His meeting with Guidubaldo di Montefeltro
Castiglione stayed in Rome until April 1504, fascinated, as well as by the archaeological beauties of the city, by the intense intellectual life promoted by the humanists, poets and prelates of different origins. In this context he came into contact with the Duke of Urbino, Guidubaldo di Montefeltro, who, after the death of Alexander VI (August 1503) and the election of Pope Giulio II, had recovered his state, which in June 1502 had been taken from him by Cesare Borgia. This revolutionary meeting sparks in Castiglione’s mind the desire to switch from Mantua to Urbino, from one master to another, as Guidubaldo appears to him to be far more similar to his human and civil ideals than Francesco Gonzaga. The moral and cultural stature of Guidubaldo is too superior to that of the Mantuan, reserved and cold, suspicious and full of envy, for Baldassarre not to feel the pressure of his dream to change his allegiance. Via his cousin Cesare Gonzaga, already related to the duke, he makes the first agreements with Guidubaldo for entering into his service.
Returning to Mantua in June 1504, he asked the Marquis Francesco Gonzaga for leave to enter the service of the Duke of Urbino. Behind this separation, heavy with consequences for the biography of Castiglione, it is presumed that there was, as well as the attraction of Guidubaldo, an insatiable antipathy for the prince of Mantua, which, caused by the incompatibility of their respectivetemperaments, had now been going on, due to obscure reasons, for some years.
Thus, no longer a youth, Castiglione decided, in order to remain faithful to himself and to his values, to dramatically sever his feudal and family ties with the Gonzagas, receiving in return, together with his freedom, a dark and permanent threat, which did not allow him to set foot at home until 1514 without risking his life. His diplomatic immunity was not enough to protect him from the rancour of the marquis. In fact, in a letter to his mother written on 1stNovember 1504, Castiglione writes: «I do not for any reason want to come to Mantua at the moment: it is enough for me now to visit the my dearest mother with these letters, and I never think of Mantua without a hair turning white. And if it were not for my dearest mother., I would never think about it» (B.Castiglione, Le lettere, by G. La Rocca, I, Milan 1978, 35).

