On 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 assembled his men to launch a counterattack, but Hawkwood’s fighters simply turned and walked away. This wasn’t an act of cowardice, but rather a result of the mercenaries’ contracts. War for these men, known as condottieri, was not about glory or conquest, but rather about getting paid.
For much of the 14th and 15th centuries, the condottieri dominated Italian warfare, taking advantage of the region’s intense political rivalries. Wealthy representatives of the Catholic Church and merchants who had grown rich from international trade competed for power and prestige by attracting talented artists and thinkers to their courts, resulting in the Italian Renaissance. Local rivalries were also expressed through military conflicts fought almost entirely by the condottieri, many of whom were veterans of the Hundred Years’ War from France and England.
When the Hundred Years’ War reached a truce in 1360, some soldiers began pillaging France in search of fortune. This attracted them to Italy, the center of the Catholic Church’s operations. Here, savvy ruling merchants saw the mercenaries as a golden opportunity, allowing them to gain an experienced army without the cost of outfitting and training locals. The mercenaries liked the deal as well, as it offered regular income and the ability to play the rulers off each other for their own benefit.
Rulers forced the mercenaries to sign elaborate contracts, or condotta, a word that became synonymous with the mercenaries themselves. Contracts specified the number of men a commander would provide, and the resulting armies ranged from a few hundred to several thousand. Individual soldiers regularly moved between armies in search of higher payments. When their contracts expired, condottieri commanders became free agents with no expectation of ongoing loyalty.
The condottieri fought primarily for themselves, leveraging their military experience to avoid taking unnecessary risks in battle. This ensured that battles rarely led to crushing victories or defeats, as the mercenaries wanted wars to be inconclusive. Of course, contracts could just as easily turn them into ruthless killers.
Over time, foreign condottieri were increasingly replaced by native Italians. War-for-profit offered an attractive alternative to farming or the church for young men from humble origins. This new generation of condottieri leveraged their military power into political influence, in some cases even founding ruling dynasties. Despite the Italian condottieri dominating warfare in the region for almost two centuries, they only truly excelled at engaging in just enough close-range combat to fulfill their contracts. Eventually, France and Spain’s large standing armies and the naval power of the Ottomans outclassed them. By the mid 16th century, these state-sponsored militaries forced all of Europe into a new era of warfare, thus ending the condottieri’s conniving war games.