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  • Writer's pictureBruce Boyce

The Condottieri

"Mercenary and auxiliary arms are useless and dangerous; and if one keeps his state founded on mercenary arms, one will never be firm or secure; for they are disunited, ambitious, without discipline, unfaithful; bold among friends, among enemies cowardly; no fear of God, no faith with men; ruin is postponed only as long as attack is postponed; and in peace you are despoiled by them, in war by the enemy."

Niccolo Machiavelli, The Prince, 1513

During the period spanning from 1350 to 1450, a notable surge in military activities occurred, characterized by an escalation in the cost and scale of wars. This era saw a prominent reliance on costly mercenary soldiers, introducing a constant threat of conflict even during peaceful times. What initially began as battles within smaller regions in the thirteenth century evolved into more significant interregional conflicts throughout the fourteenth and fifteenth centuries.

Notably, the ambitions of Milan for territorial expansion and Florence's departure from its traditional boundaries triggered hostilities that impacted a significant portion of the Italian peninsula. The rivalry between different branches of the Angevin family and the papal schism resulted in ongoing warfare within the Kingdom of Naples and the Papal States. Furthermore, Venice, which had previously held a marginal position in territorial affairs, redirected its focus inward and emerged as a significant military power during the fifteenth century. This transformation significantly influenced the dynamics and strategies of warfare during this period.

Victory of the Sienese Troops at Val di Chiana in 1363 by Lippo Vanni. c. 1373

After the mid-13th century, the interest of the German emperors in Italian affairs began to wane, leading to significant changes in the dynamics of northern and central Italy. The threat posed by large imperial and papal armies receded, and alliances like the Lombard League and the Tuscan League gradually disintegrated. As these leagues fell apart, the rivalries between individual cities took prominence, leading to a consolidation of small states and communes. Consequently, the map of Italy began to change as the number of independent states dwindled. In this evolving landscape, it was no longer the brief incursions of imperial armies that were the primary concern but rather the ongoing hostilities with neighboring cities. Warfare evolved from sporadic defenses to aggressive campaigns.

Once a reliable military force, the hastily assembled communal levy lost effectiveness. The changing nature of conflicts necessitated a more sophisticated approach to defense and warfare. Specialized infantry and professional cavalry gained importance, adapting to the evolving conflicts. Internal factionalism grew as international tensions reduced, affecting communal militias and leading to the rise of mercenary companies.

Battle of Anghiari, 1440, Unknown Florentine master, c. 1460s

Mercenaries emerged due to economic opportunities, political needs, and evolving military demands. The availability of military personnel, including political exiles and foreign troops, contributed to their rise. In cities marked by intense factional strife, a significant minority of citizens would be in exile at any time. Many early mercenaries had been ousted from their native towns due to political disputes. By the mid-fourteenth century, Italy faced economic depression and rural under-employment, further contributing to the availability of manpower for mercenary companies. The growth of mercenary forces was thus intricately tied to these economic, political, and military dynamics.

During the thirteenth century, key military technology advancements included the widespread adoption of the crossbow and, particularly in northern Europe, the long bow. The crossbow and longbow demanded significant practice to be used effectively, encouraging specialization and professionalism. These weapons also altered military techniques for those on the receiving end. Traditional infantry, armed with short lances, swords, and shields, shifted to a division between lance or pike men and shield bearers. The latter carried large, ground-resting shields to protect the pikemen and crossbowmen. The threat from crossbow bolts prompted the transition from leather and mail armor to plate armor for cavalry, necessitating horse protection and horse armor. Consequently, cavalrymen required spare horses and a small entourage for close support, giving rise to the characteristic formation of late medieval cavalry known as the cavalry "lance." Such innovations widened the gap between part-time and professional soldiers, emphasizing the need for employers to seek professionals if feasible.

Once mercenaries became an established component of the Italian military system, forming organized companies under recognized leaders became inevitable. This arrangement simplified state recruitment and offered enhanced military efficiency due to the experience of fighting together. 14th-century warfare demanded more sophisticated tactics and disciplined collaboration among troops, qualities experienced mercenary companies could provide, even though the outcomes often fell short of ideal expectations.

The Taking of Pisa, Unknown Florentine Master, c. 1460s

In the fourteenth and fifteenth centuries, Italian warfare was shaped by several key factors. First and foremost, Italian states, despite their economic potential, were more concerned with achieving security and dominance within well-defined spheres of influence rather than outright destruction of their rivals. These states faced limitations in terms of population resources compared to their wealth, leading to the reliance on small professional mercenary armies that served the needs and intentions of the employing states. Warfare in this context was characterized by devastation, capturing small political and diplomatic advantages and frustrating the enemy's attempts to do the same. Battles were calculated risks aimed at gaining advantages rather than seeking overwhelming victories, and they were rarely decisive but far from bloodless affairs.

Wars typically concluded with truces and peace treaties that involved significant indemnities. The financial burdens imposed on defeated cities were substantial, often exceeding their yearly revenue. Battles in this era were not always decisive, and winners and losers were challenging to distinguish. Expansion of territories was not solely a result of victory but often a motive for war. Territorial transfers sometimes preceded conflicts through various tactics like purchases, diplomacy, or exploiting regional rivalries.

A defining characteristic of Italian warfare during this period was its persistence. Hostilities did not end with truces, as dismissed mercenaries formed marauding bands, known as "free companies," that raided the countryside, looted, and extorted bribes from cities. These raids were integral to warfare, causing damages and costs comparable to formal campaigns. The raids were especially severe in the third decade of the fourteenth century to the opening decades of the fifteenth century, affecting regions like Tuscany, Umbria, and the Kingdom of Naples. The constant threat of such bands prompted cities to form defensive leagues (taglie) for mutual protection, contributing troops to shared armies. These leagues were a fundamental aspect of Italian military and diplomatic policy during this time, signifying the necessity for collaborative defense against the pervasive threat of marauding bands.

Condottiere Sir John Hawkwood by Paolo Uccello, 1436

As a result, mercenary troops became increasingly common and were hired through condottieri. The term "condottiere" translates to "contractor" and originates from the Italian condotta or contract, defining agreements between mercenaries and the Italian states or princedoms that hired them. It primarily refers to the leaders of these mercenary bands but technically includes any mercenary who signed such a contract or was a

part of its terms.

The condottieri system saw an influx of foreign troops, especially after the Treaty of Brétingy in 1360 ended a phase of the Hundred Years War. Unemployed soldiers, including many from England, traveled to Italy, forming free companies and offering their services under elected captains. Notable mercenary units included the White Company, Black Company, Company of the Flowers, Company of the Star, and several companies of St George. Initially led by foreigners, Italians increasingly became condottieri from the 1370s onward, dominating the system by the 15th century.

Condottieri were professional soldiers, serving employers without considering nationality or political allegiances. The system was characterized by intricate legal contracts that were mutually beneficial. By the 15th century, these contracts became standardized. They specified the condottieri's service period and payment terms, often including bonuses for bravery and provisions for injuries. Moreover, final payments often stipulated not working for the employer's competitors after the contract ended.

Battle of San Romano by Paolo Uccello, c. 1436

In return, the condottiere provided well-equipped forces, primarily comprising cavalry, dismounted men-at-arms, and archers/crossbowmen. The fundamental unit was the "lance," typically consisting of a mounted knight, a squire, a page, and two archers or men-at-arms. The condottiere would contract to provide a specific number of these lances to their employer. As the condottieri system evolved, powerful condottieri controlled a growing number of lances. For instance, in 1441, condottiere Micheletto Attendolo's band comprised 561 lances, totaling over 2,800 men. The employer received captured territories, while the condottiere could keep portable property. Discipline among troops was crucial, with looting and violence against civilians prohibited.

The equestrian statue of condottiere Bartolomeo Colleoni by Verrocchio

In the 15th century, successful condottieri often received training under renowned professional mentors, establishing schools to teach combat skills, tactics, and contract management. The training emphasized different elements based on battle tactics, whether utilizing infantry formations or coordinating with archers or crossbowmen. Italian warfare during this era mainly featured heavily armored cavalry and training in cavalry tactics was crucial for success.

All European armies were contract-based during this transition and included many foreign mercenaries. These armies' methods and organizational structures were more similar than often believed. The challenge of adapting to gunpowder usage and the need for greater organization and permanence were shared concerns across all armies. Standing armies, contracts, muster rolls, uniform pay scales, standardization of unit sizes, and central control were prevalent features across European armies, illustrating a shared evolution in military practices.

In 1494, King Charles VIII of France launched a significant invasion of Italy, swiftly gaining control of the Kingdom of Naples by February 1495. This event marked a crucial turning point in Italian history, leading to a 40-year struggle between France and Spain for dominance in the Italian peninsula. By the 1530s, Spain emerged as the victor, and much of Italy had come to terms with foreign control.

Condottiere Francesco Sforza who became Duke of Milan with Medici backing

Contemporary Italian writers like Machiavelli and Guicciardini were puzzled by Charles' swift success in Italy. They attributed Italy's military weakness to the outdated condottiere system relying on medieval cavalry tactics. Italy, sheltered by the Alps, lagged in European military advancements. European monarchs had far greater resources than individual Italian states. Italy's fragmented states, driven by self-interest, struggled to form enduring alliances for common defense.

Historically, Italian soldiers and their approach to warfare were mischaracterized as outdated. Modern scholarship is revising this view, revealing a transitional period in European warfare. This transition saw the shift from cavalry to infantry dominance, the emergence of paid professional armies, strategic changes favoring decisive blows, and a move from brute force reliance to the development of a 'science' of war.


Further Reading:

The Italian Wars 1494-1559: Michael Mallett and Christine Shaw

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