This transvaluation of values culminates in chapter 18 of The Prince, entitled, “In What Mode Faith Should Be Kept by Princes.” The writers of “mirrors of princes” believed that craftiness is a vice unbecoming a ruler.³⁵ Machiavelli concedes that it is a negative trait, but is quick to add that “nonetheless one sees by experience in our times that the princes who have done great things are those who have taken little account of faith and have known how to get around men’s brains with their astuteness; and in the end they have overcome those who have founded themselves on loyalty.”³⁶ But not content with offering an empirical observation, Machiavelli also advisesrulers to act contrary to conventional morality. This chapter thus provides the clearest example of how Machiavelli reappraises the relationship between politics and ethics.

The attack on the traditional understanding of morality and politics occurs simultaneously on two fronts: Against the Christian humanist writers of the specula principis; and against Cicero, the pagan hero of the humanists. Though Machiavelli does not mention Cicero by name in this chapter, it is manifestly clear that he and his heirs are the target of his polemic. Quoting almost verbatim from De Officiis, Machiavelli notes that “there are two ways of fighting, one with laws and the other with force. The first is the way of men, the second is the style of beasts.” Cicero went on to explain that there are also two ways to do evil: By force, the way of the lion; or by fraud, the way of the fox. Neither of them is becoming of men, but fraud is by far the more despicable. Machiavelli appropriates these same terms in order to say something altogether different. Unlike Cicero, who justified the use of force only in exceptional circumstances—when discussion and negotiation become futile, for instance—Machiavelli claims that the methods becoming of men are often ineffective, and therefore one must also be familiar with, and prepared to use, the methods of the beasts. “Thus, since a prince is compelled of necessity to know well how to use the beast, he should pick the fox and the lion, because the lion does not defend itself from snares and the fox does not defend itself from wolves.”³⁷ The combination of fraud and force is a winning formula; if, however, one must choose between the two, the fraud of the fox is preferable to the brute force of the lion. By granting legitimacy to the methods of the beasts, Machiavelli stood Cicero’s Stoic morality on its head, and with it some of Christianity’s most cherished principles.³⁸

In his Discourses on the First Ten Books of Livy,Machiavelli discusses Cicero’s political actions during the Roman civil war, the fateful results of which were the very opposite of what he had intended to achieve. Instead of weakening Mark Antony, Cicero’s actions served only to strengthen him; instead of leading the senate to victory, they brought about its defeat.³⁹ In other words, Cicero epitomizes for Machiavelli the difference between intentions and results, theory and practice, and the dangerous ease with which men are tempted into ignoring the distinction. While Cicero preached honesty, human fraternity, peaceful settlement of disputes, his Rome practiced force and deceit to create an empire.

Machiavelli does not condemn the Romans for going the way of force and fraud. On the contrary, he declares this choice a reason for their success. Had Rome acted according to Cicero’s precepts, he suggests, it would not have conquered the known world. Rather, Rome owes its glory to the fact that its policies betrayed its own moral principles.⁴⁰ To fulfill its aspirations it deceived whenever it could, and when it could not, it resorted to force. Unlike the intellectuals of the Roman republic, Machiavelli does not see the source of its power in its high ideals, but in its actions in contravention of those ideals. Nor does Machiavelli take issue with Rome’s hypocrisy; on the contrary, he recommends that all states adopt precisely the same combination of force and fraud, lion and fox: First, do what needs to be done to conquer, and only then take care that your actions enjoy the veneer of legitimacy. Such is the conclusion we must draw from the speech delivered by the anonymous leader of the popular revolt in Florence: We must behave like Romans; some Cicero will always cover our tracks. Machiavelli’s view of the relationship between politics and morality is based on this distinction between “good” theory and “evil” practice. He provides a dramatic statement of this distinction in chapter 15 of The Prince:

This quotation could well serve as the credo of political realism. It represents a complete rejection of the belief in an idealized good, either that of classical political philosophy or that of the Christian faith, both of which provided man with a lofty ideal toward which to aspire. From the point of view of classical philosophy, the fulfillment of human potential is possible only by means of an active participation in political life; from the Christian perspective, man may gain redemption only by following in the way of Jesus, who both idealized and embodied the qualities of meekness, humility, and contempt for worldly things. Machiavelli, however, starts with the actual, not the ideal. So great is the difference between the two, in his opinion, that contemplating the ideal is not only futile but downright suicidal. Hence “a prince, and especially a new prince, cannot observe all those things for which men are held good, since he is often under a necessity, to maintain his state, of acting against faith, against charity, against humanity, against religion. And so he need… not depart from good, when possible, but know how to enter into evil, when forced by necessity.”⁴²

For Machiavelli, the problem of the relationship between politics and morality is first and foremost a political one. It exists because men frequently, if not principally, judge politics from an ethical point of view. Machiavelli was fully aware of people’s moral sensitivities and of the importance they have for politics in general and the regime in particular. Just a few lines after he absolves the ruler of the need to honor agreements and keep promises, Machiavelli stresses that he nevertheless must appear “merciful, faithful, humane, honest, and religious, and to be so.”⁴³ If he fails to do this, and is then tainted by an association with the opposite traits, his days as a ruler are numbered.

Whether it is possible for a ruler to succeed in being so regarded without actually being so is a question that may be left open for now.⁴⁴ For our discussion, it is important only that Machiavelli acknowledges the fact that people expect their leaders to act in accordance with an accepted moral code. To Machiavelli it is of no consequence that these expectations are largely self-righteous and impractical.⁴⁵ What matters is the existence of such public moral expectations, which Machiavelli relates to as he would to any objective factor that a ruler must take into consideration if he hopes to survive. He does not suggest, as have others, that men are motivated solely by rational calculations of advantage and self-interest; rather, he insists that feelings, beliefs, perceptions, and even misconceptions are no less powerful than intellectual considerations. Therefore, he attaches considerable importance to the fact that people attach great importance to morality in politics.⁴⁶

Machiavelli accepts that politics cannot solve the problem that this human proclivity creates, but he nonetheless demands that politics face up to it. In his discussions of virtù he affirms that rulers do not, and cannot, act in accordance with conventional morality. The end of a ruler who does so will be as bad as his intentions were good. “A certain contemporary ruler,”⁴⁷ Machiavelli writes at the end of chapter 18 of The Prince, “never preaches anything but peace and faith, and is very hostile to both. If he had observed both, he would have had either his reputation or his state taken from him many times.”⁴⁸

The arguments made in the dizzying central chapters of The Prince reveal two central pillars of Machiavelli’s political thought. First, if we view his advice to “not depart from good, when possible” in the context of the chapter in which it appears, it is impossible to ignore the fact that it is given because it is politically expedient, and not because it is morally correct. Acting in conformity with this counsel will make the ruler appear moral and help him survive. Machiavelli examines the relationship between politics and morality from the point of view of one whose objectives are political; he instrumentalizes morality. But this does not mean that Machiavelli divorces politics from morality: Had he not believed in an intimate connection between the two, it would be impossible to attribute to him the claim that political interest is the highest consideration as well as the measure of morality.