Soldier of Fortune: Glory Days for Sir John Hawkwood, King of Mercenaries



Sir John Hawkwood was born into a life on the English countryside that was business and rebellion. From an early age, he sought power and influence outside of England’s borders. He showed off his battle skills in the Hundred Years War and won a knighthood from England’s king.

Hawkwood the man was indeed an interesting character: a brilliant tactician, and an equally brilliant politician, but in his life, he would terrorize Italy with armies and bands of mercenaries, amass a great fortune, and cement his place in history as the most famous Anglo-Italian mercenary.

Engraving representing John Hawkwood.

Engraving representing John Hawkwood. (Public Domain)

Beginnings of Business

Hawkwood was born around 1320, in the parish of Hinckford, Essex, which is located in the north-central region of the county. Essex County was known for its farming and sheep; it had a thriving business sector that produced cloth and exported raw wool. Essex also produced anti-authoritarianism. In 1381, the people revolted against the crown in a large social uprising. The county of Essex in the 14th century was indeed a business class society that did not take well to authority. This attitude harbored by the locals may have influenced the young Hawkwood early on in his life.

John was the youngest child of Gilbert de Hawkwood, but he shared the same name as his older brother. John’s social situation is contrary to what past historians claimed, said to have come from a low ranking family, and was himself a poor soldier later on in his life. This, however, is not true, for John grew up in a wealthy business family. His father was supposedly a tanner who owned land, and even had a maidservant to take care of the day-to-day chores around the house.

In 1340, John’s father died. The will Gilbert left behind divided the share each child of his received. The elder John got the largest of the share and stayed at home to run the business, while the younger John left home with his share.

Hawkwood The Military Man

The younger John Hawkwood took his share and moved to London. Once Hawkwood made it to London, he worked as a tailor or a tailor in training, an apprentice. However true this story is about Hawkwood working and training to be a tailor remains in dispute. It is also said that tailors during this period were looked down upon in terms of serving in the military. However, it did not stop Hawkwood, for when Edward III began to recruit men for his army (which he planned on taking to France in order to claim the French throne), Hawkwood tossed the needle for the sword and joined the army along with his neighbors back home – one of whom happened to be John de Vere, his lord back in Essex, and wealthy families such as the Listons, Coggeshales and Bourchiers.

John de Vere assembled an army of 40 men-at-arms, 10 knights, 29 esquires and 30 mounted archers to serve Edward III.  Wool was provided to the men as pay; a total 56 sacks of wool was to be brought with them. As for Hawkwood’s role in John de Vere’s army, this remains uncertain. However, it is said that he may have started in 1342 as an archer.

Hawkwood and the Hundred Years War

He may have had humble beginnings in the army, but Hawkwood’s ambitious goal was to one day retire to these lands and that goal would start with the battle of Crecy in 1346.

Battle of Crécy between the English and French in the Hundred Years' War. 15th century.

Battle of Crécy between the English and French in the Hundred Years’ War. 15th century. (Public Domain)

Hawkwood’s archery skills are said to have started when Edward banned games such as football, cricket, hockey, cockfighting and so on. King Edward wanted his men to focus on archery, particularly using the English longbow. Hawkwood must have been a good pupil when it came to master the bow, for at the battle of Crecy in 1346, he held the rank of captain on the battlefield and commanded a company of 250 archers led by de Vere. After the battle of Crecy in 1346, Hawkwood seems to have disappeared.

Village sign at Crécy-en-Ponthieu, Picardy commemorating the Battle of Crécy, 26 August 1346.

Village sign at Crécy-en-Ponthieu, Picardy commemorating the Battle of Crécy, 26 August 1346. (CC BY-SA 3.0)

Between Crecy and the battle of Poitiers, Hawkwood appears to be only mentioned twice, but in a negative light, so it seems. The first known record tells us he and another beat a man almost to death in a place called Finchingfield in 1350, and then he committed theft a year later. Hawkwood’s life outside the military seemed to be like that on the battlefield. In other words, Hawkwood was broke and in need of booty.

These two unflattering events are all that is known about Hawkwood outside the military, for he again disappears in the historical record and it is speculated that he returned to France and rejoined de Vere’s forces and maybe even married one of de Vere’s daughters. Nevertheless, Hawkwood’s case will always have speculation, but one can gather that he did return to France, was married, did have a daughter, and is recorded to have been at the battle of Poitiers in 1356.

In 1356, at the Battle of Poitiers, Hawkwood is said to have distinguished himself in the field of battle by winning his spurs. In other words, John Hawkwood was not just John Hawkwood anymore; he was Sir John Hawkwood, for the spurs he won made him a knight. The recommendation of knighthood that be awarded to Hawkwood was by the Earl of Oxford. After Poitiers, Hawkwood was involved in the raids on Gascony province, particularly raiding the city of Pau. Nevertheless, all well ends well or so we think, for in 1360, the treaty of Brétigny was signed between England and France, thus ending the Hundred Years War in theory.

A few historians mention Hawkwood’s status by the end of the war. The historian Philip Morant from Essex says that Hawkwood was “the poorest of knight,” while Froissart calls him “a poor knight.” Overall, Hawkwood was rich in title, but lacked the wealth to be noble. This is where his life as a mercenary was about to begin.

Hawkwood the Mercenary

John Hawkwood had only two options in his life; return home as a commoner, or stay in France and become a mercenary. This second option was preferred, as he could make money that would help him climb the ladder of nobility and service.

In 1360, Hawkwood joined up as a freebooter or mercenary group that was called “Les Tart-Venus”, which means ‘Late-Comers’. Men in positions like John Hawkwood were allowed to stay in France and conduct war. The reason is that once Edward III signed the Brétigny Treaty, he gave the order for his men to pull out of France and return to English soil. However, Edward III allowed raids to take place in France unofficially. The reason Edward allowed this was to see if he could gain a much greater deal from the French king. So how did the English soldiers stay? According to medieval author Jean Froissart, King Edward had high-ranking men encourage those seeking to return home to stay in France and continue on their destructive path—and why not? If the English soldiers returned home, they returned to nothing, for they were at the moment unemployed. However, if they turned to face the French countryside, they would soon notice that money was abundant and opportunity for warfare never-ending. All these men had to do was claim no country, as was the case of Hawkwood.

The Great Company and Heaven over Money

In December 1360, Hawkwood and his men arrived at, and captured the French town of Pont-Saint-Esprit, along with the help of other mercenaries, and together they became known as “The Great Company.”

Hawkwood had a much bigger prize in mind, however: the town of Avignon. Avignon was the capital where the Pope, himself lived.  Hawkwood saw Avignon as prime pickings, for if the Pope lived there then money was there, for the money that flowed to and from the Papacy was linked with all the major kingdoms of Christendom. Hawkwood and many others saw a great investment in harassing Pope Innocent.

The city of Avignon was surrounded and cut off by the various bands of mercenaries, including Hawkwood’s men. The city had no way of getting food, and the population was slowly beginning to starve, not to mention that the plague was back in France again. The Pope was all but powerless. He ordered the mercenaries to disperse and go home, but the mercenaries said no, so the Pope excommunicated them, but the mercenaries could care less. This left Pope Innocent with one last option. He announced a crusade to come and defeat the mercenaries that surround Avignon.

The Pope was able to summon seven thousand men to go and besiege Pont-Saint-Esprit in early February 1361. However, it failed, and Froissart mentions that the reason why the crusaders lifted the siege on Pont-Saint-Esprit was due to not being paid. The Pope had promised Heaven over money.

Despite the ‘heavenly’ offer, many of the crusaders packed up and returned home while others went over to the “Free or Great Company Side.” Because of this, the Pope and the cardinals debated as to what to do with the mercenaries. In the end, they summoned for a man by the name of Marquis of Monferrato. Monferrato was the Imperial Vicar of Piedmont as well as Lord of Turin. It was his job to hire the mercenaries and to take them back to Northern Italy to fight against Milan. Thus, the Pope paid Monferrato a huge sum of money to decontaminate the land around Avignon of plague, but also to fight Milan. Hawkwood signed up.

It is recorded that Hawkwood was sending money back home to his older brother John to make the investments for him, which in turn made the family wealthy, even during the plague years, which seemingly did not hinder their economic growth.  This could be true, for the Pope is said to have paid one hundred thousand florins to the companies: thirty thousand went to the men, while Monferrato paid the men sixty thousand more florins to hire them. This would have given each man 15 florins apiece, maybe more, for the men in charge of the bands, like Hawkwood, may have been paid more due to rank, but it is not known for certain.

White Company

Hawkwood returned to France in 1361 to fight the French as a part of the Great Company. Hawkwood finally returned and stayed permanently in Italy with a group of Anglo-German mercenaries called ‘condottieri’, effectively ‘contractors’.

Bartolomeo d'Alviano, a Condottieri.

Bartolomeo d’Alviano, a Condottieri. (Public Domain)

A man named Albert Sterz led the condottieri until December 1363.  Hawkwood took over the condottieri band of Pisa and reorganize them into the famous English mercenaries, called “White Company.” From then on Hawkwood’s fame grew ever-increasingly due to his men’s military professionalism as seasoned veterans.

In 1365, a man named Egidio Albornoz approached Hawkwood with a war chest of 200,000 florins provided by the Pope. The payment was intended for Hawkwood to attack the Visconti who had been molesting church lands in central Italy for some time. He took the battlefield and did well until he began to lose to Visconti, and Hawkwood made the decision to retreat to the castle of San Mariano.

Modern photograph of San Mariano, Perugia, Umbria, Italy.

Modern photograph of San Mariano, Perugia, Umbria, Italy. (CC BY-SA 3.0)

Hawkwood and his men held out for some time, but due to thirst, they begged for peace. The besiegers led by Albert Sterz (who was once Hawkwood’s friend), knew that it was better to keep these men alive than to kill them, for they were worth money—not as prisoners, but rather as mercenaries. In the end, 2024 men surrendered and all their belongings they had with them was given over as booty to Albert Sterz.

Sterz had won the day and was showered with glory from the people of Perugia. However, Sterz was about to betray everything he had achieved with the Perugian’s. Hawkwood and his men were now in prison, but that was not going to last long. Hawkwood managed to escape along with many of his knights. How Hawkwood did it remains unknown, but when Sterz had found out, he pursued Hawkwood.  Hawkwood and his men were on the run looking for money to pay for the men locked up in Perugian prisons. Sterz chased Hawkwood relentlessly until he had to give up. The only problem was that Hawkwood not only escaped Sterz’s grasp, he was now in the arms of the city of Genoa, which happened to seat the most powerful rulers in Italy.

Wealth and Prestige: Glory Days!

Sir John Hawkwood arrived in Milan with open arms to a man named Bernabo. He was the leader of Milan, or co-leader with his brother Galeazzo. Bernabo was a military man who led his men with the sword. So why did Bernabo want Hawkwood to lead his army? He needed an insurance policy.

Bernabò Visconti, lord of Milan.

Bernabò Visconti, lord of Milan. (Public Domain)

Bernabo was eyeing some lands to the south and he needed Hawkwood to lead an army as its general, unofficially, and at the same time mentor a person by the name of Telemachus. Both men rode out of Milan with the newly-created “Army of Saint George” numbering ten thousand in October of 1365.

Battle between condottieri.

Battle between condottieri. (Public Domain)

Their destination was the lands of Siena, where they burned and looted for over twenty miles. They also torched Santa Colomba, Marmoraia, Buonconvento, Roccastrada, Berardenga, and the abbey of San Galgano. In addition, Hawkwood defeated a militia raised by Siena, captured its leader, and ransomed him for 10,000 florins. Later Hawkwood changed his mind and brought the ransom down to 500 florins. Hawkwood left the company of Saint George in 1366.

Bernabò and his wife, Beatrice

Bernabò and his wife, Beatrice (Public Domain)

Hawkwood served the duke of Milan again from 1368 to 1372 and then for the Pope from 1372-1377. Hawkwood’s service to the Pope was one of wealth and prestige, for the mercenary extorted a large sum of money from the raids he conducted on Tuscany, which resulted in about 130,000 florins in 1375.

An Ambassador by the name of Peruzzi wanted the people of Florence to rise up against this marauder, but they would not listen and instead gave Hawkwood an annual pension of 1,200 a year with no taxes attached. One can safely say that Hawkwood bled the bank nearly dry in Florence, sparking one of the most famous wars in Italian history, the “War of the Eight Saints.”

Hawkwood not only made more money and gained some lands in Romagna, but he was also unfortunately involved in the atrocity of killing civilian populations of Faenza and Cesena. Overall, the war allowed Hawkwood to take advantage of the Pope’s money. Florence had paid him an enormous amount of money and now the Pope had to pay up to show his support.

After the war, Hawkwood served the Republic of Florence in 1377, but not exclusively. His contract was to command an army of 800 lances and 500 archers for one year. Hawkwood and his men received a double payment each month, making Hawkwood’s share 3,200 florins every month, while each lance got 42 florins, and his archers received anywhere between 16 and 28 florins. Besides his annual pay, Hawkwood sold the entire city of Faenza for 50,000 or 60,000 florins. The mercenary from Essex was making money hand over fist.

Fresco of Italian soldiers from 1467.

Fresco of Italian soldiers from 1467. (Public Domain)

With all the wealth and prestige gained by his mixed bag of adventures, Hawkwood was presented another prize— Donnina Visconti, the illegitimate daughter of Bernabo, Duke of Milan. Bernabo gave Hawkwood even more in estates and money as well as gifts of jewelry. The wedding was just more than the union of two peoples in holy matrimony; it was a political union, in which Bernabo now had the most powerful man in Italy in his hip pocket through marital ties. Hawkwood was beyond rich for he owned lands throughout Italy, received a huge pension, along with the money he made by raiding and extorting the various provinces in Italy, including the Vatican.

Hawkwood continued his bold ways throughout Italy, for after the wedding he extorted money out of the Bolognese. He then attacked Faenze, the city that he had sold two months earlier!

In 1381, Hawkwood got a request to be King Richard II of England’s ambassador to the Roman court. However, one of his biggest victories came at the battle of Castagnaro in 1387, in which he showed why the use of longbow and dismounted knights in English fighting tactics won the day, but more than that, it was a series of battles that made Sir John Hawkwood a name to be remembered. Nevertheless, all good things must end, and for Hawkwood, so did life. At the height of his power and wealth, he died of a stroke in 1394.

Sir John Hawkwood, however you take him, was a king among mercenaries.

Featured image: Detail of Funerary Monument to Sir John Hawkwood by Paolo Uccello (1436). (CC BY-SA 3.0)

By Cam Rea


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