Over the next three chapters, Machiavelli suspends his more direct critique of Christ in order to offer a critique of Christ's political legacy. He elaborates the political weakness of the papacy, the pernicious effects of its most popular politico-military strategy, and the ghastly consequences of acquiescing to the rule of the “first king among the Christians” (P 21). Using Italian and ancient examples, Machiavelli teaches a prince how to purge Italy of the corrupting influence of the Church and repel incursions by the ascendant Spanish Empire, whose success destroys the very foundations of civil society.

The title of chapter 19 is “Of Avoiding Contempt and Hatred.” Because the model Machiavellian prince described in chapter 18 would govern with Machiavellian virtue and would therefore “be praised by everyone,” one might ask why this advice is necessary. The consummate Machiavellian prince is famous, rather than infamous. Since the prince addressed here seems incapable of the height of Machiavellian virtue, chapter 19 appears to represent a descent in the argument.

This prince has not learned to abstain from taking his subjects’ property and women. He must “contrive” (ingegnarsi) to appear strong, grave, and spirited (P 19). While Machiavelli promises that the mere appearance of these qualities will prevent subjects from thinking “either of deceiving him or of getting around him” (P 19), that advice is conspicuously insouciant about the dangerous ambition of the few. Although Machiavelli cites two “failed” (P 19) conspiracies as evidence that conspiracies are difficult to accomplish, these offer little comfort: though their efforts are bungled, the conspirators nonetheless succeed in killing their respective targets. Machiavelli's advice to this defective prince is misleading. It betrays his hostility to those in power and prepares the reader for Machiavelli's conspiracy against the religious status quo, which emerges at the end of this chapter.

Internal and External Conspiracies

Machiavelli furthers his disingenuous teaching on conspiracies in the next paragraph. He notes that conspiracies can arise from within and from without. To combat “external powers,” one needs “good arms and good friends” (P 19). Machiavelli reassures the reader that the former are a sufficient guarantee of the latter.