The Scourge of Italy: the Condottieri and their mercenary armies

The Medieval Italian city states outsourced their war making to mercenary armies, a cost cutting measure that would cost them dearly.


During the late Middle Ages, while the south of Italy was unified under the Kingdom of Naples, the north was divided (see Northen Italy in the Middle Ages) amongst a plethora of small states centred on mercantile cities (see The Medieval Italian City State) such as Florence, Milan and Venice. While these cities enjoyed independence and some level of democracy, they were in constant competition for territory, trade routes and power, so much so that during this period Northern Italy was in a constant state of war.

While these city states and their citizens had become rich through trade, they had neither the resources nor the man-power to support standing armies. Instead they would raise militias when the necessity arose. Though the cities could usually call on the armed knights of a few noble families to head their armies, their numbers needed to be augmented in order to carry out the cavalry based warfare of the period. To do so, the cities needed to hire troupes of mercenaries. Their leader would negotiate a contract with the city or a condotta, thus becoming a contractor or a Condottiere.

Some of these troupes might be made up mostly of Italians, tough shepherds from the Apennines or Romagna, but most mercenaries were foreign soldiers of fortune for whom Italy had become a favourite destination. Some came with one or other of the Emperors and foreign princes who sought to intervene in Italian affairs and stayed on to ply their trade. Others came to seek their fortune when other wars, such as the Hundred Years War, abated and left them unemployed. They would take up arms for whichever city or warlord paid them, happy to change sides or withdraw if the price was right. And when the powers that hired them made peace, they were just as happy to ravage and plunder the countryside on their own account.

Despite their calling, the Condottieri tended not to engage in open battle. Reluctant to endanger themselves and their men, they avoided formal battles where possible and the hard work of winter campaigns. Instead, mercenary armies adopted the tactics of attrition, skirmishes and sieges. When facing each other, Condottieri were known for indulging in grandiose, but almost bloodless battles in which they were more intent on capturing prisoners to ransom than killing the enemy.

While for the most part, mercenaries were used in wars between city states, petty tyrants were known to make use of mercenaries against their own people, and even their own families. Cangrande II della Scala of Verona ruled with an iron fist and surrounded himself with German mercenaries, trusting that foreigners would have no sympathy for Italians and be willing to carry out his most barbarous orders. A son of the powerful Visconti clan that ruled Milan, Lodrisio Visconti fled the city after the cousin he helped to gain power, and then be captured by his enemies, was freed. He soon returned at the head of an army of German mercenaries in a failed attempt to win the city for himself.

Man on horseback on pedestal
Funerary Monument to Sir John Hawkwood by Paolo Uccello

Perhaps the most successful Condottiere was an Englishman, Sir John Hawkwood. After serving in the Hundred Years War under Edward III, Hawkwood crossed the Alps in 1362 in the service of the Marquis of Montferrat at the head of his own mercenary troupe, the White Company. Remaining in Italy, Hawkwood and his company fought under several banners, often changing sides, and exploiting shifting alliances for his own benefit. He was known for exploiting both sides of a conflict, accepting a contract from one side, then demanding payment from the other not to attack them, changing sides and keeping the payment from both, or even accepting bribes not to work for the enemy. Nonetheless, at the head of a disciplined company, Hawkwood was a successful and popular Condottiere. Towards the end of his life he became commander-in-chief of the army of Florence in their war against the expansion of Milan. Considering him the saviour of their independence, the Florentines commissioned a funerary monument for him in the Duomo.

The most fearsome of the mercenary armies was the Great Company. Its leader, the German knight, Werner von Urslingen, whose motto was ‘Enemy of God, of Pity and of Mercy,’ arrived in Italy in 1338, and it grew to number 3,000 knights alone. Between stints fighting both for and against Venice, Verona, Milan, the Papal States, Pisa, Siena, Florence and the Kingdom of Naples, the company devastated central and southern Italy, raising money by threatening to burn houses and harvests and putting prisoners to torture. In Tuscany, Werner turned against the very cities that had previously hired him. Pisa, Siena and Lucca paid him off, but when, in 1359, Florence challenged him to battle, the Great Company failed to turn up and left Tuscany without a fight.

Not all Condottieri were foreign, and by the early fifteenth century, many impoverished or landless Italian knights had taken up arms as their only viable profession. One of these was Giacomo Attendolo the son of a Romagnol nobleman. His commander nicked-named him ‘Sforza’ or ‘strength’ for his staunchness and his ability to suddenly reverse the fortunes of battles. In his early career he fought for Perugia, Milan, Florence, Ferrara and Parma. He spent the later part of his life in the service of the Kingdom of Naples, running the gauntlet of Queen Joan’s shifting favours.

However, his greatest claim to fame is to have fathered Francesco Sforza, perhaps the most famous Italian Condottiere. Francesco started his career fighting beside his father, and after his death he fought on behalf of the Kingdom of Naples, the Papal States and the Duke of Milan (switching sides twice to fight for and against both of them). Despite the Duke’s initial suspicions, Francesco married his daughter and when his father-in-law died without a son, he took control of the city and its dependencies, becoming de facto Duke, though his title was not recognised by the Emperor in his lifetime.

Study for the Equestrian Monument to Francesco Sforza by Antonio del Pollaiolo
Study for the Equestrian Monument to Francesco Sforza by Antonio del Pollaiolo

As a knight, Francesco Sforza proved himself to be an expert tactician and skilful field commander. As a ruler, he proved to be progressive and diplomatic. He modernised Milan, introduced an efficient taxation system and made his court a centre of Renaissance Culture. In foreign policy, he forged a friendship and alliance with Cosimo de’Medici in Florence and created an Italian League that stabilised almost all of Italy and succeeded in holding foreign powers at bay for the rest of the century.

However, the rise of Francesco Sforza and others like him marked the passing of the era of the independent Medieval Italian City States. While the price of independence was constant warfare, that warfare came at a high cost. War in Italy had always been destructive. With its walled cities that were almost impossible to take by storm, the systematic ravishing of its territory was the only way to put pressure on the enemy. These tactics suited the Condottieri, but the total war they created was not only exhausting but expensive. It has been estimated that the War of the Eight Saints cost Florence alone 2.5 million florins. Most of the smaller city states could not afford such costs and one by one were absorbed by the richer cities, as they, too, one by one, were taken over by powerful, ruling families.

As for the Condottieri, they plied their trade throughout the fifteenth century, but these ad hoc militias were no match for a national unified army such as the invading French army when it stormed through Italy in 1494 under Charles VIII.


© Pauline Montagna 2015

Read more about Medieval Italy…


A History of the Italian Republics by JCL de Sismondi (1968)



Back to Top