Medieval art is a treasure trove of weird trends that make you wonder what medieval minds were really thinking. From bizarre animal antics to odd theological mishaps, the period from AD 1000 to 1500 produced a parade of illustrations that still raise eyebrows today.

Weird Trends in Medieval Art

10 Murderous Rabbits

Monks tasked with creating illuminated manuscripts filled their holy books with gorgeous foliage, intricate lettering, and—occasionally—rabbits swinging clubs at unsuspecting humans. These murderous bunnies appear in countless margins, charging knights, hacking women, and even wielding axes, all with no connection to the surrounding text.

The prevailing theory is that bored monks doodled these scenes for a laugh, imagining a rabbit uprising against its hunters. One monk scolded his peers for the waste of ink, writing, “Good Lord, even if the foolishness of it all occasions no shame, at least one might balk at the expense.”

9 Cats Licking Their Butts

Long before the internet, medieval artists were already obsessed with feline anatomy—specifically, the moment a cat bends over to lick its own posterior. Sketches range from realistic depictions to contorted circles ensuring the tongue reaches the target.

These cat‑butt illustrations even made their way into religious scenes. One monk added a bored cat licking its rear to a depiction of Christ’s resurrection, proving that even sacred moments weren’t safe from this quirky fascination.

8 Women Riding Aristotle Like A Pony

For a brief spell bridging the medieval period and the early Renaissance, artists loved drawing the philosopher Aristotle on his knees while a woman rode him like a horse. Some images add a bridle, a whip, or even a full‑body nude, turning the scene into a rather explicit tableau.

The motif stems from a medieval story about Alexander the Great’s wife tricking Aristotle into a humiliating ride. Teachers used the tale to warn against female seduction, illustrating the moral that lustful impulses must be resisted.

7 Knights Fighting Snails

One of the most puzzling marginal doodles shows armored knights charging heroic battles against slow‑moving snails. Scholars have proposed allegorical readings—social struggle, mortality, discrimination—but the simplest explanation may be sheer boredom.

When monks spent endless hours copying texts, they apparently let their imaginations run wild, turning the battlefield into a surreal snail‑vs‑knight showdown.

6 Moses With Horns On His Head

For centuries, artists rendered Moses with literal horns sprouting from his scalp—a detail that seems demonic at first glance. The confusion stems from the Hebrew word keren, which can mean “ray of light” or “horn.” A mistranslation turned a shining face into a horned one.

Even Michelangelo followed the horned convention, suggesting that many medieval creators genuinely believed Moses possessed horns, or at least found the visual striking enough to repeat.

5 Mary Magdalene Covered In Body Hair

Gothic painters gave Mary Magdalene a shaggy makeover, covering her from neck down in thick body hair. The legend says that after renouncing worldly comforts, her robes fell away and hair miraculously grew over her body, turning her into a goat‑like figure.

Artists treated this miraculous hair as a visual shorthand for her ascetic transformation, resulting in a striking, if somewhat unsettling, portrayal.

4 Bored People Dying

Violent medieval scenes often feature victims who look inexplicably bored, even as they meet gruesome ends—being trampled, skinned, or sliced. This odd expression ties to the concept of Ars moriendi, the art of dying well.

According to the doctrine, a serene, even apathetic, demeanor at death signaled spiritual readiness, whereas panic suggested moral failing. Alternatively, artists may simply have struggled with facial expressions.

3 People Flying Spaceships

Some medieval panels depict tiny rockets or saucer‑like objects soaring above biblical scenes, especially those featuring Christ. One theory posits these are symbolic “alien” representations of divine presence.

A woodcut by Hans Glaser even claims to show a sky battle of flying saucers over Nuremberg, lending credence to the more out‑there explanation that medieval artists were chronicling extraterrestrial encounters.

2 Demons With Faces On Their Crotches

Medieval demonology art often gave monsters grotesque faces right on their genital regions. These crotch‑faces sometimes spewed fire, reinforcing the theme of sexual temptation and moral corruption.

The placement served as a visual warning: the true face of evil hides where lust dwells, making the demons’ anatomy a moral lesson as much as a frightful image.

1 Things Sticking Out Of People’s Butts

When monks weren’t drawing murderous beasts or crotch demons, they sometimes filled manuscript margins with people sporting objects in their rear ends. The most common motif features a trumpet—or other brass instrument—being thrust into a naked figure’s backside.

Variations include floral patterns, mooning figures, and arrows aimed at buttocks. While scholars search for symbolic meaning, the simplest answer is that medieval humor loved a good butt‑related gag, proving that fart jokes truly are timeless.

The late medieval period was a chaotic time in history. England and France were engaged in the Hundred Years’ War, and Italian city‑states were fighting one another for supremacy in the peninsula. In the absence of permanent standing armies, combatants relied on mercenary companies to do the fighting for them. The temporary peace brought about by the Treaty of Bretigny in 1360 unleashed thousands of unemployed men‑at‑arms looking to pillage to sustain themselves. Many coalesced around charismatic and intrepid leaders into what became known as “free companies.” In Italy, they were known as condottieri. This word is derived from condotta, meaning “contract,” the instrument by which they put themselves in the service of the highest bidder. These soldiers of fortune were the late medieval version of Mafia bosses, making their living with murder, extortion, and terror.

Why These 10 Swashbuckling Mercenaries Matter

Each of the ten figures below earned a reputation for ruthless efficiency, flamboyant bravado, and a willingness to switch sides for the right price. Their stories illuminate the chaotic world of medieval warfare and the shadowy economy of hired swords.

10 Roger de Flor

Roger de Flor was born in the then‑Catalonian province of Brindisi, Italy in 1267. As a boy he went out to sea and eventually became a Knight Templar. He took advantage of the Muslim capture of Acre in 1291 by robbing the refugees, and when his activities were exposed, he was expelled from the Templars. Fleeing to Genoa, he became commander of a force of Spanish mercenaries called Almogavares. Their name was derived from the Arab al‑mogauar, meaning “one who devastates,” and they were the descendants of the Iberians who accompanied Hannibal into Italy. In the seventh and eighth centuries they engaged in guerrilla operations against the Muslim invaders of Spain.

In 1303 the Byzantines recruited Roger, who was then in the service of the king of Aragon, to help fight the Ottoman Turks who had just wrested Bithynia from the Empire. In Constantinople Roger married a niece of Emperor Andronicus II Palaeologus and was made a grand duke. With 1,500 knights and 4,000 Almogavares called the Catalan Company, Roger won battles against the Turks, but he also pillaged and looted the Byzantine inhabitants of Anatolia in what is now Turkey. This led the authorities to denounce him as nothing better than a brigand, but success swelled his ego and he began dreaming of carving his own dominion in Anatolia.

Emperor Michael IX became convinced that Roger and his undisciplined Almogavares must be destroyed. In 1305 Roger was lured to Adrianople for a banquet hosted by Michael. There he was ambushed by another mercenary force and killed, along with 130 of his men. The remnants of the Catalan Company ravaged the countryside in revenge before settling in Greece and founding the Duchy of Athens in 1311.

9 Bascot de Mauleon

Bascot de Mauleon was captain of a group that marched into Burgundy with freebooters of various nationalities. Mauleon had his first experience of battle at Poitiers. Later he went to Prussia with the Count of Foix, crushing the peasant rebellion of the Jacquerie upon his return to France.

Mauleon estimated that about 12,000 men rode with him in the Loire region. This formidable force seized the castle of Brignais from the king and defeated the constable of France, amassing such wealth in ransoms and booty that the pope in Avignon feared for his safety.

Technically Mauleon fought for the king of England, but as an independent freebooter his main interest was money. Before he made it to the big time, Mauleon remembered, “Sometimes I have been so thoroughly down that I hadn’t even a horse to ride, and at other times fairly rich, as luck came and went.” His rags‑to‑riches tale was recorded by the French chronicler Froissart, who met him at a hostel in the Pyrenees. Froissart recalled, “He arrived with plenty of followers and baggage… He had as many pack horses with him as any great baron, and he and his people took their meals off silver plate.” Not a bad lifestyle for a highwayman.

8 Duke Werner von Urslingen

Taking upon himself the title of “Duke,” Werner von Urslingen stitched onto his doublet the motto “the enemy of pity, of mercy, and of God,” and lived up to it in the most horrific ways possible. Werner’s modus operandi was invading peaceful regions and robbing, raping, and killing the inhabitants before torching their property. He trumpeted his atrocities to authorities and threatened more unless he was paid, extorting vast sums from Siena, Perugia, Florence, and Bologna. In 1339 Werner and his band were denounced as “a plague of society.”

Werner founded the Great Company in 1342. At its height it numbered 6,000 men, mainly armored cavalry. He imposed strict discipline and a code of laws upon his men, including equal division of income. Later mercenary armies sought to model themselves after the powerful Great Company.

In 1347 Werner supported Queen Joanna I of Naples, sister‑in‑law of King Louis I of Hungary, after Louis invaded Naples to avenge his brother’s murder. Werner helped Joanna return to Naples and defended her against the opposing condottiere. On Joanna’s behalf Werner attacked the baronage of Meleto, raking in half a million florins’ worth of booty. Eventually both Werner and Wolfart were bought off, and Werner returned to Germany with his loot.

7 Conrad Of Landau

The German Conrad of Landau took command of the Great Company in 1354, operating in Tuscany, Umbria, the Romagna, and Lombardy. He held entire cities for ransom and reaped massive profits. As Conrad bluntly told a papal legate before invading church lands, “It is our custom to rob, sack, and pillage whoever resists. Our income is derived from the funds of the provinces we invade; he who values his life pays for peace and quiet from us at a steep price.”

On one occasion Conrad was ambushed by the Florentines on his way to Siena to fight Perugia. He was unhorsed and wounded, his force routed, and angry locals looted the remnants of the Company. It was a temporary setback, but Conrad continued to rake in vast revenues, enabling his father in Germany to buy back the family castle and lands lost to debt.

The Great Company was eventually hired by the Visconti rulers of Milan to drive away the rival White Company of Albert Sterz. In 1363 the two companies met at Canturino. Conrad held his line until his Hungarian contingents refused to fight fellow Hungarians in the opposing army. Their desertion tipped the scales to the White Company, and Conrad was killed in the ensuing battle.

6 Albert Sterz

The most infamous brigand group of all is the White Company, founded by the German Albert Sterz. It got its name from the white surcoats worn by its troops and the white banners they flew. Under Sterz, the Company was unmatched in efficiency. Its 3,500 horsemen and 2,000 infantry were impeccably organized and well equipped. Engineers even laid mines and built scaling ladders and siege towers within its ranks.

In 1360 Sterz moved the Company to Italy, the fertile field of constantly warring city‑states. Along the way he recruited an English knight named John Hawkwood, who swiftly rose through the ranks because of his negotiating skill. Sterz soon regretted his decision. Hawkwood’s men impressed him, deposed Sterz and gave command to the Englishman. The jealous Sterz sulked, biding his time for payback.

The Company drew up a contract with Pisa to attack rival Florence. The city was prepared, and Hawkwood’s attack stalled. Sterz seized his moment, switched sides, and carried his loyal men over to the Florentines. The White Company disintegrated, leaving Hawkwood with only 800 men. After the war Sterz merged the remnants with the German condottiere Hannekin Baumgarten, forming the Company of the Star, which enabled Sterz to crush Hawkwood.

5 Alberico de Barbiano

Alberico de Barbiano, a native of Cotignola in Romagna, began his career as a captain in the service of Milan. Later he was employed by Florence, Venice, Naples, and the papacy. Alberico’s most infamous moment came in 1377, when he participated in the horrific Massacre of Cesena, a town not far from his home, as captain of the forces under Cardinal Robert of Geneva (later anti‑pope Clement VII). Ordered by Pope Gregory XI to subdue the rebellious towns of Romagna, Cardinal Robert employed Breton mercenaries, “the most cruel and bestial seed of France.” Even after the townspeople surrendered their weapons, the inhabitants of Cesena were slaughtered in a three‑day bloodbath, their corpses left to be devoured by dogs.

In 1378 Alberico formed the Company of St. George, composed entirely of Italians who swore “hatred and eternal enmity” toward all foreigners. He turned against Clement VII and defeated his Breton force on behalf of Pope Urban VI, who proclaimed Italy “free of barbarians.” Yet the anti‑foreigner sentiment was empty bombast. After expelling the Bretons, Alberico began plundering Tuscan towns. His new band, the Company of the Hook, included Germans, Hungarians, and perhaps inevitably, Bretons.

At the close of the 14th century Alberico fought in wars between Florence and Milan, switching sides as it pleased him. He served Naples in the twilight of his career and died in 1409. Alberico is credited with military innovations such as improved armor and aggressive cavalry charges. His practice of recruiting troops from his own Romagnan feudatories, creating greater cohesion, is seen by some as a precursor to the eventual unification of Italy in the 19th century.

4 Muzio And Francesco Sforza

Muzio Attendolo was the first prominent member of the family that would later rule Milan. He hailed from Cotignola in Romagna and served under Alberico de Barbiano before striking out on his own. Alberico dubbed him Sforza, meaning “force,” and as an independent condottiere he made it his nom de guerre.

In 1398 Muzio entered the service of the Visconti rulers of Milan but soon departed to fight for Florence and then Ferrara. By 1412 Naples secured his services, and Muzio became constable of the kingdom. He endured a roller‑coaster career during the chaotic reign of Queen Joanna II, alternating between rewards of lands and offices and periods of imprisonment and torture. In 1424 Muzio drowned in a river while campaigning against a fellow condottiere.

Like a medieval Michael Corleone, Muzio’s son Francesco took up his father’s mantle and became the most successful mercenary captain of the 15th century. Francesco served the Visconti against Venice, then Venice against the Visconti, attacked the pope, then defended him. To bind Francesco permanently to Milan, Duke Filippo Visconti married him to his only daughter in 1441. Expecting to inherit the dukedom, Francesco was thwarted when Milan declared a republic. He besieged Milan and seized the title by force in 1450 – the Sforza name was earned.

3 Rodrigo de Villandrando

Many mercenaries were not averse to robbing their own employers. This was the case with Rodrigo de Villandrando, one of the greatest mercenaries of his era. Rodrigo was born in Castile in 1380. Seeking a military career he traveled to France and first joined the mercenary army of Amaury de Severac and the Burgundians.

Rodrigo formed his own mercenary company in 1420 and offered his services to the French Dauphin Charles. He extorted money from the cities and estates of Languedoc and pillaged the countryside, all within Charles’ realm. When Charles ordered him to attack the English, Rodrigo refused and instead went to Toulouse, recruiting more men. He eventually attacked English‑held Bordeaux and was pardoned by Charles. In a later battle at Anthon his 400 men defeated the Burgundians; one enemy soldier hid in a hollow tree, only to be crushed by his own armor. The tree was cut down in 1672, revealing his skeleton.

At his peak Rodrigo commanded 10,000 men, exacting ransoms from nobles and demanding “protection money” from locals who wished to avoid murder and pillage. His violent forays in Gascony earned him the title “Emperor of Pillagers.” Enriched, he retired in the 1440s, returned to Castile, willed his wealth to a monastery, and died in 1457.

2 Arnaud de Cervole

Born into a minor noble Gascon family, Arnaud de Cervole was the archpriest of Vélines in the diocese of Périgueux. Being a man of God didn’t stop him from mixing with brigands and men of base extraction. Deprived of his benefice by the bishop of Bordeaux, he turned to full‑time brigandage, specializing in stealing castles. At one point Arnaud and his band seized three castles in Angoulême as security until their employer paid their wages. The French crown charged him with theft when he took over a castle in Normandy, though he was then in the service of King Jean II.

After Jean II’s capture at Poitiers, Arnaud lost his patron and turned to pillaging, establishing a protection racket in the wealthy, peaceful region of Provence. He approached Avignon, terrifying the pope into a shakedown. Froissart records, “He entered Avignon with most of his followers by friendly agreement, and was received with as much respect as if he had been the king of France’s son, and dined several times with the pope and the cardinals. All his sins were remitted and when he left he was given 40,000 crowns (20,000 gold florins) to distribute among his companions.”

Shifting operations to Burgundy, Arnaud seized castle after castle until the count bought him off for 2,500 gold francs. In 1365 Pope Urban V recruited Arnaud to lead a crusade against the Turks, but the true aim was to move the freebooters away from the Rhône. Arnaud’s army reached Lyon but refused to march on. Unfed and unpaid, his men quarreled with him, which ended in his murder.

1 Sir John Hawkwood

Despite leading the murderous White Company, Sir John Hawkwood died a fairly rich man and was even honored by an equestrian fresco in the Florence Cathedral. The memorial was a personal affront to Victorian author Ferdinand Gregorovius, who lamented, “Florence, who denied Dante a resting place, erected a noble monument to a robber.”

Born to a minor Essex landowner, Hawkwood left for France to fight for Edward III at age 18. He was knighted for his role in the English victory at Poitiers, but after the Treaty of Bretigny he was left a poor knight without a job. He joined the Free Companies to support himself.

As a soldier of the king Hawkwood was an unknown, but as a freelancer he achieved astounding success. Seeking his fortune in the medieval snake pit of Italy, he became leader of the White Company, which terrorized Italy and earned a reputation as “perfidious and most wicked.” The only consolation was that “they did not mutilate or roast their victims like the Hungarians.” The locals called Hawkwood’s force “devils in human shape.”

Over the next thirty years Hawkwood’s business of murder, pillage, and blackmail prospered. His fighting skill was coveted by the pope, Florence, Milan, Pisa, and Perugia. Because his loyalty was only to money, he betrayed each client when a juicier offer appeared. Florins flowed so freely into his coffers that he rivaled banks and trading houses. The White Company employed lawyers and notaries to keep records of bribes and ransoms, accountants and secretaries to divide the plunder, and brokers to sell each soldier’s share.

Hawkwood became so influential that he arranged the marriage of Edward’s third son, Lionel, to the daughter of the Duke of Milan. He himself married the duke’s 17‑year‑old daughter when he was 57. Florence offered the richest rewards, and he ended his days as a general of the Florentines, instrumental in creating their republic. When he died in 1394, he was remembered as “the ablest military commander of the Middle Ages.”

By modern standards, legal systems in medieval Europe were unfair and weak. The 10 bizarre legal cases we examine reveal how trials by ordeal, torture, and brutal punishments were once accepted as reliable ways to determine guilt or innocence.

1. The Leprosy Scare Trials

In medieval times, leprosy was believed to be extremely contagious. Fear of the disease led Europeans to isolate lepers, branding them both unclean and suspicious. The stigma turned lepers into easy targets for blame and persecution.

In the spring of 1321, a rumor spread across southern France that lepers were conspiring to poison wells and unleash a nationwide leprosy epidemic. Supposedly, once the population was infected, the lepers would overthrow the government and seize control of the kingdom. Brutal interrogations of the accused also implicated Jews and a Muslim ruler in the imagined plot.

Although the whole story was fabricated, King Philip V ordered every leper in the realm to be arrested and tried for treason. Hysterical mobs murdered countless lepers without consequence, while those who faced formal trials were tortured and burned at the stake. By the end of the year, thousands had perished. It was not until 1338 that the Avignon Pope publicly declared the lepers innocent.

Tristan Shaw keeps a blog called Bizarre and Grotesque, where he writes about folklore, paranormal phenomena, and unsolved crime.

2. Joan Of Arc

Nearly everyone knows Joan of Arc’s infamous 1431 trial and execution, but fewer are aware of her posthumous retrial more than two decades later. The original proceeding listed seventy accusations, later narrowed to twelve, and ended with her being burned as a heretic.

In 1450, the French king ordered an investigation into the fairness of Joan’s trial. The inquiry uncovered numerous procedural flaws, especially the heavy English influence in Rouen, which was under English control at the time, rendering the original trial deeply biased.

By 1455, Pope Calixtus III authorized a new trial. After eight months of deliberation, the court declared all twelve original charges fraudulent, effectively exonerating Joan of the heresy accusation and restoring her reputation.

3. Girolamo Savonarola

In late‑15th‑century Florence, Dominican preacher Girolamo Savonarola wielded extraordinary influence, openly challenging both the civic government and the Catholic hierarchy while claiming prophetic insight.

Excommunicated in 1497, Savonarola faced a dramatic “trial by fire” in 1498, proposed by rival Francesco da Puglia. The premise: if Savonarola could walk through flames unharmed, it would prove divine favor and invalidate the papal ban.

The spectacle collapsed when a sudden thunderstorm extinguished the flames. The debacle led to Savonarola’s arrest, forced confession of false prophecy under torture, and eventual execution by hanging alongside two supporters.

4. John Rykener

John Rykener, a 14th‑century Londoner, led a double life as a male playboy and a female‑clothed prostitute known as Eleanor. His secret was uncovered in December 1395 when city officials caught him in a street stall with a client.

The client, unaware of John’s biological sex, reported the encounter. John admitted to cross‑dressing and revealed an extensive list of male patrons, including aristocratic scholars, chaplains, friars, and even priests.

He also boasted of sleeping with nuns for free while presenting as a man. The historical record does not reveal John’s ultimate fate, though it is likely he faced a sodomy conviction.

5. Stadelin Of Boltigen

Stadelin, a Swiss farmer from Boltigen between 1392 and 1406, became the target of witchcraft accusations after a bountiful harvest sparked rumors that he used sorcery to steal crops from neighboring fields and manipulate the weather.

Villagers also claimed he caused a local woman to miscarry seven times. Under torture, Stadelin confessed to consorting with demons, who summoned thunderstorms whenever he tossed a black chicken into the air. He blamed a buried lizard for the woman’s infertility.

Stadelin further implicated his wife as a witch and advised authorities not to trust her denials. Both were burned at the stake for their confessions.

6. Count Gero Of Alsleben

Trial by combat, a relic of Germanic custom, sometimes settled disputes in medieval Europe, even pitting monasteries or spouses against each other. In 979, the Holy Roman Empire arranged a duel between Count Gero of Alsleben and a Saxon named Waldo.

The exact grievance remains unclear, but Waldo brought a charge that led to Gero’s arrest. During the fight, Gero slashed Waldo’s neck, yet Waldo struck Gero’s head, winning the duel.

In a bizarre twist, Waldo collapsed and died immediately after his victory. Nonetheless, judges declared the dead man the winner, and Emperor Otto II ordered Gero’s execution by decapitation.

7. Pope Formosus

In January 897, Pope Stephen VI convened a post‑mortem trial against his predecessor Pope Formosus, who had died nine months earlier. Stephen exhumed Formosus’s corpse, propped it on a chair, and charged him with perjury, ambition for the papacy, and violations of canon law.

The dead pope was found guilty; his papacy was declared null, his appointments void, and his fingers were severed. Formosus’s body was then dumped into the Tiber River.

Public outrage forced a second trial later that year, which restored Formosus’s reputation and granted his remains an honorable burial.

8. Pandonus

Anti‑Jewish sentiment permeated medieval Europe, restricting Jews from many professions, imposing distinctive clothing, and barring them from public office or marriage to Christians.

In 14th‑century Avignon, a Jewish man named Pandonus was accused of adultery after having relations with a Christian woman. Although he confessed, jurist Oldradus de Ponte argued that without a marriage, the act could not be classified as adultery.

Two judges disagreed; one ordered Pandonus’s castration, displaying his genitals on the royal palace doors as a warning to mixed couples.

9. Rolandino Ronchaia

Rolandino Ronchaia, a 14th‑century Venetian hermaphrodite, was born with a penis yet developed full breasts and a strikingly feminine appearance. He married a woman, but the marriage dissolved because he could not achieve an erection.

After his wife left, Ronchaia moved into a relative’s house in Padua. A guest, attracted to his feminine features, made a sexual advance, prompting Ronchaia to adopt a female identity, rename himself Rolandina, and work as a prostitute.

His clientele, unaware of his biological sex, swelled until city authorities intervened. Charged with sodomy, Ronchaia was sentenced to be burned alive despite officials acknowledging his intersex condition.

10. Rose De Savage

On a chilly January morning in 1280, Rose de Savage was abducted while en route to church. John de Clifford, leader of the kidnappers, took her to his home, forced her to undress, raped her, and then locked her in an upper‑story bedroom.

Rose endured 21 months of captivity until, on St. Martin’s Day in November 1282, she escaped by leaping from a window. A trial for “rape and breach of the king’s peace” was soon convened against de Clifford.

Clifford denied the accusations, and oddly, Rose herself was imprisoned for failing to provide precise dates of the assault. Although a jury eventually found Clifford guilty, he escaped severe punishment, paying only a fine.

10 Bizarre Legal Context

The cases above illustrate the astonishingly strange and often brutal legal practices that defined medieval Europe’s quest for justice.

When you think of the Middle Ages, the image of a looming, very real Devil haunting everyday life instantly pops up. To medieval Europeans, the Devil wasn’t a distant metaphor but a palpable threat, constantly whispering promises of eternal damnation. Every sermon, every market rumor reminded folk that Hell was a very real destination, and that the Dark One would stop at nothing to drag a soul down into the abyss. These ten medieval tales capture the most chilling, cunning, and sometimes downright witty encounters between saints, villagers, and the Prince of Darkness.

10 Medieval Tales Overview

10. The Devil And The Jumping Boys

In the English hamlet of Marston Moretaine stands a solitary monolith that locals call the Devil’s Stone. Its origins have been lost to the ages, but a colourful folk tale explains the ominous name. The village church is oddly split: its bell tower sits a short distance away from the nave. Legend says the Devil, for reasons no one can quite pin down, tried to haul the tower away. Finding it too massive, he dropped it where it now rests.

Frustrated by his failed theft, the Devil scouted the surrounding fields for fresh entertainment and spotted three boys leaping over a stone in a game of leap‑frog. Since the day was the Sabbath, such games were forbidden, and the Devil decided to enforce his own twisted justice.

He challenged the boys to jump over him while he perched upon the stone. Eager to prove their daring, each boy vaulted over the Devil in turn, never pausing to see how the others fared. Unbeknownst to them, a yawning chasm yawned just beyond the stone, a portal straight to Hell. One by one, the boys vanished into the darkness.

Old maps later recorded the nearby settlement as “The Three Jumps,” a grim reminder of the reckless leaps that sent three youngsters spiralling into the netherworld.

9. St. Anthony vs. The Devil

Born into wealth, St. Anthony abandoned his comfortable life to retreat into the Egyptian desert, seeking a life of austere contemplation. The Devil, ever the relentless adversary, wasn’t about to let the hermit slip away unscathed.

First, the Devil assailed Anthony with the sins of sloth, ennui, and seductive visions of beautiful women, hoping to erode his resolve. Anthony answered each assault with deeper, more fervent prayer. When mental temptations failed, the Dark One escalated to physical violence, sending a horde of lesser demons to batter the saint until he collapsed unconscious.

Friends rescued the weakened holy man, nursing him back to health before he returned to his solitary desert cell. Undeterred, the Devil unleashed swarms of ghastly beasts—phantom wolves, snarling lions, and other nightmarish creatures—intending to frighten Anthony into abandoning his solitude. Yet the saint simply laughed, declaring, “If any of you possess authority over me, a single one would suffice to defeat you.”

8. Jack O’Kent

Folklore often warns that bargaining with the Devil is a fool’s errand, but Jack O’Kent, a roving magician, seemed to outwit the Prince of Darkness at every turn. In one infamous episode, Jack promised the Devil a share of his swine herd. To split the spoils, they agreed to divide the pigs by tail type: Jack kept the curly‑tailed ones, while the Devil took the straight‑tailed stock.

When the Devil arrived to claim his portion, Jack had already led the pigs through a cold stream, twisting every tail into a curl. The Devil’s expected prize turned into a tangled mess, leaving him empty‑handed. In another tale, the Devil demanded half of Jack’s wheat harvest. Jack handed over the lower half of the grain, keeping the prime portion for himself. Infuriated, the Devil demanded the top half of the next year’s crop, but Jack simply planted turnips, depriving the Devil of any wheat to claim.

After a string of humiliations, the Devil vowed to drag Jack straight to Hell, declaring he would take him “whether he was buried inside or outside the church.” Jack’s final trick was to have his remains bricked into a church wall, leaving him in a liminal space—neither inside nor outside—thus thwarting the Devil’s claim.

7. Transporting Gerard

Sir Gerard, a knight devoted to Saint Thomas, was famed for granting any request made in the saint’s name. Even though his generosity was saintly, the Devil was granted permission by God to test him, mirroring the trials of Job.

The Devil arrived disguised as a beggar, pleading for a cloak in Saint Thomas’s honor. Gerard, ever charitable, handed over his own fine cloak without hesitation. As soon as the beggar slipped the garment on, both vanished, leaving Gerard’s bewildered wife scolding him for parting with such an expensive piece of clothing.

Rather than lose faith in his patron saint, Gerard calmly reassured his wife: “Fear not; Saint Thomas will surely restore what we have lost.” The historical record does not preserve his wife’s retort, but the story underscores Gerard’s unwavering trust in divine providence.

6. St. Benedict And The Thorn Bush

Born into wealth, St. Benedict renounced his comfortable life to seek solitude in a remote cave, laying the foundations of Western monasticism. The Devil, unwilling to let him escape, launched a series of attacks.

First, the Devil took the form of a blackbird, buzzing annoyingly close to Benedict’s face. Benedict, unfazed, sent the bird away with a benediction, showing his spiritual authority. Next, the Devil transformed into a stunning lady, appealing to Benedict’s lingering human desires. The vision was so captivating that Benedict nearly abandoned his cave to pursue the temptress.

Instead of succumbing, Benedict hurled himself into a thorn bush, rolling amid the bristles to mortify his flesh. The painful self‑flagellation proved more effective than any cold shower, and the Devil’s temptations fell flat. Benedict emerged victorious, later revered as the father of Western monasticism.

5. St. Catherine Of Siena

St. Catherine, one of the Catholic Church’s Doctors, married Christ through a life of intense devotion, refusing the marriage arrangements her family prepared. The Devil, intent on derailing her sanctity, bombarded her with grotesque visions and lewd hallucinations that persisted for days, cutting off her communication with God.

Eventually, Catherine’s steadfast prayers dispelled the demonic onslaught. She later dictated dialogues she experienced with God during ecstatic states. In one such conversation, God explained the purpose of temptation: “I have placed the Devil in this world to test and harass My creatures, not to defeat them, but so they may conquer, proving their virtue and receiving My glory.”

While this theological reassurance offers little comfort to those condemned to eternal fire, it underscores the medieval belief that overcoming the Devil’s assaults was a path to divine triumph.

4. The Devil And The Painter Monk

Medieval churches often featured vivid frescoes to teach illiterate congregants, with “Doom” paintings depicting the Last Judgment. One monk, a skilled sculptor‑painter at the Auxerre abbey, was tasked with filling a blank wall left untouched due to a shortage of artisans.

He painted glorious scenes of Christ, the Virgin, and heavenly bliss with masterful detail. When it came time to illustrate Hell, he rendered the Devil as hideously monstrous, letting his imagination run wild. The Devil, affronted by this unflattering portrait, appeared to the monk and suggested that a handsome, charismatic adversary would have been more appropriate.

Unwilling to compromise his artistic integrity, the monk stood by his gruesome depiction. Infuriated, the Devil knocked the monk from his ladder, nearly ending his life. Only the Virgin’s intercession saved him, reinforcing the belief that steadfast faith could shield even the most daring artists from demonic retribution.

3. St. Wolfgang And The Devil’s Church

St. Wolfgang set out to build a church, using a simple method to choose the site: he climbed a mountain, hurled an axe, and let it fall where it landed. Satisfied with the spot, he realized he needed help with construction.

The Devil materialized, offering his labor on one condition: he would claim the soul of the first living being to cross the church’s threshold. Wolfgang, perhaps naïve, agreed. The finished edifice bore an unmistakable irregularity—its lines were crooked, betraying infernal craftsmanship.

Wolfgang soon feared the bargain’s price. At that moment, hunters chased a wolf that barreled straight into the open door. Wolfgang flung it inside, pointing out that the Devil’s prize was now a wolf, not a human. The Devil, bound by his own terms, accepted the beast, sparing the saint’s soul.

2. Bridge Building

Wolfgang’s clever loophole is a recurring motif in Devil‑pact folklore. Across Europe, numerous bridges are said to have been erected by the Devil himself, each with a twisty clause attached.

Villagers, desperate to span treacherous rivers or ravines, summoned the Devil for assistance. He agreed, demanding the soul of the first creature to cross the new bridge. The locals obliged, then sent an animal—be it a dog, goat, or chicken—across, ensuring the Devil received a non‑human soul and fled empty‑handed.

Variations abound: in some stories, the Devil seeks the architect’s soul. When the builder tricks him, the Devil sabotages the bridge, stealing any replacement stone and leaving a perpetual gap. These legends highlight the cunning required to outwit a demonic contractor.

1. St. Dunstan

St. Dunstan, once an adviser to an Anglo‑Saxon king, faced accusations of witchcraft and was exiled from court. He retreated to a hermitage, surviving as a harpist and blacksmith. The Devil, ever the opportunist, tried to corrupt his simple life.

While forging a horseshoe, the Devil appeared as a young woman, dancing seductively to lure Dunstan into sin. He ignored her, continuing his work. The Devil intensified his performance, lifting his skirts to reveal cloven hooves beneath.

Seizing the moment, Dunstan clamped the Devil’s nose with red‑hot tongs, forcing the demon to flee. He then hammered iron shoes onto the Devil’s hooves, binding the creature to a promise never to trouble him again. Legend says the sulfuric waters of Tunbridge Wells were tainted when the Devil quenched his scorched nose, and the tradition of hanging a horseshoe above a doorway to ward off evil stems from this very encounter.

These ten medieval tales demonstrate how ordinary people and holy figures alike wrestled with the Devil’s wiles, using wit, faith, and a dash of daring to survive the darkness.

Medieval Europe was a violent place where ruthless kings ruled with iron fists. Among the many tools of power, 10 daring assassinations stood out as shocking, brutal, and sometimes ingeniously clever ways to remove a tyrant or political rival.

10 Daring Assassinations That Shocked Medieval Europe

10 Duke Conan II Of Brittany

In 1065, William of Normandy was preparing to invade England. To secure his borders, he proposed alliances with the surrounding lords. However, Duke Conan II of Brittany hated the Normans because he believed they had poisoned his father. Conan refused to ally with William and strongly implied that he would attack Normandy as soon as the army left for England.

This turned out to be a bit of a mistake since William quickly had Conan poisoned as well. According to Orderic Vitalis, William had to be clever about it since the Breton would obviously have been careful to avoid the same fate as his father. So instead of targeting Conan’s food, William’s assassin smeared poison on Conan’s riding gloves. While out riding, Conan wiped his mouth with the back of one glove and soon suffered a fit and died.

9 Kenneth II Of Scotland

Kenneth II was assassinated in AD 995. The death is primarily notable for the absolutely insane story of the booby trap that did it. According to John of Fordun, the princes Constantine and Gryme persuaded a noblewoman named Finnguala to do the deed. Since Kenneth had killed her son, she was happy to oblige.

Finnguala rigged up her house with multiple crossbows hidden behind tapestries. The crossbows were connected by strings to a statue in the middle of the room. Finnguala then invited the king to inspect the statue. As soon as he touched it, the crossbows went off, firing a dozen arrows through him at once.

We can say for sure that Kenneth was killed in AD 995 and that Constantine and Gryme were blamed. However, most historians are skeptical of a crazy crossbow statue as the murder weapon.

8 Louis, Duke Of Orleans

Charles VI of France was insane. (Among other things, he believed that he was made of glass and might shatter at any moment.) This prompted his nobles to struggle among themselves for power.

The immediate winner was the king’s brother, Louis of Orleans, who seduced the queen and effectively became regent. Louis was opposed by John the Fearless of Burgundy, who even tried to kidnap the king’s son. In response, Louis may have tried to rape John’s wife.

Things came to a head on November 23, 1407. Louis was leaving the queen’s house in Paris when he was attacked by a gang of eight hooded men. An eyewitness said that they struck Louis repeatedly “as if they were beating a mattress” until his brains were all over the road. John didn’t even try to deny ordering the murder, insisting that it was “for the good of the realm.”

7 John The Fearless

The murder of Louis of Orleans sparked a civil war between his Armagnac supporters and John the Fearless of Burgundy. This was the last thing France needed because it was the middle of the Hundred Years War and the English were invading.

In 1419, the two sides agreed to meet to resolve their differences in a special enclosure in the middle of the Montereau Bridge. However, as soon as John the Fearless arrived, three old friends of Louis of Orleans pulled out swords and killed him in revenge.

Although the Armagnacs insisted that the murder was not premeditated, John’s son Philip allied with the English, changing the tide of the war. It was later joked that the English entered France through the hole in John’s skull.

6 Peter The Inquisitor

In the 13th century, the Catholic Church was campaigning against the Cathars, a heretical sect that believed in two gods, one good and one evil. The Albigensian Crusade had devastated the Cathar stronghold in southern France, while the Inquisition was established to hunt them throughout Europe.

One of the best inquisitors was Peter of Verona, who was known for his humble lifestyle and was unusually successful at persuading Cathars to rejoin Catholicism. As a result, the Cathar underground in Milan gathered funds and hired a pair of hit men. The killers tracked Peter to a lonely spot on the road, where they jumped him and put an axe through his head.

Peter was immediately declared a saint, and Pope Innocent IV released a bull allowing Inquisitors to use torture for the first time. Interestingly, one of the hit men, Carino of Balsamo, later repented and is now considered something of a holy man.

5 Philip De Montfort

Philip de Montfort had an interesting family history. His father and uncle were leaders of the Albigensian Crusade, while his cousin Simon was the lover of Queen Isabella of England. The couple eventually overthrew and murdered Isabella’s husband, Edward II.

Philip was Crusader Lord of Tyre. His talented leadership alarmed the Egyptian Sultan Baibars, who asked the notorious Hashishin (“Assassins”) to take care of the problem.

A Syrian Assassin was sent to Tyre, where he successfully disguised himself as a Christian and prayed daily at Philip’s church. Once the Assassin was a familiar face, he wandered up behind Philip while he was kneeling at prayer and stabbed him in the back. Baibars attacked the Crusader states a few months later.

4 Godfred Of Denmark

Godfred was king of Denmark around AD 800 when the famous Frankish Emperor Charlemagne dominated Europe. Charlemagne had conquered the pagan Saxons and forcibly converted them to Christianity, which was quite alarming to the pagan Godfred. In anticipation of a confrontation, he greatly expanded the Danevirke, a mighty series of earthen fortifications in southern Denmark.

When the Baltic city of Reric allied with Charlemagne, Godfred attacked and destroyed it. In 810, his fleets ravaged Frisia and Godfred began to talk of reconquering Saxony. According to Frankish chroniclers, Godfred boasted that he would stable his horses in Charlemagne’s palace. Furious, the emperor began building a fleet of his own.

It seemed that everything was set for a huge war between the Franks and Vikings until Godfred was suddenly stabbed to death by one of his own warriors. Many historians have suggested that the murder was ordered by Charlemagne, who presumably found assassins cheaper than fleets.

3 Godfred Of Frisia

Murdering Danes named Godfred seemed to run in the family because Charlemagne’s grandson Charles the Fat did the same thing. Charles had named a Viking called Godfred as the Duke of Frisia. In return, Godfred agreed to stop raiding Frankish lands and to keep other Vikings from doing the same.

Unfortunately, Godfred got greedy. Frisia was poor land, so Godfred demanded that Charles give him some rich, wine‑producing areas along the Rhine. This attempt at extortion seriously annoyed the Franks. They invited Godfred to discuss the issue on an island in the Rhine. To Godfred’s surprise, the previously meek Franks showed up armed to the teeth and hacked him to death.

2 Harthacnut

It’s often forgotten now, but the Norman invasion of William the Conqueror was actually the second time that England had been conquered in 50 years. Cnut (aka Canute) of Denmark made himself king of England in 1018. After his death, the throne eventually passed to his son Harthacnut.

Edward the Confessor was the son of the overthrown Anglo‑Saxon king of England. Thanks to some complicated family politics, he was also Harthacnut’s half‑brother. (They shared a mother.) If Harthacnut died, Edward was in line for the throne. As luck would have it, Harthacnut did die after suffering a mysterious fit at a banquet at age 25.

So what’s suspicious about that? Well, after Edward took the throne, the rebellious Earl Godwin of Wessex also died after suffering a mysterious fit while eating dinner with the king. Meanwhile, Edward’s half‑brother dropped dead days after returning to England from exile in Kiev. Which starts to seem a little suspicious, really.

1 Pedro The Cruel

Pedro the Cruel was not a nice guy. As king of Castile, he was accused of numerous crimes. This included the murder of his brother Fadrique, who was dining with Pedro when a guard walked up behind Fadrique and hit him with a mace. When Pedro noticed that Fadrique was still moving, Pedro gave a knife to a page to finish the job while Pedro continued eating.

Fadrique’s twin, Enrique, soon rose in revolt and besieged Pedro in his castle. Enrique was supported by the famous French knight Bertrand du Guesclin. Bertrand had a reputation as a bit of a weasel, so Pedro offered him a bribe to help him escape. Since Bertrand was actually a huge weasel, he accepted and then informed Enrique, who agreed to match the bribe if Bertrand handed Pedro over.

On March 23, 1369, Bertrand helped Pedro sneak out of the castle and led him to a tent. To Pedro’s surprise, Enrique was waiting for him. The Spanish princes immediately started throwing insults, calling each other “son of a whore” and “son of a Jew.” Then they started wrestling. Pedro was winning until someone pulled him off and sat on him while Enrique stabbed him in the stomach.

When you think of the medieval era, you might picture chivalry and castles, but the reality was often far messier. In fact, the continent was peppered with a handful of particularly audacious scoundrels. These 10 notorious rogues left a trail of terror, loot, and legend across Europe, proving that lawlessness could be as organized as any royal army.

Why These 10 Notorious Rogues Matter

Each of these villains exploited the cracks in feudal authority, turning chaos into personal empire. Their stories reveal how mercenary bands, pirate crews, and renegade nobles could rival kings, and why their names still echo in the annals of history.

10 Seguin De Badefol

Seguin de Badefol first surfaces in the chronicles as a hired sword for King John II of France. After the French king suffered defeat at the hands of the Black Prince at Poitiers, a peace treaty forced the dismissal of the royal mercenaries, leaving men of war without pay.

Rather than disperse, the bands simply morphed into marauding gangs. Badefol commanded the Margot, a formidable troupe that could muster up to two thousand men. His signature extortion scheme involved seizing a town, then demanding a hefty “leave‑our‑city” fee from its inhabitants.

When the crown finally sent an army in 1362, Badefol cleverly united the scattered companies into a single “Great Company” and crushed the royal force at the Battle of Brignais. The victory gave him free reign over eastern France, and his reign ended four years later when a poisoned quince, intended as tribute from the ruthless Charles “the Bad” of Navarre, claimed his life.

9 Geoffrey Of Mandeville

After King Henry I died without a male heir, the English throne became contested between his daughter, Empress Matilda, and Stephen of Blois. The resulting civil war—known as the Anarchy—left law and order in tatters across the realm.

Amid the turmoil, Geoffrey of Mandeville, a noble from East Anglia, rose to notoriety. Stephen initially rewarded him with the earldom of Essex for his support, but Geoffrey quickly switched sides, accepting Matilda’s promise of near‑unlimited authority over Essex. He later defected back to Stephen, trading his new lands for control of Middlesex and Hertfordshire.In 1143, Stephen attempted to curb Geoffrey’s ambitions, but the earl fled into the marshy fens of East Anglia, establishing a fortified base on the Isle of Ely. From there he launched raids, burning villages and terrorizing the countryside until an arrow struck him during a minor skirmish in 1144, ending his violent career.

8 Robert Fitz Hubert

During the Anarchy, King Stephen bolstered his forces with Flemish sellswords, a group that quickly earned a reputation for cruelty. Among them, the ferocious Robert Fitz Hubert stood out as perhaps the most brutal.

Robert arrived on English soil in 1139, but instead of entering Stephen’s service, he immediately seized Malmesbury Castle for himself. After Stephen expelled him, the mercenary turned to Matilda, offering his band for hire.

Not content with short‑term contracts, Robert slipped away from Matilda’s army and, in a daring nocturnal assault, captured Devizes Castle. He then summoned additional Flemish knights and embarked on a campaign to carve out a petty kingdom between Winchester and London. His ambitions were thwarted when John the Marshal tricked him into a false surrender, only to slam the castle gate shut as Robert entered, leading to his execution by hanging.

7 Eustace The Monk

At the height of his notoriety, Eustace the Monk was whispered about as a sorcerer‑like figure. Originally a monk, he fell from grace, was declared an outlaw, and fled to the English Channel where he became the era’s most infamous pirate.

Eustace proved a master of naval warfare, earning the attention of King John of England, who hired his fleet to wrest the Channel Islands from French control. Using the isle of Sark as a base, he raided the Norman coast and even ventured down the Seine for daring plunders.

In 1212, Eustace switched allegiance to the French, but his fleet met a brutal English counter‑attack in 1217. The English sailors hurled quicklime onto the enemy vessels, blinding crews and forcing a chaotic melee. Eustace was discovered hiding in the bilge of his own ship and was beheaded, condemned as “a traitor to the king and a most wicked pirate.”

6 Owain Red Hand

Owain Lawgoch, known as the “Red Hand,” was the last male‑line descendant of the ancient Welsh kings of Gwynedd and a celebrated warrior of the fourteenth century. Determined to reclaim his ancestral throne, he launched two separate invasions that sent shockwaves through England.

The first fleet was thwarted by a violent storm that prevented a landing, while the second expedition was diverted to aid the French king. When not attempting to seize Wales, Owain fought for France during the Hundred Years’ War, leading a company of Welsh mercenaries against Pedro the Cruel of Castile.

In 1375, he headed the Guglers—an immense mercenary army that marched into Switzerland—only to be ambushed in a night attack by enraged Swiss citizens. His life ended in 1378 when an English undercover agent assassinated him, ending the last hope of a Welsh royal resurgence.

5 Roger De Flor

Roger de Flor began his career as a member of the Knights Templar, but his disgraceful conduct during the Siege of Acre—where he commandeered a Templar galley and extorted exorbitant fees from civilians fleeing to Cyprus—earned him expulsion from the order.

After a stint as a pirate, Roger seized an opportunity when the king of Aragon dismissed thousands of soldiers following a peace treaty in 1302. He recruited roughly six thousand hardened fighters into a mercenary force known as the Catalan Company and secured a lucrative contract with the Byzantine emperor.

The Catalans achieved modest success against the Turks but quickly turned to looting Byzantine lands and clashing with imperial troops. Roger’s ambitions grew as he plotted to carve out his own kingdom in Anatolia. The Byzantines, branding him a bandit, assassinated him in 1305, ending his turbulent quest for power.

4 The Catalan Company

After Roger de Flor’s murder, the Byzantine Empire dispatched an army to eradicate his mercenaries. Though outnumbered, the veteran Catalan Company turned the tables, crushing the imperial forces at the Battle of Apros in 1305.

Following a rather feeble attempt to blockade Constantinople, the Company crossed into Greece, where the Duke of Athens recognized the threat they posed. He cleverly offered to hire the Catalans, hoping to redirect their ferocity.

The mercenaries seized extensive territories for the duke, but payment never arrived. In a bid to split the Company, the duke promised full wages and land to 500 Catalans who would turn against their comrades. Those 500 accepted the bribe, yet instead of betraying the rest, they secured their own share and delivered a stunning victory over the duke’s larger army, establishing a petty kingdom in Greece that endured for eight decades.

3 Adam The Leper

Mid‑fourteenth‑century England endured a wave of urban crime so severe that even the Black Prince’s servants were once ambushed, beaten, and robbed while buying food. The most infamous gang leader of this era was Adam the Leper, whose crew habitually targeted royal officials and wealthy merchants.

Adam’s most daring caper involved learning that Queen Philippa had entrusted a local merchant with a cache of valuable jewelry. The leper’s band surrounded the merchant’s house, demanding the jewels be handed over.

The merchant, refusing to surrender, fought back fiercely, repelling several assaults. Frustrated, Adam set the building ablaze, forcing the terrified merchant and his family to scramble for escape. In the chaos, Adam’s men held the flames at bay, compelling the merchant to surrender the precious gems. Remarkably, historical records suggest Adam escaped any punishment for this audacious theft.

2 Momcilo

Hajduk Momcilo rose from humble beginnings to become a feared Bulgarian brigand, commanding a personal army of peasants in the rugged Rhodope Mountains. Though he briefly served Stefan Dušan of Serbia, Momcilo truly came into his own during the Byzantine Civil War of 1341‑1347.

His reputation for backstabbing is legendary: he switched allegiances three consecutive years—1343, 1344, and 1345—playing both sides of the conflict to cement his own power in the contested borderlands.

Momcilo’s growing influence alarmed both the Byzantines and the emerging Ottoman Turks, prompting a joint assault on his stronghold at Peritheorion. Anticipating the tide turning against him, the city’s inhabitants locked his forces out of the gates, leading to his defeat and death at the hands of his own adversaries.

1 The Archpriest

Arnaud de Cervole, known as the Archpriest of Velines, abandoned clerical life for the chaotic world of mercenary warfare. After the Battle of Poitiers, he quickly realized that the weakened French crown could no longer contain the roaming bands of soldiers‑for‑hire.

He assembled the first “Great Company,” leading his troops into Provence, a region that had largely escaped the war’s devastation. Within months, his forces turned the once‑peaceful province into a scorched wasteland, even laying siege to Marseille with a force of three thousand men—though the city managed to hold out.

In 1358, the Archpriest cemented his notoriety by effectively holding the Pope hostage: he surrounded the Papal seat in Avignon and demanded a ransom of twenty‑thousand florins to withdraw his men. After extracting the payment, he returned to conventional mercenary work, joining the royal army that later suffered defeat at the Battle of Brignais at the hands of Seguin de Badefol’s raiders.

By 1365, Arnaud was hired to lead a crusade against the Turks—a venture whose true purpose was to remove his unruly band from French soil. During a heated dispute over supplies, he was stabbed to death, ending the career of one of medieval Europe’s most infamous mercenary leaders.

When you think of medieval Europe, you probably picture pious monks, towering cathedrals, and a strict code of chastity. Yet the continent was also a hotbed of lurid love affairs, secret trysts, and outright scandal. In this roundup we tally the 10 sex scandals that shocked medieval Europe, each more eyebrow‑raising than the last.

10 Abelard And Heloise

Why This Is One Of The 10 Sex Scandals That Shocked Medieval Europe

In the early 1100s, Peter Abelard rose to fame as the most celebrated philosopher and teacher across the continent. Crowds thronged his lectures, and wealthy students paid handsomely for his tutoring. The scandal erupted when Abelard began a clandestine liaison with one of his brightest pupils, the stunning and intellectually formidable Heloise.

Heloise happened to be the niece of Fulbert, a canon of Notre‑Dame and Abelard’s landlord. When Fulbert uncovered the affair, he demanded that the couple wed. Neither party was enthusiastic, but they consented on the condition that the marriage remain hidden. After Heloise gave birth to a son they named Astrolabe, Fulbert publicly disclosed the union, only for Heloise to deny it outright, inflaming Fulbert’s fury.

Abelard fled with Heloise to a remote convent for safety, an act that only deepened Fulbert’s wrath. In 1117 a band of men burst into Abelard’s chambers and viciously castrated him. Remarkably, Abelard survived, entered monastic life, and maintained a lifelong correspondence with Heloise.

9 Katherina Hetzeldorfer

During the late 1400s, a young, unmarried individual arrived in the German city of Speyer and quickly earned a reputation as a libertine, assaulting women and indulging in numerous affairs throughout the carnival season. The town paid little heed—until 1477, when the perpetrator’s true identity was revealed: a woman named Katherina Hetzeldorfer.

Trial records disclose that Katherina fashioned a prosthetic phallus “half as big as an arm…with a red piece of leather, at the front filled with cotton, and a wooden stick stuck into it.” She used this contraption to engage in intercourse with several women, all of whom testified that they were unaware of the deception. One of Katherina’s lovers, Else Muter, even swore that the device apparently produced “semen…beyond measure.”

Katherina met a grim fate when she was drowned in a local river. The court, recognizing that her partners had been duped, sentenced them to exile rather than death, sparing them the ultimate penalty.

8 The Swedish King And His Sister‑In‑Law

Princess Jutta, daughter of King Eric IV of Denmark, was originally consigned to a cloister, expected to live out her days as a nun. Defying expectations, she escaped to Sweden, where her sister Sophia welcomed her. Sophia’s husband, King Valdemar of Sweden, soon embarked on a passionate affair with the newly arrived Jutta, even fathering a child with her.

The scandal erupted across Sweden as rumors swirled that the king had been unfaithful to his queen with her own sister. In an attempt to atone, Valdemar embarked on a pilgrimage to Rome, seeking papal forgiveness. The Pope, however, levied a hefty fine, turning the pilgrimage into a financial burden for the Swedish populace.

The public outrage over the extra taxation, combined with the scandalous affair, led to Valdemar’s swift overthrow by his brothers, ending his turbulent reign.

7 The Naughty Nuns Of Littlemore

In 1517, a bishop inspected Littlemore Priory in Oxfordshire, England, and uncovered a series of scandalous behaviors among its inhabitants. The nuns were reported to “romp and play with boys in the cloister,” a conduct that shocked ecclesiastical authorities.

Even the prioress was implicated, having borne an illegitimate daughter with a priest from Kent. To provide for her offspring, the prioress allegedly pilfered valuable items from the convent—selling candlesticks, basins, shetts, pelouses, and even feather‑filled beds to fund a dowry.

The nuns showed little remorse. When one sister was placed in the stocks as punishment, three other nuns broke down the door, liberated their companion, set fire to the stocks, and escaped through a window, demonstrating bold defiance.

Ultimately, the scandal could not be ignored. Cardinal Wolsey ordered the dissolution of Littlemore Priory, bringing an end to its notorious reputation.

6 The Pervy Pope

John XII ascended to the papacy at the tender age of eighteen, thanks to the influence of his powerful family. He quickly demonstrated a preference for sensual pursuits over spiritual duties, transforming the papal palace into something resembling a brothel. Monks in the vicinity reportedly stopped praying for his health, instead begging him to die.

The scandal quickly spread throughout Europe. The Holy Roman Emperor dispatched a warning, accusing the Pope of homicide, perjury, sacrilege, and incest with several female relatives, including two sisters.

John XII met his end in 964 while allegedly making love with a woman named Stefanetta. Some accounts claim he suffered a stroke from the exertion; others suggest Stefanetta’s jealous husband burst into the chamber and hurled the Pope out a window, ending his notorious reign.

5 William The Conqueror

Today, William I of England is best remembered as William the Conqueror. In his own lifetime, however, he was often derisively called “William the Bastard” or “William the Tanner,” a reference to his birth from a teenage liaison between Duke Robert of Normandy and a tanner’s daughter from Falaise.

Although Robert had no other sons and William was later legitimized, the stigma of his origins haunted him. When he besieged Alençon, townsfolk dangled animal skins from the walls, chanting, “Hides, hides for the tanner! Plenty of work for the tanner!” In fury, William retaliated by catapulting severed hands at the crowd.

William’s descendants seemed to take the joke in stride. Henry II, while stitching a torn glove, recalled a bishop’s remark that he resembled his Falaise relatives, prompting Henry to burst into uncontrollable laughter.

4 The Demon‑Kings Of England

Henry II’s lineage carried a darker reputation. While his mother was William the Conqueror’s granddaughter, his father, Geoffrey Plantagenet, Count of Anjou, hailed from a family rumored to be descended from demons. Legend tells of an early count who wed the enchanting Melusine, only to discover she slipped out of church before the Eucharist.

One day, the count stood on her cloak to prevent her escape. As the priest raised the Host, Melusine screamed, sprouted wings, and flew out the window, leaving behind two demonic offspring. Though modern scholars dismiss the tale, the Plantagenets embraced it, often joking about being half‑demon.

Both Henry II and his son Richard the Lionheart were known to jest about their infernal ancestry. Bernard of Clairvaux famously summed up popular opinion: “From the Devil they came and to the Devil they will return.”

3 The King, His Son, His Wife, And Her Brother

In a particularly tangled scandal, King Henry II, his son Richard the Lionheart, and Princess Alys of France became entangled in a web of broken betrothals and rumored affairs. Alys had been betrothed to Richard in childhood and was sent to live with Henry at age nine. Despite Alys reaching marriageable age, Henry refused to sanction the union.

Rumors soon swirled that Henry had taken Alys as his own mistress. The Pope threatened to excommunicate the entire kingdom unless Richard and Alys were wed. King Louis of France demanded either a marriage or the return of his daughter. Henry grudgingly consented but delayed setting a date for years.

Complicating matters further, some historians suggest Richard may have been involved with Alys’s brother, Philip. After Henry’s death, Richard declined to marry Alys, claiming she had already given birth to his half‑brother, thereby ending the scandal in a dramatic fashion.

2 Heretical Spooning

In the later medieval period, the Church grew increasingly anxious about heretical sects, urging them to confess not only doctrinal crimes but also lurid sexual deeds. One notorious case involved a German heretic named Lepzet, who admitted that his sect convened in a cavern where their bishop would insert the handle of a silver spoon into his anus to hold an offering.

According to Lepzet’s confession, the congregation then kissed the bishop’s buttocks and even a cat’s rectum before engaging in an orgy described as “men with men and women with women.” Though some modern scholars suspect Lepzet fabricated the tale, the confession caused considerable shock.

1 Machiavelli, Da Vinci, And The Holes Of Truth

In the 1400s, Florence installed a series of public boxes known as “holes of truth,” where citizens could anonymously submit accusations for official investigation. This system proved fertile ground for rumor‑mongering and scandal.

Even Niccolò Machiavelli found himself forced to deny accusations that he had sodomized a local courtesan named La Riccia. He likely told a falsehood; in a letter he noted that La Riccia jokingly called him her “house pest” because he visited her frequently.

The most explosive allegation emerged in 1476, when several notes accused Leonardo da Vinci and three other Florentine notables of regularly having sex with a 17‑year‑old named Jacopo Saltarelli. The city buzzed with gossip, and Leonardo was summoned by the Officers of the Night for questioning. Ultimately, the charges were dropped, allowing the master artist to continue his illustrious career.

The European Middle Ages stretched across a millennium, roughly from AD 500 to AD 1500, and left behind a kaleidoscope of stories that textbooks often skim over. The top 10 fascinating relics we’re about to unveil bring the past to life, showing that medieval people loved a good gamble, a sharp sword, and even a three‑person toilet.

Why These Top 10 Fascinating Finds Matter

Each artifact below is a tangible bridge to a time when daily life was a mix of hardship, superstition, and surprising ingenuity. By digging into pots, swords, dice, and even a bed fit for a king, we gain a richer picture of the medieval world.

10 Medieval Peasant Diet

When we think of medieval cuisine, the lavish banquets of nobles dominate the imagination, while the everyday fare of peasants remains a mystery. Researchers long suspected that simple pottages and stews were the staple, but hard evidence was scarce—until a 2019 study examined 73 cooking pots from the 500‑year‑old village of West Cotton.

Chemical residue analysis revealed abundant animal fat, confirming that these earthenware vessels were indeed central to a peasant kitchen. The pots showed that the villagers regularly boiled up hearty stews, making the dreaded “peasant diet” more concrete than ever before.

Further testing identified traces of mutton, beef, cabbage, and leek, indicating a meat‑and‑vegetable stew that had never been documented in elite culinary records. Surprisingly, fish was virtually absent, suggesting either limited access or a cultural preference.

Perhaps the biggest shock came from dairy residues—about a quarter of the pots had been used for milk‑derived products. By combining these chemical clues with animal bones found on site, scholars assembled a detailed “cookbook” of medieval peasant cooking techniques, from butchering to waste disposal.

9 The Aberdeenshire Game Board

The oldest surviving Scottish manuscript, the Book of Deer, points to a monastic community in Aberdeenshire that scholars have chased since 2008. In 2018, archaeologists uncovered a stone disk-shaped gaming board at a newly discovered ruin, adding a playful twist to the scholarly quest.

The board’s carved motifs match games popular in medieval Ireland and Scandinavia, confirming cultural exchange across the British Isles. Its very presence at the site indicates that monks and laypeople alike enjoyed leisurely competition.

What truly excited researchers were the stratigraphic layers beneath the board, dated to the 7th and 8th centuries—the same period as charcoal fragments found on site. This demonstrates that the ruins were occupied, and people were gaming, centuries before the manuscript was penned.

8 The Missing Nun

While digitising the Registers of the Archbishops of York, historians uncovered a startling 1318 letter from Archbishop William Melton. He wrote of a scandalous rumor: a nun named Joan had fled her convent and even staged a fake death.

According to the letter, Joan crafted a body double—likely a shrouded dummy—to stand in for her at a funeral, allowing her to escape unnoticed. The motive cited was “carnal lust,” a vague phrase that could encompass a desire for freedom, marriage, or simply life outside cloistered walls.

The correspondence was addressed to the Dean of Beverley, situated roughly 64 km (40 mi) from York, urging him to locate and return the runaway nun. To this day, no records confirm whether Joan successfully evaded capture, leaving her daring escape shrouded in mystery.

7 The Sewer Sword

During a 2019 sewer‑installation project in Aalborg, Denmark, workers uncovered a pristine double‑edged sword lying beneath the city’s oldest pavement. The blade, measuring 1.1 m (3.6 ft), bore the hallmarks of elite 14th‑century craftsmanship, a time when only nobles could afford such weaponry.

Despite its burial in a drainage system, the sword remained razor‑sharp and displayed wear from at least three separate battles, suggesting a turbulent career before it was discarded. Its presence in the sewer was unrelated to its final resting place; rather, it likely fell during a chaotic clash on Aalborg’s streets.

Scholars have yet to agree on an exact date, but consensus points to a 1300s origin. The sword’s elite provenance and battlefield scars make it a vivid reminder of the violent world medieval warriors inhabited.

6 The Bergen Dice

Archaeologists excavating the Vagsbunnen district of Bergen, Norway, in 2018 uncovered a wooden cube beside a medieval street. Identified as a die, the artifact joins a collection of over 30 medieval dice already known from the city.

What sets this die apart is its unconventional numbering: sides for 1 and 2 are missing, replaced by duplicate 4s and 5s. The remaining faces display the standard 3‑6 dots, suggesting intentional tampering to skew odds in favour of the owner.

Given Bergen’s bustling tavern scene, it’s likely the die was used for gambling, granting its possessor an unfair edge. While some speculate a game that never required 1 and 2, the prevailing theory is that a crafty player crafted the die to cheat.

5 A Lewis Warder

In 1831, four medieval chess sets were unearthed on Scotland’s Isle of Lewis, their pieces carved from walrus tusk. Known as the “Lewis hoard,” the sets offered a window into medieval society, yet five pieces remained missing for nearly a century.

In 1964, an antiquarian purchased a small, dark‑toned statue described simply as an “antique walrus tusk warrior chessman.” The piece vanished into a private Edinburgh collection for 55 years before resurfacing at Sotheby’s for appraisal.

Experts identified the statue as the long‑lost “warder,” the medieval equivalent of today’s rook. Its grim expression, sword, and darker hue set it apart from the other figures. Astonishingly, the antiquarian bought it for just £5, while its market value now approaches £1 million (≈ $1.3 million).

4 Person Toilet

Rare as a relic, a 12th‑century three‑person toilet was discovered near the Thames, dating back roughly 900 years. Crafted from a massive oak plank, an axe had cut three adjoining holes, forming a communal seat that rested over a cesspit behind a building on today’s Ludgate Hill.

Historical records link the structure, called “Helle,” to residents such as Cassandra de Flete and her husband John, a capmaker. Researchers even sat on the reconstructed seat, finding the holes surprisingly comfortable—though personal space was certainly cramped, forcing three users to sit shoulder‑to‑shoulder.

This unusual artifact underscores how medieval urban life blended practicality with communal quirks, offering a tangible glimpse into daily hygiene practices that modern readers might find both amusing and enlightening.

3 Lost Govan Stones

Between the 10th and 11th centuries, the Kingdom of Strathclyde produced elaborate gravestones, later known as the Govan Stones after their 19th‑century discovery in Glasgow. Of the 46 original stones, 31 were safely relocated to Govan Old Parish Church, including a sarcophagus believed to hold Saint‑King Constantine.

The remaining stones were displayed against a churchyard wall until a nearby shipyard’s demolition caused them to disappear, sparking fears of permanent loss for over four decades.

In 2019, a community dig led by volunteers and professionals turned the tide. A 14‑year‑old schoolboy unearthed a missing stone, prompting further searches that recovered two additional pieces. Their recovery fuels hope that the rest of the vanished sculptures may yet be found.

2 Traveling Book Coffer

Modern readers may carry entire libraries on their phones, but medieval scholars needed portable protection for their manuscripts. Only about a hundred such book coffers survive, making each discovery exceptionally valuable.

In 2019, Oxford’s Bodleian Libraries acquired a French‑made coffer dating to the 1400s, constructed of wood, leather, metal clasps, and hand‑straps. Its age alone makes it remarkable, as most surviving examples hail from the 1500s.

Inside the lid was a rare woodcut titled “God the Father in Majesty,” a draft from a Parisian liturgical book. Scholars believe the image served as a spiritual safeguard for the coffer’s contents. Only four prints of this type are known worldwide, underscoring the artifact’s rarity.

1 Royal Marriage Bed

About a decade ago, antique dealer Ian Coulson purchased a four‑poster bed online, believing it to be a Victorian piece with armorial shields. The description proved misleading, but the bed turned out to be far more historically significant.

Experts identified the shields as the English royal coat of arms, and the timber showed hand‑tool craftsmanship, placing it firmly in a medieval workshop rather than a 19th‑century factory. Traces of ultramarine pigment—once more valuable than gold—confirmed the bed’s high‑status origins in the 15th century.

The carved motifs feature the roses of York and Lancaster, pointing to King Henry VII and Elizabeth of York as the likely owners. Commissioned before their 1486 marriage, the bed vanished during the English Civil War, when Parliamentarians destroyed many royal furnishings.

Today, this exquisitely carved marriage bed stands as perhaps the most important surviving piece of English medieval furniture, linking us directly to the Tudor dynasty’s private life.

When you think of bold adventurers, the Age of Exploration often steals the spotlight, but the medieval era was brimming with its own intrepid travelers. These ten daring explorers pushed the limits of the known world, linking continents, cultures, and ideas long before Columbus set sail. Their stories reveal a vibrant tapestry of curiosity, courage, and unexpected encounters.

10 Friar Julian

In the waning years of the ninth century, the Magyars surged out of Eastern Europe, carving a new homeland in the Carpathian Basin. Yet they never forgot a distant branch of their kin that had been cut off by a Pecheneg raid. Fast‑forward to 1235, when King Béla of Hungary dispatched four Dominican friars eastward to locate these estranged Hungarians and their forgotten territory.

Only one of the quartet, a monk named Julian, survived the arduous trek. He chronicled a route that began near the Crimean Peninsula, crossed the Caucasus, and followed the mighty Volga River. Julian claimed to have found the “Eastern Hungarians” inhabiting a region he dubbed Magna Hungaria – literally “Great Hungary.”

While there, Julian sensed a looming danger: the Mongol hordes were sweeping across Russia, threatening to spill into Europe. He raced back to Hungary, delivering the first detailed warning of the Mongol advance, and the elusive Eastern Hungarians faded once more into the shadows of history.

9 Gunnbjorn Ulfsson

Erik the Red is often credited with discovering Greenland, but the true pioneer was his kinsman Gunnbjorn Ulfsson, who reported a mysterious landmass west of Iceland in the early 900s. According to the sagas, Gunnbjorn was en route to Iceland when a fierce storm pushed his vessel off course.

He described spotting a cluster of small, barren islets—known as skerries—rising from the sea, and he inferred that a larger, habitable continent must lie beyond them. Modern scholars think Gunnbjorn may have actually witnessed a mirage called the “hillingar,” an optical phenomenon caused by light refraction off the Greenland coast.

Regardless of the exact optics, Gunnbjorn’s intuition proved correct: a massive island existed beyond those skerries. This land would later be settled by Erik the Red and serve as the launchpad for his son Leif’s famed voyages to the New World.

8 Rabban Bar Sauma

Often likened to Marco Polo, Rabban Bar Sauma was born near modern Beijing in 1220 and entered the Nestorian Christian monastic tradition. Driven by piety, he set out on a pilgrimage to Jerusalem, a journey that forced him to cross the Asian continent. He eventually reached Baghdad, but political turmoil in the Holy Land halted his progress.

After a few years in an Armenian monastery, the Mongol ruler of Persia summoned Bar Sauma for a diplomatic mission to Europe. He was warmly received in Constantinople, narrowly escaped suspicion of heresy in Rome, and later spent time at the court of King Philip of France before meeting England’s King Edward Longshanks near Bordeaux.

Returning triumphantly to Persia, Bar Sauma retired to found a monastery in Azerbaijan. He kept a meticulous diary of his travels, offering modern scholars a rare, outsider’s perspective on medieval Europe.

7 William of Rubruck

Following the first Mongol incursions into Europe, several Western powers dispatched envoys to the Great Khan’s court. The most insightful of these was the Franciscan monk William of Rubruck, who, despite not being an official ambassador, found himself thrust into the heart of Mongol territory.

During the Seventh Crusade, William petitioned King Louis IX of France for permission to travel from Palestine to the Russian lands, hoping to minister to Christians enslaved by the Mongols after their devastating raid on Hungary. Upon reaching Russia, Mongol officials mistakenly assumed he was a formal envoy and escorted him onward to the court of Mongke Khan in Mongolia.

Unable to refuse, William journeyed to Karakorum, where he engaged in a lively theological debate among Christians, Muslims, and Buddhists—an event that, according to his own account, ended with participants inebriated before the Khan could declare a winner. He later returned to France around 1255, penning a vivid, often humorous narrative that introduced Europe to Buddhism and corrected the mistaken belief that the Caspian Sea was open to the ocean.

6 Afanasy Nikitin

Afanasy Nikitin, a merchant from the Russian town of Tver, earned the reputation as perhaps the greatest Russian explorer of the medieval era. He set out in 1466 on a commercial expedition toward the Caucasus, only to be ambushed and robbed on the Volga River. Penniless but undeterred, he pressed onward, traversing Persia and eventually boarding a ship at Hormuz bound for India.

Reaching Indian shores in 1469, Nikitin found a land largely unknown to his compatriots. He traveled extensively through the Deccan plateau, forming amicable ties with Hindu communities while navigating the pressures of Muslim rulers who sought to convert him. His detailed accounts describe temples, religious rites, and his visits to both Calicut and the island of Sri Lanka, where he chronicled the famed Adam’s Peak as a sacred mountain revered by Hindus, Buddhists, Christians, and Muslims alike.

By 1472, homesickness tugged at Nikitin’s heart, prompting his return journey. Along the way he visited Ethiopia and Oman, but his travels ended tragically when he died in Smolensk, just a short distance from his beloved hometown of Tver.

5 Li Da and Chen Cheng

Li Da and Chen Cheng were two Chinese eunuchs who embarked on a perilous Central Asian expedition in the 1410s. Li Da, the seasoned traveler, had already completed two journeys deep into Asia, though he left no written record, rendering him nearly invisible to history. Chen Cheng, his subordinate, kept a meticulous diary, earning him lasting fame despite his secondary role.

In 1414, the duo set out on a diplomatic mission for the Yongle Emperor. Their trek took them across a fifty‑day desert stretch, through the world’s second‑lowest basin, and over the towering Tian Shan range. They endured salt marshes, lost most of their horses while crossing the Syr River, and finally arrived in Herat after 269 days, presenting gifts to the local sultan before returning home.

Astonishingly, Li Da repeated this arduous journey twice more, each time emerging unscathed, underscoring his extraordinary resilience and the remarkable capabilities of Ming‑era explorers.

4 Odoric of Pordenone

In the late thirteenth century, Franciscan missionaries launched a concerted effort to establish a foothold in East Asia. Among them, Odoric of Pordenone, a Czech‑born Franciscan, set out around 1316 on a grand pilgrimage that would take him across continents.

After a sojourn in Persia, Odoric preached throughout India before sailing to the Indonesian archipelago, where he visited Java, Sumatra, and perhaps Borneo. He later arrived in China, making Beijing his base while traveling widely—he was especially taken by the splendor of Hangzhou. After three years of extensive wanderings, he chose a return route that led him through Lhasa, Tibet.

Back in Italy, Odoric dictated his memoirs from a sickbed, which may explain the abrupt ending after his Tibetan episode. Though his authentic accounts were later hijacked by an anonymous writer who embellished them with fantastical beasts, the resulting work—known as “The Travels of Sir John Mandeville”—became a medieval bestseller, albeit one that distorted Odoric’s true adventures.

3 Naddodd and Gardar

According to the saga of Ari the Wise, the first Viking to lay eyes on Iceland was Naddodd, a settler from the Faroe Islands. While navigating the seas, a violent storm blew his vessel off course, depositing him on a desolate shore he christened “Snowland.” This accidental discovery was followed by the Swedish explorer Gardar Svarsson, who surveyed the coastline, wintered there, and later returned to Scandinavia, singing praises of the new land.

The saga further claims that Naddodd and Gardar were not the very first Europeans to set foot on Iceland. It suggests that Irish or Scottish hermits, known as the Papar, had already established isolated monasteries on the island but fled at the arrival of the heathen Norse, leaving behind only “Irish books.” While Ari wrote this two and a half centuries after the events, archaeological evidence for the Papar remains thin, leaving the claim open to debate.

Thanks to Naddodd’s fortune in surviving the storm and Gardar’s bold exploration, the Norse swiftly colonized Iceland, creating a lasting legacy that persists in the island’s modern population.

2 Benjamin of Tudela

Very little is documented about Benjamin of Tudela beyond the travelogue that serves as his sole biographical source. A Jewish merchant from Tudela, Spain, he embarked on his grand odyssey around 1160, meticulously recording his route.

His journey carried him through Barcelona and southern France, then onward to Rome, before he traversed Greece to reach Constantinople. From there, he set sail for the Holy Land, moving through Palestine and Syria, eventually arriving in Baghdad and Persia. His narrative later mentions distant lands such as Sri Lanka and China, though scholars suspect the latter portions became embellished, with most concluding that his travels likely ended at the Persian Gulf.

Benjamin’s greatest contribution to historiography lies in his focus on Jewish communities he encountered across the Mediterranean and Near East—populations largely ignored by other medieval chroniclers. His accounts remain a vital window into the hidden Jewish diaspora of the period.

1 Ibn Battutah

It is impossible to discuss medieval travel without invoking Ibn Battutah, the most prolific explorer of his age and arguably of all time. While many of his contemporaries journeyed for trade, diplomacy, or religious duty, Ibn Battutah traveled simply for the love of discovery, earning him the reputation of a medieval tourist.

Born into a wealthy Moroccan family, he was sent on the Hajj pilgrimage to Mecca as a teenager—a trip intended to prepare him for a future as an Islamic judge. Instead, the pilgrimage ignited an insatiable wanderlust, prompting him to wander far beyond the Arabian Peninsula.

Running low on funds, Ibn Battutah decided to head for the generous Sultan of Delhi. His route took him through Turkey, the Crimean peninsula, Constantinople, and up the Volga River into what is now Russia, before crossing the Hindu Kush into India. The Delhi Sultan lavished him with gifts and commissioned a diplomatic mission to the Yuan court in China.

However, his Chinese venture was fraught with misfortune: he was robbed, caught in a war, and shipwrecked—in that exact order—losing all the precious gifts the Sultan had entrusted to him. Fearful of returning to Delhi, he lingered in the Maldives for several years, then visited Sri Lanka, Bengal, and Sumatra before finally reaching China around 1345.

Two years later, he returned to the Middle East, only to find the region ravaged by the Black Death. After a brief sojourn in Spain, he embarked on his final great expedition, crossing the Sahara Desert and exploring the flourishing Mali Empire. In 1353, he returned to Morocco, penned his memoirs, and then vanished from the historical record.

When it comes to medieval Europe, bloodshed was practically a sport, and the phrase “top 10 shocking” fits the brutal roster of assassinations that turned the tide of history. From a Viking heir slain on a river island to a king taken down in a castle latrine, each murder left a lasting imprint on the continent.

10 William Longsword

William Longsword, the son of the audacious Viking chieftain Rollo, inherited the newly‑Christianized Duchy of Normandy and pushed its borders northward with relentless vigor. While France was mired in internal chaos, no central power could curb his ambitions—except, perhaps, his troublesome neighbor, the Count of Flanders.

As Norman forces surged north, Arnulf the Rich, Count of Flanders, expanded his own domain southward, leading to a clash in 939 over Montreuil that erupted into a brief, ferocious conflict.

Realising he could not defeat Longsword on the battlefield, Arnulf opted for a more covert approach: he summoned his rival to a rendezvous on a Seine island in 942. William, unaware of the trap, set foot on the isle only to be ambushed by three of Arnulf’s hidden men who hacked him to death.

William’s ten‑year‑old son succeeded him, only to be kidnapped by the French king and spend his life attempting to keep Normandy intact. Arnulf retained his new lands, and the rapid Viking expansion in France effectively ended.

9 Childeric II

Childeric II hailed from the famed Merovingian dynasty that ruled the Franks. By his era, the Frankish realm had fractured into three kingdoms, and the Merovingian monarchs wielded little real authority. Determined to reverse this trend, Childeric set his sights on unifying the region.

Initially king of Austrasia, the northernmost Frankish kingdom, Childeric proved capable and, by 673, had displaced his cousins to claim the thrones of Neustria and Burgundy, effectively consolidating all three realms under his rule.

Nevertheless, the three kingdoms had diverged, and the nobles of Neustria and Burgundy resented being ruled by an Austrasian. Childeric attempted to accommodate local customs, yet Burgundian chroniclers still complained that they were governed by “foolish and nearly pagan people.”

The final insult came when Childeric ordered a Neustrian named Bodilo to be beaten for a transgression. Enraged, Bodilo rallied other disgruntled Neustrians and lay in wait. During a hunting excursion, Childeric was ambushed in the forest and slaughtered alongside his pregnant wife.

8 Berdi, Qulpa, and Nurus

In 1357, the mighty Jani Beg, Khan of the Golden Horde, fell gravely ill. He promptly summoned his son Berdi, having him crowned as the new khan. Berdi, seizing the moment, murdered his ailing father to preempt any possible recovery and to cement his claim.

The Golden Horde had dominated Eastern Europe since the original Mongol invasions of the previous century, and Russian princes traveled to Berdi’s court to reaffirm their allegiance to Genghis’s descendants. Yet the Russians were about to receive an unexpected reprieve.

After assuming power, Berdi executed twelve of his brothers. The thirteenth, Qulpa, earned his brother’s trust and schemed to eliminate him. In 1359 Qulpa succeeded in assassinating Berdi and seized the throne, only to be poisoned on the orders of Nurus Beg—either another brother or an impostor posing as one.

Nurus’s reign was short‑lived; he was killed within months, and at least twenty claimants declared themselves khan. The Golden Horde fractured into civil war, allowing the Russian principalities to shake off Mongol domination permanently.

7 Constable Charles

When King Charles IV of France died childless in 1328, the throne passed to the English and Navarrese dynasties. However, the French barred both, insisting that only a male heir could inherit, prompting England to launch the Hundred Years’ War while Navarre bided its time.

The conflict intensified when Charles the Bad ascended the Navarrese throne. He loathed his cousin, King John II of France (nicknamed “the Good”), especially after John confiscated lands and granted them to Charles de la Cerda, the French Constable.

In 1354, a covert group of Navarrese mercenaries surrounded the tavern where the Constable was sleeping. Charles’s brother Phillip led four troopers into the bedroom, roused the Constable with insults, and then stabbed him more than eighty times.

John’s fury sparked a military response, but Charles negotiated an alliance with England. Unable to confront both England and Navarre, John was forced into a treaty with Charles, weakening France just as the English prepared their invasion.

6 Robert Clermont and Jean De Conflans

Serving as a royal advisor to King John II of France was perilous business. Two years after the murder of Charles de la Cerda, John suffered defeat and capture at the hands of the Black Prince at Poitiers. The teenage Dauphin Charles then assumed leadership.

The new Dauphin imposed hefty taxes to replenish the shattered army, inflaming the French populace, who resented funding a nobility that had just lost a major battle. Parisian townsfolk rallied under Etienne Marcel, a wealthy merchant demanding the dismissal of the Dauphin’s ministers in exchange for tax relief.

When the Dauphin refused, Marcel dispatched agents to free Charles the Bad from prison. The rebels stormed Paris, and Marcel himself led a mob into the royal chambers, where they murdered the Dauphin’s advisors Robert Clermont and Jean de Conflans while the king watched helplessly.

Fearing for his life, the Dauphin fled Paris, raising an army to combat the insurgents. Meanwhile, the English entrenched their gains, and France descended further into chaos.

5 Etienne Marcel

As Etienne Marcel seized control of Paris, his faction grew increasingly radical. In 1357, his assembly passed the Great Ordinance, a reform aimed at curbing noble privilege by subjecting the aristocracy to parliamentary oversight.

In 1358, a massive peasant uprising known as the Jacquerie erupted north of Paris. Marcel chose to back the rebels, hoping to forge a common cause between the countryside and the capital. This stance provoked a split with Charles the Bad, who led knights to crush the Jacquerie, while Marcel retreated into Paris.

Meanwhile, the Dauphin raised an army to march on Paris. Nervous, Marcel renewed his alliance with Charles the Bad, a move unpopular with Parisians, who resented the Navarrese and English mercenaries raiding the city. Marcel’s associate Jean Maillart secretly corresponded with the Dauphin.

In June, Maillart and his men turned on Marcel, hacking him to death with an axe. This brutal act marked the end of what could be considered France’s first revolution.

4 Thomas of Woodstock

By 1386, the Hundred Years’ War was going poorly for England, and public opinion blamed King Richard II, an aloof autocrat who relied heavily on his cronies to govern.

A faction of nobles known as the Lords Appellant formed a commission and announced their intention to wrest control from the ineffective Richard. Led by Thomas of Woodstock, the Duke of Gloucester, they defeated Richard’s forces at Radcot Bridge and seized the king.

While many of Richard’s favorites were executed or exiled, Richard bided his time, rebuilding his power base. In 1397, he lured the Duke of Norfolk away from the other Lords Appellant. Thomas of Woodstock was ambushed, banished to Calais, and soon after assassinated—accounts differ between strangulation and smothering with a feather mattress to avoid marks on the body.

The murder outraged the English populace, and Richard was eventually overthrown and starved to death, a turn of events with profound consequences for English history.

3 Isma’il and His Sons

The Nasrid dynasty, the last great Muslim ruling house in Spain, governed Granada from 1248 until its fall to Ferdinand and Isabella in 1491. Their reign was plagued by internal strife and dynastic intrigue, which hampered any sustained effort to reclaim territory from Christian forces.

Isma’il I, a dynamic and energetic leader, achieved a crushing victory over the Castilians at Vega de Granada in 1319, during which the two Castilian regents were slain—one allegedly skinned and stuffed. This triumph allowed Isma’il to press forward, conquering Baza and Martos.

Tragically, Isma’il was assassinated by his cousin over a petty personal dispute. His young son Muhammad succeeded him, only to be murdered by the Banu Abi’l‑Ula clan when he showed interest in governing.

Muhammad’s brother Yusuf then seized power, eliminating the Banu Abi’l‑Ula. Yet Yusuf met a grim end, stabbed in the back by a madman while praying in Granada’s Great Mosque.

This pattern of fratricidal violence persisted through generations, preventing the Nasrids from ever achieving lasting stability.

2 Stephen of Hungary

In the medieval world, physicians often doubled as assassins, earning widespread suspicion as medicine mingled with superstition. One striking example involves King Baldwin III of Jerusalem, who reportedly died after consuming pills prescribed by a Syrian doctor—whether murder, malpractice, or simple failure remains debated.

Stephen IV of Hungary, who briefly usurped the throne from his young nephew, fell victim to a similarly grisly medical murder. After being defeated in battle, Stephen fled to the Byzantine Empire, pursued by agents of his nephew.

Like many of his era, Stephen believed in bloodletting as a therapeutic practice. However, his attendant, bribed by his rivals, smeared the bandage covering Stephen’s wound with poison. The toxin spread throughout his body, ultimately killing him.

1 Godfrey the Hunchback

Godfrey the Hunchback rose to become Duke of Lower Lorraine in 1069. Though physically deformed, he quickly earned a reputation as a capable ruler, with contemporary chroniclers describing him as “weak in body but excelling in spirit.”

His marriage to Matilda of Tuscany, a powerful Italian magnate, could have elevated his status further, but the couple detested each other. After three years of marriage, Matilda refused even to see him. Cut off from his wife’s court, Godfrey returned to his own lands, where he met his end in a castle latrine.

Accounts differ, but all agree an assassin lay in wait within the latrine pit and struck Godfrey as he relieved himself at night. Some stories claim the killer was concealed inside the pit and impaled him with a spear, while others describe a straightforward ambush.

Chronicles attribute the murder to enemies in Holland and Flanders, not to Matilda. Nonetheless, Godfrey’s death cleared the way for Matilda to become Pope Gregory VII’s most staunch supporter in his confrontation with the Holy Roman Emperor, a pivotal political crisis of the era.