Greece occupies a central place in the book’s geography of conquest because it reveals how the character of a territory determines whether military success becomes durable rule. It appears not as a uniform possession but as a region of differing political forms, local freedoms, competing powers, and external interventions. Alexander the Great could secure the Asian kingdom of Darius after defeating its ruling house, while the Romans had to manage Greece through alliances, the humiliation of Macedonia, the expulsion of Antiochus, and eventually the destruction of cities that could not be safely governed through their own laws.

A Province of Difference and Political Fragmentation

Greece is introduced as an acquired territory whose language, usages, and laws differ from those of the conquering ruler’s original dominions. Such difference multiplies the difficulties of retention. A prince who acquires a province of this kind is advised to reside there personally, because disorders can then be detected at their beginnings and remedies applied before they become incurable. Personal residence also prevents the province from being pillaged by officials, gives inhabitants direct access to their ruler, and makes a foreign enemy more cautious about attacking a government established on the spot.

The region’s difficulty also arises from its political variety. The book contrasts centralized kingdoms, in which authority is concentrated in one prince and his servants, with kingdoms containing hereditary barons and smaller principalities whose inhabitants retain personal loyalties to local rulers. Greece is repeatedly associated with the latter, more fragmented pattern. That structure allows dissatisfied local powers to invite an outside conqueror, but it also leaves the conqueror with numerous potential centers of resistance after the initial invasion.

Alexander the Great and the Kingdom of Darius

Greece is linked to the comparison between Alexander the Great’s conquest of Asia and the acquisitions of rulers such as Pyrrhus. Alexander the Great conquered Asia within a few years and died before fully entering into possession of it. Yet the territory did not rise in rebellion against his successors. The explanation lies in the structure of the kingdom he had conquered: the government of Darius resembled the centralized rule of the Turk, where authority was concentrated in the sovereign rather than distributed among hereditary barons with independent subjects and established local affection.

Alexander the Great therefore had first to defeat Darius utterly and strip him of his dominions. Once Darius had died, the country was permanently secured to Alexander’s successors, provided that those successors themselves remained united. The disorders that later appeared arose from their ambition and mutual jealousies, not from a network of Greek-style local princes capable of independently reviving their authority. The book thus treats the contrast between Asia and Greece as a contrast in political organization, not as a difference in the personal merit of the conquerors.

Roman Intervention and Preventive War

The Romans are presented as the rulers who most deliberately understood how to secure a fragmented province. In Greece they took the Achaians and Aetolians into their pay, humbled the Macedonian monarchy, and drove Antiochus out. They accepted the assistance of weaker powers without allowing those allies to become strong enough to threaten Roman supremacy. Nor did they permit Philip or Antiochus to retain authority that might later challenge Roman control within the province.

Roman policy was directed toward future dangers as much as present enemies. The Romans recognized that disorders are easiest to cure while still remote and difficult to recognize, but easy to recognize and impossible to cure once they have matured. For that reason they chose to make war with Philip and Antiochus in Greece rather than risk facing them later in Italy. War, in this reasoning, cannot be permanently avoided; postponement merely transfers the advantage to the opposing side.

Free Cities and the Problem of Liberty

Greece also illustrates the special danger posed by cities accustomed to live under their own laws and in freedom. The book identifies three possible methods for holding such a city or province: destroy it, reside there personally, or preserve its laws while imposing tribute and entrusting the government to a small group dependent on the new prince. The last method can work only so long as the installed government understands that its survival depends on the conqueror.

The Spartan example shows the instability of ruling free cities through oligarchies. Sparta held Athens and Thebes by creating oligarchies in them, yet eventually lost both. The Roman example is harsher. Rome destroyed Capua, Carthage, and Numantia and consequently never lost them. When Rome attempted to hold Greece in the Spartan manner, leaving it free and allowing it to retain its own laws, the arrangement failed; Rome had to destroy many cities in the province before securing it.

The reason is the political memory carried by liberty and ancient law. A free city can use those names as a shield for rebellion, and neither the passage of time nor benefits bestowed by a conqueror necessarily erases them. A republic retains a stronger vitality, fiercer hatred, and keener thirst for revenge than a principality whose hereditary ruler has disappeared. Greece therefore becomes an example of how institutions survive conquest as memories and symbols, capable of turning against an occupying power when misfortune gives resistance an opening.

Greece as a Test of Military and Territorial Control

The region is also connected with the book’s broader discussion of military dependence. Cesare Borgia entered Romagna with French auxiliary troops and used them to take Imola and Forli. When those forces proved unreliable, he employed mercenaries from the Orsini and Vitelli; finding them fickle, false, and treacherous, he dismissed them and turned to troops of his own raising. The comparison reinforces the wider lesson drawn from Greece: a ruler’s reputation rises when observers see that he commands forces that are genuinely his own rather than relying on foreign powers whose interests and officers remain independent.

Greece further demonstrates that a prince must possess enough men and money either to take the field against an assailant or to defend strongly fortified towns. A ruler unable to meet an enemy in open country must strengthen the cities in which he resides and maintain his position with his subjects so that an attacker faces both physical difficulty and the danger of a hostile population. The territory’s strategic significance consequently lies not only in its conquest but in the administrative, military, and political systems required to keep it from becoming a permanent source of rebellion.