On his way to Naples (see the introduction to the previous debate), Charles VIII, King of France, entered Pisa in November 1494. The city immediately rebelled against the Florentines – who had taken her in 1406 – and came de facto under French rule. Despite his repeated assurances, the King never restored the city to Florence. As the French left Italy the following year, Lodovico Sforza, Duke of Milan, along with the Venetians, managed to prevent the Florentines from taking Pisa back. Under the pretext of defending her independence by financial and military means, both Milan and Venice were in fact attempting to bring her under their control. The Venetians went as far as sending an army into Tuscany at the end of 1498. From the beginning of the Pisa affairs, as the Venetians seemed better placed to succeed, the Duke did his best to thwart their design, first indirectly, then in an ever more manifest manner, thereby provoking a bitter resentment in Venice on account of the huge amount of money they had been spending on the enterprise.

In April 1498 Charles VIII died and was succeeded by Louis XII, who, as an Orléans, 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. The two speeches below summarise the various views that were expressed in the Venetian Senate on this issue, in an impassioned debate that lasted for days, in November 1498. The alliance was eventually signed on 9 February 1499. In August the two allies launched a simultaneous attack, and in a few weeks they managed to partition the Duchy, as stipulated in the treaty.

To Guicciardini, the reasons against the alliance were ‘cogent’ and seconded by ‘the gravest and most prudent senators’. Yet, ‘hatred and covetousness to dominate, vehement instigators of any dangerous decision’, prevailed.