This chapter presents the culmination of Machiavelli’s diplomatic service as he navigates the complex and perilous relations among Florence, France, and the papacy. It begins with his third mission to France in 1510, tasked with securing Florence’s alliance with Louis XII amid the escalating conflict with Pope Julius II. Through his encounters with French officials and insight into Louis XII’s motivations, Machiavelli grasps the ideological and theological conflict that propels the king’s actions, marking a turning point in his understanding of political-religious power. In observing the French court, Machiavelli recognizes a distinctive capacity for unifying state and religious values in ways Florence struggles to replicate. His experience with the disciplined, obedient people of France and the lack of such loyalty among the Tuscan people sharpens his perception of the Florentine republic’s vulnerabilities. This culminates during the Council of Pisa, where Machiavelli’s diplomatic and military roles converge in a tense political environment, highlighting his concerns about Florence’s unstable hold over Pisa and its fragile military structure. This chapter marks the end of Machiavelli’s public service, setting the stage for his withdrawal from political life.