Chapter 1 The Diplomat

The Humanist Background

Niccolò Machiavelli was born in Florence on 3 May 1469. We first hear of him playing an active part in the affairs of his native city in 1498, the year in which the regime controlled by Savonarola fell from power. Girolamo Savonarola, the Dominican prior of San Marco, whose prophetic sermons had dominated Florentine politics for the previous four years, was arrested for heresy early in April; soon afterwards the city’s ruling council began to dismiss his remaining supporters from their positions in the government. One of those who lost his job as a result was Alessandro Braccesi, the head of the second chancery. At first the post was left unoccupied, but after a delay of several weeks the almost unknown name of Machiavelli was put forward as a possible replacement. He was barely 29 years old, and appears to have had no previous administrative experience. Yet his nomination went through without evident difficulty, and on 19 June he was duly confirmed by the great council as second chancellor of the Florentine republic.

By the time Machiavelli entered the chancery, there was a well-established method of recruitment to its major offices. In addition to giving evidence of diplomatic skills, aspiring officials were expected to display a high degree of competence in the so-called humane disciplines. This concept of the studia humanitatis had been derived from Roman sources, and especially from Cicero, whose pedagogic ideals were revived by the Italian humanists of the fourteenth century and came to exercise a powerful influence on the universities and on the conduct of Italian public life. The humanists were distinguished first of all by their commitment to a particular theory about the proper contents of a ‘truly humane’ education. They expected their students to begin with the mastery of Latin, move on to the practice of rhetoric and the imitation of the finest classical stylists, and complete their studies with a close reading of ancient history and moral philosophy. They also popularized the long-standing belief that this type of training offers the best preparation for political life. As Cicero had repeatedly maintained, these disciplines nurture the values we principally need to acquire in order to serve our country well: a willingness to subordinate our private interests to the public good; a desire to fight against corruption and tyranny; and an ambition to reach out for the noblest goals of all, those of honour and glory for our country as well as for ourselves.


1. The Palazzo Vecchio, Florence, where Machiavelli worked in the second chancery from 1498 until 1512.


As the Florentines became increasingly imbued with these beliefs, they began to call on their leading humanists to fill the most prestigious positions in the city government. The practice may be said to have started with the appointment of Coluccio Salutati as chancellor in 1375, and it rapidly became the rule. While Machiavelli was growing up, the first chancellorship was held by Bartolomeo Scala, who retained his professorship at the university throughout his public career and continued to write on typically humanist themes, his main works being a moral treatise and a History of the Florentines. During Machiavelli’s own time in the chancery, the same traditions were impressively upheld by Scala’s successor, Marcello Adriani. He too transferred to the first chancellorship from a chair at the university, and he too continued to publish works of humanist scholarship, including a textbook on the teaching of Latin and a vernacular treatise On the Education of the Florentine Nobility.

The prevalence of these ideals helps to explain how Machiavelli came to be appointed at a relatively early age to a position of considerable responsibility in the administration of the republic. For his family, though neither rich nor highly aristocratic, was closely connected with some of the city’s most exalted humanist circles. Machiavelli’s father, Bernardo, who earned his living as a lawyer, was an enthusiastic student of the humanities. He was on close terms with several distinguished scholars, including Bartolomeo Scala, whose tract of 1483 On Laws and Legal Judgements took the form of a dialogue between himself and ‘my friend and intimate’, Bernardo Machiavelli. Moreover, it is clear from the Diary Bernardo kept between 1474 and 1487 that, throughout the period when his son Niccolò was growing up, Bernardo was engaged in studying several of the leading classical texts on which the renaissance concept of ‘the humanities’ had been founded. He records that he borrowed Cicero’s Philippics in 1477, and his greatest rhetorical work, the De Oratore, in 1480. He also borrowed Cicero’s most important moral treatise, the De Officiis, several times in the 1470s, and in 1476 he even managed to acquire his own copy of Livy’s History — the text which, some forty years later, was to serve as the framework for his son’s Discourses, his longest and most ambitious work of political philosophy.

It is also evident from Bernardo’s Diary that, in spite of the large expense involved — which he anxiously itemized — he was careful to provide his son with an excellent grounding in the studia humanitatis.[1] We first hear of Machiavelli’s education immediately after his seventh birthday, when his father records that ‘my little son Niccolò has started to go to Master Matteo’ for the first stage of his formal schooling, the study of Latin. By the time Machiavelli was 12 he had graduated to the second stage, and had passed into the care of a famous schoolmaster, Paolo da Ronciglione, who taught several of the most illustrious humanists of Machiavelli’s generation. This further step is noted by Bernardo in his Diary for 5 November 1481, when he proudly announces that ‘Niccolò is now writing Latin compositions of his own’ — following the standard humanist method of imitating the best models of classical style. Finally, it seems that — if we can trust the word of Paolo Giovio — Machiavelli may have been sent to complete his education at the university of Florence. Giovio states in his Maxims that Machiavelli ‘received the best part’ of his classical training from Marcello Adriani; and Adriani, as we have seen, occupied a chair at the university for a number of years before his appointment to the first chancellorship.

This humanist background perhaps contains the clue to explaining why Machiavelli suddenly received his governmental post in the summer of 1498. Adriani had taken over as first chancellor earlier in the same year, and it seems plausible to suppose that he remembered Machiavelli’s talents in the humanities and decided to reward them when he was filling the vacancies in the chancery caused by the change of regime. It is probable, therefore, that it was owing to Adriani’s patronage — together perhaps with the influence of Bernardo’s humanist friends — that Machiavelli found himself launched on his public career in the new anti-Savonarolan government.


The Diplomatic Missions

Machiavelli’s official position involved him in two sorts of duties. The second chancery, set up in 1437, mainly dealt with correspondence relating to the administration of Florence’s own territories. But as head of this section Machiavelli also ranked as one of the six secretaries to the first chancellor, and in this capacity he was shortly assigned the further task of serving the Ten of War, the committee responsible for the foreign and diplomatic relations of the republic. This meant that, in addition to his ordinary office work, he could be called on to travel abroad on behalf of the Ten, acting as secretary to its ambassadors and helping to send home detailed reports on foreign affairs.

His first opportunity to take part in a mission of this kind came in July 1500, when he and Francesco della Casa were commissioned ‘to proceed with all possible haste’ to the court of Louis XII of France (L 70). The decision to send this embassy arose out of the difficulties Florence had been experiencing in the war against Pisa. The Pisans had rebelled in 1496, and over the next four years they succeeded in fighting off all attempts to crush their bid for independence. Early in 1500, however, the French agreed to help the Florentines regain the city, and dispatched a force to lay siege to it. But this too turned out disastrously: the Gascon mercenaries hired by Florence deserted; the Swiss auxiliaries mutinied for lack of pay; and the assault had to be ignominiously called off.

Machiavelli’s instructions were ‘to establish that it was not due to any shortcoming on our part that this undertaking yielded no results’ and at the same time ‘to convey the impression’ if possible that the French commander had acted ‘corruptly and with cowardice’ (L 72, 74). However, as he and della Casa discovered at their first audience with Louis XII, the king was not much interested in Florence’s excuses for her past failures. Instead he wanted to know what help he could realistically expect in the future from such an apparently ill-run government. This meeting set the tone for the whole of their subsequent discussions with Louis and his chief advisers, Florimond Robertet and the archbishop of Rouen. The upshot was that, although Machiavelli remained at the French court for nearly six months, the visit taught him less about the policies of the French than about the increasingly equivocal standing of the Italian city-states.

The first lesson he learned was that, to anyone schooled in the ways of modern kingship, Florence’s governmental machinery appeared absurdly vacillating and weak. By the end of July it became obvious that the signoria, the city’s ruling council, would need to send a further embassy to renegotiate the terms of the alliance with France. Throughout August and September Machiavelli kept waiting to hear whether the new ambassadors had left Florence, and kept assuring the archbishop of Rouen that he expected them at any minute. By the middle of October, when there were still no signs of their arrival, the archbishop began to treat these continued prevarications with open contempt. As Machiavelli reported with obvious chagrin, he ‘replied in these exact words’ when assured that the promised mission was at last on its way: ‘it is true that this is what you say, but before these ambassadors arrive we shall all be dead’ (L 168). Even more humiliatingly, Machiavelli discovered that his native city’s sense of its own importance seemed to the French to be ludicrously out of line with the realities of its military position and its wealth. The French, he had to tell the signoria, ‘only value those who are well-armed or willing to pay’ and had come to believe that ‘both these qualities are lacking in your case’. Although he tried making a speech ‘about the security your greatness could bring to the possessions held by his majesty in Italy’, he found that ‘the whole thing was superfluous’, for the French merely laughed at him. The painful truth, he confesses, is that ‘they call you Mr Nothing’ (L 126 and n.).

Machiavelli took the first of these lessons profoundly to heart. His mature political writings are full of warnings about the folly of procrastinating, the danger of appearing irresolute, the need for bold and rapid action in war and politics alike. But he clearly found it impossible to accept the further implication that there might be no future for the Italian city-states. He continued to theorize about their military and political arrangements on the assumption that they were still genuinely capable of recovering and maintaining their independence, even though the period of his own lifetime witnessed their final and inexorable subordination to the vastly superior forces of France, Germany, and Spain.

The mission to France ended in December 1500, and Machiavelli hurried home as quickly as possible. His sister had died while he was away, his father had died shortly before his departure, and in consequence (as he complained to the signoria) his family affairs ‘had ceased to have any order about them at all’ (L 184). There were also anxieties about his job, for his assistant Agostino Vespucci had contacted him at the end of October to convey a rumour that ‘unless you return, you will completely lose your place in the chancery’ (C 60). Shortly after this, moreover, Machiavelli came to have a further reason for wishing to stay in the vicinity of Florence: his courtship of Marietta Corsini, whom he married in the autumn of 1501. Marietta remains a shadowy figure in Machiavelli’s story, but his letters suggest that he never ceased to be fond of her, while she for her part bore him six children, appears to have suffered his infidelities with patience, and eventually outlived him by a quarter of a century.

During the next two years, which Machiavelli spent mainly in and around Florence, the signoria became perturbed about the rise of a new and threatening military power on its borders: that of Cesare Borgia. In April 1501 Borgia was created duke of Romagna by his father, Pope Alexander VI. He thereupon launched a series of audacious campaigns designed to carve out for himself a territory to match his new and resounding title. First he seized Faenza and laid siege to Piombino, which he entered in September 1501. Next his lieutenants raised the Val di Chiana in rebellion against Florence in the spring of 1502, while Borgia himself marched north and took over the duchy of Urbino in a lightning coup. Elated by these successes, he then demanded a formal alliance with the Florentines and asked that an envoy be sent to hear his terms. The man selected for this delicate task was Machiavelli, who had already encountered Borgia at Urbino. Machiavelli received his commission on 5 October 1502 and presented himself before the duke at Imola two days later.

This mission marks the beginning of the most formative period of Machiavelli’s diplomatic career, the period in which he was able to play the role that most delighted him, that of a first-hand observer and assessor of contemporary statecraft. It was also during this time that he arrived at his definitive judgements on most of the leaders whose policies he was able to watch in the process of being formed. It is often suggested that Machiavelli’s Legations merely contain the ‘raw materials’ or ‘rough drafts’ of his later political views, and that he subsequently reworked and even idealized his observations in the years of his enforced retirement. As we shall see, however, a study of the Legations reveals that Machiavelli’s evaluations, and even his epigrams, generally occurred to him at once and were later incorporated virtually without alteration into the pages of the Discourses and especially The Prince.

Machiavelli’s mission to Borgia’s court lasted nearly four months, in the course of which he had many discussions tête-à-tête with the duke, who seems to have gone out of his way to expound his policies and the ambitions underlying them. Machiavelli was greatly impressed. The duke, he reported, is ‘superhuman in his courage’, as well as being a man of grand designs, who ‘thinks himself capable of attaining anything he wants’ (L 520). Moreover, his actions are no less striking than his words, for he ‘controls everything by himself’, governs ‘with extreme secrecy’, and is capable in consequence of deciding and executing his plans with devastating suddenness (L 427, 503). In short, Machiavelli recognized that Borgia was no mere upstart condottiere, but someone who ‘must now be regarded as a new power in Italy’ (L 422).

These observations, originally sent in secret to the Ten of War, have since become celebrated, for they recur almost word for word in chapter 7 of The Prince. Outlining Borgia’s career, Machiavelli again emphasizes the duke’s high courage, his exceptional abilities and tremendous sense of purpose (33–4). He also reiterates his opinion that Borgia was no less impressive in the execution of his schemes. He ‘made use of every means and action possible’ for ‘putting down his roots’, and managed to lay ‘mighty foundations for future power’ in such a short time that, if his luck had not deserted him, he ‘would have mastered every difficulty’ (29, 33).

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).

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?

As Machiavelli quickly discovered, the answer came in two disarmingly simple stages. Before his elevation, Julius was careful to emphasize that, ‘being a man of great good faith’, he was absolutely bound ‘to stay in contact’ with Borgia ‘in order to keep his word to him’ (L 613, 621). But as soon as he felt secure, he instantly reneged on all his promises. He not only denied the duke his title and troops, but actually had him arrested and imprisoned him in the papal palace. Machiavelli is scarcely able to conceal his astonishment as well as admiration at the coup. ‘See now’, he exclaims, ‘how honourably this pope begins to pay his debts: he simply cancels them by crossing them out.’ Nor does anyone consider, he adds significantly, that the papacy has been disgraced; on the contrary, ‘everybody continues with the same enthusiasm to bless the pope’s hands’ (L 683).

On this occasion Machiavelli felt disappointed with Borgia for allowing himself to be so ruinously outflanked. As he typically put it, the duke ought never to have supposed ‘that the words of another are more to be relied on than his own’ (L 600). Nevertheless, Borgia was undoubtedly the ruler whom Machiavelli found it most instructive to observe in action, and on two other occasions he was privileged to watch him confronting a dangerous crisis and surmounting it with a strength and assurance that earned him Machiavelli’s complete respect.

The first of these emergencies arose in December 1502, when the people of the Romagna suddenly voiced their outrage at the oppressive methods used by Borgia’s lieutenant, Rimirro de Orco, in pacifying the province in the previous year. Admittedly Rimirro had merely been executing the duke’s orders, and had done so with conspicuous success, reducing the whole area from chaos to sound government. But his cruelty had stirred up so much hatred that the continuing stability of the province was now in jeopardy. What was Borgia to do? His solution displayed a terrifying briskness, a quality that Machiavelli mirrors in his account of the episode. Rimirro was summoned to Imola, and four days later ‘he was found in the public square, cut into two pieces, where his body still remains, so that the entire populace has been able to see it’. ‘It has simply been the pleasure of the duke’, Machiavelli adds, ‘to show that he can make and unmake men as he wants, according to their deserts’ (L 503).

The other point at which Borgia evoked Machiavelli’s rather stunned admiration was in dealing with the military difficulties that developed in the Romagna at about the same time. At first the duke had been obliged to rely on the petty lords of the area for his chief military support. But in the summer of 1502 it became clear that their leaders — especially the Orsini and the Vitelli — were not only untrustworthy but were plotting against him. What should he do? His first move was simply to get rid of them by feigning reconciliation, summoning them to a meeting at Senigallia and murdering them en masse. For once Machiavelli’s studied coolness deserts him as he describes the manœuvre, and he admits to being ‘lost in wonder at this development’ (L 508). Next, Borgia resolved that in future he ought never to make use of such treacherous allies, but ought instead to raise his own troops. This policy — almost unheard of at a time when practically every Italian prince fought with hired mercenaries — seems to have struck Machiavelli at once as being an exceptionally far-sighted move. He reports with obvious approval that the duke has not only decided that ‘one of the foundations of his power’ must henceforth be ‘his own arms’, but has started the process of recruitment at an astonishing rate, ‘having already conducted a review of five hundred men-at-arms and the same number of light cavalry’ (L 419). Switching to his most admonitory style, he explains that he is ‘writing this all the more willingly’ because he has come to believe that ‘anyone who is well-armed, and has his own soldiers, will always find himself in a position of advantage, however things may happen to turn out’ (L 455).

By 1510, after a decade of missions abroad, Machiavelli had made up his mind about most of the statesmen he had met. Only Julius II continued to some extent to puzzle him. On the one hand, the pope’s declaration of war on France in 1510 struck Machiavelli as almost insanely irresponsible. It required no imagination to see that ‘a state of enmity between these two powers’ would be ‘the most terrifying misfortune that could arise’ from Florence’s point of view (L 1273). On the other hand, he could not resist hoping that, by sheer impetuosity, Julius might yet prove to be the saviour rather than the scourge of Italy. At the end of the campaign against Bologna, Machiavelli permitted himself to wonder whether the pope might not ‘go on to something greater’, so that ‘this time Italy really may find herself delivered from those who have planned to engulf her’ (L 1028). Four years later, despite the worsening of the international crisis, he was still trying to fight off his growing fears with the reflection that, ‘as in the case of Bologna’, the pope might yet manage ‘to carry everyone along with him’ (L 1244).

Unfortunately for Machiavelli and for Florence, his fears yielded better predictions than his hopes. After being hard pressed in the fighting of 1511, Julius reacted by concluding an alliance that changed the face of Italy. On 4 October 1511 he signed the Holy League with Ferdinand of Spain, thereby winning Spanish military support for the crusade against France. As soon as the new campaigning season opened in 1512, the formidable Spanish infantry marched into Italy. First they pushed back the French advance, forcing them to evacuate Ravenna, Parma, and Bologna and finally to retreat beyond Milan. Then they turned against Florence. The city had not dared defy the French, and had failed in consequence to declare its support for the pope. Now it found itself paying a costly penalty for its mistake. On 29 August the Spanish sacked the neighbouring town of Prato, and three days later the Florentines capitulated. The gonfaloniere Soderini fled into exile, the Medici re-entered the city after an absence of eighteen years, and a few weeks later the republic was dissolved.

Machiavelli’s own fortunes collapsed with those of the republican regime. On 7 November he was formally dismissed from his post in the chancery. Three days later he was sentenced to confinement within Florentine territory for a year, the surety being the enormous sum of a thousand florins. Then in February 1513 came the worst blow of all. He was mistakenly suspected of taking part in an abortive conspiracy against the new Medicean government, and after being put to the torture he was condemned to imprisonment and the payment of a heavy fine. As he later complained to the Medici in the dedication to The Prince, ‘Fortune’s great and steady malice’ had suddenly and viciously struck him down (11).

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