The Condotte


Federico da Montefeltro (Duke of Urbino) 1422 – 82 (60)  was one of the most skilled and ruthlessly focused of the Condottieri of the 14 hundreds, but his preferred image was that of Renaissance Scholar rather than horseman and slaughterer.

From the end of the War of the Sicilian Vespers (1282-1302), the Italians tried to decide for themselves what government they wanted, resulting in conflict between the Ghibellines-who supported Imperial rule-and the Guelfs-who supported papal rule. The Guelfs were successful in the first decade of the fourteenth century, ironically at much the same time the papacy moved to Avignon in 1308. Suddenly freed from either Imperial or papal influence, the large number of sovereign states in northern and central Italy began to try to exert control over their neighbors. Florence, Milan, and Venice, and to a lesser extent Lucca, Siena, Mantua, and Genoa, all profited from the early-fourteenth-century military situation by exerting their independence. But this independence came at a price. The inhabitants of the north Italian city-states had enough wealth to be able to pay for others to fight for them and they frequently employed soldiers, condottieri in their language (from the condotte, the contract hiring these soldiers) and mercenaries in ours. Indeed, the immense wealth of the Italian city-states in the late Middle Ages meant that the number of native soldiers was lower than elsewhere in Europe at the same time, but it meant the cost of waging war was much higher.

One might think that having to add the pay for condottieri to the normal costs of war would have limited the numbers of military conflicts in late medieval Italy. But that was not the case and, in what was an incredibly bellicose time, Italy was one of the most fought over regions in Europe. Most of these wars were small, with one city’s mercenary forces facing another’s, but they were very frequent. They gave employment to a large number of condottieri, who in turn fought the wars, which in turn employed the condottieri. An obvious self-perpetuating circle developed. It was fueled by a number of factors: the wealth of northern Italy; the greed of wealthier Italians to acquire more wealth by occupying neighboring cities and lands (or to keep these cities from competing by incorporating their economies); their unwillingness themselves to fight the wars; and the availability of a large number of men who were not only willing to do so, but who saw regular employment in their mercenary companies as a means to comfort, wealth, and often titles and offices. In 1416, one condottierie, Braccio da Montone, became lord of Perugia, while a short time later two others, condottieri sons of the condottiere Muccio Attendolo Sforza, Alessandro and Francesco, became the Master of Pesaro and Duke of Milan, respectively. Other condottieri became governors of Urbino, Mantua, Rimini, and Ferrara during the fifteenth century.

Venice and Genoa continued to be the greatest rivals among the northern Italian city-states. Both believed the Mediterranean to be theirs, and they refused to share it with anyone, including Naples and Aragon, nor, of course, with each other. This became a military issue at the end of the fifteenth century. The common practice was a monopoly trading contract. Venice’s monopoly with the crusader states ceased when the crusaders were forced from the Middle East in 1291, although they were able to sustain their trade with the victorious Muslim powers. And Venice’s contract with Constantinople was abandoned with the fall of the Latin Kingdom in 1261, only to be replaced by a similar contract with Genoa that would last till the city’s fall to the Ottoman Turks in 1453.

Frequently during the late Middle Ages, this rivalry turned to warfare, fought primarily on the sea, as was fitting for two naval powers. Venice almost always won these engagements, most notably the War of Chioggia (1376-1381), and there seems little doubt that such defeats led to a weakening of the political independence and economic strength of Genoa. Although Venice never actually conquered Genoa, nor does it appear that the Venetian rulers considered this to be in their city’s interest, other principalities did target the once powerful city-state. Florence held Genoa for a period of three years (1353-1356), and Naples, Aragon, and Milan vied for control in the fifteenth century. Seeking defensive assistance, the Republic of Genoa sought alliance with the Kingdom of France, and it is in this context that their most prominent military feature is set, the Genoese mercenary. During the Hundred Years War, Genoa supplied France with naval and, more famously, crossbowmen mercenaries, the latter ironically provided by a city whose experience in land warfare was rather thin.

Before the fifteenth century, the Republic of Venice had also rarely participated in land campaigns-except for leading the forces of the Second Crusade in their attack of Constantinople in 1204. Seeing the sea not only as a provider of economic security but also as defense for the city, Venetian doges and other city officials had rarely pursued campaigns against their neighbors. However, in 1404- 1405, a Venetian army, once again almost entirely mercenaries, attacked to the west and captured Vicenza, Verona, and Padua. In 1411-1412 and again in 1418-1420, they attacked to the northeast, against Hungary, and captured Dalmatia, Fruili, and Istria. So far it had been easy-simply pay for enough condottieri to fight the wars, and reap the profits of conquest. But in 1424 Venice ran into two Italian city-states that had the same military philosophy they did, and both were as wealthy: Milan and Florence. The result was thirty years of protracted warfare.

The strategy of all three of these city-states during this conflict was to employ more and more mercenaries. At the start, the Venetian army numbered 10,000-12,000; by 1432 this figure had grown to 18,000; and by 1439 it was 25,000, although it declined to 20,000 during the 1440s and 1450s. The other two city-states kept pace. At almost any time after 1430 more than 50,000 soldiers were fighting in northern Italy. The economy and society of the whole region were damaged, with little gain by any of the protagonists during the war. At its end, a negotiated settlement, Venice gained little, but it also lost very little. The city went back to war in 1478-1479, the Pazzi War, and again in 1482-1484, the War of Ferrara. The Florentines and Milanese participated in both as well.

After the acquisition of Vicenza, Verona, and Padua in 1405 Venice shared a land frontier with Milan. From that time forward Milan was the greatest threat to Venice and her allies, and to practically any other city-state, town, or village in northern Italy. Milan also shared a land frontier with Florence, and if Milanese armies were not fighting Venetian armies, they were fighting Florentine armies, sometimes taking on both at the same time.

Their animosity predates the later Middle Ages, but it intensified with the wealth and ability of both sides to hire condottieri. This led to wars with Florence in 1351-1354 and 1390-1402, and with Florence and Venice (in league together) in 1423-1454, 1478-1479, and 1482-1484. In those rare times when not at war with Florence or Venice, Milanese armies often turned on other neighboring towns, for example, capturing Pavia and Monza among other places.

Perhaps the most telling sign of Milan’s bellicosity is the rise to power of its condottiere ruler, Francesco Sforza, in 1450. Sforza had been one of Milan’s condottieri captains for a number of years, following in the footsteps of his father, Muccio, who had been in the city-state’s employ off and on since about 1400. Both had performed diligently, successfully, and, at least for condottieri, loyally, and they had become wealthy because of it. Francesco had even married the illegitimate daughter of the reigning Duke of Milan, Filippo Maria Visconti. But during the most recent wars, after he had assumed the lordship of Pavia, and in the wake of Filippo’s death in 1447, the Milanese decided not to renew Francesco’s contract. In response, the condottiere used his army to besiege the city, which capitulated in less than a year. Within a very short time, Francesco Sforza had insinuated himself into all facets of Milanese rule; his brother even became the city’s archbishop in 1454, and his descendants continued to hold power in the sixteenth century.

Genoa, Venice, and Milan all fought extensively throughout the fourteenth and fifteenth centuries, but Florence played the most active role in Italian warfare of the later Middle Ages. A republican city-state, although in the fifteenth century controlled almost exclusively by the Medici family, Florence had been deeply involved in the Guelf and Ghibelline conflicts of the thirteenth century, serving as the center of the Guelf party. But though the Guelfs were successful this did not bring peace to Florence and when, in 1301, they split into two parties-the blacks and the whites-the fighting continued until 1307. Before this feud was even concluded, however, the Florentine army, numbering 7,000, mostly condottieri, attacked Pistoia, capturing the city in 1307. In 1315 in league with Naples, Florentine forces attempted to take Pisa, but were defeated. In 1325, they were again defeated while trying to take Pisa and Lucca. Between 1351 and 1354 they fought the Milanese. From 1376 to 1378 they fought against papal forces hired at and drawn from Rome in what was known as the War of the Eight Saints, but the Florentines lost more than they gained. Forming the League of Bologna with Bologna, Padua, Ferrara, and other northern Italian cities, they warred against Milan from 1390 to 1402. While they were initially successful against the Milanese, Gian Galeazzo, Duke of Milan, was eventually able to bring Pisa, Lucca, and Venice onto his city’s side, and once again Florence was defeated. In 1406 Florence annexed Pisa without armed resistance. But war broke out with Milan again in 1423 lasting until 1454; Florence would ally with Venice in 1425, and with the papacy in 1440. Battles were lost on the Serchio in 1450 and at Imola in 1434, but won at Anghiara in 1440. Finally, after the Peace of Lodi was signed in 1454 ending the conflict, a league was formed between Florence, Venice, and Milan that lasted for 25 years. But, after the murder of Giuliano de’ Medici and the attempted murder of his brother, Lorenzo-Pope Sixtus IV was complicit in the affair-war broke out in 1478 with the papacy and lasted until the death of Sixtus in 1484. In addition, interspersed with these external wars were numerous rebellions within Florence itself. In 1345 a revolt broke out at the announcement of the bankruptcy of the Bardi and Peruzzi banking firms; in 1368 the dyers revolted; in 1378 there was the Ciompi Revolt; and in 1382 the popolo grasso revolt. None of these were extensive or successful, but they did disrupt social, economic, and political life in the city until permanently put to rest by the rise to power of the Medicis.

Why Florence continued to wage so many wars in the face of so many defeats and revolts is simple to understand. Again one must see the role of the condottieri in Florentine military strategy; as long as the governors of the city-state were willing to pay for military activity and as long as there were soldiers willing to take this pay, wars would continue until the wealth of the town ran out. In Renaissance Florence this did not happen. Take, for example, the employment of perhaps the most famous condottiere, Sir John Hawkwood. Coming south in 1361, during one of the lulls in fighting in the Hundred Years War, the Englishman Hawkwood joined the White Company, a unit of condottieri already fighting in Italy. In 1364, while in the pay of Pisa, the White Company had its first encounter with Florence when, unable to effectively besiege the city, they sacked and pillaged its rich suburbs. In 1375, now under the leadership of Hawkwood, the White Company made an agreement with the Florentines not to attack them, only to discover later that year, now in the pay of the papacy, that they were required to fight in the Florentine-controlled Romagna. Hawkwood decided that he was not actually attacking Florence, and the White Company conquered Faenza in 1376 and Cesena in 1377. However, perhaps because the papacy ordered the massacres of the people of both towns, a short time later Hawkwood and his condottieri left their papal employment. They did not stay unemployed for long, however; Florence hired them almost immediately, and for the next seventeen years, John Hawkwood and the White Company fought diligently, although not always successfully, for the city. All of the company’s condottieri became quite wealthy, but Hawkwood especially prospered. He was granted three castles outside the city, a house in Florence, a life pension of 2,000 florins, a pension for his wife, Donnina Visconti, payable after his death, and dowries for his three daughters, above his contracted pay. Florentines, it seems, loved to lavish their wealth on those whom they employed to carry out their wars, whether they were successful or not.

In comparison to the north, the south of Italy was positively peaceful. Much of this came from the fact that there were only two powers in southern Italy. The Papal States, with Rome as their capital, did not have the prosperity of the northern city-states, and in fact for most of the later Middle Ages they were, essentially, bankrupt. But economic problems were not the only matter that disrupted Roman life. From 1308 to 1378 there was no pope in Rome and from then until 1417 the Roman pontiff was one of two (and sometimes three) popes sitting on the papal throne at the same time. But even after 1417 the papacy was weak, kept that way by a Roman populace not willing to see a theocracy return to power. Perhaps this is the reason why the Papal States suffered so many insurrections. In 1347 Cola di Rienzo defeated the Roman nobles and was named Tribune by the Roman people. He governed until those same people overthrew and executed him in 1354. In 1434 the Columna family established a republican government in the Papal States, forcing the ruling pope, Eugenius IV, to flee to Florence. He did not return and reestablish his government until 1343. Finally, in 1453, a plot to put another republican government in place was halted only by the general dislike for its leader, Stefano Porcaro, who was executed for treason.

One might think that such political and economic turmoil would not breed much military confidence, yet it did not seem to keep the governors of the Papal States from hiring mercenaries, making alliances with other Italian states, or pursuing an active military role, especially in the central parts of Italy. Usually small papal armies were pitted against much larger northern city-state forces, yet often these small numbers carried the day, perhaps not winning many battles, but often winning the wars, certainly as much because of the Papal States alliances as its military prowess. This meant that despite all the obvious upheaval in the Papal States during the later Middle Ages, at the beginning of the 1490s it was much larger and more powerful than it had ever been previously.


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