A series of truces had halted any further significant fighting between Scotland and England but on April 19, 1388, English envoys sent to Scotland to again extend the ceasefire return to Richard's court empty-handed—by April 29, Robert II is conducting a council in Edinburgh to authorize renewed conflict with England.

Scottish barons charged with protecting the Anglo-Scottish border retaliate in 1388 against recent incursions by their English counterparts.

James, the thirty-year-old second earl of Douglas, together with the Earl of Moray, leads the Scots against a very large large English hunting party upon a parcel of hunting land (or chase) in the Cheviot Hills, hence the term, Chevy Chase.

The hunt is led by twenty-four-year-old Henry “Hotspur” Percy.

The Scottish Earl of Douglas had forbidden this hunt and interpretsit as an invasion of Scotland.

In response he attacked, causing a bloody battle after which only one hundred and ten people survive.

Born May 20, 1364, at Alnwick Castle in Northumberland, the eldest son of Henry Percy, 1st Earl of Northumberland, and Margaret Neville, daughter of Ralph de Neville, 2nd Lord Neville of Raby, and Alice de Audley, young Henry had been knighted by King Edward III in April 1377, together with the future Richard II and Henry IV.

He was in Ireland in 1380 with the Earl of March, and in 1383 traveled in Prussia.

He was appointed warden of the east march either on July 30, 1384 or in May 1385, and in 1385 had accompanied Richard II on an expedition into Scotland.

Sent to France in April 1386 to reinforce the garrison at Calais, he led raids into Picardy, and between August and October 1387 he was in command of a naval force in an attempt to relieve the siege of Brest.

In appreciation of these military endeavors he is in 1388 made a Knight of the Garter.

Reappointed as warden of the east march, he commands the English forces on August 10, 1388, against James Douglas, 2nd Earl of Douglas, at the Battle of Otterburn.

The English troops press so closely that, fearful of slaying their own in the gathering dusk, they loose few arrows at the Scots.

One arrow, however, finds Douglas, who, mortally wounded, instructs his soldiers to raise his standard and to keep his death a secret until victory is achieved.

His followers rally and kill twenty-seven hundred English soldiers as they flee in retreat.

Hotspur is captured and later ransomed for a fee of seven thousand marks.

The Scots army defeated the English at the Battle of Otterburn in Northumberland in August 1388, but the death, without issue, of its leader James, earl of Douglas, has triggered a series of claims on his estate—Carrick backs his brother-in-law Malcolm Drummond, the husband of Douglas's sister while Carrick's brother Fife takes the side of Sir Archibald Douglas, lord of Galloway, who holds an entail on his kinsman's estates and who ultimately succeeds to the earldom.

Archibald, called the Grim, is the sixty-year-old illegitimate son of the first Sir James, the original Black Douglas.

Fife, with his powerful Douglas ally, together with those loyal to the king, ensures at the December 1388 council meeting that the lieutenancy of Scotland will pass from Carrick (who had recently been badly injured from a horse-kick) to Fife.

There is general approval of Fife's intention to properly resolve the situation of lawlessness in the north and in particular the activities of Buchan his younger brother.

Buchan is stripped of his position of justiciar, which will soon be given to Fife's son, Murdoch Stewart.

George, the illegitimate son of William, 1st Earl of Douglas, and Margaret Stewart, Dowager Countess of Mar and Countess of Angus and Lady Abernethy in her own right, is seen as the product of incest as his mother is the widow of Earl William's wife's brother, Thomas, 13th Earl of Mar.

Earl William's legitimate wife, Margaret of Mar, had already produced an heir for her husband in 1358: James, 2nd Earl of Douglas and Mar, who had inherited the title in 1384 upon his father's death.

Margaret of Angus in 1389 had relinquished her title in favor of her son, but he does not assume it until his betrothal in 1397 to the princess Mary, daughter of King Robert III.

Margaret’s influence must have been considerable: in addition to having obtaining a royal bride for her illegitimate son, she persuades King Robert to confirm the seventeen-year-old in his style of Earl of Angus, and also to bestow upon him the lordships of Abernethy, (Perthshire) and Bonkill, (Berwickshire); and "to endow him and his spouse with the justiciary fees of the County of Forfar, to ratify all gifts, entails, and leases made or to be made by Isabel, Countess of Mar, to the said Jorge her brothir" (Maxwell).

The Good Sir James Douglas, having been killed without issue in 1388, at the Battle of Otterburn, the Earldom of Mar, and all non-entailed Douglas possessions, had passed to his sister Isabel.

The earldom of Douglas had passed to a cousin, an illegitimate son of James Douglas, Archibald the Grim.

Archibald’s descendants are to form the famed line of Black Line of Douglases, and those of George the equally famed and longer-lived Red Line.