The definition originally applied only to commanders of mercenary companies, condottiero in medieval Italian meaning 'contractor' and condotta being the contract by which the condottieri put themselves in the service of a city or lord.
Notable condottieri include Prospero Colonna, Giovanni dalle Bande Nere, Cesare Borgia, the Marquis of Pescara, Andrea Doria, and the Duke of Parma.
[4][5] Most historians would narrow it down to the years from c. 1350 to c. 1650, with a particular focus on the rise of the commanders of free companies (capitani di ventura) and their transformation into captain generals fighting for the major powers during the struggle for political and religious supremacy in Europe.
However, later in the Renaissance the condottieri line of battle still deployed the grand armoured knight and medieval weapons and tactics after most European powers had begun employing professional standing armies of pikemen and musketeers; this helped to contribute to their eventual decline and destruction.
On the conclusion (1360) of the Peace of Bretigny between England and France, Sir John Hawkwood led an army of English mercenaries, called the White Company, into Italy, which took a prominent part in the confused wars of the next thirty years.
In 1363, Count von Landau was betrayed by his Hungarian soldiers, and defeated in combat, by the White Company's more advanced tactics under commanders Albert Sterz and John Hawkwood.
From the 15th century hence, most condottieri were landless Italian nobles who had chosen the profession of arms as a livelihood; the most famous of such mercenary captains was the son of Caterina Sforza, Giovanni dalle Bande Nere, from Forlì, known as The Last Condottiere; his son was Cosimo I de' Medici, Grand Duke of Tuscany; besides noblemen, princes also fought as condottieri, given the sizable income to their estates, notably Sigismondo Pandolfo Malatesta, Lord of Rimini, and Federico da Montefeltro, Duke of Urbino; despite war-time inflation, soldier's pay was high: The condottieri company commanders selected the soldiers to enlist; the condotta was a consolidated contract, and, when the ferma (service period) elapsed, the company entered an aspetto (wait) period, wherein the contracting city-state considered its renewal.
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 honour upon themselves.In 1487, at Calliano, the Venetians successfully met and acquitted themselves against the German landsknechte and the Swiss infantry, the best soldiers in Europe at the time.
In time, the financial and political interests of the condottieri proved serious drawbacks to decisive, bloody warfare: the mercenary captains often were treacherous, tending to avoid combat, and "resolve" fights with a bribe—either for the opponent or for themselves.
Although the mercenary forces were among the first to adapt to the emerging technologies on the battlefield,[citation needed] ultimately, the advent of firearms-governed warfare rendered their ceremonial fighting style obsolete.
The most renowned condottieri fought for foreign powers: Gian Giacomo Trivulzio abandoned Milan for France, while Andrea Doria was Admiral of the Holy Roman Emperor Charles V. In the end, failure was political, rather than military, stemming from disunity and political indecision, and, by 1550, the military service condotta had disappeared, while the term condottiere remained current, denominating the great Italian generals (mainly) fighting for foreign states; men such as Gian Giacomo Medici, Ambrogio Spinola, Alexander Farnese, Marcantonio II Colonna, Raimondo Montecuccoli and Prospero Colonna were prominent into the sixteenth and the seventeenth centuries.
The end of the Thirty Years' War in 1648 and the birth of Westphalian sovereignty diminished Roman Catholic influence in Europe and led to the consolidation of large states, while Italy was fragmented and divided.