Sir John Hawkwood, Italian byname Giovani Acuto, meaning “John the Astute” (1320 – 1394) was an English soldier of fortune who plied his trade in Italy as a condotierre. As captain of a powerful mercenary band, Hawkwood played a significant role in 14th century Italy’s wars and politics, and switched sides on numerous occasions between the peninsula’s competing factions and states.
Hawkwood began his military 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 the English unit known as the White Company.
In 1364, he was elected captain-general of the White Company, and he elevated its reputation, transforming it into an elite and highly sought after mercenary unit by adopting the English longbow and tactics successfully used in France, lightened his 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 when the Holy Father stiffed Hawkwood on payment, the 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 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.