In October, 1505, Ferdinand, who had already recalled Gonsalvo de Cordova from Naples and decided to supplant him with his own son Alfonso of Aragon, Archbishop of Saragossa, determined, owing to his lieutenant’s uncertain attitude, to go to Naples himself. The ten days Gonsalvo had asked to put the defences in order and arrange his affairs had elapsed and the King’s suspicions were strengthened. It was then that he conceived the idea of using Caesar to crush Gonsalvo. Thereupon he dispatched Don Pedro de Ayala to Philippe le Beau at Medina del Campo to demand his prisoner, saying that he intended to confine him in the Castle of Ejerica until he was ready to go to Naples, when he would take him with him to command his troops.

Fate apparently was about to afford Caesar an exquisite revenge; he was to lead a Spanish army against the man who had deceived him and delivered him into the hands of the Catholic monarch. Philippe le Beau, however, had his own plans regarding Caesar, and while Ferdinand desired to avail himself of his services against Gonsalvo and Julius II., Maximilian’s son conceived the idea of using him against the Catholic sovereign himself in case he persisted in claiming the regency. From these circumstances it is clear that Caesar’s ability and energy as a military leader were universally recognised.

To lend greater authority to his refusal to surrender Caesar, Philippe le Beau stated that he would first have to refer the matter to the Council of Castile to determine whether the Duke was the prisoner of the King or of Queen Jeanne. In apprehending him in Naples Gonsalvo indubitably was acting in the interests of the kingdom of which Philippe was Regent for his wife, the legitimate heir. Moreover, the Duke would have to be held a prisoner until the suit instituted by the Duchess of Gandia was decided. Ferdinand did not give up the fight when informed of the Council’s decision, but requested Don Bernardino de Cardenas, Governor of the province of Grenada, to whose care he had committed Caesar, to surrender his prisoner. Cardenas was disposed to obey, but asked permission of the Regent, who absolutely refused to allow Caesar to be given up. The Governor then explained to the King that even if he freed Valentino, Philippe would at once seize him again as he did not have a sufficient force to oppose the Regent.

Ferdinand set sail for Naples September 4, 1506, accompanied by his young Queen, and having with him the flower of his army. About a month later, October 5th, his son-in-law Philippe, the Regent of Castile, suddenly died. The Regent was then only twenty-eight years of age, and he was so strong and active that it was believed that he had been poisoned. His widow had still sufficient sense left to ask her father to return to Spain, and to her supplications were added those of his subjects, who feared the kingdom might become a prey to the contending factions. Ferdinand, however, was making good progress in Naples and was anxious to complete his work; he therefore refused to come, and Jeanne acted as Regent during his absence.

The death of Philippe had left Caesar’s guardian, Don Bernardino de Cardenas, in a peculiar position; he had directly disobeyed Ferdinand’s orders, and now, to save himself from the King’s wrath, he proposed to Luis Ferrer, the Catholic monarch’s ambassador, to send Caesar to him in order that he might be transferred to Aragon. Ferrer, cognisant of the machinations which had been carried on by Philippe le Beau and Maximilian with Caesar in prison, promptly accepted the offer in the name of his sovereign, but asked Cardenas to keep his prisoner until he could ascertain Ferdinand’s wishes regarding him. The Spanish monarch, however, was still in Naples, and Caesar, informed by Don Bernardino of what he had done, and unwilling to trust himself to him, succeeded in making his escape, October 25, 1506. He arrived at the Court of his brother-in-law Jean d’Albret December 3, 1506, suddenly—“like the devil,” as the chronicler Moret says.

The news of his escape caused consternation in Italy; Julius II. could never rest as long as Valentino was at large; the Venetians feared him, and the King of France immediately took steps to defend himself against his machinations. Caesar’s friends in Romagna, however, immediately recovered hope.

The Castle of Medina del Campo was the largest in Spain, and for any one to escape from its gloomy walls had been deemed impossible. Erected about the middle of the fifteenth century, in 1460 it fell into the hands of Fonseca, Archbishop of Seville, who on his death left it to a cousin. In 1473 it was seized by the first Duke of Alva.

The Count of Benavente undoubtedly aided Caesar to escape. Valentino had been furnished a chaplain, and this man probably was the one who acted as his agent in dealing with the outer world and also the person who furnished the rope by means of which Valentino descended from the tower. One of the servants tried the rope first; it was found to be too short, and the unfortunate man fell into the moat, breaking some of his bones; he was left where he fell and later was apprehended, tried, and put to death. Caesar had almost reached the end of the rope when, the alarm having been given, it was cut, and he also dropped into the moat. He was injured and had to be carried to the horse which was held in waiting for him by his confederates. Putting spurs to their animals, they never stopped until they reached the little town of Pozaldez; thence they travelled to Villalon, the seat of the Count of Benavente. Caesar was now safe. He had escaped from prison, October 25th, and not until five weeks later did he reach the Court of his brother-in-law at Pamplona; it had taken nearly all this time for him to recover from his injuries and regain his strength; but he had also had time to renew his machinations with the Emperor Maximilian’s ambassadors.

The records of the investigation which followed his escape are preserved in the archives of Simancas and are exceedingly voluminous. The order for his apprehension, which was issued in the name of Queen Jeanne, reads as follows: “Sixteenth December 1506. Commission and order is given by the Queen [titles] to you, Christoval Vasquez de Acuña, and to our alcaldes and to all of those to whom this royal letter shall be shown. You are informed that the Duke of Valentinois, being a prisoner by my order in the castle of Medina del Campo, the said Duke has escaped, and I advise you that I have been informed that he went to the city of Santander; that there were two persons mounted on horseback and that they left their horses in the town of Castres with the son of Pedro Gonzales Calderon. Thence they went to Santander where it is said the Duke was apprehended by an alcalde of the said town, but that the latter released him on receiving presents from him; once free he looked for some one to conduct him safe and sound to Castro-Urdiales to take ship from there. I require that the Duke be searched for with all possible diligence; that careful inquiry be made regarding the persons who left the said horses in the town of Castres; whither they went and where they now are; whether the said alcalde actually had the Duke in his hands and who these persons were. If these persons embarked, from what port, on what vessel, and their destination. In a word I wish you to inform us of everything relevant; and you will seize the person of the said Duke wherever you may find him, be this in a church or a monastery, or any other place, however privileged it may be, and even beyond your jurisdiction, and that, this done, you keep him in your sight with a strong guard until you shall have received further orders. For this purpose I send you the said letter and direct you to begin a searching investigation wherever and among all persons who may be able to give you any information regarding this matter; and that you procure all information concerning the said Duke, and that they give you the means of apprehending him, and that the sum that you promise them on my account for this purpose, be paid them in the manner agreed upon. And if any of them conceal him, cause them to understand that they incur the risk of death and that all their goods will be confiscated. And if you learn that the persons who left their horses in the said town of Castres were unknown, they must nevertheless be held until it is ascertained what they were doing, why and whither they were travelling.

“To carry out my instructions I give you absolute power with all the warrants, writs and authority necessary; and if any one in any way interferes with you he will be liable to a fine of ten thousand maravedis to be paid into my treasury.