From the first the story of the English Pale was a story of degradation and anarchy. It needed the stern vengeance of John, whose army stormed its strongholds and drove its leading barons into exile, to preserve even their fealty to the English Crown John divided the Pale into counties and ordered the observance of the English law; but the departure of his army was the signal for a return of the disorder he had trampled under foot. Between Englishmen and Irishmen went on a ceaseless and pitiless war. Every Irishman without the Pale was counted by the English settlers an enemy and a robber whose murder found no cognizance or punishment at the hands of the law. Half the subsistence of the English barons was drawn from forays across the border, and these forays were avenged by incursions of native marauders which carried havoc at times to the very walls of Dublin. Within the Pale itself the misery was hardly less. The English settlers were harried and oppressed by their own baronage as much as by the Irish marauders, while the feuds of the English lords wasted their strength and prevented any effective combination either for common conquest or common defence. So utter seemed their weakness that Robert Bruce saw in it an opportunity for a counter-blow at his English assailants, and his victory at Bannockburn was followed up by the dispatch of a Scotch force to Ireland with his brother Edward at its head. A general rising of the Irish welcomed this deliverer; but the danger drove the barons of the Pale to a momentary union, and in 1316 their valor was proved on the bloody field of Athenree by the slaughter of eleven thousand of their foes and the almost complete annihilation of the Sept of the O'Connors. But with victory returned the old anarchy and degradation. The barons of the Pale sank more and more into Irish chieftains. The Fitz-Maurices, who became Earls of Desmond and whose vast territory in Munster was erected into a County Palatine, adopted the dress and manners of the natives around them. The rapid growth of this evil was seen in the ruthless provisions by which Edward the Third strove to check it in his Statute of Kilkenny. The Statute forbade the adoption of the Irish language or name or dress by any man of English blood: it enforced within the Pale the exclusive use of English law, and made the use of the native or Brehon law, which was gaining ground, an act of treason; it made treasonable any marriage of the Englishry with persons of Irish race, or any adoption of English children by Irish foster-fathers.

But stern as they were these provisions proved fruitless to check the fusion of the two races, while the growing independence of the Lords of the Pale threw off all but the semblance of obedience to the English government. It was this which stirred Richard to a serious effort for the conquest and organization of the island. In 1386 he granted the "entire dominion" of Ireland with the title of its Duke to Robert de Vere on condition of his carrying out its utter reduction. But the troubles of the reign soon recalled De Vere, and it was not till the truce with France had freed his hands that the King again took up his projects of conquest. In 1394 he landed with an army at Waterford, and received the general submission of the native chieftains. But the Lords of the Pale held sullenly aloof ; and Richard had no sooner quitted the island than the Irish in turn refused to carry out their promise of quitting Leinster, and engaged in a fresh contest with the Earl of March, whom the King had proclaimed as his heir and. left behind him as his lieutenant in Ireland. In the summer of 1398 March was beaten and slain in battle: and Richard resolved to avenge his cousin's death and complete the work he had begun by a fresh invasion. He felt no apprehension of danger. At home his triumph seemed complete. The death of Norfolk, the exile of Henry of Lancaster, left the baronage without heads for any rising. He insured, as he believed, the loyalty of the great houses by the hostages of their blood whom he carried with him, at whose head was Henry of Lancaster's son, the future Henry the Fifth. The refusal of the Percies, the Earl of Northumberland and his son Henry Percy or Hotspur, to obey his summons might have warned him that danger was brewing in the north. Richard, however, took little heed. He banished the Percies, who withdrew into Scotland; and sailed for Ireland at the end of May, leaving his uncle the Duke of York regent in his stead.

The opening of his campaign was indecisive, and it was not till fresh reinforcements arrived at Dublin that the King could prepare for a march into the heart of the island. But while he planned the conquest of Ireland the news came that England was lost. Little more than a month had passed after his departure when Henry of Lancaster entered the Humber and landed at Ravenspur. He came, he said, to claim his heritage; and three of his Yorkshire castles at once threw open their gates. The two great houses of the north joined him at once. Ralph Neville, the Earl of Westmoreland, had married his half-sister; the Percies came from their exile over the Scottish border. As he pushed quickly to the south all resistance broke down. The army which the Regent gathered refused to do hurt to the Duke; London called him to her gates; and the royal Council could only march hastily on Bristol in the hope of securing that port for the King's return. But the town at once yielded to Henry's summons, the Regent submitted to him, and with an army which grew at every step the Duke marched upon Cheshire, where Richard's adherents were gathering in arms to meet the King. Contrary winds had for a while kept Richard ignorant of his cousin's progress, and even when the news reached him he was in a web of treachery. The Duke of Albemarle, the son of the Regent Duke of York, was beside him, and at his persuasion the King abandoned his first purpose of returning at once, and sent the Earl of Salisbury to Conway while he himself waited to gather his army and fleet. The six days he proposed to gather them in became sixteen, and the delay proved fatal to his cause. As no news came of Richard the Welshmen who flocked to Salisbury's camp dispersed on Henry's advance to Chester. Henry was in fact master of the realm at the opening of August when Richard at last sailed from Waterford and landed at Milford Haven.

Every road was blocked, and the news that all was lost told on the thirty thousand men he brought with him. In a single day but six thousand remained, and even these dispersed when it was found that the King had ridden off disguised as a friar to join the force which be believed to be awaiting him in North Wales with Salisbury at its head. He reached Caernarvon only to find this force already disbanded, and throwing himself into the castle dispatched his kinsmen, the Dukes of Exeter and Surrey, to Chester to negotiate with Henry of Lancaster. But they were detained there while the Earl of Northumberland pushed forward with a picked body of men, and securing the castles of the coast at last sought an interview with Richard at Conway. The King's confidence was still unbroken. He threatened to raise a force of Welshmen and to put Lancaster to death. Deserted as he was indeed, a King was in himself a power, and only the treacherous pledges of the Earl induced him to set aside his plans for a reconciliation to be brought about in Parliament and to move from Conway on the promise of a conference with Henry at Flint. But he had no sooner reached the town than be found himself surrounded by Lancaster's forces. "I am betrayed," he cried, as the view of his enemies burst on him from the hill; "there are pennons and banners in the valley." But it was too late for retreat. Richard was seized and brought before his cousin. "I am come before my time," said Lancaster, "but I will show you the reason. Your people, my lord, complain that for the space of twenty years you have ruled them harshly: however if it please God, I will help you to rule them better." "Fair cousin," replied the King, "since it pleases you, it pleases me well." Then, breaking in private into passionate regrets that he had ever spared his cousin's life, he suffered himself to be carried a prisoner along the road to London.