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Facts from the Middle Ages that Are Full of Surprises

Khalid Elhassan March 15, 2021 36 min

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.

Sir John Hawkwood’s funerary monument. Wikimedia

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.

Written by

Khalid Elhassan

A lifelong history buff, I developed a particular passion for WW2 history as a child, when I spent hours listening to my grandfather, enraptured, as he recounted his wartime experiences in the British East African Campaign and with the British 8th Army in North Africa.

I graduated with a history BA from George Mason University, then went on to get a JD from the University of Virginia School of Law. After lawyering for a decade, I moved to sunny Rio de Janeiro and a less demanding career, opening a tourism agency in Copacabana.

A big chunk of my free time is spent blogging (you can follow me on Quora https://www.quora.com/profile/Khalid-Elhassan ) or freelance writing, mostly about my favorite subject, history.