Machiavelli is fully aware that his new analysis of princely virtú raises some new difficulties. He states the main dilemma in the course of chapter 15: on the one hand ‘a ruler who wishes to maintain his power must be prepared to act immorally when this becomes necessary’; but on the other hand he must be careful not to acquire the reputation of being a wicked man, because this will destroy his power instead of securing it (55). The problem is how to avoid appearing wicked when you cannot avoid behaving wickedly.
Moreover, the dilemma is even sharper than this implies, for the true aim of the prince is not merely to secure his position, but is of course to win honour and glory as well. As Machiavelli indicates in recounting the story of Agathocles of Sicily in chapter 8, this greatly intensifies the predicament in which any new ruler finds himself. Agathocles, we are told, ‘always lived a very dissolute life’ and was known for ‘appallingly cruel and inhumane conduct’. These attributes brought him immense success, enabling him to rise from ‘the lowest and most abject origins’ to become king of Syracuse and hold on to his principality ‘without any civil strife’ (30–1). But as Machiavelli warns us, in a deeply revealing phrase, such unashamed cruelties may win us power ‘but not glory’. Although Agathocles was able to maintain his state by means of these qualities, they ‘cannot be called virtú’ and they ‘preclude his being numbered among the finest men’ (31).
Machiavelli refuses to admit that the dilemma can be resolved by setting stringent limits to princely wickedness, and in general behaving honourably towards one’s subjects and allies. This is exactly what one cannot hope to do, because all men at all times ‘are ungrateful, fickle, feigners and dissemblers, avoiders of danger, eager for gain’, so that any ruler ‘who has relied completely on their promises, and has neglected to prepare other defences, will be ruined’ (59). The implication is that a prince, and above all a new prince, will often — not just occasionally — find himself forced by necessity to act contrary to humanity if he wishes to keep his position and avoid being deceived (62).
These are acute difficulties, but they can nevertheless be overcome. The prince need only remember that, although it is not necessary to have all the qualities usually considered good, it is indispensable to appear to have them (66). It is desirable to be considered liberal; it is sensible to seem merciful and not cruel; it is essential in general to appear meritorious (56, 58, 64). The solution is thus to become a great simulator and dissimulator, learning the skill of ‘cunningly confusing men’ and making them believe in your pretence (61).
Machiavelli had received an early lesson in the value of cunningly confusing men. As we have seen, he had been present when the struggle developed between Cesare Borgia and Julius II in the closing months of 1503, and it is evident that the impressions he carried away from that occasion were still uppermost in his mind when he came to write about the question of dissimulation in The Prince. He immediately refers back to the episode he had witnessed, using it as his main example of the need to remain constantly on one’s guard against princely duplicity. Julius, he recalls, managed to conceal his hatred of Borgia so cleverly that he caused the duke to fall into the egregious error of believing ‘that new benefits make important men forget old injuries’ (29). He was then able to put his powers of dissimulation to decisive use. Having won the papal election with Borgia’s full support, he suddenly revealed his true feelings, turned against the duke, and brought about his final downfall. Borgia certainly blundered at this point, and Machiavelli feels that he deserves to be blamed severely for his mistake. He ought to have known that a talent for spreading confusion is part of the armoury of any successful prince (34).
Machiavelli cannot have been unaware, however, that in recommending the arts of deceit as the key to success he was in danger of sounding too glib. More orthodox moralists had always been prepared to consider the suggestion that hypocrisy might be used as a short cut to glory, but had always gone on to rule out any such possibility. Cicero, for example, had explicitly canvassed the idea in Book II of De Officiis, only to dismiss it as a manifest absurdity. Anyone, he declares, who ‘thinks that he can win lasting glory by pretence’ is ‘very much mistaken’. The reason is that ‘true glory strikes deep roots and spreads its branches wide’, whereas ‘all pretences soon fall to the ground like fragile flowers’ (II.12.43).
Machiavelli responds, as before, by rejecting such earnest sentiments in his most ironic style. He insists in chapter 18 that the practice of hypocrisy is not merely indispensable to princely government, but is capable of being sustained without much difficulty for as long as may be required. Two distinct reasons are offered for this deliberately provocative conclusion. One is that most men are so simple-minded, and above all so prone to self-deception, that they usually take things at face value in a wholly uncritical way (62). The other is that, when it comes to assessing the behaviour of princes, even the shrewdest observers are largely condemned to judge by appearances. Isolated from the populace, sustained by the majesty of his role, the prince’s position is such that ‘everyone can see what you appear to be’ but ‘few have direct experience of what you really are’ (63). So there is no reason to suppose that your sins will find you out; on the contrary, ‘a skilful deceiver always finds plenty of people who will let themselves be deceived’ (62).
A further issue Machiavelli discusses is what attitude we should take towards the new rules he has sought to inculcate. At first sight he appears to adopt a relatively conventional moral stance. He agrees in chapter 15 that ‘it would be most praiseworthy’ for new princes to exhibit those qualities which are normally considered good, and he equates the abandonment of the princely virtues with the process of learning ‘to act immorally’ (55). The same scale of values recurs even in the notorious chapter on ‘How rulers should keep their promises’. Machiavelli begins by affirming that everybody realizes how praiseworthy it is when a ruler ‘lives uprightly and not by trickery’ (61). He goes on to insist that a prince ought not merely to seem conventionally virtuous, but ought ‘actually to be so’ as far as circumstances permit. He should ‘not deviate from right conduct if possible, but be capable of entering upon the path of wrongdoing when this becomes necessary’ (62).
However, two very different arguments are introduced in the course of chapter 15, each of which is subsequently developed. First of all, Machiavelli is somewhat quizzical about whether we can properly say that those qualities which are considered good, but are nevertheless ruinous, really deserve the name of virtues. Since they are prone to bring destruction, he prefers to say that they ‘seem virtuous’; and since their opposites are more likely to strengthen one’s position, he prefers to say that they only look like vices (55).
This suggestion is pursued in both the succeeding chapters. Chapter 16, entitled ‘Generosity and Meanness’, picks up a theme handled by all the classical moralists and turns it on its head. When Cicero discusses the virtue of generosity in De Officiis (II.17.58 and II.22.77), he defines it as a desire to ‘avoid any suspicion of penuriousness’, together with an awareness that no vice is more offensive in a political leader than parsimony and avarice. Machiavelli replies that, if this is what we mean by generosity, it is the name not of a virtue but a vice. He argues that a ruler who wishes to avoid a reputation for parsimony will find that he ‘needs to spend lavishly and ostentatiously’. As a result, he will find himself having ‘to tax the people very heavily’ to pay for his liberality, a policy which will soon make him ‘hated by his subjects’. Conversely, if he begins by abandoning any desire to act with such munificence, he may well be called miserly at the outset, but ‘eventually he will be come to be considered more generous’, and will in fact be practising the true virtue of generosity (59).