Chapter 22 — The Secretaries of Princes
The first thing one forms about a prince's intelligence is an opinion of the men around him.
Summary
The chapter opens with a diagnostic claim: the first opinion one forms of a prince's understanding is by observing the men around him. When the prince's servants are capable and faithful, he may always be considered wise, since he has been able to recognise the capable and to keep them faithful. When they are not capable, the prince's first blunder has already been made — in his choice of advisers. The argument makes the quality of the court a direct index of the quality of the ruler.
Machiavelli offers a single test for identifying loyal ministers, expressed with characteristic simplicity: when you see the servant thinking more of his own interests than of yours, and seeking inwardly his own profit in everything, such a man will never make a good servant, nor will you ever be able to trust him. The test is observable in behaviour, not in avowals of loyalty. A servant who consistently prioritises the master's affairs over his own — in small things and large, in the day-to-day management of responsibilities — is either genuinely faithful or so practised in appearing so that the difference is negligible.
The structural solution to the problem of servant loyalty is to make loyalty rational. A prince should honour his faithful servants, enrich them, share honours and cares with them, and — critically — make them aware that they cannot stand alone without the prince's support. The aim is to create a situation where the servant's own interest and the master's interest are aligned: the servant flourishes as the prince flourishes, is exposed as the prince is exposed, and has no better option than continued faithfulness. This is not an appeal to virtue but to incentive structure — which is, for Machiavelli, the more reliable foundation.
- Chapter 1Machiavelli opens not with a chapter but with a letter — one of the most celebrated dedications in European literature.
- Chapter 2The book's first chapter is a taxonomy so compressed it reads like a table of contents for the entire argument.
- Chapter 3Machiavelli's analysis of hereditary principalities is deliberately brief because the argument is simple: long-settled states are easier to hold than new ones.
- Chapter 4This is the book's first major analysis, and Machiavelli uses France's disastrous Italian campaigns as his case study.
- Chapter 5Machiavelli uses Alexander the Great's conquest of Persia versus the repeated French failures in Italy to introduce one of his sharpest analytical distinctions: the difference between states governed through a single lord with servile administrators and states governed through a lord with independent barons.
- Chapter 6Machiavelli confronts one of the hardest problems in The Prince: what to do with a conquered city that has historically governed itself.
- Chapter 7Machiavelli turns to the most admirable category: the prince who rises from nothing by his own ability.
- Chapter 8This is the chapter that establishes Cesare Borgia as The Prince's central case study — the man who came closest to the political ideal, whose eventual failure was attributable entirely to fortune rather than to any deficiency in his method.
- Chapter 9Machiavelli refuses to praise Agathocles's murders as virtù, but he cannot deny that they worked.
- Chapter 10Chapter 9 introduces Machiavelli's social analysis: every city contains two humours, the people who wish not to be oppressed and the great who wish to oppress.
- Chapter 11This short chapter introduces a practical test for evaluating a principality's stability: can the prince, if attacked, maintain himself with his own resources, or must he always rely on others? Machiavelli uses the fortified German free cities as his model — towns with strong walls, substantial reserves, and organised citizens who can defend themselves for at least a year without outside help.
- Chapter 12Machiavelli's treatment of the Church is one of the book's most revealing moments — not because it is disrespectful, but because it applies the same analytical framework to the papacy that it applies to every other state.
- Chapter 13Machiavelli's hatred of mercenary armies is the most consistent passion in The Prince, and this chapter is its fullest expression.
- Chapter 14Auxiliaries — troops borrowed from a foreign power — are worse than mercenaries, Machiavelli argues, because at least mercenaries are divided among themselves.
- Chapter 15The chapter is short and absolute.
- Chapter 16Chapter 15 is the hinge on which the entire book turns.
- Chapter 17The argument of Chapter 16 runs against the ordinary wisdom of every medieval mirror-of-princes tradition: a reputation for liberality, sincerely maintained, is ruinous.
- Chapter 18Chapter 17 contains the most famous argument in the book, and it is more careful than its reputation suggests.
- Chapter 19Chapter 18 is the most disputed in the book and the one that earned Machiavelli his reputation as the theorist of bad faith.
- Chapter 20The longest chapter in the book synthesises the ethical analysis of the preceding chapters into a comprehensive theory of internal security.
- Chapter 21Machiavelli surveys the range of defensive strategies princes have used — disarming subjects, fostering internal factions, building fortresses, cultivating those they mistrusted — and delivers a nuanced verdict.
- Chapter 22Chapter 21 turns from the negative task of avoiding hatred and contempt to the positive task of building a reputation that sustains power.
- Chapter 23This short chapter on the choice of ministers is a compressed theory of institutional trust.
- Chapter 24The problem of flattery is, for Machiavelli, an epistemic problem before it is a moral one.
- Chapter 25Chapter 24 applies the book's principles to the immediate Italian political situation and delivers a harsh verdict.
- Chapter 26Chapter 25 contains the book's most sustained philosophical argument and its most famous image.
- Chapter 27The book's final chapter drops the cool analytical register of everything that preceded it and becomes a plea.