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 Barbour’s Bruce, are familiar from Scott’s Tales of a Grandfather and Castle Dangerous. His half-brother, Sir Archibald, defeated Edward Baliol at Annan in 1332, and had just been appointed regent of Scotland for David II. when he risked a pitched battle at Halidon Hill, where he was defeated and killed (1333), with his nephew William, lord of Douglas. The inheritance fell to his brother, a churchman, Hugh the “Dull” (b. 1294), who surrendered his lands to David II.; and a re-grant was made to William Douglas, next referred to.

(c. 1327–1384), had been educated in France, and returned to Scotland in 1348. In 1353 he killed in Ettrick Forest his kinsman, William, the knight of Liddesdale (c. 1300–1353), known as the “Flower of Chivalry,” who had been warden of the western marches during David II.’s minority, and had taken a heroic share in driving the English from southern Scotland. Liddesdale had in 1342 lost the king’s favour by the murder of Sir Alexander Ramsay of Dalhousie, whom David had made constable of the castle of Roxburgh and sheriff of Teviotdale in his place; he was taken prisoner at Nevill’s Cross in 1346, and only released on becoming liegeman of Edward III. for the lands of Liddesdale and the castle of the Hermitage; Liddesdale was also accused of contriving the murder of Sir David Barclay in 1350. Some of his lands fell to his kinsman and murderer, who was created earl of Douglas in 1358. In 1357 his marriage with Margaret, sister and heiress of Thomas, 13th earl of Mar, eventually brought him the estates and the earldom of Mar. During a short truce with the warden of the English marches he had served in France, being wounded at Poitiers in 1356. He was one of the securities for the payment of David II.’s ransom, and in consequence of the royal misappropriation of some moneys raised for this purpose Douglas was for a short time in rebellion in 1363. In 1364 he joined David II. in seeking a treaty with England which should deprive Robert the Steward, formerly an ally of Douglas, of the succession by putting an English prince on the Scottish throne. The independence of Scotland was to be guaranteed, and a special clause provided for the restoration of the English estates of the Douglas family. On the accession of Robert II. he was nevertheless reconciled, becoming justiciar of southern Scotland, and the last years of his life were spent in making and repelling border raids. He died at Douglas in May 1384, and was succeeded by his son James. By his wife’s sister-in-law, Margaret Stewart, countess of Angus in her own right, and widow of the 13th earl of Mar, he had a son George, afterwards 1st earl of Angus.

(c. 1358–1388), married Lady Isabel Stewart, daughter of Robert II. In 1385 he made war on the English with the assistance of a French contingent under John de Vienne. He allowed the English to advance to Edinburgh, wisely refusing battle, and contented himself with a destructive counter-raid on Carlisle. Disputes soon arose between the allies, and the French returned home at the end of the year. In 1388 Douglas captured Hotspur Percy’s pennon in a skirmish near Newcastle. Percy sought revenge in the battle of Otterburn (August 1388), which ended in a victory for the Scots and the capture of Hotspur and his brother, though Douglas fell in the fight. The struggle, narrated by Froissart, is celebrated in the English and Scottish ballads called “Chevy Chase” and “The Battle of Otterburn.” Sir Philip Sidney “never heard the olde song of Percy and Douglas that I found not my heart mooved more than with a trumpet” (Apologie for Poetrie). The 2nd earl left no legitimate male issue. His natural sons William and Archibald became the ancestors of the families of Douglas of Drumlanrig (see ) and Douglas of Cavers. His sister Isabel became countess of Mar, inheriting the lands of Mar and his unentailed estates.

The earldom and entailed estates of Douglas reverted by the patent of 1358 to, called “The Grim” (c. 1328–c. 1400), a natural son of the “good” Sir James. With his cousin, the 1st earl of Douglas, he had fought at Poitiers, where he was taken prisoner, but was released through ignorance of his real rank. On his return to Scotland he became constable and sheriff of Edinburgh, and, later, warden of the western marches, where his position was strengthened by his becoming lord of Galloway in 1369 and by his purchase of the earldom of Wigtown in 1372. He further increased his estates by his marriage with Joanna Moray, heiress of Bothwell. During the intervals of war with the English he imposed feudal law on the border chieftains, drawing up a special code for the marches. He was twice sent on missions to the French court. The power of the Black Douglas overshadowed the crown under the weak rule of Robert III., and in 1399 he arranged a marriage between David, duke of Rothesay, the king’s son and heir, and his own daughter, Marjory Douglas. Rothesay was already contracted to marry Elizabeth Dunbar, daughter of the earl of March, who had paid a large sum for the honour. March, alienated from his allegiance by this breach of faith on the king’s part, now joined the English forces. A natural son of Archibald, Sir William of Douglas, lord of Nithisdale (d. 1392), married Egidia, daughter of Robert III.

Archibald the Grim was succeeded by his eldest son,, 1st duke of Touraine, lord of Galloway and Annandale (1372–1424), who married in 1390 Lady Margaret Stewart, eldest daughter of John, earl of Carrick, afterwards King Robert III. In 1400 March and Hotspur Percy had laid waste eastern Scotland as far as Lothian when they were defeated by Douglas (then master of Douglas) near Preston. With the regent, Robert, duke of Albany, he was suspected of complicity in the murder (March 1402) of David, duke of Rothesay, who was in their custody at Falkland Castle, but both were officially declared guiltless by the parliament. In that year Douglas raided England and was taken prisoner at Homildon Hill by the Percys. He fought on the side of his captors at Shrewsbury (1403), and was taken prisoner by the English king Henry IV. He became reconciled during his captivity with the earl of March, whose lands had been conferred on Douglas, but were now, with the exception of Annandale, restored. He returned to Scotland in 1409, but was in constant communication with the English court for the release of the captive king James I. In 1412 he had visited Paris, when he entered into a personal alliance with John the Fearless, duke of Burgundy, and in 1423 he commanded a contingent of 10,000 Scots sent to the help of Charles VII. against the English. He was made lieutenant-general in the French army, and received the peerage-duchy of Touraine with remainder to his heirs-male. The new duke was defeated and slain at Verneuil (1424) with his second son, James; his persistent ill-luck earned him the title of the Tyneman (the loser).

(c. 1391–1439), succeeded to his father’s English and Scottish honours, though he never touched the revenues of Touraine. He fought at Baugé in 1421, and was made count of Longueville in Normandy.

His two sons, (1423?–1440), and David, were little more than boys at the time of their father’s death in 1439. They can hardly have been guilty of any real offence when, on the 24th of November 1440, they were summoned to court by Sir William Crichton, lord chancellor of Scotland, and, after a mock trial in the young king’s presence, were beheaded forthwith in the courtyard of Edinburgh Castle. This murder broke up the dangerous power wielded by the Douglases. The lordships of Annandale and Bothwell fell to the crown; Galloway to the earl’s sister Margaret, the “Fair Maid of Galloway”; while the Douglas lands passed to his great-uncle, called the “Gross,” of Balvany (1371–1444), lord of Abercorn and Aberdour, earl of Avondale (cr. 1437), younger son of the 3rd earl.

The latter’s sons, (c. 1425–1452) and James (1426–1488),