Condottieri (Italian: [kondotˈtjɛːri]; singular condottiero or condottiere) were Italian captains in command of mercenary companies during the Middle Ages and of multinational armies during the early modern period. They notably served popes and other European monarchs during the Italian Wars of the Renaissance and the European Wars of Religion. Notable condottieri include Prospero Colonna, Giovanni dalle Bande Nere, Cesare Borgia, the Marquis of Pescara, Andrea Doria, and the Duke of Parma.
The term condottiero in medieval Italian originally meant "contractor" since the condotta was the contract by which the condottieri put themselves in the service of a city or of a lord. The term, however, became a synonym of "military leader" during the Renaissance and Reformation era. Some authors have described Guido da Landriano (the real figure behind the legendary Alberto da Giussano) as the "first condottiero" and Napoleon Bonaparte (in virtue of his Italian origins) as the "last condottiero". According to this view, the condottieri tradition would span a huge diverse period from the battle of Legnano in 1176 to the Battle of Waterloo in 1815. 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.