From 1494 onward, foreign armies walked the length of Italy almost unopposed. French, Spanish and papal forces took cities, sold them, lost them and took them again, while the peninsula's republics and duchies hired mercenary captains who changed sides for money. The books available to anyone thinking about this were mirrors for princes: advise the ruler to be just, merciful, truthful and pious, and providence will attend to the rest. Held up against what was actually happening at Senigallia or Prato, that literature described nothing at all.
A clerk in the Florentine chancery decided to write about politics as it is practised rather than as it ought to be. That is the whole of the scandal, and it has never stopped being one.
He had an unusual seat from which to look. Made second chancellor of the republic in 1498 at twenty-nine, with no legal training and no previous office, he spent fourteen years on the road as Florence's eyes — at the court of the French king Louis XII, at the conclave that produced Julius II, the warrior pope, and with Cesare Borgia, the son of Pope Alexander VI, in December 1502, when Borgia lured his mutinous captains to Senigallia and had them strangled. Machiavelli's dispatches recorded the technique without flinching. They also drew a practical conclusion: hired soldiers fight for pay and therefore do not fight. In 1506 he pushed through an ordinance raising a citizen militia from the Florentine countryside, and in 1509 that militia took Pisa back.
Three years later it could not hold Prato. Spanish and papal troops stormed the town in August 1512, the republic collapsed, the Medici, Florence's ruling family, returned, and the man who had built the army lost everything with it — dismissed, made to post a bond of a thousand florins, confined to Florentine territory. In February 1513 his name turned up on a list carried by a conspirator he did not know. He spent three weeks in prison and was hoisted repeatedly on the strappado, the rope that dislocates the shoulders under the body's own weight. A papal amnesty released him, and he went out to a small farm at Sant'Andrea in Percussina with nothing to do.
He wrote The Prince there, in a few months of 1513, describing it to his friend Francesco Vettori, Florence's ambassador in Rome, as a little work on principalities. It argues that a ruler who insists on being good among men who are not will be destroyed, that cruelty concentrated at the start costs less than cruelty spread out, and that fortune governs about half of what happens. It was not published, and circulated in manuscript for nineteen years.
The same exile produced the Discourses on Livy, which holds that the best state is a republic and that the running quarrel between the nobles and the people gave Rome its liberty. The Art of War went back to the militia he had raised in 1506. Set as a day's conversation in a Florentine garden with Fabrizio Colonna, a veteran commander, it argues that a state should be defended by its own citizens, trained on the model of the Roman legions, and not by hired captains. It was also the only one of his major prose works to appear in print while he lived. In 1520 the Medici, the family that had tortured him, commissioned a history of Florence from him; he delivered it in 1525.
When Rome was sacked in 1527 and the Florentine republic came back, he applied for his old post and was turned down — too compromised by the Medici. He died that June.
The Prince was printed in 1532 with papal permission and placed on the Index of forbidden books in 1559. English playwrights turned his name into a stock stage villain within decades. The argument since has been about which book is the real one. Rousseau took The Prince for an exposure of tyranny written by a republican; the political philosopher Leo Strauss took it at its word and called him a teacher of evil; a long line of historians reads him as the source of a republican tradition running to the American founders. He wrote both books in the same exile, and readers have been choosing between them ever since.