8. The White Company: The English Freebooters Who Terrified Italy
Sir John Hawkwood (1320 – 1394) was an English mercenary who worked in Italy as a condottiere. Frequently switching sides, he played a significant role in 14th-century Italy’s wars and politics. He began his career during the Hundred Years War in the armies of England’s king Edward III, who knighted Hawkwood for exceptional service. When that war was temporarily interrupted by a peace treaty in 1360, Hawkwood left for Italy at the head of a company of mercenaries, and joined an English unit known as the White Company. In 1364, he was elected captain-general of the White Company, and he elevated its reputation. Hawkwood transformed the White Company into an elite and highly sought-after unit by adopting the English longbow and tactics successfully used in France. He also lightened his men’s armor and equipment, which made them famous for the rapidity of their movements, and instilled strict discipline.
During the 1370s, Hawkwood served the Pope, but the Holy Father stiffed him on payment. So 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 Pope 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, and was appointed its captain-general. He remained in Florence until he finally decided to sell his Italian properties and retire to England to spend his last years, but died in 1394 before he could do so.