10. From Freebooter to Captain-General of Italy’s Most Flourishing City
John Hawkwood further improved the White Company by lightening the men’s armor and equipment, which made them famous for the rapidity of their movements and instilled strict discipline. During the 1370s, he served the Pope, but then the Holy Father stiffed Hawkwood on payment. The medieval mercenary bided his time, and when the pope sent him to put down a rebellion in Citta di Castello, Hawkwood captured and kept the city in order to compel payment. Strapped for cash, the Holy Father was forced to invest Hawkwood with the city, granting it to him in return for uncompensated services.
Between 1372 and 1378, Hawkwood repeatedly switched sides between serving the Pope and his rival, the duke of Milan, whose illegitimate daughter he married in 1377. In 1378, after quarreling with his new father-in-law, Hawkwood switched sides and signed a contract with Milan’s rival, the city of Florence. The Florentines appointed him their Captain-General, and he remained in Florence until he finally decided to sell his Italian properties and retire to England to spend his final years. However, he died in 1394 before he could do so.