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As the Medieval age was coming to a rapid close, Italy was divided into many small city states. Each of these tiny principalities had their own rulers, who fought constantly to overthrow or kill one another for land, wealth, and power. None of these principalities had enough subjects to build their own armies. But they did have plenty of money. Italy at that time was a land made wealthy by trade. The lords and rulers realized that the only way to protect themselves and their tiny kingdoms was to use some of their vast wealth to hire mercenaries, or free soldiers.

These first “condotta” (mercenary companies) were soldiers from various nations like England, Germany, Spain, and France. The Hundred Years War was raging at the time. There were often lulls in the fighting and soldiers found themselves out of work for months or years at a time. With nothing else to do these “free soldiers” formed their own companies, then swept through large areas of the countryside, looting and leaving destruction in their wake. Some of these free companies eventually crossed into Italy, where other more permanent bands of mercenaries had already established themselves. These soldiers were much more organized and headed by leaders called “condottiere”.

One of the first mercenary bands to have such formal organization was called the Grand Company and was headed by a man named Montreal d’Albarno. His soldiers not only became organized, they had a strict code of honor, were heavily armed cavalry and fought with the most modern weaponry of the day. Yet despite the beginnings of stricter organization and more rigid codes of conduct, most free soldiers continued to be untrustworthy, disorderly, and often changed their allegiance just before or halfway through a battle.

The most famous non-Italian condottieri was Sir John Hawkwood who came to Italy in around 1360, after serving with Edward III in the French wars. It’s believed Hawkwood earned a knighthood but historical records are not clear on that point. He left France for Italy and joined a band of English mercenaries called the White Company. His prowess as a longbowman, military tactician and disciplinarian had him quickly moving up the ranks until he became leader of the White Company, a title he held for 30 years. Later in his career Hawkwood alternately carried the title of duke and pope of Milan until his retirement in 1378.

By the 14th century the condottiere were no longer satisfied with the large sums of money they and their companies earned fighting wars for nobles and kings. They began to conquer principalities and nation states for themselves.

One of the most famous, or infamous, of the Italian condottiere and the first to establish his own state, was named Braccio da Montone. His hunger for wealth and political gain initiated a lifelong rivalry between himself and another well-known condottieri, Muzio Sforza. During the early 15th century very few military campaigns in Italy were fought without either Braccio’s or Sforza’s leadership. Both condotierre died in 1424, and within a few weeks of one another, bitter rivals to the end. Their animosity did not end there - both mens’ sons would carry on their own power struggle for decades.

As the 15th century came to a close, the continuous wars between the Italian principalities were also coming to an end. Power structures shifted and Italy became a staging ground for other wars that involved more powerful armies from France, Spain and Germany. Against these armies the condottiere, and their own mercenary armies, could not hold their ground. They had a choice, to join the conquering forces or be annihilated. By the year 1450 the day of the condottieri and his brotherhood of mercenaries had come to an end.