The great rebellion began with a personal quarrel between Owen and his arrogant neighbour Lord Grey of Ruthin. In 1400 the king had summoned Owen to assist him in his Scottish expedition. The summons had been entrusted to Lord Grey to deliver; but he, wishing to sow discord between Henry and Owen, neglected to transmit it. The king was angry with Owen, and with greater justice Owen was angry with Grey. Owen's wrath took the eloquent form of a merciless raid upon his enemy's estates, in the course of which certain members of his household were slain. Grey, determined to retaliate, gathered together his forces and marched against Glyndyfrdwy. But the whole country was now up in arms; and supported by a strong body of followers, Owen was able to burn the town of Ruthin to the ground. Owen then openly declared himself the deliverer of Wales from the English yoke; and so serious a view did the king take of the situation that, without delay, he marched into Carnarvonshire. He was greatly incensed; and his anger was proved by the burning, without any provocation, of the house of the Franciscans at Llan Vaes. Owen, not strong enough as yet to meet the king in battle, retired into the mountain recesses, and Henry had to content himself with declaring all his lands forfeited. Meanwhile the flame of rebellion spread; and Owen was joined not only by people from every part of Wales, but by young Welshmen from Oxford, from London, and from beyond the seas. He had now planted his standard of the red dragon on the slopes of Plinlimmon; and there, safe from the clutches of all invading armies, he proceeded with the task of organization, making frequent dashes into the neighbouring counties, and capturing towns, castles, and abbeys. The capture of the strong castle of Conway by nephews of Owen in the spring of 1401 brought Henry again to Wales, this time accompanied by Earl Percy. Conway was quickly recaptured. Percy, after marching through Carnarvonshire, reached the foot of Cader Idris, where he won a victory. Nevertheless the crushing of the rebellion, and the capture of Owen, seemed to be as remote as ever. In the autumn of the same year the energetic and persistent king came again, marched through Merionethshire, harried Cardiganshire, and stabled his horses near the high altar of the abbey of Strata Florida. Owen meanwhile hung on the skirts of his army, capturing stragglers, and cutting off supplies; and again the baffled monarch was compelled to return to his own country.

Up to the close of 1401 Owen had been nothing more than a guerrilla leader who, had he been captured, might with perfect justice have been put to death as a rebel. And had that fate befallen him then, his career would have but little interest save for the curious and the professional student. It was the next two years that proved that Owen was a statesman of the first rank, as well as an able military leader. He began at once to look out for suitable alliances, and in making them he met with marked success. His early enemy, Lord Grey, fell a prisoner into his hands, and was converted into an ally by marriage with one of Owen's daughters. At the same time successful negotiations were entered into with the native chieftains of Ireland, the French king, the king of Scotland, and the discontented Percies. At the battle of Bryn Glas Edmund Mortimer was captured. He, likewise, was married to one of the Welsh leader's daughters, and encouraged to desert Henry, and to claim the throne of England for his own nephew the Earl of March. For the third time Henry marched into Wales, this time with an immense army. But the elusive and ubiquitous Glyndwr could nowhere be brought to bay; and wind, rain, and floods played havoc with the English hosts. Henry had now quarrelled openly with the Percies. Owen, Mortimer, and Percy Hotspur met on the shore of remote and desolate Aberdaron; and there they agreed upon a plan for the tripartite division of England and Wales.

Owen was then at the height of his power, but in the very hour of triumph he on two occasions only barely escaped death at the hand of an assassin. On the first occasion he was walking with his cousin Howel Sele in his park at Nannau near Dolgelly. Suddenly a doe appeared, and Owen called upon Howel to shoot. But the faithless Howel turned his bow against Owen; and the arrow glanced off from the coat of mail which he invariably wore beneath his ordinary dress. From that hour no man ever saw Howel Sele; but years afterwards a human skeleton was discovered in a hollow tree close to the spot where the encounter must have taken place. The second attempt was made by Davydd Gam. He had come to Machynlleth to attend the Parliament which Owen had summoned there. Fortunately for him, as well as for his intended victim, the plot was discovered, and Davydd lived to meet a more honourable death on the field of Agincourt.

The alliance concluded at Aberdaron was destined to be short-lived; for the Percies were crushed by Henry at the battle of Shrewsbury. Owen has been repeatedly blamed for wasting time in ravaging South Wales instead of keeping tryst with his allies, and joining them before the king's forces had come upon the scene. The censure is probably undeserved. It was vital to the success of their plans that South Wales should be left behind them incapable of further resistance; and, furthermore, it is likely that the Percies had, at the last moment, altered their plans and marched on Shrewsbury, instead of meeting Owen in the vicinity of Ludlow. But we cannot so readily exonerate Owen from blame for neglecting to fall upon the king's army, tired and disorganized as it must have been after the battle. Not to do so was the greatest blunder of his whole career.

Prince Henry, afterwards to become so famous as the victor of Agincourt and the conqueror of France, had now been appointed Lieutenant of Wales, and the war was carried on with increased vigour and ruthlessness. Henry ravaged North Wales, and burned to the ground Owen's home of Sycherth. Nevertheless the power of Owen steadily increased. In 1404 he summoned Parliaments to Dolgelly and Machynlleth. These Parliaments were not a revival of Llewelyn's Council of Princes, but deliberate imitations of the English Parliament. He was now styling himself "Owen by the grace of God Prince of Wales"; and he was treated by foreign potentates as sovereign of an independent country. He had his own Great Seal, his Privy Seal, his chancery, and his courts of law. He concluded an alliance with France in January 1405, and some time later a force of fifteen hundred Frenchmen landed at Milford, and captured Carmarthen. They remained in Wales until early in the following year; but the assistance which they rendered to the national cause appears to have been negligible. But the friendship between Owen and Charles of France continued; and in 1406, in a letter addressed from Pennal, we find Owen telling the French king what his aims were, i.e., to create a Wales territorially free, to create an independent Welsh Church, and to create two Universities, one for North, and one for South Wales.

Owen had also succeeded in winning the support of the Pope, or rather of one of the Popes; for those were the days of the Great Schism, and there were rival claimants for the throne of St. Peter. Owen decided to withdraw the spiritual allegiance of Wales from the Roman Pope, Gregory XII, and to transfer it to Peter de Luna, then dwelling in Avignon, and calling himself Pope Benedict XIII. In return, of course, Owen expected the Pope to acknowledge the independence of Wales. John Trevor, bishop of St. Asaph, had already gone over to the nationalist side; and Owen, with the Pope's consent, nominated Llewelyn Bifort to the see of Bangor. Apparently this prelate was never recognised by the English Church; but he was present some years later at the Council of Constance, signing himself as "Ludovicus Bangorensis." In the North Wales dioceses, at least, the national party was supreme between 1404 and 1408, and in a lesser degree in those of the South as well.

The project of founding two national Universities, it seems, never found any sort of realization in Owen's day, nor indeed for close upon five centuries afterwards. But the plan in itself is sufficient to rebut the ridiculous calumny that Owen was an uncivilized barbarian. It is a pity that the age which saw the founding of Universities at St. Andrews, Prague, Vienna, Louvain, Cracow, Cologne, Padua, Heidelberg, Leipzig, Erfurt, Pesth, Würtzburg, and Rostock, should not have witnessed the founding of one in Wales as well. What a difference the existence of such an institution would have made in the national character, and in the whole outlook of the people, we can only regretfully conjecture. For centuries young Welshmen flocked eagerly to Oxford, to Cambridge, and to some of the famous European seats of learning; but the culture of Wales ran in other channels, undisciplined and amateurish, and, despite its wonderful charm and fascination, lacking in classic restraint and breadth of outlook.

Owen's success reached its culmination in 1405. From that time on his star was steadily on the wane, although for years he kept up a brave, and sometimes successful, resistance. A plan to secure the person of the young Earl of March, and to proclaim him King of England, miscarried. Slowly but surely the pressure of Henry's armies, and those of the Lords Marchers, was beginning to tell. Most of the grievances of the peasants had wisely been redressed, and they longed for the time when they could till their fields in peace, unmolested by the armies of either friend or foe. Owen's high ideals were beyond the comprehension of the selfish and illiterate labouring classes upon whom he had depended for his strength; and they now deserted in hundreds from his camp. The general débâcle was assisted by the young Henry's policy of studied clemency. He was no foreigner, but a rival Prince of Wales; and he strove to prove that he cared just as much as did Owen for the welfare of his Welsh subjects. The abbot of Valle Crucis was perfectly right when he told Owen that he had risen a century too soon.

In the closing years of his life Owen was no better than a fugitive. Indeed, so completely had all traces of rebellion disappeared, that no particular effort was made to effect his capture. Where he lived, and how he lived, was unknown to his contemporaries as it is to us. Sometimes he would appear, clad as a common labourer; then vanish again, and not be seen for months. In its poverty and its loneliness it is a pathetic close to so splendid and so romantic a career. The young Henry had succeeded his father as King of England in 1413, and in 1415 he offered a free pardon to Owen. The pardon was, however, refused. That is the last fact which we know about the fallen leader. When he died, or where he is buried, we do not know; but a tradition, to which perhaps some credence may be given, tells us that at the end he came home to his beloved Glyndyfrdwy, and that his bones lie close by at Corwen. All his friends had long since been dispersed; some were dead, some languished in English prisons, others were living abroad in exile. Of the State which Owen had attempted to construct not a vestige remained, and the ideals which he had cherished remained for centuries forgotten. But in tradition his name always loomed large on both sides of the border. How powerfully he had impressed the people of England is proved by the place which is accorded to him by Shakespeare. The Glendower of the great dramatist is a compound of cunning and simplicity, of amiability and uncouthness; but his considered verdict is that—

"In faith he is a worthy gentleman,
Exceeding well read, and profited
In strange concealments; valiant as a lion,
And wondrous affable, and as bountiful
As mines of India."