While he admired Borgia’s qualities of leadership, however, Machiavelli felt an element of uneasiness from the outset about the duke’s astounding self-confidence. As early as October 1502 he wrote from Imola that ‘as long as I have been here, the duke’s government has been founded on nothing more than his good Fortune’ (L 386). By the start of the following year he was speaking with increasing disapproval of the fact that the duke was still content to rely on his ‘unheard-of good luck’ (L 520). And by October 1503, when Machiavelli was sent on a mission to Rome, and again had an opportunity of observing Borgia at close quarters, his earlier doubts crystallized into a strong sense of the limitations of the duke’s capacities.
The main purpose of Machiavelli’s journey to Rome was to report on an unusual crisis which had developed at the papal court. The pope, Alexander VI, had died in August and his successor, Pius III, had in turn died within a month of taking office. The Florentine signoria was anxious to receive daily bulletins about what was likely to happen next, especially after Borgia switched sides and agreed to promote the candidacy of Cardinal Giuliano della Rovere. This development looked potentially threatening to Florence’s interests, for the duke’s support had been bought with a promise that he would be appointed captain-general of the papal armies if Rovere were elected. It seemed certain, if Borgia secured this post, that he would begin a new series of hostile campaigns on the borders of Florentine territory.
Machiavelli’s earliest dispatches accordingly concentrate on the meeting of the conclave, in which Rovere was elected ‘by an enormous majority’ and took the name of Julius II (L 599). But once this matter had been settled, everyone’s attention shifted to the struggle that started to develop between Borgia and the pope. As Machiavelli watched these two masters of duplicity beginning to circle around one another, he saw that his initial doubts about the duke’s abilities had been thoroughly justified.
Borgia, he felt, had already displayed a lack of foresight in failing to see the dangers inherent in switching his support to Rovere. As he reminded the Ten of War, the cardinal had been forced ‘to live in exile for ten years’ under the pontificate of the duke’s father, Alexander VI. Surely, he added, Rovere ‘cannot have forgotten this so quickly’ that he now looks with genuine favour on an alliance with the son of his enemy (L 599). But Machiavelli’s most serious criticism was that, even in this equivocal and perilous situation, Borgia continued to place an altogether hubristic reliance on his uninterrupted run of good luck. At first Machiavelli simply noted, in some apparent surprise, that ‘the duke is allowing himself to be carried away by his immense confidence’ (L 599). Two weeks later, when Borgia’s papal commission had still not arrived, and his possessions in the Romagna had begun to rise in widespread revolt, he reported in more acid tones that the duke ‘has become stupified’ by ‘these blows of Fortune, which he is not accustomed to taste’ (L 631). By the end of the month, Machiavelli had come to the conclusion that Borgia’s ill Fortune had unmanned him so completely that he was now incapable of remaining firm in any decision, and on 26 November he felt able to assure the Ten of War that ‘you can henceforth act without having to think about him any more’ (L 683). A week later he mentioned Borgia’s affairs for the last time, merely observing that ‘little by little the duke is now slipping into his grave’ (L 709).
As before, these confidential judgements on Borgia’s character have since become famous through their incorporation into chapter 7 of The Prince. Machiavelli repeats that the duke ‘made a bad choice’ in supporting ‘the election of Julius as pope’, because ‘he should never have let the papacy go to any cardinal whom he had injured’ (34). And he recurs to his basic accusation that the duke relied too heavily on his luck. Instead of facing the obvious contingency that he might at some point be checked by a ‘malicious stroke of Fortune’, he collapsed as soon as this happened (29). Despite his admiration, Machiavelli’s final verdict on Borgia — in The Prince no less than in the Legations — is thus an adverse one: he ‘gained his position through his father’s Fortune’ and lost it as soon as Fortune deserted him (28).
The next influential leader whom Machiavelli was able to assess at first hand was the new pope, Julius II. Machiavelli had been present at several audiences at the time of Julius’s election, but it was in the course of two later missions that he gained his fullest insight into the pope’s character and leadership. The first of these was in 1506, when Machiavelli returned between August and October to the papal court. His instructions at that point were to keep the signoria informed about the progress of Julius’s typically aggressive plan to recover Perugia, Bologna, and other territories previously held by the Church. The second chance arose in 1510, when Machiavelli was sent on a new embassy to the court of France. By this time Julius had resolved on a great crusade to drive the ‘barbarians’ out of Italy, an ambition which placed the Florentines in an awkward position. On the one hand they had no desire to offend the pope in his increasingly bellicose mood. But on the other hand they were traditional allies of the French, who immediately asked what help they could expect if the pope were to invade the duchy of Milan, recaptured by Louis XII in the previous year. As in 1506, Machiavelli thus found himself anxiously following the progress of Julius’s campaigns, while hoping and scheming at the same time to preserve Florence’s neutrality.
Watching the warrior pope in action, Machiavelli was at first impressed and even amazed. He started out with the assumption that Julius’s plan of reconquering the papal states was bound to end in disaster. ‘No one believes’, he wrote in September 1506, that the pope ‘will be able to accomplish what he originally wanted’ (L 996). In no time at all, however, he was having to eat his words. Before the end of the month Julius had re-entered Perugia and ‘settled its affairs’, and before October was out Machiavelli found himself concluding his mission with the resounding announcement that, after a headlong campaign, Bologna had surrendered unconditionally, ‘her ambassadors throwing themselves at the feet of the pope and handing their city over to him’ (L 995, 1035).
It was not long, however, before Machiavelli began to feel more critical, especially after Julius took the alarming decision to launch his slender forces against the might of France in 1510. At first he merely expressed the sardonic hope that Julius’s boldness ‘will turn out to be based on something other than his sanctity’ (L 1234). But soon he was writing in much graver tones to say that ‘no one here knows anything for certain about the basis for the pope’s actions’, and that Julius’s own ambassador professes himself ‘completely astounded’ by the whole venture, since ‘he is deeply sceptical about whether the pope has the resources or the organisation’ to undertake it (L 1248). Machiavelli was not yet prepared to condemn Julius outright, for he still thought it conceivable that, ‘as in the campaign against Bologna’, the pope’s ‘sheer audacity and authority’ might serve to convert his maddened onrush into an unexpected victory (L 1244). Basically, however, he was beginning to feel thoroughly unnerved. He repeated with obvious sympathy a remark by Robertet to the effect that Julius appeared ‘to have been ordained by the Almighty for the destruction of the world’ (L 1270). And he added with unaccustomed solemnity that the pope did indeed ‘seem bent on the ruin of Christianity and the accomplishment of Italy’s collapse’ (L 1257).