Serving Italian Factions
In the following years, the White Company fought under many banners and switched sides many times. In 1364, it fought for Pisa against Florence. In 1369, Hawkwood fought for Perugia against the Papal forces. In 1370, he joined Bernabò Visconti in his war against an alliance of cities including Pisa and Florence. In 1372, he fought for Visconti against his former master, the Marquis of Monferrato. After that, he resigned his command and the White Company moved to the service of the Pope for a time.
In 1368, he attended the wedding of Lionel of Antwerp to Violante, daughter of Galeazzo II Visconti, in Milan. Also in attendance were the literary stars of the era Chaucer, Jean Froissart and Petrarch.
Under Hawkwood's command, the company gained a good reputation and he became a popular mercenary commander. His success was varied, but he exploited the shifting allegiances and power politics of Italian factions for his own benefit.
Italian cities concentrated on trade and hired mercenaries instead of forming standing armies. Hawkwood often played his employers and their enemies against each other. He might get a contract to fight on one side and then demand a payment from the other in order not to attack them. He also could just change sides, keeping his original payment. Sometimes one party hired him so that he would not work for their enemies.
If not paid, mercenaries like Hawkwood could threaten their employers with desertion or pillage. However, part of the White Company's reputation was built upon the fact that Sir John's men were far less likely to desert in dangerous situations than other mercenaries and Hawkwood soon grew much richer than many other condottieri. He bought estates in the Romagna and in Tuscany, and a castle at Montecchio Vesponi. Despite all this, it is claimed that he was illiterate. His education was rudimentary at best; contemporaries specifically remarked on his lack of oratorical skills, and much of his business and correspondence was done by proxy and later by his wife.
In 1375, when Hawkwood's company was fighting for the Pope against Florence in the War of the Eight Saints, Florence made an agreement with him and paid him not to attack for three months.
In 1377, Hawkwood led the destruction of Cesena by mercenary armies, acting in the name of Pope Gregory XI. One tale claims that he had promised the people that they would be spared, but Cardinal Robert of Geneva ordered them all killed. Shortly after, he switched allegiance to the anti-papal league and married Donnina Visconti, the illegitimate daughter of Bernabò Visconti, the Duke of Milan. A quarrel with Bernardo soon ended the alliance, and Hawkwood instead signed an agreement with Florence.
John and Donnina had a son and three daughters.
In 1381, Richard II of England appointed him as ambassador to the Roman Court.
In 1387, Hawkwood, fighting for Padua, fought Giovanni Ordelaffi from Forlì, fighting for Verona in the Battle of Castagnaro, and won.
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