Renaissance Knights & Condottieri ~ Chapter I

Adam Alexander
9 min readOct 14, 2023

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condottiero /kondotˈtjɛro/ — Captain of Mercenary Soldiers in medieval and renaissance Italy.

The following is a (mostly) accurate description of some of the characters, conflicts, and politics of the War of the League of Cambrai during the years 1509–1512.

Republic of Venice ~ June 1508

The Most Serene Republic of Venice is gathering mercenaries towards it. The Serenissima is at the apex of its power in the summer of 1508. She has grown rich from trade; as a sea-faring city-state her naval power dominates the Adriatic and her influence stretches far across the waters of the Mediterranean.

At the same time, her influence in the mainland has grown, and now stretches all the way west to the River Adda, across which sits the Duchy of Milan, now a stronghold of the French King Louis XII.

King Louis and the Venetians had previously been allies, and had split the Duchy of Milan between them after successfully dispossessing the House of Sforza in 1499. But now their friendship is failing and King Louis claims all of the Duchy for himself.

Cadore, Republic of Venice ~ March 1508

A new wave of mercenaries have arrived in Venice and sold their swords to the Republic, just in time to join the latest clash of steel that is brewing in the mountains.

To the north of Venice lies the province of Cadore, at the foot of the Alps and bordering on the Germanic lands of the Holy Roman Empire, including those of the Emperor himself, Maximilian Habsburg.

Habsburg’s relationship with the Venetians has broken down in recent years, leading the Venetians to become anxious at news that he is gathering an army after being crowned Holy Roman Emperor. Recent weeks have seen reports arriving in Venice of Germanic mercenaries, those known as Landsknecht, have entered town in Venetian territory and taken control. When Venice had first questioned Habsburg about his intentions with his army, he insisted that he would be peaceful, but the Venetians had not trusted him and prepared for war.

By February, war was official and the Venetians sent for their best Condottiero in the field: Bartolomeo d’Alviano. An experienced Condottiero in his early 40s, Alviano immediately heads for Cadore to face the Imperial foe. Having been suspicious of the Imperials from the start, Alviano and the Venetians have spent the preceding weeks reinforcing their positions and are ready for the fight.

Alviano targets the Castle of Pieve di Cadore, perched at the top of a winding path in the cold mountains. In late February it was taken by Imperial Forces, and now flies the black, double-headed Imperial Eagle banner of the Empire.

Alviano is advancing on the fortress, but as he approaches his army grinds to a halt when it is hit by a vicious snow storm. Stuck in the ice, the Republic’s mercenaries begin to lose morale as doubt and fear creeps in. Alviano summons his captains. He has heard that some of the mercenaries have been breaking their contracts and deserting. From now on, there will be rewards for killing deserters. Then he promises rich rewards for what’s coming next. He’s up for this fight and there will be plunder for those who go with him. Survivors with injuries will be compensated and the most heroic acts will be worth bags of gold. He turns to the Stratioti, vicious Balkan horsemen who take the heads of their conquered foes as prizes. Alviano offers to pay them for each of those heads.

They don’t have to wait long, and resume their march when the blizzard ends. They soon encounter the Imperials, and the fighting comes to a head on the frozen banks of the Rio Secco, where the snow is stained red and pink from the slaughter. In the midst of the carnage, the man bearing the crimson banner of the Republic (a golden winged sword-wielding Lion of Saint Mark) engages in a duel with the Imperial Commander. The Venetian takes a wound before ultimately knocking the German from his saddle with a fatal slash of his halberd. Seeing the doubt that this caused amongst the Imperials, Alviano orders an all-out attack, leading to a definitive victory. The defeated Germans ask for mercy but find none.

The Imperial survivors who manage to escape the battle by the river make their way to the Castle of Pieve di Cadore, their last stronghold in the region. Amidst the swirling snow, Alviano’s forces gather round the castle and prepare for the assault. Alviano, lacking sufficient supplies for a prolonged stay and therefore eager to resolve matters quickly, offers the Germans safety in exchange for surrender. However, the Landsknecht say they will need to discuss it, and they delay their response in the hope of imminent reinforcements. When Alviano sees this attempt to stall he orders a big assault on the castle rather than continuing to wait for their reply. A few volleys of cannonfire follow and eventually the doors are blown open and the remaining Germans surrender.

The Venetian forces flood into the castle, ravenous for plunder. The gold that they find is taken to Alviano, but he orders it distributed amongst his men. They take the gold and jewels but the fame belongs to him.

Innsbruck, Holy Roman Empire ~ June 1508

Maximilian Habsburg is in a bad mood. As a result of his failed invasion of Cadore, Habsburg has not only had to retreat back north, but has also lost some of his own lands to Alviano’s counterattack. Having been soundly defeated he had no choice but to sue for peace. The Venetians, taking advantage of his bad position, drew up a humiliating peace treaty for him to sign. Not long afterwards, he receives a guest. Cardinal Georges d’Amboise is visiting from Rome. Fifty years old, Cardinal Amboise has one foot in two of the main fulcrums of power in northern Italy. Coming from French nobility, he is a close confidante of French King Louis XII, who holds not just the Kingdom of France but also the Duchy of Milan. As a Cardinal, he also holds favour with the current Pope, Julius II.

Pope Julius has several bones to pick with the overly-ambitious Republic of Venice: First, they currently control some lands and cities previously held by the Papal States. The reasons for that lie with the previous administration, that of the Borgia Pope, Alexander Sextus, the current Pope’s sworn enemy. Now there’s a new Pope in town and he wants them back as part of the Papal States.

Second, there’s an ongoing dispute between Portugal and the Mamluk Sultanate of Egypt. The Venetians, for financial reasons, have been lending support to the heathen Mamluks against the Catholic Portuguese, which is clearly not permissible.

The Monarch’s of France and Spain share the Pope’s enmity for the Republic. Both Kings possess territories in Italy: Louis holds the Duchy of Milan after kicking out the Sforza, while Ferdinand holds the Kingdom of Naples. Both realms used to include towns currently controlled by the Venetians that the Kings want back. However, the Republic still has a formidable mercenary army and Pope Julius knows he can’t take them on with just his Papal Army. Maximilian’s Imperial Army didn’t fare so well either, hence the embarrassing peace treaty. Neither the Pope nor the two kings nor any other power in Italy can face the Venetians alone, but together they can humble the Republic and divide her lands amongst themselves.

Venice ~ March 1509

The League was officially formed in the French town of Cambrai in December 1508 and by early 1509 The Republic of Venice is preparing for war again. They are now aware of the powerful alliance against them. King Louis of France, King Ferdinand of Spain, The Holy Roman Emperor Maximilian Habsburg, and Pope Julius Secundus all wish to tear apart their Most Serene Republic and divide it amongst themselves. But the Venetians are determined not to lose what it has taken them and their ancestors centuries to gain.

Reports have reached Venice from Milan, where King Louis of France controls the city from the Castello Sforzesco. A French Army is gathering there to claim the entire Duchy of Milan for their king. To oppose it, The Republic has hired a mercenary army almost as large. To lead it, they have turned to Niccolò Orsini, The Count of Pitigliano, a grizzled sixty-something Condottiero. Pitigliano has been in Venetian service for the past fifteen years and, as the Captain-General, is their highest-ranking officer.

Alongside Pitigliano is Bartolomeo d’Alviano, who has just been richly rewarded for his heroics in Cadore, with his salary doubled from fifteen to thirty-thousand ducats plus bonuses, and his rank raised to Captain-General, the same as Pitigliano.

Furthermore, The Republic has decided to split command of their mercenary army between Alviano and Pitigliano, who are actually cousins from two different branches of the ancient House of Orsini. The older and more experienced Pitigliano is placed in overall command, although the more dynamic and decisive Alviano will lead half of the troops.

Sforza Castle, Milan ~ April 1509

Inside the Castello Sforzesco in Milan, the French commanders prepare for their first strike against the Republic. Amongst them is Charles d’Amboise, the second-highest ranking French Commander there (after Louis de la Trémoille). Aged in his mid-thirties, Charles leads the French Vanguard. Beside him is the Governor of Milan Gian Giacomo Trivulzio, aged in his sixties, an Italian Condottiero in service to the French. Menacing and battle-hardened, Trivulzio is one of the highest-ranking and most respected commanders in the French Army. Yet the most famed and respected man amongst the French ranks, noble knight and peasant conscript alike, is Pierre Terrail, known as Le Chevalier de Bayard. Aged in his early-thirties, Bayard has been gaining renown since his youth and is widely considered the finest knight in all France. Deeply loyal, devoutly catholic, unwavering moral, and insanely brave, he is already feared and respected throughout Italy.

The French Army are known for their heavy cavalry known as Gendarmes, l and their massive cannons. Their infantry, previously having a bad reputation, has been cleaned up by Bayard and are now well-drilled and disciplined.

On the 15th, King Louis leaves Milan and heads east towards the River Adda, which marks the boundary between his lands and those of the Republic of Venice.

Countryside near the River Adda ~ May 1509

The rain has begun to fall, and in the small town of Treviglio just east of the River Adda, Pitigliano and Alviano continue to disagree on their strategy for dealing with the French advance. Alviano favours an aggressive approach and wants to attack the French before they reach the town of Crema. Pitigliano disagrees. They are to slow the French with skirmishes but avoid a direct engagement and keep moving until they can find a better position. Before the two Orsini cousins can resolve the matter, a messenger arrives to say that the French have crossed the Adda at Casano, prompting the Venetians to move. The two halves of their army begin to march south in parallel columns.

Not far away, near the town of Agnadello, a detachment of French Cavalry under Gian Giacomo Trivulzio are preparing for an attack on Alviano’s rearguard. Alviano himself has already passed through the town and is further down the road at Pandino when Trivulzio’s cavalry charges at his rearguard. As the two armies meet for the first time, Alviano is forced into a decision. Despite half of their forces being several miles away with Pitigliano, Alviano decides to go to the aid of his rearguard and turns around to engage the French.

As the rain continues to pound down, the two sides face up against each other. Alviano positions his troops on a ridge near some vineyards as more French troops arrive. A cavalry charge of French Gendarmes is launched against the Venetians, but they hold their lines. Next to try them are the Swiss Pikemen, but they are likewise unable to make progress up the muddy incline towards the Venetian positions.

Alviano decides to send a message to Pitigliano, marching in parallel but several miles away. Alviano calls for reinforcements, believing that if the other half of their army arrives they can win a swift victory right here and now at Agnadello. The messenger rushes off but when he reaches Pitigliano the request is denied. Pitigliano wants to continue looking for a better position before risking a battle. He sends the messenger back to Alviano with instructions not to engage in a pitched battle and to continue moving south as planned. The messenger hurries back to Alviano’s position, but it’s too late. While Pitigliano failed to reinforce Alviano, the French were joined by their own reinforcements, including the king himself, and started to surround Alviano’s army.

The battle itself is short but violent. As night falls, Alviano’s army lies shattered. The French trudge through the mud finishing off the wounded survivors, while only the highest ranking officers are taken alive, including Alviano himself. The rest of the survivors are put to the sword.

Venetian Camp ~ Later that night

As Pitigliano’s army settles down for the night, word quickly spreads of what befell their counterparts under Alviano,who recently looked invincible but is now dead or captured, his army gone, and with it any chance of the Republic winning this war. Slowly and quietly, hundreds of mercenaries slip away into the night.

The next morning, Pitigliano and his remaining Condottieri wake to find the majority of their army gone. With the French army on the move again, they have no choice but to flee back to Venice in defeat.

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