The circumstances connected with the inveiglement of this poor boy,—who for fifteen out of the twenty-four years he had lived, had been a close prisoner, and so shut out from all knowledge of the outer world, that he was said "not to know a goose from a capon,"—into a confession of complicity with Perkin Warbeck's attempt, and then his barbarous murder,—for it was nothing less,—on Tower Hill, is one of the darkest of the many selfishly revengeful crimes that stain with indelible cruelty the reign of the first Tudor king, as the equally detestable slaying of the lad's aged sister the Countess of Salisbury, in 1541, appals by the horror of its incidents, the second. "The truth was," says Rapin, "the real crime that cost him his life, was his being the last male heir of the house of York." He was beheaded 14 Nov., 1499, and Sir Robert lived to witness the wretched fate of the noble youth he had four years previously brought a captive to London, and in his death the extinction of the hope of the White Rose.

At the conclusion of Henry's first Parliament in 1485, in company with his friend Sir Giles Daubeney, Sir Robert had the honour of the peerage conferred on him, by the title of Baron Willoughby de Broke, but the writ of summons does not appear to have been issued until 12 August, 1492. About the same time he was constituted one of the king's Privy Council. In 1489, he was created a Knight of the Garter, being the two hundred and forty-fourth on the roll of that noble order.

Lord Willoughby de Broke's first important public function appears to have been his despatch from Portsmouth by Henry, with an army "to the number of eight thousand choice men and well armed, who, having a fair wind, in a few hours landed in Brittany" in March, 1489, professedly to protect at her own proper costs and charges the girl-duchess Ann, then about twelve years old, from the aggression of the French king, Charles VIII., who was encamped with a hostile force within her territory, but which province he eventually added to his kingdom, together with the hand of its young mistress.

Here he remained in inglorious ease until November, when the little army, with the exception of the five hundred left to occupy the "cautionary towns" until payment for the expedition was made, returned; during which time, and for a considerable portion of the year ensuing, a game of dissimulation and feints at fighting was carried on between the three monarchs, Henry, Charles, and Maximilian, practically over the destiny of the young Duchess.

Then the scene of this playing at war shifts suddenly from Brittany to Flanders, where the subjects of Maximilian—the proxy husband of Ann—at Ypres and Sluys were in open revolt, respecting "an unpalatable edict concerning coin," and to aid whom Charles VIII. had sent Marshal d'Esquerdes with large succours of help, thus attacking the would-be bridegroom and his child fiancée, on each side, and at once; a game that proved successful in the end.

Maximilian in his turn sent ambassadors over to the wary calculating Henry, then holding the scales between the monarchs, as he was at the same time also engaged in negociations with Charles, who was procrastinating and not intending to give any definite answer, nor but little frightened at Henry's preparations, as he was well assured within himself how matters would eventually terminate.

Henry was however seriously annoyed at the French king's dissimulation, and despatched with all speed a little expedition of a thousand men over to Calais, the command being entrusted to the Lords Morley and Willoughby de Broke. Lord Daubeney was at that period Governor of Calais, and to this force he added another thousand men, drawn from the garrisons of Calais, Hammes, and Guisnes; and they had "secret instructions to aid Maximilian and raise the siege of Dixmude" where the citizens, soldiers, and their allies were encamped. The English soldiers appear to have stolen an effective surprise upon the Flemings and their French allies in the night, for they had apparently no idea of the attack, and routed them with great slaughter, said to have been eight thousand in number, while only a hundred or thereabout of the English were killed, a statement to be received with caution, as Lord Morley, Sir James Tyrrell, Captain of Guisnes, Sir Humphrey Talbot, Marshal of Calais, Sir Gilbert Talbot, and others, were among the slain. The pursuit over, the English army retired to Newport, where Marshal d'Esquerdes appears to have followed and attacked them without result. As this was the first touch of real hostilities, such as they were, between Henry and Charles, for the time it "bred a great coldness" between the belligerent monarchs.

But the coldness did not last long, and meanwhile a complete tangle of matters enveloped these three royal players, over the destiny of their hostage the girl-princess of Brittany, secretly wedded by proxy to Maximilian, practically a prisoner in her little kingdom, unprotected, and in the eyes of the French king a very desirable alliance for him, and so incorporate that province under the crown of France, of which nation it formed an integral portion. Ambassadors came over from the Duchess to sound Henry's intentions of protection toward her, others were despatched across in February, 1491, to the French king by Henry, and these were followed again by further ambassadors from Ann, vainly waiting in London for an answer. So things progressed, and Charles who by his agents was busily plying the young Duchess with his suit, in his turn amused the English envoys, until he found he had won her and had the game in hand; then he cut the knot of the difficulty by marrying her 16 Dec., 1491, and Henry's ambassadors returned discomfited.

This climax came as a bomb-shell among the great personages. Maximilian was furious at the loss of his bride, and threatened immediate invasion of France for so deadly an affront; this however did not much trouble Charles. What he was most concerned with was the attitude of Henry who was also greatly enraged, and who, beside openly boasting he should at once prepare for war against him, was also influencing Ferdinand of Spain—whose daughter Katharine was espoused to his son Arthur—to join him in the conflict. Thus France was threatened on three sides at once, Charles however had little fear of Maximilian or Ferdinand.

In the meantime Henry had another trouble nearer his door, with the Scotch, and no settlement appeared to be in view, while the complication in France continued, the French king being probably moving behind to prevent. Ambassadors again came over from Charles to negociate, but Henry who had the ulterior object of getting well paid for what he was about to do, and the old debt due by Ann of Brittany discharged, aided by liberal subsidies from Parliament, assembled an army of twenty-five thousand foot, and sixteen hundred horse, and on the second of October crossed over to Calais, to make conditions on his adversary's soil, never meaning to fight, but by show and menaces, see what he could get.