The Prince — who's who

Former second chancellor of the Florentine Republic. Diplomat to the French court, to Cesare Borgia, to Pope Julius II. Arrested and tortured in 1512 when the Medici returned. Writes The Prince on a small farm at Sant'Andrea in Percussina, in the evenings, after changing into the robes of office he no longer holds. The voice of every chapter is his: empirical, combative, impatient with received wisdom, and — in the final chapter — openly passionate about Italy.

An abstraction more than a person, but the addressee of every chapter. He is the man who acquires or holds a state — by inheritance, by his own arms, by another's arms, by fortune, by virtù, by crime, or by civic election. Through the book he acquires shape: he should not be hated; he should appear merciful, faithful, religious while being prepared at need not to be; he should keep his subjects busy with great undertakings; he should choose ministers wisely; he should look to the historical record before his own preferences.

Lorenzo II de' Medici, Duke of Urbino (1492–1519), not his famous grandfather. The Medici family installed him as the de facto ruler of Florence after their return in 1512. Machiavelli dedicated The Prince to him in the hope of employment. By every account, Lorenzo never read it — or read it and forgot. The closing exhortation to redeem Italy is addressed to him by name.

Son of Pope Alexander VI. Carved the Romagna into a personal state using his father's papal resources and Louis XII's French alliance. Machiavelli met him as a Florentine envoy, watched him operate, and returned to Florence convinced he had seen how new principalities were actually built. The pacification of the Romagna through his lieutenant Remirro de Orco — and Remirro's subsequent public execution — is Machiavelli's paradigm of cruelty well used. His state collapsed when Alexander died; Machiavelli absolves him: he did everything a man could do.

Not a goddess in any pious sense, but the personified accident of history — the river in flood, the unexpected death, the foreign army crossing the Alps. Machiavelli treats fortuna as the arbiter of roughly half of what happens in human affairs, leaving the other half to human virtù. His most quoted image, in chapter 25, is that fortune is like a raging river: where dykes have been built in advance, she is manageable; where no preparation was made, she devastates. The closing image — that fortune favours the bold — is the most famous and the least nuanced passage in the book.

Machiavelli's social analysis, sketched in chapter 9, holds that every city contains two humours — the popolo, who do not wish to be oppressed, and the grandi, the great men, who wish to oppress them. A prince comes to power either with the help of the people or the great, and the choice shapes everything that follows. Machiavelli's preference is for the popular base: the people are more numerous, more reliable, and easier to satisfy — they ask only not to be crushed.