The unique culture of the Italian city-states produced a unique military structure. Initially, each city gathered a local militia under the command of its aristocracy, in which the lower classes from the city and its subject territories served as infantry, while the upper classes served as knightly cavalry. The militia conducted regular training sessions and was well-suited to defending its domain or conducting short-term campaigns. However, by the early 1300s this system was collapsing. Increased inter-state violence, a growing preference among wealthy townsmen to hire others to fulfill their military duties, and the despots’ often justified distrust of arming their own subjects led to an almost complete reliance on paid mercenaries, the condottieri.
Named for the condotta, the contract specifying the terms of military service, the condottiero was the consummate professional; well-armed, highly trained and able to remain in the field indefinitely — or at least as long as his employer could make good on his payments; it was quite common for a military captain to switch sides as soon as his contract was either fulfilled or negated. The least savory captains sometimes simply shifted alliances if the tide seemed to be turning.
The first condottieri appeared at the end of the 13th century, and were foreign mercenaries of principally German and Spanish origin. They were generally small bands, sometimes little more than well-armed highwaymen, and were viewed as one more evil by-product of inter-city feuding. This changed in the early 1300s when these bands were joined by the first true Compagnia di Ventura (“Adventuring Company”), led by a German knight, Werner von Urslingen. This company differed from its predecessors by having an internal law code that provided specific rules of organization, behavior, discipline and the division of income. This band swelled with foreign and native Italian mercenaries, until it had over 3,000 barbute, or units. A barbuta (“helmet”) was comprised of a fully armed and mounted knight and a more-lightly armed sergeant. This new “Great Company” became a serious threat to city militia, and the Italian states were forced to respond.
The first of those responses came from a Milanese noble, Lodrisio Visconti (c. 1280 – 1364) who was destined to meet the Great Company in battle in the final chapter of a biography worthy of a novel. Lodrisio had a long-standing rivalry with his cousin Azzone, whom he had captured during one of the internal feuds that characterized the House of Visconti. In 1338, Azzone escaped captivity, raised an army and besieged his rival, destroying his castle. But Lodrisio escaped to Vicenza, where its lord, Mastino II della Scala, hired him to build an army to attack Milan. By January of 1339, Lodrisio had mustered a large army of primarily German mercenaries, including 2,500 cavalry, nearly 1000 infantry and 200 crossbowmen. Naming this force La Compagnia di San Giorgio (“The Company of St. George”), he marched against his familial lands. The expedition did not go well. Only a month after invading Milanese territory, Lodrisio’s army was defeated at the Battle of Parabiago on 20 February 1339, a brutal battle that left over 6,000 dead or wounded, and Lodrisio and his son Ambrogio became prisoners of the hated Azzone.
Azzone had little interest in collecting ransom from his cousins. Instead, Lodrisio and his son were taken to the Castello da San Colombano, and kept in an iron cage, which their captor would bring out to display to guests. They remained in this cruel captivity for ten years, until Azzone died and they were freed by the new Count of Milan, Archbishop Giovanni Visconti. Suddenly, Lodrisio found himself not only free, but in favor at court. Only a few years later, despite his advanced age, he was appointed as the Milanese commander of an expedition to capture territory in the Piedemont. The 76 year old knight began recruiting a new company and prepared for war once more.
Meanwhile, a number of cities saw the fall of Piedmont as a threat to their own security, and wanted to check the growing power of the Visconti. Uniting into an informal anti-Visconti league, they approached the Great Company with the offer of a condotta. Werner von Urslingen had been executed in Rome in 1347, and the captaincy of the Company had passed to another German knight, Konrad von Landau. In 1356, Landau accepted the contract and marched into Piedmont to meet Lodrisio’s newly-formed army, which was a combination of feudal and mercenary forces. The old wolf could still hunt; for the first time, the unbeatable Great Company was broken and driven from the field. Lodrisio returned to Milan a hero, and remained at court until his death in 1364.
While Lodrisio remained a hero, Landau and the Great Company’s fates were less fortunate. In 1362, the Company was utterly defeated by a new foe, a mercenary army of English, French, Burgundian and German mercenaries, led by an Englishman, John Hawkwood (1320-1394). This new “White Company” had a great deal of practical experience fighting in the Anglo-French dynastic struggle now known as the Hundred Years War. It also had a contingent of the vaunted English longbowmen and a new method of organization. The barbuta was replaced with a lancia (“lance”), consisting of a knight and sergeant mounted on heavy war-horses, plus a groom mounted on a lesser-quality horse. Five lancie formed a posta (“position”) and five positions formed a bandiera (“banner”). Hawkwood and his private army would dominate Italian military affairs for decades, showing that the day had dawned for this new style of warfare.
Throughout the 14th century, native companies sprang up across the peninsula. The captains of these new companies were Italians, but they founded the companies around themselves instead of being chosen by their men. Ambrogio Visconti reformed the Compagnia di San Giorgio, while Astorre I Manfredi, (who was destined to run afoul of Niccolò III d’Este, Fiore dei Liberi’s patron) founded the Compagnia della Stella (“Company of the Star”). Niccolò da Montefeltro founded the Compagnia del Cappelletto (“Little Hat Company”), beginning a family tradition of condottieri that would reach its apex with his descendant, the unparalleled Federigo da Montefeltro, first Duke of Urbino.
Equally knight and bandit, the profession of condottiero created opportunity and social mobility unlike anything seen in the rest of Europe. Poor men took up the sword to make their fortunes, such as the Sforze – horse ranchers whose successes as mercenary captains allowed one of their number to become Duke of Milan. The great lords of old noble families, such as the Este family of Ferrara and the Montefeltro family of Urbino, used the position of captain-general to bolster their coffers and greatly expand their own borders. Throughout the 15th century, these “merchants of war” would paradoxically defend Italy’s borders against German, Spanish, French and Turkish incursions, while themselves contributing to the internal feuding and destabilization that would ultimately lead to the peninsula’s fall to outside invasion in the century that followed.