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This account of the pope’s progress reappears virtually unaltered in the pages of The Prince. Machiavelli first concedes that, although Julius ‘proceeded impetuously in all his affairs’, he ‘was always successful’ even in his most unrealistic enterprises. But he goes on to argue that this was merely because ‘the times and their circumstances’ were ‘so in harmony with his own way of proceeding’ that he never had to pay the due penalty for his recklessness. Despite the pope’s startling successes, Machiavelli accordingly feels justified in taking an extremely unfavourable view of his statecraft. Admittedly Julius ‘accomplished with his impetuous movement what no other pontiff, with the utmost human prudence, would ever have accomplished’. But it was only due to ‘the shortness of his life’ that we are left with the impression that he must have been a great leader of men. ‘If times had come when he needed to proceed with caution, they would have brought about his downfall; for never would he have turned away from those methods to which his nature inclined him’ (91–2).

Between his papal legation of 1506 and his return to France in 1510, Machiavelli went on one further mission outside Italy, in the course of which he was able to appraise yet another prominent ruler at first hand — Maximilian, the Holy Roman Emperor. The signoria’s decision to send this embassy arose out of its concern about the emperor’s plan to march into Italy and have himself crowned at Rome. Announcing this intention, he demanded a large subsidy from the Florentines to help him overcome his chronic lack of funds. The signoria felt anxious to oblige him if he were indeed coming; but not if not. So was he in fact going to come? In June 1507 Francesco Vettori was dispatched to find out the answer, but reported in such confusing terms that Machiavelli was sent after him with additional instructions six months later. Both men remained at the imperial court until June of the following year, by which time the proposed expedition had definitely been called off.

Machiavelli’s comments on the head of the house of Hapsburg contain none of the nuances or qualifications that characterize his descriptions of Cesare Borgia and Julius II. From first to last the emperor struck Machiavelli as a totally inept ruler, with scarcely any of the right qualifications for conducting an effective government. His basic weakness, Machiavelli felt, was a tendency to be ‘altogether too lax and credulous’, as a result of which ‘he has a constant readiness to be influenced by every different opinion’ put to him (L 1098–9). This makes it impossible to conduct negotiations, for even when he begins by deciding on a course of action — as with the expedition to Italy — it is still safe to say that ‘God alone knows how it will end’ (L 1139). It also makes for hopelessly enfeebled leadership, because everyone is left ‘in continuing confusion’ and ‘nobody knows what he will do at all’ (L 1106).

Machiavelli’s portrait of the emperor in The Prince largely reproduces these earlier judgements. Maximilian is discussed in the course of chapter 23, the theme of which is the need for princes to listen to good advice. The emperor’s conduct is treated as a cautionary tale about the dangers of failing to handle one’s councillors with adequate decisiveness. Maximilian is described as so ‘pliable’ that, if ever his plans ‘become generally known’ and are then ‘opposed by those around him’, this throws him off course so completely that he is immediately ‘pulled away from them’. This not only makes him frustrating to deal with, since ‘no one ever knows what he wishes or intends to do’; it also makes him downright incompetent as a ruler, since ‘it is impossible to rely’ on any decisions he makes, and ‘what he does one day he destroys the next’ (87).

The Lessons of Diplomacy

By the time Machiavelli came to record his final verdicts on the rulers and statesmen he had met, he had reached the conclusion that there was one simple yet fundamental lesson which they had all misunderstood, as a result of which they had generally failed in their undertakings, or else had succeeded more by luck than sound political judgement. The basic weakness they all shared was a fatal inflexibility in the face of changing circumstances. Cesare Borgia was at all times overweening in his self-confidence; Maximilian was always cautious and over-hesitant; Julius II was always impetuous and over-excited. What they all refused to recognize was that they would have been far more succcessful if they had sought to accommodate their personalities to the exigencies of the times, instead of trying to reshape their times in the mould of their personalities.

Machiavelli eventually placed this judgement at the very heart of his analysis of political leadership in The Prince. However, he first registered the insight much earlier, in the course of his active career as a diplomat. Furthermore, it is clear from his Legations that the generalization first struck him less as a result of his own reflections than through listening to, and subsequently thinking about, the views of two of the shrewdest politicians with whom he came into contact. The point was first put to him on the day of Julius II’s election to the pontificate. Machiavelli found himself drawn into conversation with Francesco Soderini, cardinal of Volterra and brother of Piero Soderini, the leader (gonfaloniere) of Florence’s government. The cardinal assured him that ‘not for many years has our city had so much to hope for from a new pope as from the present one’. ‘But only’, he added, ‘if you know how to harmonise with the times’ (L 593). Two years later, Machiavelli met with the same judgement in the course of negotiating with Pandolfo Petrucci, the lord of Siena, whom he was later to mention admiringly in The Prince as ‘a very able man’ (85). Machiavelli had been commissioned by the signoria to demand the reasons for ‘all the tricks and intrigues’ which had marked Pandolfo’s dealings with Florence (L 911). Pandolfo responded with an effrontery that evidently impressed Machiavelli very much. ‘Wishing to make as few mistakes as possible,’ he replied, ‘I conduct my government day by day, and arrange my affairs hour by hour; because the times are more powerful than our brains’ (L 912).

Although Machiavelli’s pronouncements on the rulers of his age are in general severely critical, it would be misleading to conclude that he regarded the entire record of contemporary statecraft as nothing more than a history of crimes, follies, and misfortunes. At several moments in his diplomatic career he was able to watch a political problem being confronted and resolved in a manner that not only commanded his unequivocal admiration, but also exercised a clear influence on his own theories of political leadership. One such incident occurred in 1503, in the course of the protracted battle of wits between Cesare Borgia and the pope. Machiavelli was fascinated to see how Julius would cope with the dilemma raised by the duke’s presence at the papal court. As he reminded the Ten of War, ‘the hatred his holiness has always felt’ for Borgia ‘is well-known’, but this hardly alters the fact that Borgia ‘has been more help to him than anyone else’ in securing his election, as a result of which he ‘has made the duke a number of very large promises’ (L 599). The problem seemed insoluble: how could Julius hope to achieve any freedom of action without at the same time violating his solemn pledge?