Why Generosity Ruins Leaders—And What to Do Instead — The Prince

Machiavelli takes up liberality first among the praised and blamed qualities. It would be well to be reputed liberal, yet liberality that earns no reputation injures you, and maintaining a liberal name forces a prince into magnificence until he consumes his property, taxes his people, becomes odious and poor, offends many while rewarding few, and falls at the first danger. If he then tries to stop, he is suddenly called miserly.

A wise prince therefore should not fear a reputation for meanness. Economy keeps revenues sufficient for defense and enterprise without burdening subjects, so he is liberal toward all from whom he takes nothing, who are numberless, and mean toward the few he does not pay. Machiavelli says the great deeds of his time came from men considered mean, not from spenders.

Julius II reached the papacy partly through a reputation for liberality but did not keep it up when he made war on France; his long thriftiness funded many wars without extraordinary taxes. The present King of Spain, Ferdinand, could not have undertaken so many conquests if he had been reputed liberal.

Machiavelli answers the Caesar objection: liberality helps a man rising to power but destroys a prince who keeps spending once established. Spending falls into three buckets: your own, your subjects', and others'. Be sparing with the first two; with others' wealth, especially on campaign through pillage, liberality is necessary and even Cyrus, Caesar, and Alexander gained glory by giving away what was not theirs. Squandering your own wastes power fast and leads to poverty, contempt, or rapacity and hatred. Better a mean reputation that brings reproach without hatred than liberal pretensions that end in rapacity with hatred.