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A similar paradox appears in the following chapter, entitled ‘Cruelty and Mercifulness’. This too had been a favourite topic among the Roman moralists, Seneca’s essay On Clemency being the most celebrated treatment of the theme. According to Seneca, a prince who is merciful will always show ‘how loath he is to turn his hand’ to punishment; he will resort to it only ‘when great and repeated wrongdoing has overcome his patience’; and he will inflict it only ‘after great reluctance’ and ‘much procrastination’ as well as with the greatest possible clemency (I.13.4, I.14.1, II.2.3). Faced with this orthodoxy, Machiavelli insists once more that it represents a complete misunderstanding of the virtue involved. If you begin by trying to be merciful, so that you ‘overindulgently permit disorders to develop’ and only turn to punishment once ‘killings and plunderings’ have begun, your conduct will be far less clement than that of a ruler who possesses the courage to start by making an example of the ringleaders involved. Machiavelli gives the example of his fellow Florentines, who wanted to avoid seeming cruel in the face of an uprising and in consequence acted in such a way that the destruction of an entire city resulted — an outcome hideously more cruel than any cruelty they could have devised. This is contrasted with the behaviour of Cesare Borgia, who ‘was considered cruel’, but whose harsh measures ‘restored order to the Romagna, unifying it and rendering it peaceful and loyal’ by means of his alleged viciousness (58).

This leads Machiavelli to a closely connected question which he puts forward — with a similar air of self-conscious paradox — later in the same chapter: ‘whether it is better to be loved than feared, or vice versa’ (59). Again the classic answer had been furnished by Cicero in De Officiis. ‘Fear is but a poor safeguard of lasting power’, whereas love ‘may be trusted to keep it safe for ever’ (II.7.23). Again Machiavelli registers his total dissent. ‘It is much safer’, he retorts, for a prince ‘to be feared than loved’. The reason is that many of the qualities that make a prince loved also tend to bring him into contempt. If your subjects have no ‘dread of punishment’, they will take every chance to deceive you for their own profit. But if you make yourself feared, they will hesitate to offend or injure you, as a result of which you will find it much easier to maintain your state (59).

The other line of argument in these chapters reflects an even more scornful rejection of conventional humanist morality. Machiavelli suggests that, even if the qualities usually considered good are indeed virtues — such that a ruler who flouts them will undoubtedly be falling into vice — he ought not to worry about such vices if he thinks them either useful or irrelevant to the conduct of his government.

3. The title-page of Edward Dacres’s translation of The Prince, the earliest English version to be printed.

Machiavelli’s main concern at this point is to remind new rulers of their most basic duty of all. A wise prince ‘should not be troubled about becoming notorious for those vices without which it is difficult to preserve his power’; he will see that such criticisms are merely an unavoidable cost he has to bear in the course of discharging his fundamental obligation, which is of course to maintain his state (55). The implications are first spelled out in relation to the supposed vice of parsimony. Once a wise prince perceives that miserliness is ‘one of those vices that enable him to rule’, he will cease to worry about being thought a miserly man (57). The same applies in the case of cruelty. A willingness to act on occasion with exemplary severity is crucial to the preservation of good order in civil as in military affairs. This means that a wise prince ‘should not worry about incurring a reputation for cruelty’, and that it is essential not to worry about being called cruel if you are an army commander, for without such a reputation you can never hope to keep your troops ‘united and prepared for military action’ (60).

Lastly, Machiavelli considers whether it is important for a ruler to eschew the lesser vices and sins of the flesh if he wishes to maintain his state. The writers of advice books for princes generally dealt with this issue in a sternly moralistic vein, echoing Cicero’s insistence in Book I of De Officiis that propriety is ‘essential to moral rectitude’, and thus that all persons in positions of authority must avoid all lapses of conduct in their personal lives (I.28.98). By contrast, Machiavelli answers with a shrug. A wise prince ‘will seek to avoid those vices’ if he can; but if he finds he cannot, then he certainly will not trouble himself unduly about such ordinary moral susceptibilities (55). 

Chapter 3

The Theorist of Liberty

With the completion of The Prince, Machiavelli’s hopes of returning to an active public career revived. As he wrote to Vettori in December 1513, his highest aspiration was still to make himself ‘useful to our Medici lords, even if they begin by making me roll a stone’. He wondered whether the most effective way of realizing his ambition might be to go to Rome with ‘this little treatise of mine’ in order to offer it in person to Giuliano de’ Medici, thereby showing him that he ‘might well be pleased to gain my services’ (C 305).

At first Vettori seemed willing to support this scheme. He replied that Machiavelli should send him the book, so that he ‘could see whether it might be appropriate to present it’ (C 312). When Machiavelli duly dispatched the fair copy he had begun to make of the opening chapters, Vettori announced that he was ‘extremely pleased with them’, though he cautiously added that ‘since I do not have the rest of the work, I do not wish to offer a final judgement’ (C 319).

It soon became clear, however, that Machiavelli’s hopes were again going to be dashed. Having read the whole of The Prince early in 1514, Vettori responded with an ominous silence. He never mentioned the work again, and instead began to fill up his letters with distracting chatter about his latest love affairs. Although Machiavelli forced himself to write back in a similar spirit, he was barely able to conceal his mounting anxiety. By the middle of the year, he finally came to realize that it was all hopeless, and wrote in great bitterness to Vettori to say that he was giving up the struggle. It has become obvious, he declares, ‘that I am going to have to continue in this sordid way of life, without finding a single man who remembers the service I have done or believes me capable of doing any good’ (C 343).

After this disappointment Machiavelli’s life underwent a permanent change. Abandoning any further hopes of a diplomatic career, he began to see himself increasingly as a man of letters. The main sign of this new orientation was that, after another year or more of ‘rotting in idleness’ in the country, he started to take a prominent part in the meetings held by a group of humanists and literati who forgathered regularly at Cosimo Rucellai’s gardens on the outskirts of Florence for learned conversation and entertainment.

These discussions at the Orti Oricellari were partly of a literary character. There were debates about the rival merits of Latin and Italian as literary languages, and there were readings and even performances of plays. The effect on Machiavelli was to channel his creative energies in a wholly new direction: he decided to write a play himself. The result was Mandragola, his brilliant if brutal comedy about the seduction of an old judge’s beautiful young wife. The original version was probably completed in 1518, and may well have been read to Machiavelli’s friends in the Orti before being publicly presented for the first time in Florence and Rome in the course of the next two years.