With his condemnation of modern Christian politics in chapters 1 through 13, Machiavelli has sought like-minded malcontents. Chapter 14 presents a scheme for their basic training, and establishes an appropriate, non-Christian model of imitation: the Greek prince, Philopoemen. In obedience to ancient orders, Machiavelli discloses the best way to correct the weak and vain education of Christianity: “a prince should have no other object, nor any other thought, nor take anything else as his art but that of war and its orders and its discipline” (P 14). The rest of the chapter consists of three sections: an exhortation for princes to think constantly of war; a comparison of war to hunting that reintroduces the landscape metaphor of the dedicatory letter; and finally, a prescription to read histories so that one might correctly imitate ancient men.

Machiavelli asserts that knowledge of the art of war is sufficient “to one who commands” (P 14). Being unarmed, on the other hand, makes one “contemptible,” since it is not “reasonable” (P 14) for the armed to obey the unarmed. Although Machiavelli does not allude to the Gospels here, Christ's relationship to Roman soldiers generally confirms his judgment that being unarmed produces scorn among the armed.

According to Machiavelli, even a prince who is at peace is obliged to think constantly of war. To prepare the body for war, Machiavelli recommends a combination of military exercises and hunting. The latter activity also constitutes mental preparation: while hunting, “he should learn the nature of sites, and recognize how mountains rise, how valleys open up, how plains lie, and understand the nature of rivers and marshes—and in this invest the greatest care” (P 14).