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Henry VII land. But in 1501 he again abruptly left England and fled to the Emperor Maximilian, who had promised a friend of his to aid him to obtain the crown. He was welcomed by Maximilian in the Tyrol, but on 20 June 1502 a treaty was made between Henry and Maximilian, and confirmed by the latter on 28 July, by which Henry gave the emperor 10,000l. in aid against the Turks, and the emperor promised not to receive English rebels of whatever rank. Suffolk accordingly had to seek other protectors, but Henry had so many allies upon the continent that hardly any country now was safe for him. In 1504 he was made prisoner by the Duke of Gueldres, who handed him over in 1505 to Philip, archduke of Austria, then king of Castile.

On the death of Prince Arthur in 1502 the Spanish sovereigns demanded restitution of the dowry that Catherine brought with her to England; but to this Henry considered himself in no wise bound. The Spanish sovereigns were ready, however, to settle the dispute by marrying Catherine to Arthur's younger brother Henry when he should come of age. To this in itself Henry was not ill inclined, but he was determined not to agree to it until the Spanish sovereigns expressly renounced all claim in any event to the restitution of the dowry. While things were in this state Henry became a widower, and immediately made a monstrous proposal to marry his own daughter-in-law himself. Her mother Isabella was greatly shocked, and wrote to her ambassador not to press the demand for restitution of the dowry, but to get Catherine by all means back to Spain. The result was that a treaty was immediately agreed to in England for Catherine's marriage with her late husband's brother, with an express renunciation by Ferdinand and Isabella of all claim to restitution of the dowry, and it was confirmed by each of the Spanish sovereigns separately in the following September.

In 1504 Isabella of Castile died, and her kingdom descended by inheritance to her daughter Joanna and Joanna's husband, the Archduke Philip. Henry was deeply interested to know how much authority over Castile Ferdinand still possessed as governor in the absence of the new king and queen, and in 1505 he sent three gentlemen to Spain mainly to report on this subject, though ostensibly to offer terms for an alliance against France to which he had been much solicited. They were also instructed to visit Valencia, where two dowager queens of Naples (mother and daughter) lived, and to make careful observations, in reply to a regular set of questions by no means delicate, of the stature, complexion, and personal qualities generally of the younger lady, who had been suggested by Queen Isabella as a second wife to Henry to divert him from the thought of her daughter. The inquiries on this head were satisfactory, except as regards the young queen's jointure. As to Ferdinand's position in Castile, Henry's agents satisfied him that the nobles there were anxious for Philip's coming to emancipate them from his control.

In January 1506 Philip and Joanna actually set sail for their new kingdom; but meeting with a violent storm on the way they were obliged to land in Dorsetshire. Henry at once invited them to Windsor, where he showed them every attention, made Philip a knight of the Garter, and led him to sign a treaty of alliance which involved the surrender of Suffolk. A treaty of commerce was also arranged between England and the Low Countries, which the Flemings called the Intercursus Malus, as it was so much in favour of the English merchants. Suffolk was brought to England just after Philip's departure, and thrown into the Tower. Henry promised Philip to spare his life, and did so, though he was put to death by Henry VIII in 1513.

Philip died in Spain in September 1506, and Henry immediately offered to marry his widow, with a view to becoming master of Castile. The lady was insane, as Henry knew, and her father Ferdinand certainly did not wish him for a rival in the peninsula; but Ferdinand promised, if she could be induced to listen to any project of marriage, that she should have no other husband than Henry. The scheme, however, was not seriously entertained on either side, and Henry endeavoured to attain his object otherwise by marrying his daughter Mary to Philip's son Charles (afterwards the emperor Charles V), which was one of the matches proposed at the interview between him and Philip at Calais, although the parties were still mere children. Relations were becoming strained between Henry and Ferdinand, and it was said in Spain that Henry was collecting a fleet to invade Castile. Matters went no further, however, than a war of diplomacy. Ferdinand made alliance with France, which dragged him into the league of Cambray against Venice; while Henry made treaties with Maximilian, and endeavoured to negotiate for himself a marriage with the emperor's daughter, Margaret of Savoy, which would have placed the government of the Low Countries in his hands.

A great embassy came over from Flanders towards the close of 1508, and the marriage of Mary to Prince Charles of Castile was celebrated by proxy on 17 Dec. But the king's health now began to decline under complicated