JAMES, 2ND EARL OF DOUGLAS AND MAR (c. 1358-1388), mar ried 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. In 1388 Douglas captured Hotspur Percy's pennon in a skirmish near Newcastle. Percy sought revenge in the battle of Otterburn (Aug. 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, nar rated by Froissart, is celebrated in the English and Scottish ballads called "Chevy Chase" and "The Battle of Otterburn." 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 QUEENSBERRY) 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 ARCHIBALD DOUGLAS, 3RD EARL OF DOUGLAS, called "The Grim" (c. 1328—c. 1400), a natural son of the "good" Sir James. He was warden of the western marches, lord of Gallo way in 1369, increased his estates by his marriage with Joanna Moray, heiress of Bothwell, and by his purchase of the earldom of Wigtown in 1372. 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. 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, ARCHIEALD, 4TH EARL OF DOUqLAs, 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 140o 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 10,00o 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).