During the turbulent last decade of the 1300s, anarchy ruled in Scotland. Alexander Stewart, Earl of Buchan, fourth son King Robert II, and known as the notorious "Wolf of Badenoch", ruled the whole north of Scotland in the name of his father, as the "Justiciar and Lieutenant of the North". His older brother, Robert Earl of Fife had been the Governor and Regent of Scotland since 1388 and had been the real power behind their father’s throne. Their competition led to the "Wolf" being excommunicated for seizing the lands of the bishop of Moray. In revenge Alexander burned and plundered the towns of Forres in May and Elgin and its cathedral in June 1390. Upon their father’s death, their elder brother, John Earl of Carrick, was crowned as King Robert III at Scone in August 1390. Alexander was forced to submit to his brothers at Perth and make full restitution to the bishop and humbly seek absolution from the pope. Earl Alexander’s rage, as his nickname implies, led him to encourage his natural son, Sir Duncan, in raising a force in 1392 and sending him south to teach some of his older brother’s supporters a lesson and get even with Earl Robert for this humiliation.

Sir Duncan Stewart, with some of his followers and accompanied by the Roses and their adherents from Strathnairn came south into Rannoch country to meet up with our second Chief, Robert de Atholia who had become chief around 1355 upon the death of "Stout Duncan" of Bannockburn fame. Our chief had been looking for a reason to "visit" the Lindsays in Angus and this opportunity was perfect.

Robert’s first wife had been the younger daughter of Sir John Sterling (de Striviling) of Glenesk and a co-heiress of the lands of Glenesk in Angus. Sir John’s other daughter had married Sir Alexander Lindsay. Their son, Sir David Lindsay of Glenesk, was afterward created Earl of Crawford in 1397. The Lindsays held about two thirds of the county of Angus and in addition were overlords of the highland district of Strathnairn, the home of the Roses and others of Sir Duncan Stewart’s Clan Chattan followers.

The dispute between the two families was probably over her heritable lands which had somehow passed to Sir David Lindsay on his wife’s death, or possibly for some other reason now unknown, but our Chief now saw an opportunity to settle this score. Sir David Lindsay, expecting some trouble from his deceased aunt’s family, arranged a tryst with the Robertsons to mollify them and that meeting was not kept. Lindsay later sent a scout into Atholl to find out what was going on and the scout was never seen again. What was happening, of course, were secret meetings between our Chief and his younger half brothers with Sir Duncan Stewart. No hint of the impending foray into Angus leaked out and everything seemed peaceful and quiet.

One night, six hundred years ago, a small army of our clansmen were mustered under our Chief’s three half brothers from their father’s ("Stout Duncan") second marriage. These half brothers were Patrick of Lude, Thomas of Strowan and Gibbon. Along with Sir Duncan Stewart and his followers, they secretly assembled and over three hundred men moved eastward into Angus to raid the Lindsays and their Ogilvy allies.

During the initial raid, many Ogilvys and Lindsays were slain, their homes burned and their cattle driven off westward toward Rannoch. Of course, the leaders of Glenesk, Glenisla and other districts of Angus quickly gathered as many survivors as possible for pursuit and caught up with the highlanders near Blairgowrie, where a bloody battle was fought at Glasclune in revenge for the raid and to recapture the large herd of stolen cattle. The Angus men were beaten off with heavy losses and the highlanders continued moving westward at a leisurely pace up the valley of Strathardle toward home.

Meanwhile, news of the raid had been spread throughout Angus and most of the remaining Angus lairds gathered their forces under Sir Walter Ogilvie and rushed westward to join the defeated Angus men retreating from the previous battle. Reorganized and once again pursuing our clan, the Angus men, although inferior in numbers, caught up with the raiders in the western portion of Strathardle at a site now known as Dalnagairn or ‘field of the cairns’ at the very head of Glenbrierachan, which in Gaelic means ‘valley of the stream of the grey heights’, lands which later belonged to the Robertsons of Balnaguard. The name of this site, Dalnagairn, comes from the ancient custom of the highlanders to raise cairns over the slain both as monuments to the fallen and also to prevent wolves and foxes from later scratching up the dead.

At Dalnagairn, about six miles northeast of Pitlochry, a second battle took place, which is generally considered to have been one of the more savage fights throughout the entire history of clan conflicts. This fight was between the pride of Angus chivalry, led by some threescore men mounted on horseback, fully clad in steel armor and carrying long lances against wild highlanders afoot and armed with claymore, targe and dirk. The highlanders sent the cattle on before them and stood their ground on rough defensive terrain difficult for horsemen. The Angus chivalry and their followers attacked and were instantly overwhelmed by the ferocity of the defenders, they panicked and were then routed. The hereditary Sheriff of Angus, Sir Walter Ogilvie, was killed along with his brother and nearly a dozen other knights and according to reports over sixty more of the Angus men were slain. Sir David Lindsay was wounded and the report of how he was wounded illustrates the ferocity of the battle. Sir David had lanced and pinned one of the raiders to the ground. The mortally wounded man pulled himself up the lance and with his claymore almost severed Lindsay’s foot by slashing through the stirrup and armored steel boot and cutting through to the bone. The Angus survivors retreated again. The raiders, not content to have just defeated the men of Angus a second time, followed. The Angus men bravely made two vain attempts to rally after this second defeat. First at a site which is called to this day Dail-Chosnaidh or 'the field of contending' and then later at a pass five hundred yards further down the glen known as Clais-Chatha or ‘the battle hollow’. A number of men were killed in this pass and their bodies were thrown into a small loch now called An Lochan Dubh. The hollow to which the cattle were driven before the fight at Dalnagairn and up which the highlanders marched triumphantly home with their thousands of cattle and other hard won booty, is still called the 'pass of thanksgiving'.

The vanquished survivors did not meekly submit to this total defeat and appealed to their ally and Regent, Robert Earl of Fife, for redress. With their report, he pushed through an Act of Parliament, by which the Chief’s half brothers were declared outlaws and the clan was laid under forfeiture. Our Chief had to give up all claim to the north side of Loch Rannoch to have this forfeiture removed. These lands had been given to our Chief’s father (Duncan) by Robert the Bruce for our part in the victorious Battle of Bannockburn in June 1314.