The relationship between virtù, fortuna, and free will is one of the most interesting philosophical problems posed by The Prince. But Machiavelli probably did not intend to present a comprehensive philosophy that would explain human action and human failure; rather, he was simply making observations based on his own experience, and perhaps for this reason, his explanation is filled with contradictions.
The figure of the goddess Fortuna, luck or fortune, was derived from Classical Roman mythology, where she was often portrayed in a positive light. Though she was fickle and uncertain, she was also the bringer of good luck and abundance, and one of her symbols was an overflowing cornucopia. The Christian philosopher Boethius, however, focused on Fortuna's dark side in his Consolation of Philosophy, and although her Classical elements survived, subsequent images of her in medieval Europe focused on her ability to dash human hopes and ambitions. Her symbol was the turning wheel, which people rode to the top, only to be thrown to the bottom at the next turning. Fortuna embodied the tawdry and transitory glory of the world that the thoughtful Christian must seek to transcend by focusing on the unchangeable goods of virtue and faith, which had eternal glory in Heaven. The figure of Fortuna makes an appearance in Chapter 25 of The Prince, but the concept of fortune is present throughout. In general, Machiavelli uses fortuna to refer to all of those circumstances which human beings cannot control, and in particular, to the character of the times, which has direct bearing on a prince's success or failure. Whether fortune obeyed the will of God or was simply an impersonal natural force was a subject of debate throughout the Middle Ages and Renaissance. However, nowhere in The Prince is there an indication that one should try to transcend fortune; rather, one should meet it head on and bend it, if possible, to one's own will.
Virtù is the human energy or action that stands in opposition to fortune. While Machiavelli's use of the word does not exclude the idea of goodness or virtuous behavior, it does not necessarily include it, either. Virtù is drive, talent, or ability directed toward the achievement of certain goals, and it is the most vital quality for a prince. Even criminals like Agathocles or extremely cruel rulers like Severus can possess virtù. Machiavelli sometimes seems to say that virtù could defeat fortuna if it was properly applied. If a prince could always adapt his virtù to the present circumstances, he would always be successful. Then again, Machiavelli implies that there is a connection between the two. In his statement that virtù is wasted if there is no opportunity, and opportunity is wasted if there is no virtù, Machiavelli implies that there is some kind of cooperation between the two forces—they cannot operate independently. It may not be possible to completely cancel out the effects of changing fortune, but by decisive action, it is possible to prepare for changes and to mitigate their bad effects.
Here lies the central contradiction of the philosophy. Machiavelli is quite specific in deciding that human beings do have free will; if they did not, energy and ability would be useless qualities. He admonishes the Medici by saying that God wants people to act, not to sit around waiting for things to happen. But Machiavelli also limits the power of free will to only half of human affairs; the other half, the realm of fortuna, cannot be controlled. The reasoning behind this remains obscure. Machiavelli says that people can only act according to their natures, which people are not flexible enough to alter. If, by nature, a prince is impetuous, and the times are ripe for impetuous action, the prince will be successful; but when the times change, a prince cannot change his natures with them, and this brings about his failure. Because a prince can neither choose his nature nor change it, free will seems illusory indeed, and virtù, for all its admirability, begins to look like a cruel trick played by God, or Fortuna, or some other uncontrollable force, on humankind. Although Machiavelli seeks to deny fatalism, he also seems to argue himself into it. Many critics have found in Chapter 25 of The Prince the lowest depths of Machiavelli's cynicism, because the logical conclusion of his argument is that nothing the prince does particularly matters, because he is a mere political time server.
If this is really his final conclusion, however, Machiavelli scarcely seems aware of it, and it does nothing to dampen the enthusiasm of his plea to the Medici to liberate Italy. It is difficult to accept that Machiavelli would spend so much effort honing his sharp advice to the prince if there is no real point in following it. This apparent contradiction has kept readers debating over the real meaning of Machiavelli's philosophy for centuries.