It soon became clear what the Orsinis intended to do, and not only the Orsinis. In the first week of October a meeting which boded ill for the Borgias took place at Cardinal Orsini’s castle of La Magione, near Perugia. The conference was attended by the Cardinal, as head of the clan, with his nephew Francesco, Duke of Gravina, Paolo Orsini, lord of Palombara, Gian Paolo Baglioni and his brother Gentile, Oliverotto da Fermo, another of Cesare’s captains, and even Vitellozzo, who appeared groaning with pain carried on a litter. Other lords who had been threatened or injured by the Borgias were represented. Giovanni Bentivoglio sent his son Ermes, Guidobaldo his nephew Ottaviano Fregoso, and Pandolfo Petrucci of Siena two of his intimates. None of the major Italian powers was represented; Ferrara and Mantua were Cesare’s allies, Florence feared the Orsinis and Vitellozzo, while Venice, secretly sympathetic, dared not come out openly against the King of France. Nonetheless the conjunction of these men was dangerous for Cesare: between them the conspirators commanded forces numerically superior to his. Bentivoglio, poised on his northern frontier, was strategically placed for a damaging attack on the Romagna, while Guidobaldo could be the spark to ignite a partisan uprising in Urbino.
Feeling against Cesare ran high at La Magione, with Gian Paolo Baglioni taking the lead. He represented to his fellow conspirators the danger that threatened them ‘of being one by one devoured by the dragon’, if they did not take preventive action, and told them that he had intercepted a papal brief instructing Cesare to invite himself, Vitellozzo, Oliverotto and the Orsinis to Imola and seize them. Violent words followed, with Vitellozzo and Bentivoglio swearing to kill Cesare if they had the chance. Yet it seemed that the conference would produce little more than words; united as they were in their hatred and fear of Cesare, that fear and their intimate knowledge of him made them wary of undertaking open action against him. There was not a true leader amongst them; they were all subordinate officers with their own lordships to look to, while behind Cesare stood the King of France, so that neither Florence nor Venice would help them. While the Baglionis and Oliverotto were for all-out war against il Valentino, the Orsinis, Bentivoglio and Petrucci were having second thoughts about the wisdom of confronting a man with his proven reputation and backing. Cesare, typically, further disturbed the unity of the conspirators by sending one of his gentlemen, Roberto Orsini, with instructions to win over his relations, and particularly the gullible Paolo, with offers of better conditions for his condotta and hints of Alexander’s gratitude. But while Bentivoglio and Fregoso left the conference in disgust, the revolt of the key fortress of San Leo in Urbino against Cesare on 7 October put new life into the conspiracy. On arrival at La Magione, the leader of the rising was told bitterly by Gian Paolo Baglioni that ‘against his own opinion, and only through the action of Paolo Orsini, suborned by the promises and words of il Valentino, the League had not yet been concluded, but that the following morning he would speak to the Cardinal and the others to make every effort so that the agreements should be signed’. Gian Paolo, who had known Cesare Borgia longer and better than the others and was not beguiled by his smooth words, was now able to bring the others into line behind him, and on 9 October the league was signed. Cesare was to be attacked on two sides, in the Romagna by Bentivoglio and in Urbino by the Orsinis in support of the uprising. In the exhilaration of the moment the confident conspirators planned the division of Valentino’s states between them.
Alexander, when the news of La Magione and the revolt of San Leo reached Rome, was described as ‘raging like a bear’ against the Orsinis, but Cesare at Imola reacted with amazing calm to a situation which he had doubtless foreseen, at least as far as the conspirators were concerned. To Machiavelli, who arrived at camp on the 7th with assurances of Florentine support, he made a most revealing remark. After showing him a letter from Louis promising him 300 lances against Bologna, he referred to the confederates: ‘Believe me that this thing is to my advantage, and they cannot reveal themselves at an hour when it will damage me less, nor can I, to strengthen my states, wish for a thing that will be more useful to me; because I shall know this time against whom I have to protect myself, and I shall recognize my friends. And if the Venetians reveal themselves in this matter, which I do not expect, I shall be the better pleased …’ And when he read Gian Paolo Baglioni’s account of the confederate forces, he laughed:
He said that those 600 men-at-arms, of whom those enemies of his boast, would turn out to be less each one on the parade ground: and laughing said to me: ‘They do well to say “men-at-arms on paper”, which means nothing. I do not want to boast, but I would like the results, whatever they may be, to show what kind of men they are and who I am. And I think the less of them, the more I know them, both themselves and their troops; and Vitellozzo, who enjoys such a reputation, I cannot say I have ever seen him do anything as a valiant man, excusing himself on the ground of the French disease: he is only good at devastating defenceless places, and robbing those who dare not show him their face, and at these kind of betrayals …’
Yet despite Cesare’s contempt for his former condottieri, and his relief that they had at last revealed themselves, the situation to observers on the spot like Machiavelli looked extremely dangerous. His immediately available forces did not exceed 2500 foot and some 750 men-at-arms, and if the condottieri were to make a swift concerted attack they could overwhelm him. The nearest French troops were at Milan, too far away to afford immediate help, and if his cities of the Romagna followed the example of Urbino he would be lost. Machiavelli, unaware that Cesare had been expecting a situation of this kind since June, was amazed at the speed, decision and confidence with which he reacted to the crisis. Urbino for the moment was to be considered lost; he concentrated on securing the Romagna and speedily recruiting new troops and more trustworthy Italian condottieri. Ramiro de Lorqua, military governor of the Romagna, rode through the country putting the towns and fortresses in a state of defence, while Ugo de Moncada on the borders of Urbino was ordered to retreat to Rimini, and Michelotto dispatched to recruit a thousand infantry in the Romagna. Within a few days Cesare had raised 800 of the famous infantry from the Val di Lamone, and according to Machiavelli had inspected a further 6000 foot-soldiers from the Romagna. Meanwhile he sent to engage 500 Gascons at Milan, and 1500 Swiss, the best infantry in Europe. Alexander backed him up by forwarding 18,000 ducats from Rome to pay the troops. Couriers and messengers were dispatched from Imola to Rome, France, Ferrara and Milan to obtain money, troops and invaluable intelligence as to enemy movements. One of the secrets of Cesare’s success was the excellence of his intelligence service and the money he was prepared to spend on it. As Machiavelli wrote in what was intended as a backhanded reproach to his government for their short-sighted parsimony in this respect: ‘He has spent, in the two weeks since I have been here, as much money for couriers and special messengers as anyone else would have spent in two years …’
Michelotto and Ugo de Moncada, retreating from Urbino into the Romagna, took cruel revenge on the rebels, sacking Fossombrone and La Pergola, where Giulio Cesare Varano was strangled in the castle for good measure. At Imola, Cesare revealed the strong streak of superstition in him when he described to Machiavelli ‘what Don Ugo and Don Michele had done … saying thus joyfully that this year the planets showed themselves evil towards those who rebelled’. However, during the second week of October the planets showed themselves favourable to the conspirators as things went from bad to worse in Urbino, and the Orsinis fell upon Ugo de Moncada and Michelotto at Calmazzo and routed them, taking Ugo prisoner and forcing the remainder to retreat upon Fano. On the 18th Guidobaldo, amid general rejoicing, re-entered Urbino, which was now the condottieri headquarters. From Bologna, Giovanni Bentivoglio sent forward 2300 troops to Castel San Pietro, only seven miles from Cesare’s headquarters at Imola.
On the face of it the situation looked discouraging, but in fact the worst was over. Over two weeks had passed since the signing of the league at La Magione and t
he outbreak of the revolt in Urbino, and since then the conspirators had accomplished little beyond the retaking of the duchy. Cesare’s Romagna cities had remained loyal to him, and, what was more important, none of his other commanders, Romagnol, Italian or Spanish, had joined the revolt. The Orsinis and their adherents had revealed themselves as an isolated clique. Events had proved Cesare right in his estimate of the confederates and their psychology, or, as he had put it to Machiavelli, what kind of men they were and who he was. Fear of his reputation for luck and invincibility had prevented them from making a direct attack on him and destroying him when he was weak; now with his defensive arrangements in order, with troops and money pouring in from all sides, he was too strong for them. His masterly inactivity as far as the conspirators were concerned, and his prudent refusal to be drawn into the field against their superior forces, had confused them. Machiavelli, considering the situation from Imola on 23 October, thought that Cesare had won the first round:
The state of this Lord, since I have been here, has been governed only by his good fortune; the cause of which is the general opinion that the King of France will support him with troops and the Pope with money, and another thing which is no less responsible for it; and this is the tardiness of his enemies in pressing him. Nor do I think that at this time they are any longer in a position to do him much harm, because he has garrisoned all the important places with infantry, and the fortresses he has provided for most excellently; so that, as their spirits cool in the face of such provisions, he can feel secure enough to wait for reinforcements.
By the end of October, reinforcements in the form of French heavy cavalry were on the march from Lombardy.
Fear had united the conspirators against Cesare, and fear was to disunite them, enabling him to drive a wedge between them. Even while acting against him in Urbino, they continued separately to send him messages of friendship. As Cesare told Machiavelli on 23 October: ‘Thus you see how they govern themselves: they keep up negotiations for an agreement, write me friendly letters, and today the lord Paolo is to come to see me, and tomorrow the Cardinal [Orsini]; and thus they play games with me in their way. I, on the other hand, temporize, listen to everything, and bide my time.’ Machiavelli failed to note the sinister implications of Cesare’s final phrase, and it was not until a week later that the truth began to dawn upon him. Cesare was perfectly content to play a cat and mouse game with his condottieri, building up his strength while pretending to believe in their assurances of friendship. By the end of October he had already succeeded in separating Bentivoglio from the rest: Machiavelli reported on the 30th that there had been constant comings and goings between Cesare and Bentivoglio, and that Bentivoglio ‘when he sees he can secure his own affairs with this lord, would be content to leave the Orsinis to his discretion’. At the time of La Magione, Cesare had picked upon Paolo Orsini with unerring instinct as the weak link among the conspirators; now once again he used him as his instrument to induce the others to play into his hands. The wretched Paolo easily fell victim to the charm which Cesare could exert when he wanted to, and hurried to do his bidding with such officious eagerness that Guidobaido’s partisans called him ‘my lady Paolo’, intimating that he was infatuated with il Valentino. Machiavelli, as Paolo rode back and forth between Imola and Urbino, was at a loss to comprehend the motives of either side in making this agreement. He wrote on 27 October:
As to the suggested understanding, respecting the terms of which I am still in ignorance, I do not augur well of it. For when I consider the two parties concerned, I see on the one hand Duke Cesare, vigorous, courageous, confident in his future, blessed with exceptional fortune, backed by the favour of Pope and King, and now suffering at the hands of faithless servants the loss of a signory [Urbino] which he had just made his own. Confronting him, we have a group of lords who, even whilst they were his friends, were in anxiety for their possessions, and fearful of his growing power; and now, having thus injured him, and become his declared enemies, naturally more apprehensive still. So that I fail to understand how, on the one part, such injury can be expected to find forgiveness, and how, on the other, such fears are to be assuaged …
Despite his bewilderment, and the difficulty of gleaning information at Cesare’s close-mouthed court where ‘things to be kept silent are never mentioned to us, and are carried on with wonderful secrecy’, Machiavelli’s perception enabled him to divine the truth. The agreements were no more than a temporary truce in the high game for survival which both sides were playing. It is hard to see how the condottieri, in the situation into which they had led themselves, could have done anything else but sue for peace. They had rebelled to save themselves and their lordships from extinction; they made peace for the same reasons. For the present, Cesare, surrounded by trustworthy troops and squadrons of French men-at-arms, was untouchable, but there might always be another chance to catch him unawares. With the exception of Francesco Orsini, the condottieri were tough, ruthless, and practised in deceit – men like Gian Paolo Baglioni, whom Machiavelli later reproved for his treachery as ‘a stumbling horse whom no one would ride for fear of breaking his neck’, and Oliverotto da Fermo, who the previous year had lured the uncle who had fostered him from childhood into a trap and murdered him with all his family and followers in order to seize power at Fermo. It is difficult to believe that such men, knowing Cesare as they did, would ever have expected him not to take his revenge. Cesare, as he had told Machiavelli, let them play their games with him, listened to everything, and bided his time.
The separate agreements with Bentivoglio and with the Orsinis and the rest were finally signed in the last week of November. Cesare was probably sincere, at least for the moment, in making an alliance with Bentivoglio. It was Alexander rather than Cesare who was bent on the acquisition of the former papal city, a huge prize which, according to Machiavelli, Cesare realized would be too difficult for him to digest at present, and whose friendship was essential to him for the security of his northern frontier. Moreover Bologna promised to supply him with troops, 200 men-at-arms and 200 light horse, and to give him a condotta for eight years at 12,000 ducats per annum. Not the least of the advantages of the Bologna agreement from Cesare’s point of view was the bad blood which it created between Bentivoglio and his former friends; although it was supposed to be kept secret, Cardinal Orsini got wind of it and raged at the Bolognese envoy in the presence of the Pope.
As far as the terms of agreement with the condottieri were concerned, Cesare’s confidential secretary Agapito Geraldini, who knew his master as well as anyone could know so secretive and complex a man, told Machiavelli that ‘even children would laugh at such articles’ – a remark which perfectly illustrated the seriousness with which Cesare regarded them. Both sides were to end their enmity with remission of all injuries; Cesare would receive all the confederates in perpetual alliance, and promise to defend their states, reserving only the interests of the Pope and the King of France, while the confederates promised to aid him to recover Urbino and also Camerino, which had fallen to Ercole Varano. Cesare promised to keep on all the condottieri in his service, although only one of them at a time was obliged to serve in the field. The controversy between the Church and Bologna, the ostensible cause of the whole outbreak, was to be decided between Cardinal Orsini, Pandolfo Petrucci – and Cesare.
Cesare, through his own cool-headedness, diplomatic skill and knowledge of men, had turned disaster into triumph. He had separated the confederates and brought them to sign agreements with him on his own terms. They had pledged themselves to help him recover both Urbino and Camerino, thus abandoning Guidobaldo and the Varano family, while Cesare had not lost one single city in the Romagna. He had shown himself able, in the face of adverse odds, to confront fortune, to outface and outwit some of the most experienced, tough and treacherous captains in Italy, to divide them and bring them crawling to his feet. Baglioni and Petrucci sent representatives to Imola to assure him that their purpose had been to make him King of
Tuscany, while the much-admired Vitellozzo, Machiavelli reported, wrote ‘the most submissive and pleasing letters, excusing himself and offering his services, and saying that if he ever spoke to him personally he had no doubt that he would be able to justify himself absolutely and make him understand that the past events were never intended to offend him’.
If the condottieri really intended to fool Cesare with fair words they underestimated him even more than they had at the time of La Magione. As one of his circle remarked to Machiavelli of Vitellozzo’s letter: ‘Here is a man who has stabbed us in the back and then thinks to heal the wound with words.’ In Rome, Giustinian, with more information at his disposal than Machiavelli, had seen clearly which way the wind was blowing. Alexander was bent on vendetta against the Orsinis; he had not forgotten Juan Gandia, although he never spoke of him. The punishment of Vitellozzo and the others was incidental – for him the real targets were the Orsinis. On 6 November Giustinian wrote that in signing the agreement the Orsinis ‘could be certain of having taken a terminal poison’. He saw, too, how the Orsinis and their allies had played into the Borgias’ hands; everyone, he said, vituperated them because ‘like stupid brutes they took the initiative and with unconsidered fury, then more stupidly made an agreement with little security, indeed greater peril to their interests, and also thus made themselves guilty and deserving of every punishment, which at some time the Pope may give them: the common opinion is that with justification he may and should do so’.
As November turned into December, Machiavelli at Imola gained a sense of impending tragedy, and his dispatches are full of repeated references to Cesare’s ‘bad feelings’ about the condottieri and his occasional ‘sinister’ references to them. They were also full of pleas for his own recall; he was ill, and he was doing nothing of use to the city. Cesare was repeating his demands for an alliance and a condotta from Florence, which the Florentines, as before, had no intention of giving him. As Cesare perceived this, and his need for Florence became less pressing as the crisis passed, so his treatment of Machiavelli changed from the intimate frankness of early October when he had seemed to take the envoy flatteringly into his confidence, admitting his mistakes and asking for opinions, to his usual elusiveness. Machiavelli’s admiration for Cesare remained undimmed, but he was embarrassed at the false position into which his government’s temporizing placed him in his relations with il Valentino:
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