Knight Tales: The 9 Greatest Knights of the Middle Ages

Knight Tales: The 9 Greatest Knights of the Middle Ages

Alexander Meddings - September 4, 2017

The knight in shining armor and the damsel in distress are two of the Middle Age’s most enduring clichés. Through his strength, his devotion and his undying love, the knight finds a way to rescue his lady from peril, winning her heart and reinforcing his reputation as a great knight along the way. Such is the stuff of fantasy. But, since fantasy and history rarely go hand-in-hand, we should ask what historically constituted a great knight?

To be a knight, in the most basic sense, was to be a man of aristocratic standing, wealthy enough to fight as a heavy cavalryman when called upon, and initiated into a chivalric circle through having been “dubbed”. To be the perfect knight demanded more than that. Certain military attributes were required: being a brave and able fighter, willing to serve one’s liege honorably and loyally, and being a protector of the weak.

To achieve chivalric greatness, a knight also had to aspire to—and indeed realize—some more abstract ideas. Unfaltering religious piety was important. And while it was difficult when it came to Christian knights having to fight Christian knights, there were always various papal-sanctioned Crusades that provided an outlet. The best knights also participated in tournaments and jousts (and won them too, ideally) and engaged in the rituals of courtly love.

Despite the dozens of works defining what it meant to be the perfect knight, there was, in reality, no such thing; no one man could fill all these criteria. However, the Middle Ages were saturated with knights who can be considered great. Here are 9 of them.

Knight Tales: The 9 Greatest Knights of the Middle Ages
Contemporary illustration of the Battle of Poitiers. Geoffrey de Charny is depicted holding the Oriflamme of St. Denis (the red banner on the left). Wikipedia

Geoffrey de Charny (1300 – 1356)

When it comes to chivalric perfection, few ever came closer than Geoffrey de Charny. Even during his own lifetime, people were calling him “the true and perfect knight”, and his military achievements, unwavering loyalty to French crown and fighting prowess all marked him out for the title. However, there could be another reason he fits so well into the definition of the perfect knight: as the author of three works on what it meant to chivalric, it’s a definition he helped create.

Geoffrey de Charny—not to be confused with the Knight Templar of the same name who was burned at the stake in 1307—lived, and ultimately died, by the sword. After first seeing action in Gascony in 1337, he served a series of French kings fighting the English in Tornai, Brittany, and Calais. He also participated in a crusade against the Turks (though it was ultimately unsuccessful) led by Humbert II of Viennois in 1345. He suffered defeats during his career, but it was his victories he was recognized for, earning him his initiation into John the Good’s Order of the Star.

Geoffrey de Charny fought his last battle at the Battle of Poitiers between the English and the French in 1356. The battle is described in some detail by the French chronicler Froissart (who also gives us much of our information about the Black Death and the Hundred Years War in general). Charny had been entrusted as the standard-bearer of the red silken Oriflamme of St. Denis, the king’s sacred standard. Naturally, the standard was an effective rallying point; according to legend, Charlemagne had borne it to the Holy Land. It also inspired fierce fighting, as its very presence on the battlefield signaled that no quarter was to be given.

The Oriflamme was also, however, a valuable prize, and for this reason, often drew the heaviest—and bloodiest—of the fighting. So it was Poitiers, when its 55-year old bearer abandoned any hope of surrender (still an honorable option under the chivalric code) and fought to the death. Along with most of the flower French knights, Charny was ultimately cut down, completely surrounded by English soldiers, the Oriflamme still in his hand. In defining what made the perfect knight, Geoffrey de Charny had once written that “he who achieves more is more worthy.” Judging himself by his own standard, it’s hard to think of any worthier.

Knight Tales: The 9 Greatest Knights of the Middle Ages
Effigy of William Marshal. Get History

William Marshal (1147 – 1219)

Most of what we know about William Marshal comes from his biography, which was commissioned by his son and executors in the mid-1220s. He was born to very minor nobility, and after his father’s failed rebellion against King Stephen, the young William was given to the king as a hostage. Favored by Stephen, he eventually made his way into the house of William de Tancarville of Normandy. As a teenager, William developed a reputation as a lazy, self-indulgent glutton. But as he approached his twenties, he began to demonstrate his phenomenal fighting prowess.

He entered his first tournament (a very violent kind of mock battle) in 1166, coming up against fought against forty “finely-equipped” knights, including the King of Scotland and his retinue. Surpassing all expectations, the young William came out victorious. This furthered more than just his knightly reputation as a warrior as anything won during the tournament became the property of the victor. So although Marshal had begun the day as a relatively under-equipped warrior, by the end of he found himself in possession of four fine packhorses as well as a heap of weaponry and armor.

William Marshal also played a pivotal role in the politics of the time. He served under five Angevin kings. William knighted the first one, Henry II, himself. But despite their shared passion for all things chivalric, William soon found himself expelled from court, accused of seducing the young Henry’s wife. While in exile he fought in numerous tournaments and in the mid-1180s even embarked on a Crusade to the Holy Land, something we know remarkably little about other than that he linked up with the Order of the Knights Templar. Upon returning from the Crusade, the 40-year-old William married an 18-year-old heiress. It proved a successful, loving marriage, however, and established William as the Earl of Pembroke.

As well as being Earl of Pembroke, William was now also Regent of the Realm. He went on to fight in this capacity under Richard I (the Lionheart) who he had once almost killed in battle, and after Richard’s death under King John I. John was despised by the English barons, and after their rebellion was ultimately forced to sign the famous Magna Carta in 1215. But despite this, William remained loyal to him; so much so that John’s last words were allegedly about William’s unfailing, loyal service. William Marshal fought his last battle for Henry III against the English rebels and the French at the Battle of Lincoln in 1217. Aged 70, he led the charge himself and won the royal forces the battle. William, by this stage recognized as one of the greatest knights to have ever lived, died just two years later.

Knight Tales: The 9 Greatest Knights of the Middle Ages
Don Pero Niño carrying out a naval attack against the English.

Don Pero Niño (c. 1378 – 1453)

Most of what we know about Don Pero Niño comes from the mid-fifteenth century chronicle El Victorial. As a historical source, the chronicle is far from impartial. Written by Gutierre Diaz de Gamez—the man who was Pero Niño’s standard-bearer for almost 50 years—it portrays the Spanish privateer much in the mould of the great chivalric knight (and the previous man on this list) William Marshal, with its lengthy list of Pero Niño’s chivalric feats. But exaggerated or not, it tells us the story of a man who totally dedicated his life to warfare, and bore the scars to prove it.

Pero Niño was raised in the Spanish Royal Household and had his first experience of battle aged just 15. Over the course of his long career, he would fight against the Portuguese, the North African Muslims, and—for the most part—the English, carrying out constant raids along the south coast of England and Jersey. Although one of his weapons of choice was the crossbow, when not at sea, he would often show off his talents with the lance as a formidable jouster, earning such celebrity status that he managed to successfully woo the widow of a recently deceased admiral of France.

Even for the standards of the time, Don Pero Niño was as hard as nails. In 1403, while skirmishing near Tunis, he was wounded in the leg. His comrades carried him back to their ships, but he outright refused to abandon the expedition. The choice nearly cost him his life: by the time he and his men made it back to Spain his wound had began to fester. Carrying a high fever, Don Pero Niño was slipping in and out of consciousness, and the surgeons accepted that there was only one way they might save him: by amputating his leg.

Don Pero Niño, however, refused. Instead, he asked that they cauterized the wound, singing the flesh with a white-hot iron. The surgeon agreed, but at the last moment refused to perform the procedure, not wanting to inflict the degree of pain they knew it would cause. But Pero Niño, by now a master of inflicting and sustaining physical pain, grabbed the iron from him and applied it to himself, rubbing it up and down the length of his leg. He spent the later years of his life (apart from the brief interlude of being exiled) serving the Spanish monarchy, and died at a remarkably old age for a knight who had lived so rashly.

Knight Tales: The 9 Greatest Knights of the Middle Ages
Statue of El Cid “Campeador” in Burgos, Spain. Alchetron

El Cid (1040/43 – 1099)

Immortalized by Charlton Heston in the eponymous 1961 film, El Cid, whose real, quintessentially Spanish-sounding name was Rodrigo Diaz de Vivar, was born to minor nobility in the Castilian town of Vivar. He was raised at the court of King Ferdinand the Great and served as the standard-bearer to the prince, Sancho II of Castile and León.

By the time Sancho took over as king in 1065, Rodrigo had proven himself militarily. He was an exceptional individual fighter, according to legend defeating an Aragonese knight in single combat (from which he got the pseudonym El Campeador, meaning, in Spanish, the unsurpassed warrior). He was also a strategic genius, leading successful campaigns against Sancho’s brothers, García II of Galicia and Alfonso VI of León, as well as Muslim armies in Al-Andalus (once Muslim Spain).

In serving Sancho, however, Rodrigo backed the wrong horse. When the childless king was assassinated just seven years into his reign, the new king Alfonso VI forced Rodrigo—now related to the king through marriage—into exile at one of the earliest opportunities. Rodrigo first offered his services to the rulers of Barcelona, but they refused. So he traveled south, and having spent the first 40 or so years of his life fighting against the Moors, he then spent his latter years fighting largely with them (it was the Moors, in fact, who gave him the name El Cid, meaning “the Lord”).

He entered into the service of the Moorish King of Zaragoza, Yusuf al-Mu’taman ibn Hud, exercising his tactical and strategic genius in defending Zaragoza against their Spanish enemies, Barcelona and Aragon. Then, in 1086, Alfonso VI suffered a major defeat at the hands of the North African Almoravid armies. Realising he desperately needed an able general, he recalled Rodrigo from exile. Rather than becoming too involved, though, he sat back and watched the two sides wear each other down. This was because he had set his eyes on a bigger prize: the Kingdom of Valencia.

Rodrigo took Valencia in 1094 after a lengthy siege, and ruled essentially as a king, styling himself Alfonso VI. He died, either from famine or disease, during another siege of Valencia (one that had him in the role of defender) in 1099. Legend goes that his corpse was dressed in armor, mounted on a horse, and sent forth to lead the charge against the enemy; an assault that won the battle, but ultimately not the war. Whether true or not, it’s a testament to the loyalty that he commanded.

Knight Tales: The 9 Greatest Knights of the Middle Ages
The effigy of “the Black Prince” in Canterbury Cathedral.

Edward “The Black Prince” (1330 – 1376)

Born to royal parents, the warmongering English King Edward III and Philippa of Hainault, Edward Woodstock was always destined for military life. Aged just 16, he led the English against the French at the Battle of Crécy in 1346, winning a stunning victory. It was the Welsh longbowmen, in particular, who inflicted considerable damage on the heavily armored, yet heavily outgunned, French. Just ten years later, he fought again at the Battle of Poitiers (in which the French King John the Good was captured and the first knight on this list, his standard-bearer Geoffrey de Charny, was killed).

Historians dispute the origins of his epithet “the Black Prince“. It may have come from the color of his shield and armor, however, it may also have come from his reputation for brutality, particularly against the French at Aquitaine. One particular event marked him out: the massacre of 3,000 men, women, and children after the sack of Limoges in 1370. But while this was documented by the contemporary chronicler Jean Froissart, two other sources have come to light that cast doubt over Froissart’s claim; one saying that he just captured 200 men at arms, another that there were a total of 300 deaths during the sack of the city. It’s likely we’ll never know the truth.

Though still despised by the French, in the English tradition the Black Prince is often credited with upholding some of the best chivalric ideals, especially in the way he treated his captives with honor and dignity. But this was not always the case. In 1355 he launched one of his many chevauchée (mounted raids) across Languedoc in southern France. Attacks of this kind were not made for the purpose of fighting battles or consolidating positions, but to obtain plunder and ravage the lands. Even at the time, chevauchée were considered to be thoroughly unchivalrous as the people who suffered most in losing their lands, and indeed their lives were not knights but ordinary peasants.

Though becoming the founding member of the Order of the Garter (still in existence today) Edward’s greatness never translated into kingship. While campaigning to restore Don Pedro the Cruel to the Castilian throne in 1366—going by the name, one has to question Edward’s choice in candidate—Edward contracted what most people think was amoebic dysentery. His health went into sharp decline over the next ten years, and though he did manage at one stage to rise from his sickbed, don armor and defend Aquitaine against the French, he died in 1376 at the age of 45, just one year before his father. He is buried in Canterbury Cathedral, where his effigy is still open for visit by the public.

Knight Tales: The 9 Greatest Knights of the Middle Ages
Contemporary representation of Ulrich von Liechtenstein.

Ulrich von Liechtenstein (c. 1200 – 1275)

Anyone who’s seen the 2001 film “A Knight’s Tale” might remember the protagonist William Thatcher, played by the late, great Heath Ledger, taking on the name of Ulrich von Liechtenstein when he assumes a knight’s identity and starts entering into jousts. Despite the cameo appearance of several historical figures, particularly the English poet and composer of “The Canterbury Tales”, Geoffrey Chaucer, the film is neither historical nor autobiographical. However, in introducing even a fictional von Liechtenstein into a story that revolves around love, jousting, and chivalric honour, it pays fitting tribute to the real figure.

Ulrich von Liechtenstein was born into an aristocratic family in Styria, modern-day Austria. He received his accolade—the shoulder tap with a sword or, more traditionally, a rather hard strike across the face that conferred knighthood—at the betrothal ceremony of the Duke of Austria’s daughter. He then served as an administrator in his home duchy of Liechtenstein. Like all knights of the age he saw battle, fighting for Philip of Sponheim, the Archbishop of Salzburg, who had been deposed by Pope Alexander IV. The opposing forces met in 1252 at the Battle of Sachsenburg, and Philip’s forces won a decisive victory, with Ulrich being one of the seven men charged with mediating the ensuing peace.

Rather than his knightly career, it was through being one of the Minnesänger, a group of German nobles renowned for composing verse poetry, that he is better remembered. He wrote three works in High Middle German dispensing advice for how a knight should live by the chivalric code and, more famously, how to win over a lady through noble deeds His first work, the Frauendienst (Service of the Lady) is often regarded as autobiographical, and essentially outlines how in the guises of various legendary figures he roamed the lands breaking lances and winning jousts in order to please his lady and bring her honour.

Winning jousts alone wasn’t enough for his demanding damsel, however, and the indignities von Lichtenstein had to suffer were so extreme that we have to question how much of what we’re told was true. At one stage he had to dress as a leper; at another he had to endure being urinated on by a night watchman as he lay in wait outside his lady’s castle. Despite being physically unattractive (he had a hare lip, we are told) he did finally win her around by signing up to an event guaranteed to impress any medieval lady of high renown: a Crusade.

Knight Tales: The 9 Greatest Knights of the Middle Ages
Effigy of Bertrand du Guesclin in Paris’s Basilica of St. Denis. Wikipedia

Bertrand du Guesclin (1320 – 1380)

He may be an obscure figure to those who are unfamiliar with medieval French history (which I suspect would be most of us), but Bertrand du Guesclin was one of France’s greatest ever warriors and the finest knight of his age. Born into minor Breton nobility, Bertrand entered his first tournament in the nearby town of Renne aged just 17. Short of stature and physically rather ugly, upon his arrival he was mercilessly mocked by the other knights at the tournament and barred from entering. He did, however, manage to enter the jousts in disguise, and achieved the amazing feat of unhorsing 15 well-trained, fully armored knights in the day’s events.

Bertrand was destined for greater things than winning tournaments though. As an active knight throughout the Hundred Years War, he took part in many battles. He won a great number of them, most notably at Cocherel in 1364 against the French pretender to the throne Charles of Navarre, and against the English at Limoges in 1370. That was the same year, in fact, that Bertrand was granted the most prestigious military title in the realm: Constable of France. His leadership during the Hundred Years War consisted of exercising effective hit-and-run tactics, avoiding engaging the English in many pitched battles.

In 1357 Bertrand participated in one of the most fundamentally chivalric acts of personal prowess there was: a duel. When Thomas of Canterbury took Bertrand’s brother captive after attacking his hometown of Dinan, Bertrand in his rage challenged him to a duel. Thomas accepted and the two men donned armour and lances and mounted their horses. They fought on horseback, first with lances and then with swords, until Thomas was disarmed. Bertrand then dismounted his horse, killed Thomas’s from under him, and while the English knight was lying on the ground Bertrand punched him squarely in the face with his iron gauntlet, thus ending the duel.

Bertrand spent his final years leading smaller military campaigns against the old English enemy. As a man who had committed his life to warfare, it was almost fitting that he died on campaign, succumbing to an unknown illness while his forces were besieging the town of Chateauneuf-de-Randon. Testament to the high regard his contemporaries held him in, Bertrand du Guesclin was buried among the tombs of the French royalty in Paris’s Basilica of St Denis.

Knight Tales: The 9 Greatest Knights of the Middle Ages
Baldwin II ceding the Temple of Solomon to Hugues de Paynes and Godfrey de Saint-Omer. Wikipedia

Hugues de Payens (c. 1070 – 1136)

Remarkably little is known about Hugues de Payens, and for this reason alone it’s controversial to count him as one of history’s greatest knights. But it is less for his life than his legacy that Hugues de Payens is best remembered: for along with his close friend Saint Bernard of Clairvaux, Hugues co-founded, and was the First Grand Master of, the Order of the Knights Templar in 1128.

Regarding his early life, we know only that he came from either the Champagne or Burgundy regions of France and that after Pope Urban II’s incendiary speech that launched the First Crusade in 1095, he joined other European nobles on the journey to the Holy Land. We don’t know whether he was in one of the splinter groups that launched vicious pogroms against the Jews in the Rhineland in 1096, or whether he traveled directly to the Holy Land via Byzantium. We do know, however, that he was there for the fall of Jerusalem in 1099 and that he stuck around in the aftermath.

Hugues’s Order of the Templars were essentially seen as militia christi: Christ’s militia. They are the first historical example of doctrinally driven military Christianity. And it is the religiously sanctioned element that explains much of their appeal, for the idea of fighting against those branded enemies by the church provided an outlet for the excess military energies of the European knightly class who for years had been told that shedding Christian blood would send them to hell.

Hugues de Payens probably died in Palestine in 1136. We don’t know the cause of death, but the Templars would commemorate him on the 24th of every month on the assumption that he died of old age. His Order went on to have a long and turbulent history. Abandoning its absolute dedication to piety and poverty, it became an order of bankers—the first and foremost financial powerhouse in the Holy Land— with a vast network of monasteries stretching all across Europe.

It was common practice for banks to lend money to kings. Where the Templars made the mistake was lending money to a king who couldn’t repay his loan. Drowning in debt, the French King Philip IV conspired to have the Templars crushed, and on the fateful night of Friday 13th, 1307 he had them arrested, interrogated and, ultimately, sentenced. This marked the end of the Order, with many members burned at the stake including their leader, Jacques de Molay (from which we get the word “immolation”).

Knight Tales: The 9 Greatest Knights of the Middle Ages
Fresco of John Hawkwood in Florence’s “Duomo”. Pinterest

John Hawkwood (c. 1323 – 1394)

Little is known about the origins of this formidable fighter. Nobody knows, for example, where, when or by whom he was knighted, though some suggest he received the accolade from the Black Prince after the Battle of Poitiers in 1356. What we do know about Hawkwood comes from the period shortly following the battle. He was the leader of the famous White Company: a band of men at arms that left France when the Anglo-French War came to a temporary halt and the work ran out in 1360. After a short stint of plundering the Papal enclave in Avignon, they made their way to Italy. There, their commander entered into the role of a condottiero, a ruthlessly efficient mercenary willing to fight for the highest bidder.

Hawkwood fought first for Pisa against the Florentines before shifting allegiance to Pope Gregory XI in the War of the Eight Saints (1375). Things soon turned ugly, however, and after being coerced into carrying out the massacre of civilians in Cesena in 1377 he switched sides, allying himself with Milan, Florence, and their allies. His greatest victory came at the Battle of Castagnaro in 1387. In command of a Paduan army, he managed to completely outflank the Veronese by hiding his cavalry in a nearby wood. His last few years were spent fighting for the Florentines against the Milanese.

For foreign adventurers, Italy was a playground in which they could earn their fame and fortune through endless fighting opportunities. Few exploited this more effectively than John Hawkwood. But for normal Italians, these foreign adventurers were a scourge. We are told that John Hawkwood was once greeted at the gates of the Italian city of Montecchio by two clergymen. They wished him peace, to which he replied: “Do you know that I live by war and that peace would be my undoing?” It’s easy to see how, with such a moral code, many wouldn’t have seen him as a chivalrous knight, but as a bandit.

John Hawkwood died in Florence in 1394. He was buried in the Basilica Santa Maria del Fiore (known more commonly today as “the Duomo”. But the Florentines, eternally grateful to the man who had once been their general, did not stop there. To commemorate his memory, the Florentine Republic commissioned the artist Paolo Uccello to design a fresco of him. The fresco was placed inside the Duomo. And it remains there to this day, gawked at by masses of tourists every day. Not bad for an obscure English knight.


Sources For Further Reading:

Classic of Strategy and Diplomacy – Geoffroi de Charny, The Book of Chivalry

BBC – William Marshal: A combination of ‘Muhammad Ali and Kissinger’

Queen Mary University – The Crusades and The Medieval Knight William Marshal, Changing Perception and Stimulating Engagement

History Channel – Chivalry Was Established to Keep Thuggish, Medieval Knights in Check

History Net – The Genius of El Cid

Camino Del Cid – Biography Of El Cid: Life and Facts

Historic UK – Edward the Black Prince

Medievalists – John Hawkwood: Florentine Hero and Faithful Englishman