On Whether the Emperor Should Be Magnanimous towards the King of France, Whom He Holds Prisoner, or Impose Severe Terms on Him

This chapter follows up on the previous debate, as the Venetians consider the fate of King Francis, who had been previously captured in a sensational battle at Pavia, where the French army had been overwhelmed. One side of the debate argues that the king of France be set free upon congenial terms, with no attempt made to take advantage of his situation. The other side, on the other hand, argued that this victory must be taken advantage of, and Francis would soon find himself with rather harsh conditions upon which he would be set free: among other things, he was to give up all his claims to Italy, Flanders and Artois, and restore to Charles Burgundy and all the dominions that had been annexed by the French crown in 1477.

On Whether the Venetians Should Ally with the Emperor or Stick to the Alliance with the King of France

This chapter considers how, once again, the Venetians had found themselves under steady pressure from two sides — this time between the new king of France, Francis I, and Charles of Habsburg, the king of Spain as well as the Holy Roman Emperor. Although they had not come to a clear rupture with the Emperor, the Venetians had dutifully performed their role in the war on the French side, and were now rather at sea as to what they should do next. On the one hand, Francis incited them to hold on, for he would soon send another army into Italy; on the other hand, Charles was trying to detach them from the French alliance with various reassurances and offers.

On Whether or Not the Venetians Should Sign an Offensive Alliance with the King of France

This chapter summarises an impassioned debate held in the Venetian Senate in 1498. The issue was a potential alliance with the next king of France, Charles' successor Louis XII. As an Orléans, Louis had claimed rights to the Duchy of Milan. In order to second his ambitions, the new French king needed the support of Venice, in exchange for which he was ready to cede a part of the Duchy to her. Thus, Venice had a fair opportunity to expand her dominion significantly, at the cost, though, of finding herself with a far more powerful prince than the Duke as a neighbour.

On Whether or Not the Florentines Should Launch a War of Aggression against Lucca

This chapter takes up the events following the war with the Duke of Milan, when the Florentines resumed their century-long design to take Lucca, the conduct of whose lord, during the last war, had provided a pretext. Here, Guicciardini comments that the desire to take Lucca was so irresistible that it prevented the Florentines from seeing the difficulties and the dangers that the enterprise entailed and, in such a large assembly, ‘where votes were not weighed but counted, the prudent men turned out much less numerous than the imprudent men, with whom the partisans (i.e. the supporters of the Medici) had joined’.

On Whether the Venetians Should Ally with the King of the Romans or Stick to the Alliance with the King of France

This chapter considers the delicate position that the Venetians had found themselves in during the spring of 1507. At the time, Maximilian I, King of the Romans, was getting ready to pass into Italy for the sake of being finally crowned emperor by the Pope and, in particular, of settling matters with Louis XII, King of France, over the Duchy of Milan, to which both monarchs claimed rights and which the French had seized in 1499. To that purpose, he asked the Venetians for leave to pass through their dominion and invited them to make an alliance with him against the French. Should they refuse his offer, he threatened to find an agreement with Louis at their expense. The French King, in turn, invoked the existing alliance with the Venetians, urged them to oppose the coming of Maximilian, and offered a new alliance and the assistance of all his forces.

On Whether or Not the Florentines Should Accept the Peace Agreement that the Duke of Milan is Offering

This chapter concerns the offer of a treaty of peace from Duke Filippo Maria Visconti of Milan as he attempted to restore his family's lost territories — a plan that the Florentines had good reason to oppose, though they accepted the treaty nevertheless. To Guicciardini, the decision reflected in particular the desire not to antagonise the popular party, whose members suspected that those who spoke against Filippo's peace plan stood to gain some personal advantage from war. Thus, the supporters of the peace became more vocal, those who held a different view turned more reserved, and those in between embraced the prevailing opinion, ‘whose good was evident and whose evil was so hidden that only a perspicacious eye could see it’.

On Whether or Not the Venetians Should Make an Agreement with the Emperor or Risk War against Him

This chapter showcases a debate on whether or not the Venetians should make an agreement with Charles. At the time there was a possibility that Charles could find a pretext to seize the Duchy of Milan, in which case the Venetian Republic would have found itself squeezed in between Habsburg and imperial dominions on all sides. In addition, the French eclipse from Italian affairs meant the disappearance of the only credible counterweight to Charles's power. At the same time, the Venetians could not challenge the Emperor on their own. The year was thus spent in negotiations with Charles, on the one hand, and with all those who had reason to oppose his triumph, on the other — especially Pope Clement VII and the French regency.

On Whether or Not the King of France Should Make Peace with the Duke of Milan

This chapter discusses a peace treaty between the King of France, Charles VIII, and the Duke of Milan, following the king's attempt to claim dynastic rights over the Kingdom of Naples. Charles had passed into Italy in 1494, during which time the inability of the Italian states to coordinate their moves paved the way to an effortless campaign. The very ease with which the enterprise had been accomplished, however, induced the Italian states to take action. A large coalition was thus created in early 1495 to counter the French, and a few months later, Charles would engage in negotiations with the enemy coalition, especially the Duke of Milan. A truce was signed, which allowed for the evacuation of the French, and the Duke submitted a proposal for what amounted to a separate peace with the King of France, which is the subject of this chapter's debate.

On Whether or Not the Florentines Should Wage War against the Church

This chapter discusses the tensions between the Florentines and the papal legates. In the years 1374–6, the strained relationship between the people of Florence and Legate of Bologna came to a head when Sir John Hawkwood and his mercenary company had passed into Tuscany, presumably upon the Legate's encouragement, for it was believed that the latter intended to take revenge on the Tuscan cities that had refused to contribute funding for his war against the Visconti, thus forcing him to suspend it. The ensuing outrage had driven the Florentines to consider war against the Church — which eventually occurred, though Guicciardini had been critical of such a decision — to him, considerations relating to the ‘just indignation’ prevailed over those relating to ‘expediency’.

On Whether the Emperor Should Make an Agreement with the Italian States or the King of France

This chapter considers where the Holy Roman Emperor's allegiances might sway. In a triangular relationship involving the Emperor, France, and the Italians, everybody was sitting simultaneously at two tables, trying both to prevent the other two from joining their forces and to extract as many concessions as possible from each of them. It was Charles who had the upper hand in the game. With his usual lucidity, Guicciardini captures the essence of the situation in a few lines: ‘and nothing [was] more easy to [Charles] than by feeding the French with hopes to divert them from the thoughts of taking up arms, and by this artfulness to keep the Italians in suspense, so that they should not venture to take new resolutions’.