Condottieri (singular condottiero, rarely condottiero) were mercenary leaders employed by the Italian city-states from the late Middle Ages until the mid-sixteenth century. The word meant "contractor" in contemporary Italian; it is a synonym of "mercenary captain" in modern English historiography, and connotes nothing about the nationality of the person given the label.
The word is also sometimes used in English writings —up through Napoleonic times or in histories about that era (well into the second half of the twentieth century), as the practice of keeping a large standing army was not prevalent until well into the Napoleonic wars and when a brigade size military unit was frequently considered an army— with the general sense of any "mercenary captain (or general, contractor, etc.)" and which quite frequently might carry the rank of colonel, if the captain had the means to provide circa a thousand or more men or commanded such a body. Perhaps the best known mercenary contractor often called a Condottiere was the Bohemian count Albrecht von Wallenstein of the Thirty Years' War, who was both active primarily in Northern Europe, and had little to do with Italy.
The very first of these bands (called in contemporary Italy masnada, plural masnade) appeared between the end of the thirteenth and the beginning of fourteenth centuries and were not of Italian origin. Soldiers came mainly from Germany, Brabant (brabanzoni), Aragon and Catalonia: the last, for example, had come to Italy following King Peter III of Aragon in October 1282 and had remained there afterward searching for employers. Other mercenaries came in 1333 alongside John of Bohemia, and therefore served Perugia in its war against Arezzo with the name Compagnia della Colomba ("Dove Company"). Some of these masnade were merely a grouping of bandits and other desperate men.
Later these bands were joined by the first true organized Ventura Companies, those of Duke Werner of Urslingen and Count Konrad von Landau. The Italian noble Lodrisio Visconti countered by creating the "Company of St. George." Werner's company differed from the previous ones by a code of laws which imposed a rigid discipline and an equal division of income. This company was increased until it turned into the fearsome "Great Company", which had up to 3,000 barbute, each barbuta including a knight and a sergeant.
The bands of condottieri became notorious for their caprice. They soon realized that they held a monopoly on military power in Italy and began dictating terms to their ostensible employers. Many, such as Braccio da Montone and Muzio Sforza, became powerful political figures in the fourteenth century. Since many of the condottiere were fairly educated men and they had acquainted themselves with Roman military manuals, such as Vegetius's Epitoma rei militarii, they began to view warfare more on scientific viewpoint rather than bravery, a departure from the traditional Medieval model of chivalry. As consequence, most condottieri viewed it a better idea to out-maneuevre the opponent and fight his ability to wage war rather than risk the fortune at actual field battles. Since the condottieri developed the Medieval art of war and tactics further than anyone before, and rather fought the enemy indirectly than directly, the condottieri also became reluctant to place themselves or their men in harm's way and rather avoided battles than fought them. This was mis-interpreted by Machiavelli that condottieri fought each other in grandiose but often pointless and nearly bloodless "battles". They still retained grand armored knights and medieval weapons and tactics long after the rest of Europe had converted to more modern armies composed of pikemen and musketeers.
Cola di Rienzo had Werner executed in Rome in 1347, and Landau took over the Great Company. Landau, betrayed by his Hungarian soldiers, was defeated in 1362 by Albert Sterz and John Hawkwood's "White Company", which used more advanced combat tactics and formations. The barbuta was replaced by the lancia comprising three men: a capo-lancia and groom, both mounting a battle horse, plus a boy using a lesser quality horse. Five lance formed a posta, five poste a bandiera ("flag"). Now the condottieri comprised as many Italian companies as foreign, creating soon a host of national companies: they included the Astorre I Manfredi's Compagnia della Stella ("Star's company"), a new Company of St. George under Ambrogio Visconti, Niccolò da Montefeltro's Compagnia del Cappelletto ("Little Hat Company"), and Giovanni da Buscareto and Bartolomeo Gonzaga's Compagnia della Rosa, the last using a name of its own.
From the 15th century onward the companies' leaders were mainly Italian: they were nobles who for some reason had not been able to succeed in their lands and had therefore chosen the fighting life. In that century, the most famous condottiero was Giovanni dalle Bande Nere from Forlì, son of Caterina Sforza. He was also known as "the last condottiero". His son was Cosimo I de' Medici, Grand Duke of Tuscany.
Sometimes even princes fought for some periods as condottieri in order to increase their revenues: the most notable cases are Sigismondo Malatesta, lord of Rimini, and Federico da Montefeltro, duke of Urbino. Incomes were high indeed, though it should be noted that inflation was high in Italy during the period:
The leaders of these new condottieri companies were not chosen by their men, but vice versa. The condotta become a consolidated form of contract. When the contract period (ferma) ceased, the company had to wait another period called aspetto ("wait") in which the State kept the possibility of renewing it. If the contract ended in a definitive way, the condottiero could not declare war upon the other contracting party before two years had passed. This usage was well respected: the reputation and credibility was everything to the condottiero, and if he deceived his employer, his reputation was essentially ruined.
The condotta was also applied for sea mercenaries. This was called contratto d'assento, and assentisti were the captains and venturers hired in this way. These were mainly used by Genoa and the Papal States from the 14th century. Venice considered it a humiliating way to hire sailors and never used it, even in the most dangerous periods of her history.
The condottieri were masters of the battles fought in Italy for the whole 15th century. By the time of the wars in Lombardy, Niccolò Machiavelli observed, "None of the principal states were armed with their own proper forces":
Thus the arms of Italy were either in the hands of the lesser princes, or of men who possessed no state; for the minor princes did not adopt the practice of arms from any desire of glory, but for the acquisition of either property or safety. The others (those who possessed no state) being bred to arms from their infancy, were acquainted with no other art, and pursued war for emolument, or to confer honor upon themselves.
Throughout the 15th century Italian armies had defeated most, though not all, incursions by hostile neighbors, be they French, Swiss, German, Austrian, Hungarian or Turkish. At Calliano in 1487 the Venetians met, and more than held their own against, German landsknechte and Swiss infantry, troops who were then regarded as the best in Europe.
The end of the condottieri age began in 1494 with the first great foreign invasion in more than a century: Charles VIII's national French army proved quite a match for the divided Italian states and smaller condottieri armies. Some of the most renowned condottieri chose therefore to fight for foreign powers: Gian Giacomo Trivulzio, for example, abandoned Milan for France, while Andrea Doria became admiral of the Holy Roman Emperor Charles. In the end, however, the failure was political rather than military, and stemmed from a disunity and a lack of political determination.
The condotta had disappeared by 1550. The term condottiero remained to indicate great Italian generals mainly fighting for foreign states. Figures like Marcantonio II Colonna and Raimondo Montecuccoli were prominent well into the sixteenth and the seventeenth centuries.