Knight Tales: The 9 Greatest Knights of the Middle Ages
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

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