By September 1498, the soldiers of Florence were coming close to ending the Pisan rebellion, after three long years of wearing campaigns and diplomatic stalemates. As a result of an all-out offensive, the army had eventually occupied a large area of the enemy countryside, seizing the towns of Buti, Calci, Vico, and Ripafratta. Only the city of Cascina did not surrender to the captain-general, Paolo Vitelli, whose mastery of siege artillery was a significant determinant of this successful, brisk operation.

Once again, however, a decisive victory was hampered by an external intervention. The Venetian invasion of the mountain region of Casentino, in October 1498, diverted Florentine attention from the reconquest of Pisa. The menace of a heavy defeat represented a serious problem for the troubled Republic, now compelled to fight on two fronts, “with a daily expenditure of one thousand and fifty hundred florins.” Only after five months of stalemate did the opponents, encouraged by Ludovico Sforza, enter into negotiations. They were both wearied by “the draining of wells full of ducats” and “the bargaining, the extortion” of their mercenaries.

In the first days of April 1499, however, the two peace agreements proposed by the duke of Ferrara, Ercole d’Este, dissatisfied each one of the three contenders. Pisans protested firmly against the numerous, important concessions to Florentines, such as the cession of public incomes, the relinquishment of city fortresses, and the appointment of foreign criminal judges. Considering the pact as the beginning of the end of the “popular freedom,” they said they would prefer to abandon the city, or to die bravely, defending the walls against their “bloodthirsty” enemy, rather than “live under Florentine custody.”