Said to have been the son of an Essex tanner and to have been born around 1320CE, John Hawkwood served in the English army under Edward III and the Black Prince during the Hundred Years War with France. At some point he was knighted by the Black Prince, but history appears ignorant of the circumstances.
Around 1360, after the peace of Bretigny, Hawkwood struck out on his own and formed the "White Company", a band of men-at-arms, mostly English (at least to begin with). They hired themselves out as mercenaries during the 14th century Italian wars, serving (among others, and at different times) the Marquis of Montferrato, the Pisans, Pergugia, and Bernab Visconti. In 1372, after assisting Visconti against Montferrato, he resigned his command, allowing the Company to serve the Pope against whom they had previously fought.
In 1375 he accepted money from the city of Florence not to engage the city in battle for 3 months. The engagement lasted for over 20 years, during which time, in 1377, he married Donnina Visconti (Bernab's illegitimate daughter) in Milan (curiously shortly after he had, on a cardinal-legate's orders, massacred the inhabitants of Cesena).
During the 1390s, fighting for Florence against Gian Galeazzo Visconti (who had murdered Bernab), Hawkwood became the city's general and command-in-chief. He died in 1394, was given a vast public funeral and burial, and ought to have had a marble monument in the Florentine cathedral but it never came to pass. Later his body was returned to England.
He was also known to Jean Froissart as "Haccoude" and to Machiavelli, under the name "Acuto".
His arms were Argent, on a chevron sable three escallops of the field.