The Rise And Fall Of Italy’s Warriors-For-Hire

The Dawn Attack of July 29th, 1364

On the morning of July 29th, 1364, John Hawkwood, an English soldier turned contract mercenary, led a surprise attack against a sleeping army of Florentine mercenaries. The enemy commander quickly awoke and rallied his men to launch a counterattack. However, as soon as the defending army was ready to fight, Hawkwood’s fighters simply turned and walked away. This was not an act of cowardice. These mercenaries, known as condottieri, had simply done just enough fighting to fulfill their contracts. For Italy’s condottieri, war wasn’t about glory or conquest: it was purely about getting paid.

The Dominance of the Condottieri

For much of the 14th and 15th centuries, the condottieri dominated Italian warfare, profiting from and encouraging the region’s intense political rivalries. The most powerful of these regions were ruled either by wealthy representatives of the Catholic Church or merchants who’d grown rich from international trade. These rulers competed for power and prestige by attracting the most talented artists and thinkers to their courts, leading to a cultural explosion now known as the Italian Renaissance. But local rivalries also played out in military conflicts, fought almost entirely by the condottieri.

The Arrival of Foreign Mercenaries

Many of these elite mercenaries were veterans of the Hundred Years’ War, hailing from France and England. When that war reached a temporary truce in 1360, some soldiers began pillaging France in search of fortune. The riches they found in Catholic churches drew their raiding parties to the center of the Church’s operations: Italy. But here, savvy ruling merchants saw these bandits’ arrival as a golden opportunity. By hiring the soldiers as mercenaries, they could control the violence and gain an experienced army without the cost of outfitting and training locals.

The Business of War

The mercenaries liked this deal as well, as it offered regular income and the ability to play these rulers off each other for their own benefit. Of course, these soldiers had to be kept on a tight leash. Rulers forced them to sign elaborate contracts, or condotta, a word that became synonymous with the mercenaries themselves. Divisions of payment, distribution of plunder, non-compete agreements—it was all spelled out clearly, making war merely another dimension of business.

The Rise and Fall of the Condottieri

Over time, foreign condottieri were increasingly replaced by native Italians. For young men from humble origins, war-for-profit offered an attractive alternative to farming or the church. And this new generation of condottieri leveraged their military power into political influence, in some cases even founding ruling dynasties. However, despite cornering the market on Italian warfare for nearly two centuries, the condottieri only truly excelled at engaging in just enough close-range combat to fulfill their contracts. Over time, they became 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 forced all of Europe into a new era of warfare, putting an end to the condottieri’s conniving war games.