MISSION TO THE DUKE OF VALENTINOIS.
October 5, 1502.

Cesare Borgia, second son of Pope Alexander VI., was originally intended for the Church, and had been made Cardinal of Valence by his father. But after the assassination of his elder brother, the Duke of Gandia, charged by all the writers of the day upon Cesare, he doffed the cardinal’s hat and eagerly seized the sword as more congenial to him. His father, the Pope, granted him a bull of secularization, and sent him with letters of credence and strong recommendations to King Louis XII. of France, as bearer of the Pope’s bull dissolving the marriage of the King with the Queen Jeanne, thus enabling Louis XII. to marry Anne of Brittany, widow of King Charles VIII., of whom he had been enamored whilst yet Duke of Orleans. At the same time Cesare Borgia was bearer of the cardinal’s hat for Georges d’Amboise, Archbishop of Rouen and prime minister of Louis XII. In recognition of these services the king, who had already made Cesare Duke of Valentinois, gave him for wife Carlotta d’Albret, daughter of the Sieur d’Albret; and from Cardinal d’Amboise he obtained the promise of aid and support in the establishment of a state for himself in the Romagna, which had been given him by his father, Pope Alexander VI., together with the command of the papal forces. The Romagna, however, was at that time occupied by a number of petty lords and despots, some of whom were employed by the Duke of Valentinois as captains of his troops. These fearing lest the Duke would dispossess them, met in secret at Magione, in the Perugian territory, to devise measures for thwarting the Duke’s projects. Immediately after his return from France, however, the Duke pushed his military movements with extraordinary energy and skill, and very quickly made himself master of Faenza, Urbino, etc. Feeling the importance of having the support and alliance of the Florentine republic, whose territory adjoined the Romagna, Cesare requested the Signoria of Florence to send an ambassador to him with whom he could treat of these matters. The Signoria accordingly sent Francesco Soderini, Cardinal of Volterra, and Niccolo Machiavelli to him at Urbino; but the demands of the Duke for an alliance and a change in the government of Florence, by which he hoped to facilitate his future plans of conquest in Tuscany, were such as the envoys could not accede to. The Duke gave them four days for a final reply, during which Machiavelli returned to Florence for the purpose of consulting the government; the result

of which was that the Signoria wrote to Soderini to inform the Duke of the impossibility of their complying with his demands.

Meantime, however, the Florentine government became still more alarmed by the disturbances in the Val di Chiano and Arezzo, which had been stirred up by some of the Duke’s captains, especially Vitellozzo Vitelli. Although these disturbances were quieted and Arezzo restored to the Florentines by the intervention of the French, yet they had produced such an impression upon the Florentine government that they resolved on the 5th of October, 1502, to despatch Machiavelli on a special mission to the Duke of Valentinois and to remain near him and watch his movements. This is the mission that gave rise to the following despatches from Machiavelli to the Signoria, which are of the highest interest, especially as they contain an authentic account of the proceedings of the Duke of Valentinois at Sinigaglia in killing Vitellozzo Vitelli, Oliverotto da Fermo, and the Signor Paolo and the Duke Gravina Orsini.