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.
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.
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 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.
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.
Research and create a timeline of key events from the article. Include the Dawn Attack of July 29th, 1364, the dominance of the condottieri, the arrival of foreign mercenaries, and the rise and fall of the condottieri. Use images and brief descriptions to make your timeline visually engaging.
Divide into small groups and role-play a scenario where you are condottieri negotiating a contract with a ruler. Each group should create a contract that includes terms for payment, plunder distribution, and non-compete clauses. Present your contract to the class and explain your negotiation strategy.
Use a map of Europe to trace the journey of the foreign mercenaries from France and England to Italy. Mark key locations mentioned in the article and write a brief explanation of why these locations were significant to the mercenaries and the rulers who hired them.
Hold a class debate on the ethics of mercenary warfare. One side will argue that the condottieri were justified in their actions as they were fulfilling contracts and earning a living. The other side will argue that their actions were morally wrong and contributed to prolonged conflicts. Use evidence from the article to support your arguments.
Imagine you are a young Italian condottiero in the 15th century. Write a diary entry describing a day in your life, including your thoughts on the business of war, your aspirations, and your experiences in battle. Use historical details from the article to make your entry realistic and engaging.
attack – verb – The act of initiating an aggressive action against someone or something. – The enemy launched a surprise attack on the unsuspecting troops.
soldier – noun – A person who serves in an army, usually trained in warfare and combat. – The brave soldier fought valiantly on the battlefield.
mercenary – noun – A professional soldier who is hired to fight in a foreign army in exchange for payment. – The wealthy ruler hired a group of mercenaries to protect his kingdom.
army – noun – A large organized group of soldiers trained for warfare and led by officers. – The army marched in formation, ready for battle.
counterattack – noun – An offensive action taken by a defending force against an attacking force. – The troops launched a counterattack to regain control of their position.
condottieri – noun – Mercenary leaders in Italy during the Middle Ages who commanded bands of soldiers for hire. – The condottieri were renowned for their military expertise and leadership.
warfare – noun – The activity or process of engaging in or conducting war or military operations. – The country was ravaged by years of brutal warfare.
mercenaries – noun – Plural form of mercenary, referring to a group of professional soldiers for hire. – The mercenaries were known for their loyalty to the highest bidder.
contracts – noun – Legally binding agreements between two or more parties, outlining the terms and conditions of a specific task or job. – The mercenaries signed contracts with the kingdom, specifying their duties and compensation.
combat – noun – The act of fighting or engaging in armed conflict. – The soldiers engaged in hand-to-hand combat, using their training and skills to defeat the enemy.
