TO GUIDO MACHIAVELLI

IMOLA, 2 APRIL 1527

On the day Machiavelli wrote this warm and seemingly carefree letter to his teenage son Guido, he also sent a dire missive to Florence warning the city to fortify itself against the Holy Roman Emperor, Charles V, who was marching against the Medici pope Clement VII and his allies. Florence, Machiavelli warned, should not attempt to pay the emperor off: “It is better to spend ten florins so we can categorically remain free than forty florins that will fetter and destroy us.”

Machiavelli ends this letter to his son asking him to reassure his mother that he will be back “before any trouble comes.” This was, however, among Machiavelli’s last letters, as he fell ill after returning to Florence and died on June 21, 1527.

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Guido, my dearest son, I received a letter from you that has made me very happy, above all because you write that you are now recovered. What good news! If God grants you life, and me as well, I believe I can make you a man of standing, as long as you are prepared to do your part. Among the great friendships I have I can count a new one with Cardinal Cybo,⁴³ a friendship that is so close that I myself am astonished This will be to your advantage. But you must study and, as you no longer have your illness as an excuse, exert yourself learning literature and music, since you can see how much honor my few accomplishments have secured for me. Thus, my dear boy if you want to make me happy and bring advantage and honor to yourself, you must study, do well, and learn. Everyone will help you if you help yourself.

Since the little mule has gone mad, it must be handled in the opposite way one would treat a man who has gone insane. A madman might be tied up, but I want you to untie the animal. Give it to Vangelo and tell him to take it to Montepugliano, remove its bridle and halter, and let it roam wherever it wants, making its own way to free itself of its madness. The village is big and the beast is small. It will not do anybody any harm. So without having to worry ourselves in any way we shall see what it wants to do, and we can always catch it again should it come to its senses. As for the horses, do whatever Ludovico⁴⁴ has told you to do. Thank God he is cured and has sold them. I am certain he has made a good profit, as he sent some money, but I am surprised and saddened that he has not written.

Greet Madonna Marietta⁴⁵ and tell her that I have been hoping to leave any day now, and am still hoping. I have never wished to be in Florence more than now, but I have no choice. Just tell her that regardless of what she hears she should be of good cheer, since I will be there before any trouble comes. Kiss Baccina, Piero, and Totto,⁴⁶ if he is there—I very much want to know if his eyes are well again. Live cheerfully and spend as little as you can. And remind Bernardo to mend his ways: I have written him two letters in the past two weeks and have not received a reply. May Christ watch over you all.

On the second day of April 1527

Niccolò Machiavelli in Imola

43. Cardinal Innocenzo Cybo (1491–1549) was the son of Francesco, the illegitimate son of Pope Innocent VIII and Maddalena de’Medici. In 1521 he had come close to being elected to the pontificate himself. Machiavelli had stayed at his palazzo in Bologna the previous month.

44. Machiavelli’s son Ludovico was in Constantinople.

45. Machiavelli’s wife.

46. Machiavelli’s daughter and sons. The infant, Totto, was away with his wet nurse.