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Charles VIII of France
France (Valois)

Charles VIII of France

King of France

BornJune 30, 1470 · Amboise, France
DiedApril 7, 1498 · Amboise, France
EducationBarely schooled; raised on tales of chivalry and crusade
Pre-warKing of France from the age of thirteen

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Charles VIII of France

June 30, 1470April 7, 1498

Did you know?

He conquered the length of Italy with the first true mobile siege train in history, achieved nothing by it, and died at twenty-seven by walking into a door lintel on his way to watch a game of tennis.

"I go to claim what is mine by right, and Italy shall be the road to Jerusalem."

A small, physically frail, poorly educated young king with a head full of chivalric romances, Charles VIII inherited a France that was — for the first time in centuries — unified, solvent, and possessed of the best artillery in the world. He decided to use it to claim the throne of Naples through a tenuous Angevin inheritance, and beyond Naples he imagined a crusade to retake Jerusalem. In September 1494 he crossed the Alps with 25,000 men and forty bronze guns on horse-drawn carriages, and Italy simply opened. Fortresses built to hold out for months fell in hours; the condottieri system, which had made war in Italy into a manageable and rarely lethal business, evaporated on contact. He reached Naples in four months having barely fought. Then the Italian states, Spain, and the Empire allied against him, and he had to cut his way home at Fornovo. He got nothing and started everything. Four years later he hit his head on a door lintel at Amboise and died at twenty-seven, leaving no heir and a war that would run for another sixty-one years. Guicciardini wrote that all the calamities of Italy dated from his arrival, and that judgement has never really been revised.

Key Battles

charles viii invasionbattle of fornovo

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Gonzalo Fernández de Córdoba
Habsburg Spain & the Empire

Gonzalo Fernández de Córdoba

El Gran Capitán; Viceroy of Naples

BornSeptember 1, 1453 · Montilla, Córdoba, Castile
DiedDecember 2, 1515 · Granada, Castile
EducationRaised as a page at the Castilian court; learned war in the Granada campaign
Pre-warCommander in the final conquest of Granada

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Gonzalo Fernández de Córdoba

September 1, 1453December 2, 1515

Did you know?

Asked to account for his spending in Naples, he produced the legendary "Accounts of the Great Captain" — an itemised bill including sums for spies, pickaxes, and "two hundred million ducats for the patience with which I listened to a king who demanded accounts from the man who had given him a kingdom."

"Better the bread of the arquebusier than the plumes of the knight."

The most important soldier of the age and the one who understood first what was happening. A veteran of the Granada campaign, Gonzalo went to Italy in 1495, was beaten by the French and their Swiss pikes, and — instead of demanding better knights — rebuilt Spanish infantry from scratch around the arquebus and the spade. At Cerignola in 1503 he dug a ditch, lined it with arquebusiers, and let the French gendarmerie charge into it. The finest heavy cavalry in Europe was shot to pieces at point-blank range for the loss of about a hundred Spaniards — generally counted the first battle in history decided by handheld gunpowder weapons. Eight months later he crossed the flooded Garigliano on a secret pontoon bridge in freezing rain and destroyed the French again. Naples was Spanish for two hundred years. His reorganisation of infantry into self-contained mixed units of pike, sword, and shot became the *coronelía* and then the tercio, which dominated European battlefields until the Dutch broke it at Nieuwpoort ninety-seven years later. Ferdinand of Aragon, suspicious of a subject that famous, recalled him and left him in honourable idleness for the rest of his life.

Key Battles

battle of cerignolabattle of garigliano

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Cesare Borgia
The Italian States

Cesare Borgia

Duke of Valentinois and Romagna; Gonfalonier of the Church

BornSeptember 13, 1475 · Rome or Subiaco, Papal States
DiedMarch 11, 1507 · Viana, Navarre
EducationStudied law and theology at Perugia and Pisa; made a cardinal at eighteen
Pre-warCardinal — the first ever to resign the office

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Cesare Borgia

September 13, 1475March 11, 1507

Did you know?

He is the model for *The Prince*. Machiavelli watched him at close range as Florence’s envoy, saw him have his own governor cut in half and displayed in a public square, and concluded he was the most instructive man in Italy.

"Aut Caesar, aut nihil. — Either Caesar, or nothing."

The illegitimate son of Pope Alexander VI, made a cardinal at eighteen and the first man in history to resign the office, Cesare Borgia used French arms and papal money to carve a state for himself out of the Romagna in three ruthless years. He was fast, treacherous, and effective: he took town after town, and when his brutal governor Remirro de Orco had served his purpose, Cesare had him cut in half and left in the piazza at Cesena — a gesture Machiavelli, who was there as Florence's envoy, recorded with something close to admiration. He also lured four rival captains to a friendly parley at Senigallia in 1502 and had them all strangled. Machiavelli called it *la bellissima ingannazione* — the most beautiful deception. He spent months watching Cesare at close range and concluded he had seen the future: a prince who understood that a state is built by force, held by fear, and legitimated afterwards. The whole edifice rested on his father, and when Alexander VI died suddenly in 1503 — while Cesare himself lay near death from the same fever — the enemies he had made elected Julius II, who destroyed him within a year. He died in an obscure skirmish in Navarre at thirty-one. Machiavelli's verdict was that he had done everything right and been ruined by fortune, which is the whole argument of *The Prince*.

Key Battles

battle of fornovobattle of agnadello

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Pope Julius II
The Italian States

Pope Julius II

Pope; Il Papa Terribile, the Warrior Pope

BornDecember 5, 1443 · Albisola, Republic of Genoa
DiedFebruary 21, 1513 · Rome, Papal States
EducationEducated by the Franciscans; his uncle was Pope Sixtus IV
Pre-warCardinal for three decades before taking the papacy

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Pope Julius II

December 5, 1443February 21, 1513

Did you know?

He commissioned the Sistine ceiling, rebuilt St. Peter’s, founded the Swiss Guard, and personally led armies in armour — and funded the building with the indulgences that provoked Martin Luther four years after his death.

"Fuori i barbari! — Out with the barbarians!"

Giuliano della Rovere waited a decade for the papacy while he loathed the Borgias, took it in 1503, and immediately did what no pope had done: he put on armour and led armies in the field. Contemporaries called him *Il Papa Terribile*. Erasmus, who saw him ride into Bologna at the head of his troops, wrote a savage satire imagining him refused entry to heaven. His politics were pure expediency in service of one aim — a papacy strong enough that no foreigner could dictate to it. He assembled the League of Cambrai to destroy Venice in 1509, then, having succeeded, reversed his alliances entirely and built the Holy League to expel the French he had brought in, and adopted the cry *fuori i barbari*. He gained and lost allies at a speed that made him almost impossible to negotiate with. He also commissioned the Sistine ceiling from a sculptor who insisted he was not a painter, tore down the old St. Peter's to build the current basilica, hired Raphael for the Stanze, and founded the Swiss Guard in 1506 — the same Guard that would die almost to a man at the Sack of Rome twenty-one years later. He paid for the building with indulgences, and the indulgences helped produce Martin Luther.

Key Battles

battle of agnadellobattle of ravenna

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Niccolò Machiavelli
The Italian States

Niccolò Machiavelli

Second Chancellor of the Florentine Republic

BornMay 3, 1469 · Florence, Republic of Florence
DiedJune 21, 1527 · Florence, Republic of Florence
EducationHumanist schooling in Latin and the classics; largely self-taught in politics
Pre-warCivil servant and diplomat of the Florentine Republic

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Niccolò Machiavelli

May 3, 1469June 21, 1527

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.

"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.

Key Battles

battle of agnadellobattle of ravenna

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Gaston de Foix
France (Valois)

Gaston de Foix

Duke of Nemours; Lieutenant-General in Italy

BornDecember 10, 1489 · Mazères, Ariège, France
DiedApril 11, 1512 · Killed at Ravenna, Italy
EducationRaised at the French court as a prince of the blood
Pre-warRoyal nephew; given his first independent command at twenty-one

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Gaston de Foix

December 10, 1489April 11, 1512

Did you know?

His entire military career lasted about six months. In it he became the most celebrated soldier in Europe, invented the enfilade of field entrenchments, and died at twenty-two chasing infantry he had already beaten.

"Speed is the only advantage that costs nothing."

Louis XII's nephew was twenty-one when he was given command in Italy and twenty-two when he died, and in the six months between he ran one of the most brilliant campaigns in military history. Contemporaries called him the Thunderbolt of Italy. Facing the Holy League on three sides, he relieved Bologna by a forced march through snow, turned and destroyed a Venetian army at Brescia within days, stormed the city, and then marched south to force a battle at Ravenna. At Ravenna he did something new. Unable to attack the Spanish entrenchments frontally after Cerignola's lesson, he manoeuvred his guns to fire along the length of the trenches — enfilade — until the Spanish had to come out and fight in the open, where he broke them. It was the bloodiest day Italy had ever seen: 12,000 dead. Then he saw Spanish infantry retreating in good order, charged them with a handful of companions to make the victory complete, and was killed. He was twenty-two. France lost Italy within months, because the victory at Ravenna was worth nothing without the man who had won it — the campaign was him, and no one else could carry it.

Key Battles

battle of ravenna

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Pierre Terrail, Chevalier de Bayard
France (Valois)

Pierre Terrail, Chevalier de Bayard

Captain; le chevalier sans peur et sans reproche

Bornc. 1476 · Château Bayard, Pontcharra, Dauphiné
DiedApril 30, 1524 · Killed on the Sesia, near Romagnano, Italy
EducationPage in the household of the Duke of Savoy; trained as a knight from childhood
Pre-warMinor nobility of the Dauphiné; a soldier from adolescence

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Pierre Terrail, Chevalier de Bayard

c. 1476April 30, 1524

Did you know?

He executed captured arquebusiers because he thought the weapon dishonourable — and was killed by an arquebus ball in the spine in 1524, propped against a tree facing the enemy because he had never turned his back on one.

"I have never in my life turned my back on an enemy, and I do not mean to begin now."

The knight without fear and beyond reproach — the last man in Europe to be that, and he knew it. Bayard fought in every French campaign from 1494 to 1524 and became the age's model of chivalry: he refused ransoms, returned prisoners, and once held a bridge at the Garigliano against a large Spanish force almost alone. After Marignano in 1515, Francis I asked to be knighted by him on the field rather than by a prince — the King of France taking the accolade from a minor Dauphinois gentleman because he was the best knight alive. He also despised gunpowder, and said so. He is reported to have executed arquebusiers he captured, on the grounds that it was dishonourable for a base-born man with a tube to kill a nobleman who had trained since childhood. He was not being merely reactionary; he could see exactly what the weapon was doing to his world. In 1524, covering a French retreat across the Sesia, he was hit in the spine by an arquebus ball. He had himself propped against a tree facing the enemy, refused to be moved, and died there. The Constable of Bourbon — a Frenchman now fighting for the Emperor — came to express his pity, and Bayard reportedly answered that pity was not owed to him but to a man who bore arms against his own king. The perfect knight, killed by the weapon that ended knighthood.

Key Battles

battle of fornovobattle of gariglianobattle of ravennabattle of marignanobattle of bicocca

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Francis I of France
France (Valois)

Francis I of France

King of France

BornSeptember 12, 1494 · Cognac, France
DiedMarch 31, 1547 · Rambouillet, France
EducationHumanist tutoring; raised by an ambitious mother and sister as the heir presumptive
Pre-warDuke of Valois; became king at twenty

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Francis I of France

September 12, 1494March 31, 1547

Did you know?

He brought Leonardo da Vinci to France and was reportedly at his bedside when he died — which is why the *Mona Lisa* is in the Louvre and not in Italy. He also allied with the Ottoman sultan against Charles V and let an Ottoman fleet winter at Toulon.

"All is lost, save honour — and my life, which is safe."

Francis I came to the throne at twenty in 1515, marched into Italy at once, and beat the undefeated Swiss at Marignano within months — then asked Bayard to knight him on the field. It was the best day of his life and he spent the next thirty years failing to repeat it. He lost the imperial election of 1519 to Charles V, and thereafter France was encircled by a single dynasty holding Spain, the Netherlands, Germany, Naples, and the Americas. Francis fought him for the rest of his life and mostly lost. At Pavia in 1525 he charged at the head of his gendarmes, masked his own artillery, rode into Spanish arquebusiers hidden among trees, watched the French nobility die around him, and was captured. He wrote to his mother that all was lost save honour. He signed away Burgundy in a Madrid prison, was released, and repudiated the treaty immediately on the grounds that it had been extracted under duress. He then allied with Suleiman the Magnificent against a fellow Christian monarch, which scandalised Europe and worked, and wintered an Ottoman fleet at Toulon. At home he was the great patron king: he brought Leonardo da Vinci to France, where he died — and the *Mona Lisa* hangs in the Louvre because Francis I bought it.

Key Battles

battle of marignanobattle of bicoccabattle of paviasack of romebattle of ceresole

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Charles V, Holy Roman Emperor
Habsburg Spain & the Empire

Charles V, Holy Roman Emperor

Holy Roman Emperor; King of Spain; Lord of the Netherlands

BornFebruary 24, 1500 · Ghent, Flanders
DiedSeptember 21, 1558 · Monastery of Yuste, Extremadura, Spain
EducationRaised in the Netherlands under Margaret of Austria and Adrian of Utrecht
Pre-warDuke of Burgundy from six; King of Spain at sixteen; Emperor at nineteen

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Charles V, Holy Roman Emperor

February 24, 1500September 21, 1558

Did you know?

He ruled the largest empire in the world and voluntarily gave all of it away — abdicating in 1556, splitting it between his son and his brother because no one man could hold it, and retiring to a monastery to repair clocks.

"I came, I saw, and God conquered."

Charles inherited more of the world than anyone before him: Spain and its new American empire from his mother, the Netherlands and Franche-Comté from his father, Austria and the imperial title from his grandfather. He was nineteen when he became emperor, and he spent forty years discovering that it was too much for one man. He beat Francis I at Pavia and took him prisoner, and it gained him nothing — Francis repudiated the treaty the moment he was free. His own unpaid army sacked Rome in 1527 and imprisoned the Pope without his orders, an event he could neither prevent nor disown. He fought the Ottomans in Hungary and the Mediterranean, Lutherans in Germany, and France in Italy, essentially simultaneously, for four decades, financed by American silver that arrived late and was always already mortgaged to his bankers. Spain declared bankruptcy in 1557; so did France. In 1556 he did something no emperor had done: he abdicated everything, split the inheritance between his son Philip and his brother Ferdinand because no successor could hold it all, and retired to a monastery at Yuste to tend clocks. He died two years later, and the Peace of Cateau-Cambrésis that finally ended the Italian Wars was signed by his son a few months after that.

Key Battles

battle of paviasack of romebattle of ceresolebattle of st quentin

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Charles III, Duke of Bourbon
Habsburg Spain & the Empire

Charles III, Duke of Bourbon

Constable of France, then Imperial Commander

BornFebruary 17, 1490 · Montpensier, Auvergne, France
DiedMay 6, 1527 · Killed on the walls of Rome
EducationRaised as heir to the greatest fief in France
Pre-warConstable of France — the kingdom’s supreme military officer

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Charles III, Duke of Bourbon

February 17, 1490May 6, 1527

Did you know?

Benvenuto Cellini claimed in his memoirs to have personally shot him off the walls of Rome. Bourbon’s death left the army leaderless, which is precisely why the sack was so total — there was no one left with the authority to stop it.

"I have no country now. I have an army, and it must be paid."

The greatest magnate in France and its Constable — the supreme military office — Bourbon fought brilliantly for Francis I at Marignano and was then systematically ruined by him. Francis's mother Louise of Savoy laid claim to his inheritance, the courts obliged the crown, and Bourbon lost his lands to a legal manoeuvre. In 1523 he defected to Charles V and became the most infamous traitor in French history. He commanded Imperial forces at Pavia, where the king who had ruined him was captured. Then he was handed the thing that destroyed him: an army in Italy that Charles V could not pay. Unpaid German landsknechts and Spanish veterans do not disband, they mutiny, and by 1527 Bourbon was less their commander than their hostage — they marched on Rome to pay themselves and he went with them because he could not stop them. He was shot dead scaling the walls on the first morning, reportedly by Benvenuto Cellini, who claimed the credit in his memoirs. It was the worst possible outcome: the army took Rome with nobody in command at all, and destroyed it for eight days. Bourbon is the age in one man — a feudal lord ruined by lawyers, who died leading mercenaries he could not control against a city nobody had ordered him to attack.

Key Battles

battle of marignanobattle of paviasack of rome

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