From Mercenary Might to Fading Glory: Italy's Condottieri Chronicles

In the early morning of July 29th, 1364, John Hawkwood, originally an English soldier turned contract mercenary, executed a surprise attack against a group of Florentine mercenaries who were caught sleeping.

Upon the enemy commander's swift awakening, he rallied his men to launch a counterattack. However, Hawkwood's fighters surprisingly chose not to engage in battle and instead withdrew. This wasn't an act of cowardice; rather, these mercenaries, known as condottieri, were simply fulfilling their contractual obligations, doing only what was necessary to get paid. In 14th and 15th century Italy, the condottieri held sway over the realm of warfare, capitalizing on and fueling the region's intense political rivalries.

The most influential regions in Italy were governed either by wealthy representatives of the Catholic Church or prosperous merchants who had thrived from international trade. In their quest for power and prestige, these rulers sought to attract the finest artists and intellectuals to their courts, a movement that marked the glorious period known as the Italian Renaissance.

However, these local power struggles often played out through military conflicts, predominantly orchestrated by the condottieri. Many of these elite mercenaries were veterans of the Hundred Years' War, having origins in France and England. When that conflict reached a temporary truce in 1360, some soldiers sought wealth by pillaging France, eventually being drawn to Italy due to the riches found within Catholic churches.

Seeing an opportunity to control the violence and amass a trained army without the burden of outfitting and training locals, shrewd ruling merchants hired these soldiers as mercenaries. The arrangement suited the mercenaries as well, granting them a stable income and the ability to exploit the rivalries among the rulers for their personal gain. The mercenaries, in turn, were subject to strict control, bound by detailed contracts or "condotta," which became synonymous with their identity. These agreements specified the number of soldiers a commander would provide, leading to armies ranging from a few hundred to several thousand. Soldiers frequently moved between armies to secure higher payments, and once their contracts expired, they became free agents with no obligation of loyalty.

John Hawkwood's attack against the Florentine condottieri was done on behalf of Pisa, but he later fought for Florence and other enemies of Pisa. Nevertheless, regardless of the contracting parties, the condottieri primarily fought for their self-interests. Their vast military experience enabled them to avoid unnecessary risks during battles, resulting in clashes that rarely yielded decisive victories or defeats. Condottieri commanders preferred inconclusive battles since a prolonged peace would have meant an end to their profitable business.

In instances where one side emerged victorious, enemy combatants were typically held captive and later released to fight another day. This approach was not driven by mercy but rather by the desire to preserve their lucrative enterprise. In some cases, contracts transformed the condottieri into ruthless killers, such as the massacre Hawkwood led in 1377 against a famine-stricken town that dared to rebel against the local government.

As time passed, foreign condottieri were gradually replaced by native Italians, especially among young men from humble backgrounds seeking a more attractive career path compared to farming or the church. This new generation of condottieri leveraged their military power to attain political influence, and some even established ruling dynasties.

Despite their dominance over Italian warfare for nearly two centuries, the condottieri were ultimately outclassed by the gunpowder weaponry of France and Spain's large standing armies, as well as the naval might of the Ottomans. By the mid-16th century, these state-sponsored militaries ushered Europe into a new era of warfare, marking the end of the condottieri's cunning war games.