History’s Most Notorious Knights

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Today we will be taking a look at some of the most notable and notorious knights from history.

Just for clarity, we know that knighthoods are still awarded regularly, but we will be sticking with the knights of the medieval variety — the ones with the swords and the armor. We’re also going with real knights, so no legendary figures, either.

10. Pierre Terrail

We start off with a man who embodied all the virtues that we associate with knights – chivalry, bravery, loyalty, nobility, and piety. Of course, most of the times, these qualities are a lot easier to find in the romanticized knights from fictional stories than the real ones, but they did seem to apply to Pierre Terrail, known as “le Bon Chevalier” or “the Good Knight.”

Born at Château Bayard in the south of France circa 1476, Terrail came from a noble family with a long history going back centuries of fighting for the king and dying with honor in battle. Unsurprisingly, this was the fate that Terrail envisioned for himself, as well.

The Good Knight took part in many battles and sieges, all of them during the Italian Wars of the late 15th – early 16th centuries. He first served as a man-at-arms in 1490 and was knighted five years later by King Charles VIII of France for his role at the Battle of Fornovo. His greatest feat came at the Battle of Garigliano where, according to legend, Terrail defended a bridge by himself by holding out against 200 Spanish soldiers.

Soon enough, thanks to his actions, Terrail was being hailed as le chevalier sans peur et sans reproche, meaning “the knight without fear and without reproach.” Noblemen, mercenaries, even the pope tried to entice him to their side, but Terrail showed no interest in betraying his king. He died from an arquebus shot at the Battle of the Sesia in 1524, while protecting the rearguard as his army was retreating. 

9. James Douglas

Born in 1286 in Scotland, James Douglas had some big shoes to fill. He was the eldest son of Sir William Douglas “the Hardy,” a nobleman and a staunch supporter of William Wallace. When the English invaded Scotland in 1296, William sent his son to Paris, both for safety and so he could train uninterrupted in the ways of a knight. The elder Douglas was captured in the war and subsequently died in the Tower of London.

When James Douglas returned home, he asked the English King Edward Longshanks to restore his family lands and titles, a request the king, unsurprisingly, refused. Therefore, Douglas allied himself with another famed fighting Scot, Robert the Bruce.

James Douglas had several notable fights during the War for Scottish Independence. He was present at the Battle of Bannockburn which was a crucial victory for Scotland, but more infamous was his fight to retake his own family seat, Douglas Castle. In 1307, on Palm Sunday before Easter, Douglas and his men hid in wait for the English soldiers to attend mass and charged them on the way to church. There was no mercy. All the English men who survived the attack or surrendered were taken to the castle cellar and beheaded, with their heads mounted on broken wine casks. The massacre itself became known as “the Douglas Larder,” while the knight was called “the Black Douglas” by the English for his ferocity.

8. Guy of Lusignan

Because we are talking about notorious knights, not the best knights, we should also mention Guy of Lusignan, a man who earned his fame through a failure which shaped the course of history.

He was born in the Duchy of Aquitaine circa 1150, the son of Hugh VIII of Lusignan. At some unknown time during the 1170s, Guy traveled to Jerusalem where he entered the patronage of King Baldwin IV, also known as “the Leper King” because, well, he had leprosy. Guy married the king’s sister, Sibylla. However, King Baldwin wasn’t really impressed with his new brother-in-law’s military skills so he named Sibylla’s young son from a previous marriage, Baldwin V, as his heir. The Leper King died in 1185 but, unfortunately for him, the young Baldwin also perished the following year and Guy of Lusignan became the new King of Jerusalem.

Soon afterwards, war broke out with the Ayyubid Dynasty led by Saladin. After the disastrous loss at the Battle of Hattin in 1187, Guy was taken prisoner and Jerusalem fell a few months later. After that came the Third Crusade, the one led by Richard the Lionheart, King of England, Holy Roman Emperor Frederick Barbarossa, and King Philip II of France. Guy himself was released and given sovereignty over Cyprus where he ruled for a couple of years more before dying without an heir.

7. John Hawkwood

Loyalty is a trait we value highly in knights, but the truth is that it was possible to become a successful and powerful knight without this particular quality thanks to mercenary work. A perfect example of this is Sir John Hawkwood, an Englishman who became Italy’s most renowned mercenary during the 14th century.

Details about his early life are scarce. He was born circa 1320, but we’re not even sure if his family was poor or rich. We know that he was knighted at one point because the inscription of a famous fresco dedicated to him in the Duomo in Florence reads “John Hawkwood, British knight, most prudent leader of his age, and most expert in the art of war.” 

While we are unsure of the exact circumstances, the knighthood had to come thanks to Hawkwood’s actions in the Hundred Years’ War. There, he joined an infamous mercenary band called the White Company and eventually became their leader. After the Treaty of Brétigny in 1360 marked a temporary peace between England and France, the White Company accepted orders from the pope to fight in Italy during the Western Schism. 

That would become Hawkwood’s role for the next 30 years. He was a condotierro, meaning the commander of a mercenary company. He fought for multiple factions, but his greatest victory is usually considered the Battle of Castagnaro from 1387, which he won for the city-state of Padua. 

6. Hugues de Payens

We now move on to a French knight whose life is very poorly documented. His name was Hugues de Payens or Payns, and he was born circa 1070 in the Champagne province. Even though we know so little about him, de Payens earned his place on this list by founding one of the most mysterious and controversial groups from medieval times, the Poor Fellow-Soldiers of Christ and of the Temple of Solomon, better known as the Knights Templar.

Sometime at the start of the 12th century, Hugh, Count of Champagne went on a pilgrimage to the Holy Land. Undoubtedly, Hugues de Payens and his other knights accompanied him. This was only a few years after the First Crusade. While it had been successful, most crusaders began heading home with their vows fulfilled, leaving pilgrims vulnerable to attacks. Seeing this, de Payens and a few other knights decided to stay behind to protect them and, with the approval of King Baldwin II of Jerusalem, formed the religious military order known as the Knights Templar, with Hugues de Payens serving as their first Grand Master.

The Templars quickly grew in power and wealth. They received donations from many European noblemen and were even granted special privileges by the pope. Since then, they have been associated with many legends, secrets, and conspiracies, becoming the default shadowy organization of the Middle Ages.

5. Roger Mortimer

If there is one knight whose exploits would make for an exciting movie, it would probably be Sir Roger Mortimer, 1st Earl of March. His life included war, intrigues, betrayals, romance, fights, a prison break, and was capped off by a violent death.

Mortimer was born in 1287 at Wigmore Castle into a powerful and influential family. He became a Marcher Lord like his father, meaning a nobleman who owned and protected lands located at the border between England and Wales. Alongside 266 other men, Roger Mortimer became a knight in 1306, at a unique event dubbed the Feast of the Swans where he and all the other knights swore fealty to the new King Edward II.


Over the next two decades, Mortimer’s loyalty to the king eroded thanks to the favoritism and privileges that the monarch afforded to another noble family called Despenser. Mortimer wasn’t the only one and, in 1321, he led a revolt against King Edward II known as the Despenser War. The king won and Mortimer barely escaped execution by being sentenced to life imprisonment in the Tower of London.

A month later, with outside help Mortimer managed to drug his guards, escape prison and flee to France. A few years later, the king’s wife Isabella, who was the sister of the King of France, traveled to her native country on a diplomatic mission. There, she met Mortimer and the two began an affair. They rallied strong support behind them and, in 1327, invaded England to depose Edward II.

They succeeded. Edward II was forced to abdicate, dying a few months later in prison under “suspicious circumstances,” which most likely means that Mortimer had him assassinated. The son, Edward III, was now king but, because he was underage, Roger Mortimer served as his regent, making him the de facto ruler of England. 

This only lasted for three years. Like many before him, Mortimer was corrupted by greed and power and, soon enough, all the other noblemen wanted him dead. When Edward III came of age, they persuaded him that the knight was a traitor, so Roger Mortimer was arrested, condemned and hanged. 

4. Edward of Woodstock

The Black Knight is a very popular stock character from medieval tales, one who usually plays the main villain of the story. Looking at his real counterparts, there were a few knights who shared this sobriquet, such as Sir James Stewart, the Black Knight of Lorn, but most notorious of all was Edward of Woodstock, aka the Black Prince.

Born in 1330, he was the eldest son of the aforementioned Edward III and heir to the throne of England. He joined his father in battle from an early age and received his knighthood during his first military campaign in Crécy in 1346, when he was just 16 years old.

Edward proved to have a keen military mind. He had multiple notable victories in the Hundred Years’ War against France, but none were more stunning than the Battle of Poitiers in 1356. The English led by the Blac Prince were outnumbered almost 2-to-1, but pulled off a decisive triumph where they sustained minimal casualties, and managed to take prisoner 2,000 enemy soldiers and almost 100 noblemen, including the King of France himself, John II, and his heir.

Everyone respected Edward’s combat prowess, including his enemies. He seemed destined to become one of England’s greatest kings, but this was not to be, as he died of dysentery before taking the throne.

As far as his moniker is concerned, it’s actually uncertain why Edward was called the Black Prince. He did have one giant black spot on his record. When the town of Limoges revolted against English control, he laid siege on it and massacred 3,000 civilians in anger. Therefore, the sobriquet came from the “blackness of his soul.” Recently-found documents, however, suggest that this massacre may have never actually happened, and that the nickname came from Edward’s black armor and heraldry that he used in jousting tournaments.

3. Suero de Quiñones

Speaking of Black Knights, there is a famous scene in Monty Python and the Holy Grail where King Arthur encounters a Black Knight guarding a tiny bridge, demanding that all who want to pass must fight him. Believe it or not, such a knight actually existed and his name was Suero de Quiñones.

Born in the Kingdom of León in the early 15th century, Suero de Quiñones and a group of nine other knights decided to block the bridge over the Orbigo River for 30 days in the summer of 1434, with their goal being to take on all challengers and “break” 300 lances. To accomplish this, the knights had to either literally break their opponents’ weapons, draw first blood, or knock them off their horses. 

This was done entirely with the approval of the king and knights from far and wide came to prove themselves and test their mettle. Dozens of tents were erected near the bridge for the fighters and their retinue and wooden platforms were built next to the bridge to accommodate a public audience. It was quite a spectacle, although it ended before Suero and his men “broke” 300 lances because they were too injured to continue.

Such an event was not as rare as you might expect. It was called a pas d’armes or “passage of arms.” It was one of the medieval combat games that knights took part in but, for some reason, it hasn’t really captured the imaginations of the modern public the way jousts and tournaments have.

2. El Cid

His real name was Rodrigo Diaz de Vivar, a minor nobleman born circa 1043 in the town of Vivar in the Kingdom of Castile. From there, he became a knight, and then a prince and, eventually, turned into one of Spain’s most celebrated heroes, known simply as El Cid.

From a very young age, Diaz impressed with his military acumen. When Sancho II came to power in Castile, he nominated Diaz as his standard-bearer and commander of his troops, even though he was still just 22 years old. However, when Sancho was assassinated in 1072, his brother Alfonso became King of Castile and Leon. He believed El Cid was way too popular with the people, so first he took away his position and, eventually, exiled him.

Diaz originally built his reputation by fighting the Moorish kings present on the Iberian Peninsula, or Al-Andalus as the Muslims called it. However, it was those same kings now who were interested in his services as they respected his skills. El Cid went to the court of Al-Mu’taman Billah, ruler of Zaragoza, and helped him fight against the Kingdom of Aragon. 

Meanwhile, King Alfonso’s lands were being threatened by an Almoravid invasion from Morocco. After suffering a crushing defeat at the Battle of Sagrajas in 1086, he wanted El Cid back. He gave the knight back his command, as well as the right to keep the lands he conquered. 

To that end, Diaz decided that he would conquer the Moorish Kingdom of Valencia and rule over it as an independent principality. It took him six years but, after a long siege, El Cid accomplished his goal and became Prince of Valencia in 1094. His kingdom only lasted for five years before the Almoravids laid siege themselves and El Cid died in 1099. However, it became an iconic moment in the 800-year period of Spanish history known as Reconquista. 

1. William Marshal

We end this list with William Marshal, a man who was suitably called “the greatest knight to be found in all the world.” What exactly did he do to earn such a reputation? Well, he was successful in jousts and tournaments, he served five different kings, he went on crusade, he became the de facto ruler of England on two separate occasions, he was a skilled fighter and diplomat, and he also helped draft the Magna Carta.

All of this almost never happened as Marshal had a close call when he was a young boy. Born circa 1146, he was the son of a minor nobleman named John Marshal. His father sided against King Stephen during a civil war known as The Anarchy. During a siege, the king took young William hostage and demanded that his father surrender his castle otherwise he would execute the boy. John Marshal pretty much told him to go ahead as he could make more sons but, fortunately for William, the king was not as cold-blooded as his father and spared him.

When he was around 12, William Marshal went to Normandy to live with one of his uncles and begin his training as a knight. When he turned 20, he participated in his first battle, earned his knighthood and also took part in his first tournament where his skill as a fighter became evident. Henry II was King of England at this time, and he appointed Marshal to be tutor-in-arms to his son and heir, Young King Henry.  

At one point, the Young Henry declared war on his father and on his brother, the future King Richard the Lionheart. Marshal joined him and, although he lost, he was considered too valuable to be punished. In fact, when Richard became king, he rewarded Marshal by marrying him to Isabel de Clare, one of the richest women in England, and then basically left him in charge of the country as Lord Protectorate while Richard was away on crusade.

This respect was also extended by King John who, on his deathbed, named Marshal regent and protector of his own heir, Henry III. Marshal’s crowning achievement was the negotiations between King John and the barons which ultimately led to the signing of the Magna Carta. The importance of his role is evident as his signature on the document is second, right after that of the king.


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