
Second Chancellor of the Florentine Republic
"A prince must have no other object, nor any other thought, but war."
Machiavelli is on this list because the Italian Wars are the reason he exists. As Florence's second chancellor he spent fourteen years as a diplomat inside the catastrophe — envoy to Cesare Borgia, to Julius II, to Louis XII, to the Emperor — watching Italian states be dismantled by foreigners while their rulers made clever arrangements that did not work. He drew two conclusions. First, that mercenaries were the disease: condottieri had no reason to win decisively or die trying, so he raised a citizen militia for Florence — which promptly ran away at Prato in 1512, and the Republic fell. Second, that politics had to be described as it is rather than as preachers said it should be. When the Medici returned he was sacked, tortured on the rope, and exiled to a small farm, and there he wrote *The Prince* in 1513 — partly as a job application, which failed. It closes with an anguished plea for a prince to unite Italy and drive out the barbarians. Nobody did. He died in 1527, weeks after the Sack of Rome confirmed everything he had argued, and his name became a synonym for the behaviour he had merely reported.
Did you know?
He raised a citizen militia to prove that mercenaries were ruining Italy. It broke and ran at Prato in 1512, the Republic fell, and he was tortured and exiled — and wrote *The Prince* on a farm, as a job application that was ignored.
May 14, 1509 · 6,000 total casualties
The high-water mark of Italy's humiliation, and a lesson in the wars' logic: the same Julius who organised the destruction of Venice reversed his alliances within two years to expel the French he had invited, then reversed again. Machiavelli watched this from a Florentine desk. Venice survived by conceding everything and waiting, and eventually got most of it back — proof that in this war diplomacy outperformed armies.
April 11, 1512 · 12,000 total casualties
A victory that won nothing. Ravenna showed artillery could break the field fortifications that had made Cerignola possible, and it killed 12,000 men in a day — a scale of slaughter Italy had never imagined. But Gaston died in the pursuit, France lost the only commander who could have finished the campaign, and within months the French were expelled from Italy entirely. The wars' recurring lesson: battles were decided, and nothing was.
May 3, 1469
🌅 Birth
Born in Florence to a struggling lawyer
June 19, 1498
📍 Posting
Becomes second chancellor of the Republic
October 7, 1502
📍 Posting
Envoy to Cesare Borgia; takes notes that become The Prince
August 29, 1512
⚔️ Battle
His citizen militia breaks at Prato; the Republic falls
February 12, 1513
🕊️ Postwar
Tortured on the rope and exiled from Florence
December 10, 1513
🕊️ Postwar
Writes The Prince at his farm at Sant’Andrea
June 21, 1527
✝️ Death
Dies weeks after the Sack of Rome proves him right