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Updated: June 9, 2025
The king secured his release by paying his ransom; and he led the companies into Spain to help the cause of Henry of Transtamare, who had a dispute for the throne of Castile with Peter the Cruel. The Black Prince supported Peter, and, for a time, with success. In 1369 Henry was established on the throne, and with him the French party.
Protected by the Black Prince, he was at first victorious against Henry of Transtamare his rival; and Du Guesclin was defeated in the battle of Najara in 1367. Afterwards Peter was obliged to surrender, and was killed by the dagger of Henry in a personal encounter. CONSTITUTIONS OF ARAGON AND CASTILE. The political institutions of Aragon and Castile are specially worthy of note.
"Nay, Sir Nigel," said Felton, peering at the prisoner through the uncertain light, "I have twice seen Henry of Transtamare, and certes this man in no way resembles him." "Then, by the light of heaven! I will ride back for him," cried Sir Nigel. "Nay, nay, the camp is in arms, and it would be rank madness.
The first use Du Guesclin made of it was to go and put his name and his sword at the service first of the Duke of Anjou, governor of Languedoc, who was making war in Provence against Queen Joan of Naples, and then of his Spanish patron, Henry of Transtamare, who had recommenced the war in Spain against his brother, Pedro the Cruel, whom he was before long to dethrone for the second time and slay with his own hand.
"'After the great battle of Navarette, when Henry of Transtamare had relieved his brother, King Pedro, of the troublesome burden of the crown, "'And likewise of that still more troublesome burden, which is called life, then Don Henry's victorious magnanimity had to deal with his brother's children. "'He has adopted them, as an uncle should; and he has given them free quarters in his own castle.
When the English and Gascon chieftains who had followed Du Guesclin into Spain heard of the resolutions of their king, Edward III., and the preparations made by the Prince of Wales for going and restoring Don Pedro to the throne of Castile, they withdrew from the cause which they had just brought to an issue to the advantage of Henry of Transtamare, separated from the French captain who had been their leader, and marched back into Aquitaine, quite ready to adopt the contrary cause, and follow the Prince of Wales in the service of Don Pedro.
There was, in point of fact, a civil war raging in Spain between Don Pedro the Cruel, King of Castile, and his natural brother, Henry of Transtamare, and that was the theatre on which Du Guesclin had first proposed to launch the vagabond army which he desired to get out of France.
Charles V. on his side vigorously pushed forward his preparations; he had begun them before he showed his teeth, for as early as the 19th of July, 1368, he had sent into Spain ambassadors with orders to conclude an alliance with Henry of Transtamare against the King of England and his son, whom he called "the Duke of Aquitaine."
The states bordering on France, amongst others Spain and Italy, were a prey to discord and even civil wars, which could not fail to be a source of trouble or serious embarrassment to France. In Spain two brothers, Peter the Cruel and Henry of Transtamare, were disputing the throne of Castile.
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