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.
