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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).