As shown by his letter of dedication, Machiavelli's work eventually came to be dedicated to Lorenzo di Piero de' Medici, grandson of "Lorenzo the Magnificent", and a member of the ruling Florentine Medici family, whose uncle Giovanni became Pope Leo X in 1513. It is known from his personal correspondence that it was written during 1513, the year after the Medici took control of Florence, and a few months after Machiavelli's arrest, torture, and banishment by the in-coming Medici regime. It was discussed for a long time with Francesco Vettori - a friend of Machiavelli - whom he wanted to pass it and commend it to the Medici. The book had originally been intended for Giuliano di Lorenzo de' Medici, young Lorenzo's uncle, who however died in 1516. It is not certain that the work was ever read by any of the Medici before it was printed. Machiavelli describes the contents as being an un-embellished summary of his knowledge about the nature of princes and "the actions of great men", based not only on reading but also, unusually, on real experience.
The types of political behavior which are discussed with apparent approval by Machiavelli in The Prince were regarded as shocking by contemporaries, and its immorality is still a subject of serious discussion. Although the work advises princes how to tyrannize, Machiavelli is generally thought to have preferred some form of free republic. Some commentators justify his acceptance of immoral and criminal actions by leaders by arguing that he lived during a time of continuous political conflict and instability in Italy, and that his influence has increased the "pleasures, equality and freedom" of many people, loosening the grip of medieval Catholicism's "classical teleology", which "disregarded not only the needs of individuals and the wants of the common man, but stifled innovation, enterprise, and enquiry into cause and effect relationships that now allow us to control nature".
On the other hand, Strauss (1958:11) notes that "even if we were forced to grant that Machiavelli was essentially a patriot or a scientist, we would not be forced to deny that he was a teacher of evil". Furthermore, Machiavelli "was too thoughtful not to know what he was doing and too generous not to admit it to his reasonable friends".
Machiavelli emphasized the need for realism, as opposed to idealism. In The Prince he does not explain what he thinks the best ethical or political goals are, except the control of one's own fortune, as opposed to waiting to see what chance brings. Machiavelli took it for granted that would-be leaders naturally aim at glory or honor. He associated these goals with a need for "virtue" and "prudence" in a leader, and saw such virtues as essential to good politics and indeed the common good. That great men should develop and use their virtue and prudence was a traditional theme of advice to Christian princes. And that more virtue meant less reliance on chance was a classically influenced "humanist commonplace" in Machiavelli's time, as Fischer (2000:75) says, even if it was somewhat controversial. However, Machiavelli went far beyond other authors in his time, who in his opinion left things to fortune, and therefore to bad rulers, because of their Christian beliefs. He used the words "virtue" and "prudence" to refer to glory-seeking and spirited excellence of character, in strong contrast to the traditional Christian uses of those terms, but more keeping with the original pre-Christian Greek and Roman concepts from which they derived. He encouraged ambition and risk taking. So in another break with tradition, he treated not only stability, but also radical innovation, as possible aims of a prince in a political community. Managing major reforms can show off a Prince's virtue and give him glory. He clearly felt Italy needed major reform in his time, and this opinion of his time is widely shared.
Machiavelli's descriptions encourage leaders to attempt to control their fortune gloriously, to the extreme extent that some situations may call for a fresh "founding" (or re-founding) of the "modes and orders" that define a community, despite the danger and necessary evil and lawlessness of such a project. Founding a wholly new state, or even a new religion, using injustice and immorality has even been called the chief theme of the Prince. For a political theorist to do this in public was one of Machiavelli's clearest breaks not just with medieval scholasticism, but with the classical tradition of political philosophy, especially the favorite philosopher of Catholicism at the time, Aristotle. This is one of Machiavelli's most lasting influences upon modernity.
Nevertheless Machiavelli was heavily influenced by classical pre-Christian political philosophy. According to Strauss (1958:291) Machiavelli refers to Xenophon more than Plato, Aristotle, and Cicero put together. Xenophon wrote one of the classic mirrors of princes, the Education of Cyrus. Gilbert (1938:236) wrote: "The Cyrus of Xenophon was a hero to many a literary man of the sixteenth century, but for Machiavelli he lived". Xenophon also, as Strauss pointed out, wrote a dialogue, Hiero which showed a wise man dealing sympathetically with a tyrant, coming close to what Machiavelli would do in questioning the ideal of "the imagined prince". Xenophon however, like Plato and Aristotle, was a follower of Socrates, and his works show approval of a "teleological argument", while Machiavelli rejected such arguments. On this matter, Strauss (1958:222–223) gives evidence that Machiavelli may have seen himself as having learned something from Democritus, Epicurus and classical materialism, which was however not associated with political realism, or even any interest in politics.
On the topic of rhetoric Machiavelli, in his introduction, stated that “I have not embellished or crammed this book with rounded periods or big, impressive words, or with any blandishment or superfluous decoration of the kind which many are in the habit of using to describe or adorn what they have produced”. This has been interpreted as showing a distancing from traditional rhetoric styles, but there are echoes of classical rhetoric in several areas. In Chapter 18, for example, he uses a metaphor of a lion and a fox, examples of cunning and force; according to Zerba (2004:217), “the Roman author from whom Machiavelli in all likelihood drew the simile of the lion and the fox” was Cicero. The Rhetorica ad Herennium, a work which was believed during Machiavelli’s time to have been written by Cicero, was used widely to teach rhetoric, and it is likely that Machiavelli was familiar with it. Unlike Cicero's more widely accepted works however, according to Cox (1997:1122), “Ad Herennium ... offers a model of an ethical system that not only condones the practice of force and deception but appears to regard them as habitual and indeed germane to political activity”. This makes it an ideal text for Machiavelli to have used.