Machiavelli was painfully aware of living in a disastrous moment of Italy's history: foreign invasions, occupations and shattered states. He was harshly critical of Italy's princes (such as Francesco Sforza), its professional military class (especially Cesare Borgia), and the Church (Pope Julius II), and this is a study of his evaluation of their failures and of their underlying causes.

He believed that the root of Italy's political weakness was the excessive ambition of its elite classes, who, like their counterparts in ancient Rome, were prepared to overthrow governments that obstructed their ambition. Machiavelli formulates this phenomenon, first theoretically, then historically in the context of the Florentine Republic's descent into family-based factionalism, which culminated in the brittle Medici regime. The most damaging tyranny, according to Machiavelli, was the collective tyranny of wealthy elites ready to undermine law and government to preserve and augment their power and wealth.