Machiavelli dedicates The Prince to Lorenzo di Medici, offering his knowledge of great men's actions as a valuable gift.

Machiavelli establishes that all states are either republics or principalities and focuses the book on principalities alone.

Machiavelli argues that hereditary principalities are the easiest to maintain because people are already accustomed to the ruling family.

Machiavelli warns that annexing new territories creates enemies of those harmed and those who supported the conquest but remain unsatisfied.

Machiavelli recommends that a prince completely destroy the ruling family of any annexed territory to prevent future rebellion.

Machiavelli argues that princes who rise to power through their own ability are far more secure than those who rely on fortune.

Cesare Borgia's poor choice in supporting Julius II as Pope—a longtime family enemy—leads directly to his eventual downfall.

Machiavelli describes how Agathocles assembled Syracuse's senate and ordered his soldiers to kill them all, seizing the city.

Machiavelli explains that civil principalities arise when a private citizen becomes ruler through the favor of the people or the nobles.

Machiavelli declares mercenary soldiers useless and dangerous, arguing that Italy's ruin was caused entirely by reliance on them.

Machiavelli concludes that no principality can be truly secure unless it is defended by its own native forces.

Machiavelli argues that a wise prince must know how to do wrong and use that knowledge when necessity demands it.

Machiavelli concludes that when a prince must choose, it is far safer to be feared by his people than to be loved.

Machiavelli argues a prince does not need to possess virtuous qualities, but he must always appear to have them.

Machiavelli makes a direct plea to the Medici family to raise a native army and liberate Italy from foreign invaders.

The Prince opens with Machiavelli dedicating his work to Lorenzo di Medici, framing his political knowledge as a valuable gift meant to earn favor with the ruling family. He establishes a foundational framework, explaining that all states are either republics or principalities, and offers strategies for seizing and holding each type. Moving through the types of principalities, Machiavelli draws on examples like Cesare Borgia and Agathocles to illustrate how rulers can acquire states through fortune, ability, or outright wickedness. The military section stresses that mercenaries are dangerous and that no state is secure without its own native army. In the behavioral section, Machiavelli delivers his most famous conclusions: a prince must know how to do wrong when necessary, fear is safer than love, and appearing virtuous matters more than being virtuous. The work closes with a passionate call for the Medici family to raise a native Italian army and drive out foreign powers.

The core arguments of The Prince from principalities to Italy's liberation.

Machiavelli states he will not discuss republics and limits the book's scope entirely to the governance of principalities.

Machiavelli recommends sending colonists to annexed territories rather than armies, arguing it is less costly and offends fewer people.

Machiavelli contrasts the Ottoman sultan's centralized servant-based rule with France's powerful hereditary noble families holding regional power.

Machiavelli outlines three methods for holding annexed states that previously lived under their own laws and enjoyed freedom.

Machiavelli cites Moses, Cyrus, Theseus, and Romulus as examples of armed prophets who successfully imposed new political orders.

Oliverotto of Fermo orders soldiers to kill his uncle and all dinner guests at a banquet held in his own honor, seizing the city.

Machiavelli argues that ruling through wickedness may win a prince his state but will never earn him true glory or virtue.

Machiavelli measures principality strength by whether a prince can defend himself using his own resources or always needs outside assistance.

Machiavelli explains that ecclesiastical principalities are uniquely easy to hold regardless of how a prince lives or governs.

Machiavelli notes that Pope Alexander VI transformed the church into a major temporal power through the use of money and arms.

Cesare Borgia progresses from relying on French auxiliary troops to mercenaries and finally builds his own army, earning his greatest reputation.

Machiavelli argues a prince should study military history and keep troops drilled and organized even during times of peace.

Machiavelli warns that excessive generosity exhausts a prince's resources, forces higher taxation, and ultimately causes the people to hate him.

Machiavelli argues that a prince who disarms his subjects earns their hatred by signaling distrust and forces himself to rely on mercenaries.

Machiavelli argues that Italian princes lost their states through sloth and complacency rather than misfortune, having failed to prepare in calm times.

Pool 2 covers the secondary arguments that give The Prince its depth and practical texture. Machiavelli limits the book's scope to principalities and then works through detailed recommendations—sending colonists to annexed territories, contrasting governance styles through the Ottoman and French examples, and explaining how to hold formerly free states. The section on acquiring principalities is enriched by the example of Oliverotto's banquet massacre and the church's rise to temporal power under Alexander VI. The military arguments trace Borgia's evolution from borrowed foreign soldiers to his own reliable army and conclude that no prince is safe relying on outside forces. Behavioral chapters warn that generosity leads to resource exhaustion and hatred, while disarming subjects breeds distrust and dependence on mercenaries. The pool closes with Machiavelli's sobering diagnosis that Italian princes lost their states through complacency and sloth, not bad fortune.

The supporting arguments, historical examples, and practical recommendations of The Prince.

In the dedication, Machiavelli compares his perspective on princes to a painter who steps low to capture the height of mountains.

Machiavelli notes that annexed territories sharing the same language and customs as the main principality are far easier to hold.

Machiavelli recommends that a prince personally reside in a newly annexed territory to quickly suppress disorder and deter invaders.

Machiavelli warns that people in formerly free republics never forget their past freedoms and will seek vengeance against a new ruler.

Machiavelli cites Francesco Sforza as an example of a man who rose from private citizen to Duke of Milan through ability alone.

Machiavelli advises that when cruelties are necessary, a prince should commit them all at once and then win the people over with benefits.

Machiavelli argues that the people's desire to avoid oppression is more righteous than the nobles' desire to rule and oppress.

Machiavelli warns that auxiliary troops are even more dangerous than mercenaries because their loyalty belongs entirely to a foreign ruler.

Machiavelli points to Cesare Borgia's pacification of the Romagna as proof that a reputation for cruelty can restore peace and loyalty.

Machiavelli uses Hannibal, whose cruelty kept a diverse army unified, contrasted with Scipio, whose clemency caused his Spanish army to rebel.

Machiavelli introduces the fox and lion metaphor to argue that princes need both cunning to avoid traps and force to overpower enemies.

Machiavelli argues that a prince who remains neutral in a conflict between neighboring states will lose the respect of both sides.

Machiavelli advises that a prince reward talent, encourage subjects to prosper in their trades, and entertain the people with festivals.

Machiavelli argues that fortune governs only half of human affairs while free will allows rulers to direct the remaining half.

Machiavelli compares fortune to a raging river, arguing that a ruler who prepares canals and dams in calm times can withstand any flood.

Pool 3 traces the sharper revelations and pivotal arguments that give The Prince its lasting controversial reputation. Beginning with Machiavelli's painter metaphor in the dedication, the pool moves through his insights on holding annexed territories—the advantages of shared culture, the importance of personal presence, and the permanent threat posed by peoples who once knew freedom. Historical figures like Francesco Sforza and Cesare Borgia illustrate how ability, cruelty, and timing determine a ruler's fate. The behavioral section delivers some of the book's most provocative claims: that all necessary cruelties should be committed at once, that Borgia's reputation for cruelty brought lasting peace to the Romagna, and that Hannibal's inhuman discipline kept his diverse army from mutiny while Scipio's clemency caused rebellion. The fox and lion metaphor encapsulates Machiavelli's philosophy of cunning power, and the pool ends with his argument that fortune governs only half of destiny—leaving the prepared ruler to shape the rest.

The key revelations, pivotal metaphors, and illustrative examples that define The Prince.