Condottieri were mercenary leaders employed by Italian city-states from the late Middle Ages until the mid-fifteenth century.

Portrait, called the "Condottiere," by Antonello da Messina, dated 1475 (Louvre)

In the thirteenth and fourteenth centuries Italian city-states were becoming enriched by their trade with the Orient. These cities, such as Venice, Florence, and Genoa had woefully small armies and were increasingly becoming targets of attack by foreign powers as well as envious neighbors. The noblemen ruling the cities soon resorted to hiring companies of mercenaries known as "condotta" to defend their territories. Each condotta was led by a "condottiere." Often the administration of the cities was also in the hands of a foreign podestà hired for one year.

The bands of condottieri became notorious for their caprice. They would often change sides to a higher paying rival before and even during battle. The condottieri soon realized that they held a monopoly on military power in Italy and began dictating terms to their former employers. Many, such as Braccio de Montone and Muzio Sforza, became powerful political figures in the fourteenth century. The condottieri also became lethargic in regards to the changing nature of warfare and began fighting each other in grandiose but often pointless and nearly bloodless "battles." The condottieri still retained grand armored knights and medieval weapons and tactics long after the rest of Europe had transitioned to more modern armies composed of pikemen and musketeers.

In the 15th century, with the French invasion of Italy and the Papal States's plea to the Spanish for help, the lavishly adorned but ineffective condottieri were defeated by wave after wave of invasions from the armies of almost every nation in Western Europe. The condottieri were no match for the Swiss pikemen, English musketeers, French cavalry, and Spanish tercios, and the condotta had disappeared by 1450.

Famous condottieri

"Sir" John Hawkwood ('Giovanni Acuto'), (Essex, ca. 1320 - Florence 1394) arrived in Italy ca 1360, hardened in the Hundred Years War in France, at the head of the White Company served Pisa against Florence, then the Visconti in Milan, then, Gregory XI, and ended his career serving Florence. He was appointed Capitaine de la ville (in English?), being paid 130,000 golden ducats. wound up as duke in Milan. Retired 1378. The city did him magnificent funerals, still remembered by a fresco monument in Santa Maria Novella, Florence.

Facino Cane de Casale (Casale Monferrato, 1360 - Pavia, 1412) began in the service of Gian Galeazzo Visconti, in his struggles against Mantua. After Visconti's death in 1402 he adventured throughout northern Italy, gained a Byzantine princess for a bride -- who brought his lands to Filippo Maria Visconti after the adventurer's demise.

Andrea Fortebracci, called Braccio da Montone (Perugia 1368-Aquila 1424) rival to Muzio 'Sforza', bitter rivals who died within weeks of one another in 1424, leaving their sons to carry on their feud. Braccio was master of Perugia in 1416 and briefly controlled the city of Rome. He was killed laying siege to Aquila on behalf of Ladislas, king of Naples.

Muzio Attendolo, called Sforza ("Strong") (Cotignola, 1369 - near Pescara, 1424) Condottiere from the Romagna serving the Angevin kings of Naples; the most successful dynast of the condottieri after receiving from Joan II of Naples the title of grand connétable (Grand Constable in English?).

Bartolomeo Colleoni,(Solza, near Bergamo ca 1400 - Malpaga 1475) immortalized in Andrea Verrochio's equestrian bronze, at Campo dei Santi Giovanni e Paolo, Venice. He began under Braccio da Montone and then under Muzio Sforza. He switched sides between Milan and Venice, before settling his fortunes on Venice, where he was general for many years. A great patron of artists.

• Biography. (http://www.kfki.hu/~arthp/database/glossary/illustri/colleoni.html)

Sigismondo Malatesta , lord of Rimini, by Piero della Francesca

Malatesta da Verruchio (1212 - 1312), founder of the Malatesta dynasty, master of Rimini in 1295. Father of Giovanni Malatesta (d. 1304) who killed his wife Francesca da Rimini, who had taken his handsome brother Piero for a lover, earning them all places in Dante's Inferno.

Sigismondo Malatesta (1417 - 1468), lord of Rimini, a capable condottiere in the family tradition, was hired by the Venetians against the Turks (unsuccessfully), 1465, and was patron of Leone Battista Alberti, whose Tempio Malatestiana at Rimini is one of the first entirely classical buildings of the Renaissance.

Erasmo da Narni "Gattamelata" (Narni 1370 - Padua 1443) the butcher's boy from Narni immortalized in Donatello's mounted sculpture (1447) the first equestrian bronze since Antiquity. He began with Montone, served Pope and Florence equally, served Venice in 1434 in the battles with the Visconti of Milan, then became dictator of Padua in 1437.

Niccolò Piccinino ('Little Nick') (Pérugia 1380 - Milan, 1444), was in arms at the age of 13. In 1424, at the death of his commander, he took charge of the company of mercenaries and sold his services to Florence, then to Milan in 1426. His rapacious ambition made his employer, the duke of Milan, uneasy, who decided instead to hire Francesco Sforza, the personal enemy of Piccinino. The growing rivalry between the two eventually led to a showdown in 1443. Defeated, Piccinino died next year.

Giovanni Vitelleschi (died 1440), the condottiere of Pope Eugenius IV, who made him archbishop of Florence and a cardinal, while he commanded the papal armies against René of Anjou in Naples.

Francesco Bussone da Carmagnola (1390 - 1432) fought for Filippo Maria Visconti of Milan, before taking orders from the republics of Florence and of Venice. Suspected of treasonous actions, he was executed in 1432.

Cesare Borgia See separate article.

Giovanni delle Bande Nere, son of Caterina Sforza, fighting in the service of Pope Leo X.