this time Berwick was back in English hands but William played a part in the towns recapture (again, however, they failed to capture the castle). This had come in the face of a defeat that Douglas experienced at the hands of the English at the Battle of Nesbit Moor. A later ambush by Douglas against the English at Melrose nearly saw Douglas capturing King Edward. Edward had been retreating back to England due to another successful Scottish scorched earth campaign. Once Scotland had been freed of this latest invasion Douglas travelled to France to join the French war-effort against the English there. He was knighted on the morning of the battle of Poitiers by the French king. The battle was a disastrous French defeat, and Douglas had to retreat (leaving behind his cousin, the Good Sir James’ youngest son, Archibald the Grim). Returning to Scotland, peace negotiations between the Scottish and English crowns resulted in success and Douglas became a March warden and, soon after in 1358, he was styled the Earl of Douglas. He soon erected Tantallon Castle where his sister-in-law (a widow, and his mistress), Margaret Stewart, the 3rd countess of Mar, took up residence. Here they had an illegitimate son, George Douglas, who would later become the Earl of Angus and the first Red Douglas. Douglas spent the rest of his life carrying out -and repelling- raids to and from England. He died in 1384 and records are conflicted as to whether this was the result of a fever or a seizure (or both).
James Douglas, 2nd Earl of Douglas and Mar (1358-1388)+ unknown mother = Willaim Douglas, 1st of Drumlanrig (an illegitimate son) and Archibald (also illegitimate: he would become the ancestor of the Douglasses of Cavers).
James Douglas was born around 1358 and he died in 1388, only a few years after succeeding his father as Earl. He received the lands of his father’s once-time ally turned enemy, Douglas of Liddesdale in 1380 (by which point he had already been knighted). While negotiations between Scotland, France, and England were underway in 1384, Douglas and some other Scots joined forces with a renegade group of French knights and raided England. A short truce brought a pause to the fighting and saw his French allies returning to the continent but when the peace expired in 1385 he attacked the English again (the French, having promised to aid him, did indeed come back to do so). The English forces, under Richard II, were numerically superior so Douglas did not meet them in battle and instead returned to the old tactic of scorched earth. The English, however, sacked Melrose, Newbattle, Dryburgh and burned Haddington and Edinburgh. All Douglas could do was rely on guerrilla tactics while his cousin, Archibald the Grim, launched a diversionary invasion of Carlisle from Galloway. Infighting weakened the Scots under Douglas which led to the departure of his French comrades: but he still managed to launch a raid deep into England in 1386, burning Cockermouth. By 1388 the context had changed, Richard II of England was busy with his own rebellious barons and Douglas seized the opportunity to avenge the destruction of 1385. However, he met Henry Hotspur Percy in Battle at Otterburn near Newcastle and was soundly defeated. He was killed in the battle and his body interred at Melrose Abbey. Douglas married Robert II of Scotland’s daughter, Isabel but they had no legitimate heirs.
Archibald ‘the Grim’ Douglas, the 3rd Earl of Douglas (c.1330-1400) + Joanna de Moravia, Lady of Bothwell = Archibald, 4th Earl of Douglas; James Douglas, 7th Earl of Douglas, Marjorie Douglas (who married the Duke of Rothesay and then later married the treasurer of Scotland); Helen Douglas (who married the governor of Edinburgh Castle). See The Story of Black Archibald for more information.
He also had an illegitimate son, William Douglas of Nithsdale with an unknown mother. He was with the Franco-Scottish army that besieged Carlisle in 1385 (unsuccessfully). He married a princess of Scotland, Egidia Stewart, in 1387 (she was the daughter of King Robert II). He was involved in wars in Ireland and was part of the war that culminated in Otterburn (but in a separate campaign). Thereafter he joined the Teutonic crusade in Lithuania and was later killed in Danzig by a contingent of English crusaders due to a feud with Lord Clifford in 1391.
Archibald Douglas, 4th Earl of Douglas (c.1369-1424) + Margaret Stewart, princess of Scotland = Archibald Douglas, 5th Earl of Douglas and others.
Archibald Douglas was born to ‘the Grim’ and Joanna de Moravia around 1369 and he died at the Battle of Verneuil in Normandy in 1424. As well as inheriting his father’s titles he was also made the Duke of Touraine and Marshal of France. He is often given the epithet ‘Tyneman’ which is old Scots for loser but this might be a misidentification with his great uncle, another Archibald, who died at Hallidon Hill in 1333. By 1390 he had married the princess Margaret of Carrick, a daughter of King Robert III. In 1400 Robert made him Keeper of Edinburgh Castle for life. In 1400 Hotspur, the man who had led the Englsih force that defeated and killed his Kinsman James, the 2nd Earl, invaded Scotland. Archibald 4th surprised them in a night raid at their camp near East Linton, pursuing the English back to Berwick. Later that year he was involved in the defence of Edinburgh castle when Henry IV of England besieged it (unsuccessfully). At Christmas that year his father died and he became the largest and most powerful magnate in Scotland. In 1402 Douglas probably conspired with the Duke of Albany to arrest the the prince, the Duke of Rothesay, Douglas’ own brother-in-law (the Duke died soon after in suspicious circumstances). Albany, the uncle of the departed Duke, and especially Douglas were, however, too valuable to the weak crown of Robert III (who was ailing in health). In the context of renewed English hostility they were acquitted in what historians consider a whitewash. In that hostility the Scots were sorely defeated at Nesbit Moor so Archibald raided into England for revenge. Here the Scots, including Douglas, were outsmarted by Hotspur and summarily defeated at the Battle of Homildon Hill. Douglas possibly hesitated to charge his force into the fight and when he did, it was too late. Many Douglasses, including Archibald 4th and George Douglas (the 1st Earl of Angus) were captured. Archibald himself had been gravely wounded and had lost an eye in the battle. Douglas and his fellow captives were soon freed however: Percy entered into rebellion against his own king in 1403. In exchange, Archibald decided to join the English rebels. This culminated in the battle of Shrewsbury (the aforementioned Earl of March, in exile from Scotland and in open feud with the Douglasses since the Grim undercut his dowry, fought on the side of the English crown). The battle was a disaster and Douglas was now a captive of King Henry of England. To make matters worse: the Scots were struggling to raise funds for the ransom of Homildon hill, the prince of Scotland was then captured by English pirates in 1406, and Robert III died shortly after. With no Douglasses wielding power in Scotland, the realm was now in the hands of the Duke of Albany.
Douglas was allowed to return to Scotland in exchange for hostages, but he failed to keep his oath to his captor. However, Douglas and Albany had managed to reconcile with the Earl of March and Douglas and Albany strengthened their ties with a dynastic marriage between their children. Soon, in 1416, the Scots would go on the offensive again against the Englsih but their attempts at seizing Beriwck and Roxburgh (Douglas being in charge of the latter campaign) failed when a large force of English forced a retreat. The warring was not over, however: Douglas soon sailed to France with his son (who had been fighting for the French King and who had been present at the victory at the Battle of Bauge). He arrived with an army in 1424 and was awarded the Duchy of Touraine. He was soon killed, however, at the defeat at the battle of Verneuil in August 1424.
Archibald Douglas 5th Earl of Douglas (c.1391 – 1439) + Euphemia Graham = William Douglas 6th Earl; Margaret Douglas, Fair Lady of Galloway, and David Douglas.
Archibald the 5th Earl was born around 1391 and died in 1439. He is interred in St Bride’s kirk. Not much is known about his early years but we do know that he was fighting for the French in the hundred years war and saw victory at the battle of Bauge in 1421. He inherited his father’s swathes of land (comprising all of Southwestern Scotland) upon his father’s death at Verneuil in 1424. He also inherited the title of Duke of Touraine although we do not think he ever actually went there. After his father’s death Douglas went to England to negotiate the ransom of James I of Scotland. Later, in 1425, he was one of the 21 knights who convicted the Duke of Albany for treason which resulted in the execution and virtual annihilation of the family: an important political rival, if not closely connected to the Douglasses. When James I was murdered in 1437 it was this Douglas who sevred as regent for James II until he died of a fever in 1439. At some time in the mid 1420’s he married Lady Eupheme Graham (who lived to 1468), daughter of the Earl and Countess of Strathearn.
William Douglas, 6th Earl (1424-1440)was young when he was murdered and so did not have any children that we know of. He was born in 1424 and died aged 16 when he was murdered in 1440 at Edinburgh Castle. He was married to Lady Janet Lindsay, the daughter of the Earl of Crawford. He inherited his father’s vast estates when he died in 1439. Following his father’s death the regency over James II was shared by William Crichton, Alecander Livingston, and James Douglas, the earl of Avondale: William’s great uncle. These three men conspired to break up William’s vast estate: he was too powerful, and too young! He and his younger brother, David (aged 10), were invited to Edinburgh Castle for an event which is known to history as ‘the Black Dinner’ (the infamous inspiration for the graphic ‘Red Wedding’ scene in George R.R. Martin’s Game of Thrones). During the dinner a black bulls’ head was served, a symbol of death, and the two boys were beheaded there and then on trumped up charges all while the very young James II screamed in protest (he would have been around 10 years old at the time). The Black Douglas estate was broken up: Annandale and Bothwell went to the Crown, Galloway to Margaret Douglas (the boy’s sister) and the rest of the Douglas lands, including the earldom of Douglas, passed to the next in line: to James Douglas, the 7th Earl, who was present at the murder and more-than-likely played an instrumental hand in the affair. Members of the Douglas family soon laid siege to Edinburgh castle which was surrendered to the Crown.
James Douglas, 7th Earl of Douglas (and 1st Earl of Avondale, also known as ‘James the Gross’ meaning ‘the fat’ and James of Balvenie) (1371-1443) + Beatrice Sinclair (2nd wife) = Beatrice Douglas; William Douglas (8th Earl); James Douglas (9th Earl); Archibald Doglas, Earl of Moray (the twin of the 9th Earl); Hugh Douglas, Earl of Ormonde; John Douglas, Lord of Balvenie, Janet Douglas; Margaret Douglas; and one other daughter who never married (we don’t know her name).
James the Gross was the second son of Archibald the Grim and, as such, had been passed over in the inheritance of the Douglas Earldom for his brother (Archibald, 4th Earl) and his descendants. Prior to the events of the Black Dinner, however, James had experienced his own rise to prominence. After the disaster at Homildon Hill, where his brother was defeated and captured, James acted as regent of Douglas for 7 years until his brother’s return in 1409. He was rewarded for this with estates, including Abercorn Castle (the seat of his power) and the title of councillor. When James I returned to the throne from English captivity in 1424 James Douglas became one of his councillors too: the close relationship with the Crown opened the door for him being made the Earl of Avondale in 1437 although it is possible this came after James I’s murder and was in fact a gift made to James the Gross by the man who ruled Scotland in the turmoil that ensue (James the Gross’s nephew, Archibald, the 5th Earl who was, at that time, the lieutenant governor of the country). James the Gross and his nephew, Archibald the 5th Earl of Douglas seem to have had a positive relationship. The two acted together on the jury which convicted -and summarily obliterated- the house of Albany for treason against James I. After James I’s own killing, the two Douglasses acted in consort once again, with Albany’s long gone it was only natural that the Earls of Douglas would hold the power in Scotland and we know that James the Gross backed his nephew, Archibald the 5th Earl, when he assumed the title of Lieutenant governor and, as such, became regent of the young James II. It was the unexpected death of his nephew in 1439 that triggered the events that would culminate in ‘the Black Dinner’. With Archibald, the Earl of Douglas and the Regent of Scotland deceased: power in Scotland did not lie with the young king but with the three next most powerful men in the country: James the Gross, William Crichton, and Alexander Livingston. When James the Gross’ two young great nephews (aged 16 and 10), one being the new Earl of Douglas, were invited to Edinburgh Castle in 1440 the three men had the two boys beheaded on trumped up charges of treason. Much of the Douglas estates were subsequently broken up but the Earldom of Douglas itself passed to James the Gross as the next in line. He was now the most powerful man in the country. He died shortly afterwards in 1443 and to his son’s went the Douglas inheritance.
William 8th Earl of Douglas, and 2nd Earl of Avondale (1425-1452): William was 18 when he inherited his father’s two earldoms. He was the most powerful man in the country but he had even more clout: he was the son of Beatrice Sinclair, the daughter of the Earl of Orkney. William may have taken part in the Black Dinner conspiracy but if that is true he would have been only 15 at the time. He married Margaret Douglas, the Fair Maid of Douglas (the sister of the boys who had been murdered at the Black Dinner, she was the middle child and was around 13 years old at the time). Through this marriage he restored the full Douglas inheritance; Bothwell and Galloway. He was, simply, too powerful and a threat to the throne of James II. When William Douglas went to Rome in 1450/51 James II attacked his lands and relations remained strained. In 1452 James II summoned him to Stirling Castle and granted him safe passage. When he arrived the King demanded that Douglas dissolve the allegiance between himself, John of Islay, and Alexander Lindsay (the Tiger Earl of Crawford, a family with which the Douglasses had close kinship ties). When Douglas refused, the king and his companions murdered him and threw his body from a window. The window (and garden below it) are still referred to as the Douglas garden and Douglas window to this day.
William died without an heir and so he was succeeded by his younger brother, James.
James, 9th Earl of Douglas (1426-1491) the last Black Douglas.
James inherited his brothers’ vast territory upon the murder of his brother, William, at the hands of King James II at Stirling Castle in 1452. This prompted James to immediately rebel against the King. He, alongside his younger brothers, attacked Stirling within a month. Famously, he drove a horse through the town with the safe conduct his brother had received from the king pinned to its’ tail. In retribution, the King attacked the Douglas lands. An uneasy peace was brokered -compelled by the loss of allies by both parties- in 1452. At this time James received permission from the King to marry his brother’s widow, Margaret, the Fair maid of Galloway (herself also a Douglas). We do not know if this marriage actually took place, but it had certainly been arranged. Nevertheless, conflict would soon erupt once more. The Red Douglasses declared their backing for the king and finding himself short of allies, James fled to England for help. The warring continued, however, and in 1455 James’ brothers, who had remained in Scotland, met the kings forces -comprised of their kin, the Red Douglasses- at the Battle of Arkinholm. One brother was killed (James’ twin, Archibald, the Earl of Moray), one was captured and executed (Hugh, Earl of Ormonde), and one escaped to join his brother in exile (John, Lord of Balvenie). Later that year, the last loyal stronghold of the Black Douglas family, Threave castle, fell. James Douglas was attainted in 1455 and his lands and estates were forfeited to the crown to be divided amongst his political rivals: to the Red Douglasses, the Earls of Angus, went the Lordship of Douglas. James would return later in an attempt to reclaim Berwick and Roxborough but he never succeeded. In exile he continued to conspire against the Stewart monarchy (now in the hands of James III). He joined English invasions into Scotland and aided their political intrigues in an attempt to foster rebellion. It was during one such episode of intrigue that his brother, the last of the Black Douglasses, was captured and executed (1463). James’ planned marriage to Margaret was either cancelled or they were divorced (a decision taken by Margaret herself) and so he married Anne Holland (daughter of the Duke of Exeter): they never had any children. In 1484 he was captured at the Battle of Lochmaben Fair (another civil conflict between James III and his domestic rivals, aided by England) and he died in captivity in 1491. With him died the Black Douglas dynasty: none of his brothers had any legitimate children and all their estates had been forfeited.
Margaret Douglas, Countess of Douglas and Fair Maid of Galloway (1427-1473) was the daughter of Archibald Douglas, the 5th Earl and Eupheme Graham. Her brothers were murdered at the Black Dinner when she was still a child. In the wake of their deaths she inherited Galloway. Margaret married the son of the man who probably instrumented her brother’s murder (James the Gross, the 7th Earl). Her union with William Douglas, the 8th Earl was designed to keep the Black Douglas inheritance intact (she brought Galloway and Bothwell with her). After his murder she obtained permission from the pope to marry her late-husband’s younger brother although we are unsure if the wedding ever actually took place. What we do know is that she petitioned to James III to end her marriage in the wake of the battle of Arkinholm in 1455. She then married John Stewart, 1st Earl of Athol (he was the King’s half-brother). John Stewart was the son of Joan Beufort (King James II’s mother, the widow of James I) and her second husband James Stewart, who had been a staunch Douglas ally. The Douglasses and Stewart had planned on deposing James II but Joan was arrested in 1439 alongside John Stewart and his brother; as the civil conflict between James II and James III and the Black Douglasses evolved to its’ effective end at Arkinholm, the importance -and threat- of these Stewarts dissolved. Margaret died in 1473 and John Stewart would go on to re-marry. We think he died at the Battle of Flodden in 1513.
The story of the Good Sir James:
The Douglas Larder: Barbour states that this particular event occurred on Palm Sunday in 1307 (it may have been in 1308, but the details of Barbours account certainly does suggest the earlier date). Barbour, in fact, states that this act was the first real success the Scottish rebels had in establishing themselves in the Southern theatre of the war. Concealing his army through the night -with local support and the aid of his kinsman, Thomas Dickson, Castellan of the Douglas Castle- Douglas entered the Church alongside his forces and some local supporters while the English garrison was holding mass. Many English were killed and others were captured. Moving to the castle James had the stores piled together, the prisoners beheaded, and everything -bodies, supplies, and the castle- burned. The wells were then poisoned with the bodies of dead horses and salt. It was soon after this, according to Barbour, that the English started to call him ‘the Black Douglas’. Douglas would soon be involved in a string of battles between the Bruce (and his brother) and their enemies (Comyn loyalists as well as the English invaders) throughout Scotland, including the now famous Battle of Loudon Hill in May 1307. When, in 1310, the new king of England, Edward II, came north Douglas and the Bruce’s continued to engage in guerrilla war tactics. Meaning that, by the year of Bannockburn in 1314, the English presence in Scotland was confined to the strongest castles. In February that year Douglas captured Roxburgh castle (again timing his attack around the holy calendar, the assault was held in the ‘wee hours’ between Shrove Tuesday and Ash Wednesday). This attack was carried out in the darkness, with Douglas’ forces pretending to be cattle -literally crawling on their hands and knees and covered by their cloaks- until they were close enough to the Castle walls to scale them using hooks and ropes. Due to the surprise assault, the defence was futile and afterwards -like Douglas’ own castle- this castle too was destroyed to prevent the English from re-occupying it.
On the morning of Bannockburn, June 24, Douglas -according to Barbour- was knighted. He was more than likely already a knight, so it is more plausible that he was made a knight banneret meaning he was given permission to lead a portion of his King’s army under his own colours -a great honour at the time. The battle, as is well known, was won by the Scots but Douglas was not finished: he sought -and was granted- permission to pursue the fleeing invaders. He pursued them all the way to Dunbar Castle (a distance greater than 60 miles). The Battle and its’ immediate aftermath ended the invasion: only Berwick remined in English hands. It did not, however, end the war: Edward would not abandon his claim to Scotland. Thus, Douglas took the war into the North of England, where he raided with impunity. He would soon be named Guardian of Scotland and tutor to Robert Bruce’s son, the future king (this was after Edward Bruce, the kings’ brother, died in the Irish campaign in 1318). Later that year Douglas played a role in the final recapture of Berwick which had remained under English control since his father’s defence of the town. This prompted another invasion by the English king but Douglas and his kinsman, Moray, evaded being pinned down in the North of England and instead attacked York (which is where the English Queen had taken up residence while Edward II was hunting Douglas in Northumbria). By the time Douglas and the rest of the Scottish force reached York the Queen had been evacuated, and the only resistance was a hastily put together defence force organised by the bishop of York. It largely consisted of priests and clerics and the result of the battle between these and the experienced commanders of Scotland was inevitable (this is known as the Battle of Myton). Yorkshire was raided and Edward had to bring his army back South, abandoning any hope of recapturing Berwick. Douglas would return to raid Yorkshire and the North of England again in 1322: the English had launched another failed invasion which was repulsed not by battle but by Bruce’s scorched earth campaign inflicting starvation upon the invaders who had managed to get as far as Edinburgh before hastily retreating. It was in this retreat that Douglas and other Scottish commanders launched this latest offensive. The Scottish army, again, getting so close to the Royal Court of England (at Byland abbey, where Douglas played another instrumental role in the rout) that the King and Queen had to retreat again. Any peace that this episode won the Scots was short lived: the English Queen had her husband deposed in a coup in 1327 and peace agreements were immediately annulled. Douglas once again raided England, reaching Weardale. The Scots could not be pinned down again and soon Douglas once again launched a night raid on Edward III’s army. A French eye-witness recorded: “The Lord James Douglas took with him about two hundred men-at-arms, and passed the river far off from the host so that he was not perceived: and suddenly he broke into the English host about midnight crying ‘Douglas!’ ‘Douglas!’ ‘Ye shall all die thieves of England’; and he slew three hundred men, some in their beds and some scarcely ready: and he stroke his horse with spurs, and came to the King’s tent, always crying ‘Douglas!’, and stroke asunder two or three cords of the King’s tent.”
Edward III, only by miracle, escaped but it was in the aftermath of this humiliation and the resultant un-opposed Scottish raiding of England that the treaty of Northampton was signed in 1328: England, finally, recognised Scottish independence and Bruce as king.
Teba: Douglas’ story was not yet over. The following year his friend and comrade, King Robert Bruce, died (1329). As a mark of penance Bruce requested his friend to take his heart to the Holy Land (Barbour recorded that Bruce only asked that this heart be carried into battle against enemies of Christ). Douglas departed with his king’s heart in 1330, setting sail from Berwick with seven knights and around 20 squires: this was not a war party. While stopping in Flanders, Douglas learned of Alfonso XI’s upcoming campaign against the Muslims of Granada. Alfonso was Edward III’s cousin, but Barbour records that James was accepted by him with honours at Seville. Soon they set out to lay siege to the castle of Teba.
Uthman ibn Abi al-Ulla marched with his army of Berbers to support the besieged castle which lay on the border between Castille and Granada. According to Spanish sources, Douglas died in the battle when he made a premature assault on the Berbers, possibly in an attempt to win access to water. The Spanish sources detail how Uthman lured the Christians into an assault by launching a small diversionary offensive (while holding the bulk of the army back in hopes of flanking and routing the Christians). Alfonso, expecting this, dispatched a small force to meet Uthman’s fake assault (hoping to spring a trap on the Berbers who would think they were approaching an unsuspecting camp). Douglas and his retinue, it would seem, were a part of this small dispatch. When Uthman’s real assault came to a well fortified and prepared camp, he instead sent the full weight of his army against the party whom Alfonso had sent out. Douglas, although winning the smaller battle, was about to be surrounded. Despite this, Douglas and the rest of the Christian force managed to drive Uthman’s smaller assault back by a distance of 10 miles but, when the main force of Uthman’s army finally arrived the Christian soldiers would have been exhausted and hopelessly outnumbered and it was at this point that he was killed.
Barbour’s description agrees with all of this to a point: he has Douglas present when the enemy broke and fled and he describes Douglas as being part of the Christian contingent that pursued the enemy across those 10 miles or so. But soon Douglas and a handful of his retinue were too far in front of their companions. Despite trying to turn back to their comrades they were hopelessly isolated and soon, they were subjected to a fatal counter-attack. Soon, one of Douglas’ companions from Scotland, Sir William St Clair of Rosslyn, was in danger of being surrounded. He rallied his men and attempted a rescue but by this point they were outnumbered 20 to 1 and overrun. It is during these final moments that the legend of the Bruce’s heart is set: Douglas took the silver casket containing Robert’s heart and threw it into the fray crying “Now pass thou onward as thou wert wont, and Douglas will follow thee or die.” This was added to Barbours poem in the 1500’s (so likely an embellishment) and in that version this actually happened at the opening stage of the battle. Walter Scott, in the 1900’s is the one who modified this embellishment to be the dying act of the Good Sir James. Barbour’s account states that Douglas and the entire Scottish contingent were killed in the skirmish. Other Spanish accounts state that a ‘foreign count’ was killed several days prior to this in a skirmish which was the fault of said count’s own rash behaviour.
Regardless, his body was recovered (some accounts state the Moors were so shocked to find who they had killed that they returned his body with honours to Alfonso). His heart was removed and placed in a casket and his body was boiled so that his bones (and his heart) could return to Douglasdale to be interred in what is now the Church of St Brides. This was carried out by the only surviving Scot of the adventure (Sir William Keith of Galston, who had broken his arm some days prior). Bruce’s heart was also recovered and later interred under the high alter at Melrose Abbey.
The Story of Eleanor and le Hardi
Eleanor was the widow of William de Ferrers of Groby, second son of William de Ferrers, 5th earl of Derby. She was also the daughter of Matthew de Lovaine, great grandson of Godfrey III, count of Louvain. She was ‘abducted’ in 1288 by Le Hardi from Castle Fa’side near Tranent. This was possibly something Eleanor was signed up to -or she was exchanged. Eleanor would go on to be a staunch defender of le Hardi and, besides, how else would he have gotten her out of a castle which was being besieged, but which never capitulated. Nevertheless, she was a powerful person and Douglas’ stealing away of her was referred to as an abduction at the time for which a warrant was put out for le Hardi’s arrest. Eleanor’s brother-in-law was Alexander Comyn, Earl of Buchan and guardian of Scotland (le Hardi’s brother-in-law was James Stewart, the 5th High Steward of Scotland at this time). Nevertheless, the couple obtained permission to marry soon after the siege and le Hardi managed to avoid arrest due to them both having their aforementioned ‘friends in high places’. The English King was nevertheless angered by the development and did manage to imprison Douglas in 1290. Eleanor bailed him from prison in soon after alongside 4 of his fellow in-mates (who were all her cousins). She was fined £100 and as payment had some of her manors in England taken by the English Crown some time later in 1296. By 1291 le Hardi had managed to offend the English king once more (we don’t know what he did): he had already had his lands in Northumberland seized and now the king confiscated Douglasdale as well.
When John Balliol was declared King of Scots in 1292, Douglas defaulted and was soon imprisoned by John in 1292. When the Scots rebelled against Balliol and set up a new guardianship in 1295, Douglas sided with the new faction and was soon appointed governor of Berwick. He led the defence there when it was sacked in 1296 by the English (after which he was imprisoned again and the last of his English estates -in Essex- were seized). He was only freed after signing the infamous Ragman roll, swearing fealty to Edward of England, regaining his Scottish estates in doing so (not his English ones, in fact, de Umfraville, the man who had tried to kill him so many years before, was gifted his old Northumbrian titles). Fate, being poetic, would see le Hardi’s descendant (his great grandson, George, the first Red Douglas, gaining the Earldom of Angus in 1389. Le Hardi was summoned by Edward in 1297 in response to Wallace’s rebellion but he, instead, joined Wallace (who was from Lanark, not far from Douglasdale). Douglas helped the rebels to capture the English treasury and used this to finance further attacks on English authority. Robert the Bruce, aged 22, was dispatched by Edward to take retribution on Douglasdale but he, instead, joined the Douglas rebels too. Bruce and his father ahd both been present at Berwick when Douglas led the defence of the town. Le Hardi was captured once more at the capitulation of Irvine in July 1297 and imprisoned at Berwick castle (so often being an inmate there that there is a tower of Berwick castle called ‘Douglas Tower’ to this day). Following the surprise victory at Stirling Bridge in September that year, le Hardi was transferred to the Tower of London where he died, probably sue to maltreatment, in January 1298.
The Story of Black Archibald
Archibald ‘the Grim’ Douglas was the youngest illegitimate son of the Good sir James and we think he was born in 1330, the year his father died. He lived to 1400, dying at Threave Castle and being buried in Bothwell. He inherited his cousin’s estate of Douglas when he was left as the candidate with the best legitimate claim when James, the 2nd Earl of Douglas, was killed at the battle of Otterburn in 1385. As an illegitimate son who had been passed over numerous times for succession, Archibald likely held no ambitions of becoming the most powerful magnate in Scotland: but that is exactly what happened. Soon, in the 1390’s, he arranged for his house’s ties to the Scottish crown to be strengthened Robert III was a weak ruler). His son and heir married princess Margeret in 1390 and in 1399 his daughter, Marjorie, married another of Robert III’s children: David Stewart, the duke of Rothesay. This later marriage alienated the Earls of March who had already paid a large dowry for their own daughter to marry the duke, resulting in March siding with the English.
Contemporary writers have left some pen descriptions of Archibald: Walter Bower described him as “He was dark and ugly more like a coco [cook-boy] than a Noble”. While Jean Froissart’s chronicle describes him in later life as a large man capable of wielding a giant sword. He was likely not even born by the time his father departed with Bruce’s heart. We do believe he was born in Scotland but it is very likely that he spent much of his life, especially his younger years, in France at the exiled court of David II. This is likely why he so readily entered the service of the French King. It is in this context that he makes one of his first appearances in the records: at the battle of Poitiers in the service of John II against Edward, the Black Prince of England. He had travelled to serve the English as part of his cousin’s retinue (William Douglas, 1st Earl). While William escaped, Archibald was captured (he was wearing what was described as finely made armour and his horse had a fine made harness, so he was correctly assumed to be a valuable captive for ransom).
The armour is relevant to the story of his escape. One of his companions as a captive, Sir William Ramsay pretended that he had stolen the armour and that he was but a squire before beating him with one of Archibald’s own shoes. When the English guards intervened, trying to protect who they assumed to be a valuable hostage, Ramsay convinced them he was but a thief and that the owner of the armour had died in the battle. Convincing the guards that Archibald was a lowly squire, Ramsay duly paid 40 shillings for Archibald’s ransom (the low, going rate for someone of such a station) and Archibald was thus able to travel back to Scotland.
By 1360 Archibald the Black or Grim was made Sheriff of Edinburgh and constable of the Castle as well as Warden of the Western March. In his role of the latter office he conducted several raids into English held territory. Further rise to prominence came in 1362 when he married the Lady of Bothwell, the widowed Joanna de Moravia (an heiress of the Earl of Srathearn). Records state that for the right to Joanna’s hand he offered to fight five English knights in single combat. The King was happy with this, as it ensured that the Moravia estate would pass into loyal and capable hands. With this marriage Archibald also gained the lands of Bothwell (the estate of Joanna’s late husband). He now controlled large swathes of Scotland. Power breeds power and soon after, in 1369, he was named Lord of Galloway by David II as a reward for taking war so effectively to the English. Within a few short years he had solidified control over the unruly territory of Galloway which is why his seal has two ‘barbarians’ on either side. 1378 saw more war with England (the result of a surprise, and successful attack on Berwick by the Scots). This war culminated in Archibald gaining a decisive victory over a much larger English force at Melrose. It is around this time that he started to build Threave castle: he was now so powerful that he was superior to his cousin, William, who had inherited his father’s estate of Douglas. Nevertheless: it would not be long until he inherited those lands also, in the wake of the Battle of Otterburn in 1388 and the death of James Douglas the 2nd Earl.