When you hear “10 pivotal days” in the context of the Crusades, you might picture epic battles, daring leaders and sweeping religious fervor. In fact, a handful of specific dates acted like fulcrums, tipping the balance of power, belief, and geography across centuries of holy war. Below we stroll through each of those decisive moments, unpacking the drama, the personalities, and the lasting ripples they sent through medieval Europe and the Near East.

10. The Siege And Fall Of Acre

Acre, perched on Israel’s western Galilee coast, boasts a history that stretches back to at least 1900 B.C. The modern city’s layout sits atop layers of earlier settlements, and buried beneath its streets are the remnants of a Crusader fortress that once dominated the region.

Over the course of the Crusades the city changed hands many times. Crusaders first secured it in 1104, only to lose it to Muslim forces in 1187. After Richard the Lion‑heart’s campaign, the city was recaptured in 1191, fortified, and transformed into the capital of the Latin Kingdom of Jerusalem, complete with churches and massive defensive works.

Unlike many towns that were periodically pillaged, Acre grew into a massive stronghold. It housed the headquarters of the Hospitallers, the Templars, and the Teutonic Knights. When the final siege broke on May 18, 1291, the city fell forever. The Grand Master of the Templars perished, the Hospitallers fled wounded leaders, and most Teutonic Knights were slain. A handful of survivors fled to Italy and Cyprus, but never managed to re‑establish a foothold. The loss of Acre marked the end of a Christian heart‑beat in the Holy Land.

9. Peter The Hermit

When Pope Urban II called for a holy war against the infidels, it was the charismatic preacher Peter the Hermit who turned the papal proclamation into a mass movement, setting the tone for the First Crusade.

Peter, a wiry, dark‑haired figure who traveled on a mule, criss‑crossed villages preaching the cause. His oratory was so compelling that he not only swayed public opinion; he actually assembled an army of common folk eager to take up the cross.

These eager volunteers were impatient. Rather than wait for a papal‑organized force, they marched on their own. By April, Peter’s ragtag force of roughly 13,000 had reached Cologne, and some contingents, led by the enigmatic Gautier Sans‑Avoir, pushed even farther east.

By August 1, 1096 Peter arrived in Constantinople. The trek had been anything but peaceful; his army absorbed every stray, including outcasts and bandits, leading to rampant looting and violence across Germany, Hungary, and the Byzantine Empire. Once they reached the Bosporus, the troops scattered into smaller groups, and Turkish forces began picking them off one by one.

8. Indulgences

Indulgences, the medieval equivalent of a “get‑out‑of‑hell‑free” card, promised that the faithful could secure heavenly forgiveness by either performing penance or contributing financially to the Church’s cause.

The practice began in earnest on November 25, 1095, when Pope Urban II, eager to muster a massive army, declared in his Clermont sermon that anyone who took up the cross and fought the non‑Christians would automatically receive absolution for their sins.

This promise sparked a wave of controversy. The notion that the Church could essentially sell salvation raised ethical questions that would echo for centuries. Over time, even those unable to travel to the Holy Land could purchase indulgences, contributing money in exchange for the same spiritual benefits. The Pope’s assurance that this was a just war made the policy appear divinely sanctioned.

7. Stephen Of Cloyes

The Children’s Crusade of 1212 stands out as a tragic episode where youthful zeal collided with harsh medieval realities. Thousands of teenage boys abandoned farms and families, hoping to secure the Holy Land for Christ.

In the spring of 1212, a French boy named Stephen of Cloyes claimed to have received a divine vision instructing him to march to Jerusalem. He convinced a small band of believers to accompany him to Paris, where he sought an audience with King Philip II. The king dismissed the petition and sent the youngsters home, but not all obeyed.

Later that summer, another group of youths, led by a boy named Nicholas, set sail for the Holy Land. Their journey was fraught with disaster: many perished in shipwrecks near Sardinia, some were sold into slavery, and the majority never reached their intended destination. While the exact numbers remain debated, the Children’s Crusade ultimately failed to achieve any lasting military or spiritual impact.

6. Frederick Barbarossa

German emperor Frederick Barbarossa met a watery demise while attempting to cross a river en route to the Holy Land, a loss that reverberated through the Third Crusade’s strategic plans.

Barbarossa led a massive German army through Constantinople and the Taurus Mountains, answering Pope Gregory VIII’s call to join forces with the French and English contingents under Philip Augustus and Henry II. At the time, the Crusader coalition was already strained, with only the fortress of Tyre holding out against Saladin’s forces.

The combined forces presented a formidable front, and the temporary truce between England and France demonstrated a rare unity against a common enemy. However, the death of Barbarossa caused the German army to fracture: some troops returned home, others pressed on to Tripoli, while the heir ventured to Cilicia to bury his father.

Barbarossa’s sudden death also sowed doubt among his men; a number of soldiers abandoned Christianity altogether, interpreting the tragedy as divine disfavor toward the Crusade.

5. Saladin And Raynald

Raynald de Chatillon, a notorious Crusader lord, had a reputation for cruelty and defiance. After spending years imprisoned for his misdeeds, he resumed raiding, flagrantly violating a fragile truce with Saladin.

When Saladin set his sights on reclaiming Jerusalem in 1187, he first targeted Raynald’s holdings. The two forces clashed at the Battle of Hattin on July 4, 1187. Saladin’s army decisively defeated the Crusaders, capturing King Guy of Lusignan and Raynald.

According to chronicler Baha al‑Din, Saladin offered King Guy a drink of water, which the king passed to Raynald. While hospitality protected the king, Raynald was not afforded such mercy; Saladin beheaded him on the spot.

The crushing defeat left Jerusalem virtually defenseless, paving the way for Saladin’s capture of the city on October 2, 1187. The loss reshaped the power balance in the Levant for years to come.

4. The Tournament Of The Fourth Crusade

In 1199, as the Church prepared the Fourth Crusade, it turned to a grand tournament to rally the nobility, secure funding, and inspire martial enthusiasm.

The event, held on November 28, 1199 at Ecry‑sur‑Aisne in France, was marketed as the pinnacle of chivalry, entertainment, and courtly spectacle. Yet the battlefield remained brutally real: participants wielded genuine weapons, and lances were not designed to break, resulting in a blood‑soaked melee.Both hosts of the tournament boasted Crusader lineage. Count Louis of Blois had previously fought in a Crusade, while Count Thibaut of Champagne’s father had been a high‑ranking official in Jerusalem. Their families’ histories added gravitas to the gathering.

The tournament succeeded in forging camaraderie among the elite, leading many nobles to take the cross and join the Fourth Crusade, which would later divert to Constantinople.

3. The Great Schism

On September 20, 1378, a faction of thirteen cardinals grew weary of Pope Urban VI’s abrasive leadership and elected a rival pontiff, Pope Clement VII, establishing his papal court in Avignon.

The split stemmed largely from Urban VI’s harsh temperament and suspicion toward his peers, prompting many cardinals to withdraw to Avignon and crown their own pope. This schism fractured the Catholic Church, with two competing popes issuing bulls, excommunicating each other, and vying for secular support.

Both papal claimants summoned saints to their cause, and many European monarchs aligned with Clement VII. The internal conflict prompted calls for a new Crusade, championed by St. Catherine of Siena, who argued that a common enemy could reunite the divided Church.

The Great Schism persisted until 1417, when Pope Martin V was elected, finally restoring a single papacy. In the intervening years, several Crusades were launched against the Ottomans, Mahdia, Hungary, Bulgaria, and Syria.

2. The Crusading Bull

By the mid‑12th century, the image of crusading armies sweeping across Europe to the Holy Land had become iconic, yet the motives behind these campaigns grew increasingly complex.

Pope Eugenius III, on December 1, 1145, issued a papal bull calling for what would become the Second Crusade. In his proclamation, he invoked the memory of fallen saints, the desecration of relics, and the blood of Christians slain by infidels, urging a renewed holy effort.

The bull also promised crusaders the same privileges as clergy: exemption from debts, relief from interest‑bearing loans, and tax relief. Moreover, participants were assured that confession would cleanse them of sin, reinforcing the notion that the campaign was divinely sanctioned.

1. Jan Hus

Not every Crusade was fought in the Levant; the death of Czech reformer Jan Hus on July 6, 1415 ignited a series of holy wars against heretical Christians in Bohemia.

Hus, a revolutionary priest, challenged the Catholic hierarchy and its moral authority. Convicted of heresy, he was burned at the stake, an act that transformed him into a martyr for reform. The University of Prague decried his execution as murder, and his ideas rapidly spread among nobles and peasants alike.

By 1418, Pope Martin V declared a crusade against the Hussites. Over the next decade, five separate crusades were launched, pitting Catholic forces against the Hussite rebels. The conflict culminated in a decisive Hussite victory, making it one of the most unusual Crusades—Christians fighting Christians under the banner of the same God.

The Crusades were a series of religious wars that left a trail of heroic triumphs and spectacular blunders. In this roundup we highlight the 10 embarrassing flops that prove even medieval zealots could stumble spectacularly. From megaphone preachers fleeing the battlefield to cannibalistic sieges, these cringe-worthy moments still echo through history.

10 Embarrassing Flops Overview

10 Pastor Of The First Crusade Runs Away

In 1095, Pope Urban II convened the Council of Clermont in France and urged a holy war against the Turks. Peter the Hermit, a charismatic monk from Amiens, answered the call with fervor, eloquence, and a talent for rallying crowds. He quickly became the medieval equivalent of a megachurch preacher, amassing a massive following eager to join the First Crusade.

However, preaching prowess did not translate into battlefield competence. In 1096, Peter set out with his followers months before the main crusading armies, only to see his force decimated in Turkey. He was forced to linger in Constantinople, awaiting the arrival of the larger crusader contingents.

By 1098, the chaos of the First Crusade was evident. Realizing the danger, Peter attempted to abandon the campaign, but he was captured by his own comrades. He pleaded for forgiveness and was compelled to rejoin the crusade, highlighting the precarious nature of his leadership.

9 Lionheart’s Sister Rejects Saladin’s Brother

The Third Crusade (1189–1192) is famed for its two titanic personalities: England’s Richard the Lionheart and the Kurdish sultan Saladin. Their interactions were often portrayed as a model of chivalry and mutual respect.

In 1191, Richard concocted a diplomatic gambit: he offered his sister Joan in marriage to Saladin’s brother al‑Adil, but only if al‑Adil converted to Christianity. Saladin consented, yet the religious stipulation proved an insurmountable obstacle. Joan, unwilling to marry a Muslim, rejected the proposal outright.

Richard then considered substituting his niece for his sister, but Saladin dismissed the notion. The marriage scheme collapsed, and the crusade continued with the Muslims eventually retaking Jerusalem, while Richard negotiated a settlement that allowed limited Christian access.

8 The Crusade Of Frederick II

Frederick II, grandson of Frederick Barbarossa, wore many crowns: Holy Roman Emperor, King of Germany, King of Sicily, and Duke of Swabia. In 1229 he even claimed the title King of Jerusalem.

Despite his intellect, Frederick was notoriously unreliable—much like a friend who habitually breaks promises. The papacy repeatedly urged him to lead a crusade, and each time he pledged support only to delay or abandon the effort. Eventually, the Pope excommunicated him for his vacillations.

After his excommunication, Frederick finally launched a crusade in 1228‑29 without papal approval, reinforcing his ban. Rather than a battlefield campaign, he negotiated a treaty with Egypt’s Malik al‑Kamil, ceding Jaffa, Bethlehem, Nazareth, and Jerusalem to the Christians, while the Muslims retained the Temple and left Jerusalem undefended. This arrangement sparked a ten‑year truce between the faiths.

Frederick then proclaimed himself King of Jerusalem—a title rejected by both the Catholic Church and European nobility—leading to a second excommunication. When the treaty expired, Muslim forces swiftly reclaimed Jerusalem, which remained under Muslim control until 1917.

7 The Children’s Crusade

The Crusades were fueled not only by seasoned knights but also by fervent laypeople. Yet the Catholic Church withheld official sanction for the ill‑fated Children’s Crusade of 1212, fearing that untrained masses would jeopardize the cause.

Two charismatic leaders emerged: French peasant Stephen of Cloyes and German youth Nicholas of Cologne. Stephen rallied a peasant army of up to 30,000, hoping to petition the French king to embark on a crusade. The monarch’s lukewarm response—essentially “how cute”—meant Stephen’s group never reached the Holy Land.

Nicholas led his followers to Genoa, anticipating a miraculous sea crossing that never materialized. Many stayed in Genoa as cheap labor, while others trekked to Rome, where the Pope advised them to return home. Tragically, Nicholas’s father was executed by enraged parents for encouraging his son’s venture.

6 The Many Woes Of Byzantium

The Byzantine Empire, the premier Christian power of the Middle Ages, struggled to repel Muslim advances. When Alexius I sought aid from Pope Urban II, his plea helped ignite the First Crusade.

Upon the arrival of Western feudal lords in Constantinople, Alexius realized his request might have backfired. The Latin crusaders followed Roman Catholicism, while the Byzantines adhered to Greek Orthodoxy, fostering mutual distrust. Crusaders often kept reclaimed Byzantine lands, leaving the empire to fend for itself.

This tension peaked during the Fourth Crusade (1202‑04), led by Venetians, French, and Germans. To fund a Venetian fleet aimed at Egypt, the crusaders struck a deal with Byzantine prince Alexius IV, promising to install him after deposing his usurper uncle Alexius III. In exchange, Alexius IV pledged financial support.

The crusaders seized Constantinople with little resistance, crowning Isaac II and Alexius IV as co‑emperors. However, Alexius IV could not deliver the promised funds, prompting the crusaders to rationalize a full‑scale war: they argued that Constantinople should submit to the Catholic Church, labeling the Byzantines as heretics, thereby justifying a crusade against fellow Christians.

The resulting sack of Constantinople in 1204 was brutal and devastating, installing a Western European ruler and marking a catastrophic reversal of Alexius I’s original plea for help.

5 The French King Destroys The Knights Templar

The Knights Templar, a military order devoted to the Crusades, also pioneered early banking. They devised a system allowing pilgrims to deposit funds in Europe and retrieve them safely in the Holy Land, effectively protecting travelers from robbery.

Although individual Templars swore vows of poverty, the order amassed considerable wealth. French monarch Philip IV, hearing rumors of their treasure, coveted the riches for himself.

Philip persuaded Pope Clement V—who held jurisdiction over the Templars—that the order was heretical and corrupt. Lacking solid evidence, Clement yielded, leading to the mass arrest of Templars, seizure of their assets, and execution of knights across Europe.

Grand Master Jacques de Molay was burned at the stake in 1314. Ironically, both Clement and Philip died later that same year, underscoring the dramatic fallout of their actions.

4 The Eighth Crusade: Death By Dysentery

By the late 13th century, crusading zeal was waning, yet King Louis IX of France remained a steadfast believer. Renowned for his chivalry, generosity, and piety, Louis embodied the ideal medieval Christian monarch.

In 1248, Louis launched the Seventh Crusade, aiming to retake Jerusalem after its loss following Frederick II’s treaty expiration. He targeted Egypt, the heart of Muslim power, but the campaign faltered: Louis was captured, ransomed, and forced to retreat.

Undeterred, Louis embarked on the Eighth Crusade in 1270, this time focusing on Tunisia, hoping that securing its ports would ease future Egyptian campaigns.

Upon landing in North Africa, dysentery ravaged his army, claiming Louis’s life in August. Despite his devout commitment, the crusade ended in disaster. Louis was later canonized in 1297, cementing his legacy despite the failure.

3 Women’s Scorn Leads To The Crusade Of 1101

After the First Crusade’s success, many who had sworn the crusader’s oath in 1096 balked at actually marching east. Some veterans even deserted, fearing the campaign’s prospects. One such deserter was Stephen of Blois, whose wife Adela of Blois pressured him to fulfill his vow.

When Jerusalem fell, Pope Paschal II threatened excommunication for any crusader who had taken the vow but not proceeded. Embarrassed and shamed, families forced oath‑breakers back into the fray. Stephen’s wife, Adela, urged him to rejoin the effort.

Yielding to pressure, Stephen and other reluctant nobles joined the Crusade of 1101. The venture ended in disaster: Turkish forces defeated the crusaders at each engagement, and Stephen perished at Ramula in 1102.

2 Starving Crusaders Eat Saracen Buttocks

During the First Crusade in 1098, the crusaders besieged the Syrian city of Ma’arra. After a month, the Muslim defenders surrendered under the promise that the crusaders would spare the inhabitants. The crusaders broke their word, slaughtering the population.

With the city’s food stores exhausted, the starving crusaders turned to cannibalism. Historical accounts describe them cutting pieces from the victims’ buttocks, boiling adult flesh, and roasting children on spits. Some even ate raw human meat, driven by desperation.

Later medieval romance Richard Coer de Lyon fictionalized Richard the Lionheart as tasting Saracen flesh that surprisingly resembled pork. In the tale, Richard laughs upon discovering the truth and declares his army will never starve again.

1 The Inadvertent Slaughter Of Jews

The official Crusade targets were Muslim forces in the Holy Land and pagan groups in Europe. Yet the crusading movement inadvertently sparked waves of anti‑Semitic violence.

Crusaders rationalized that Jews were enemies of Christianity for rejecting Jesus, leading to attacks on Jewish communities despite papal admonitions for restraint. In 1096, crusaders assaulted three prosperous Rhineland towns, forcing Jews to convert or die; many chose death over conversion. After Jerusalem fell in 1099, its Jewish residents were enslaved and tasked with cleaning the city.

Anti‑Jewish violence persisted with each new crusade. In 1320, the Shepherd’s Crusade—a popular uprising in France—mobilized roughly 40,000 mostly teenage peasants to assault Jewish communities, destroying over 100 towns and killing thousands.

The Shepherd’s Crusade was condemned by clergy and nobility; the Pope excommunicated participants, and Christian authorities executed the ringleaders.

In the Middle Ages, the Catholic Church fashioned a special kind of holy journey that promised forgiveness of sins. These expeditions, known as crusades, were not limited to the well‑trodden paths to the Holy Land; many obscure and oddly motivated campaigns also carried the papal seal. Below we uncover the ten most bizarre crusades that have slipped through the cracks of history, each a wild mix of politics, ambition, and occasional blunder.

10 Bizarre Crusades Overview

10 The Crusade Against Markward

The crusade against Markward of Annweiler represents a clear departure from purely religious warfare, venturing straight into the realm of political intrigue. When Emperor Henry VI passed away, his infant heir was slated to inherit the throne of Sicily, a realm that Pope Innocent III was entrusted to safeguard. Yet Markward, a trusted steward of the late emperor, claimed a secret testament naming him regent of Sicily, and he moved to occupy the island against papal wishes.

This bold claim sparked outrage, as Markward was a devout Christian who had even taken part in the Third Crusade. Undeterred, the Pope declared a crusade, rallying a force under the leadership of Walter of Brienne. However, the campaign fizzled when Markward unexpectedly died, leaving the papacy with a conveniently resolved dispute but a precedent for future politically‑styled crusades.

Although the conflict ended without the fanfare of a battlefield victory, the episode set a troubling example: papal authority could be wielded to settle secular power struggles under the banner of holy war, a template that would echo in later, equally strange crusading ventures.

9 Humbert’s Crusade

In 1343, Pope Clement VI launched an ambitious plan to seize the Turkish port of Smyrna, enlisting the Venetians and the Hospitallers for the task. The initial expedition floundered, prompting Clement to issue a broader call to the western nobility. The response was tepid at best, with only one eager volunteer stepping forward: Humbert, the energetic Dauphin of Viennois.

Elevated to commander, Humbert set sail with roughly nine hundred men. Their journey was immediately jeopardized when Genoese forces, suspecting a secret attack on the island of Chios, engaged the tiny crusading fleet in the Aegean. Despite the skirmish, Humbert pressed on, finally anchoring at Smyrna in 1346, only to discover that internal strife between the Hospitallers and Venetians had already torn the original mission apart.

Disillusioned by the chaos and lacking any substantial support, Humbert ordered his men back to Europe, effectively ending one of the most under‑whelming crusading attempts ever recorded.

8 The Battle Of Nicopolis

When the Ottoman Empire pushed into Europe, the Kingdom of Hungary called for a crusade to halt the advance. Despite the schism between the Roman and Avignon popes, both pontiffs agreed to sanction a holy war, and an army of eager French and Burgundian nobles assembled, hoping to prove their valor.

The expedition, led by the twenty‑four‑year‑old son of the Duke of Burgundy, turned into a flamboyant competition of armor and extravagance. After crossing into the Balkans in 1396, the crusaders clashed with Sultan Bayezid the Thunderbolt’s forces at Nicopolis. Ignoring counsel from the more cautious Hungarians, the western knights launched a reckless uphill charge against fortified positions, resulting in a devastating slaughter that abruptly ended the campaign.

The defeat at Nicopolis underscored the perils of overconfidence and highlighted how a crusade driven more by chivalric bravado than strategic sense could swiftly collapse under superior tactics.

7 The Stedinger Crusade

The Stedingers were a band of independent peasants in northern Germany who refused to pay tithes or perform forced labor for the Archbishop of Bremen. When the archbishop raised an army to subdue the rebels, the Stedingers achieved a surprising victory in 1229, demonstrating both their resolve and military skill.

Incensed, the archbishop escalated the conflict by accusing the Stedingers of heresy, a charge that allowed him to petition Pope Gregory IX for a crusade against the peasants. In reality, the Stedingers were not doctrinally deviant; they simply resisted ecclesiastical taxation. Nevertheless, the Pope granted indulgences to any who would fight, framing the campaign as a holy endeavor.

The crusaders managed to defeat the Stedingers once, but a fresh papal army in 1234 finally crushed the rebellion, ending the crusade and reaffirming the church’s willingness to weaponize crusading rhetoric against its own flock.

6 The Anti‑Colonna Crusade

Late in the thirteenth century, Rome’s power balance was a three‑way tug‑of‑war among the Orsini, the Caetani, and the Colonna families. In 1294, the Orsini and Caetani succeeded in electing Benedetto Caetani as Pope Boniface XIII, a move that enraged the Colonna, who retaliated by looting the papal treasury in 1297.

Pope Boniface responded by kidnapping the Colonna cardinals Giacomo and Pietro, demanding the stolen funds be returned. Though the money was eventually handed back, the Colonna felt deeply betrayed and launched a series of attacks against the Caetani. Accusing the Pope of heresy and murder, they intensified the feud, prompting Boniface to formally demote the Colonna cardinals and declare a crusade against the entire family.

The Colonna fled Rome and allied with the French king, culminating in a violent assault on the Pope’s residence in Anagni. During the melee, the French barely prevented Sciarra Colonna from killing Boniface. Though the Pope was rescued by a mob, the ordeal hastened his death, effectively ending the anti‑Colonna crusade.

5 The Italian Crusades

Following the inconclusive anti‑Colonna effort, popes continued to entangle themselves in the petty politics of northern Italy, repeatedly invoking crusading language against rival city‑states and noble houses throughout the fourteenth century. In 1309, a dispute over Ferrara sparked a papal crusade against Venice, though the Venetians withdrew before any fighting began.

Later, in 1317, a broader crusade targeted the Estensi of Ferrara, the Visconti of Milan, and the warlord Frederick of Montefeltro. The conflict dragged on for years, expanding in 1324 to include Mantua and, by 1327, even Emperor Louis IV. Subsequent crusades in 1355 and 1363 focused on various Romagna families and the Visconti again, respectively.

These campaigns were largely fought by mercenary companies who, despite their profit‑driven motives, were granted full indulgences and the spiritual benefits traditionally reserved for holy warriors. The Italian crusades illustrate how the crusading ideal could be twisted to serve secular ambitions across the continent.

4 The Aragonese Crusades

Pope Martin IV, effectively a puppet of the French royal line, found himself at odds with the Crown of Aragon when Peter of Aragon seized Sicily. The Pope excommunicated Peter and demanded that the kingdom be handed over to a French prince. Peter’s refusal prompted Martin to declare a crusade against Aragon, framing the conflict as a holy war despite its overtly political nature.

The French king Philip III marshaled a massive army, crossing the Pyrenees to besiege Girona. However, the Aragonese navy disrupted French supply lines, and an outbreak of dysentery ravaged the invading troops, striking even the king himself.

Fearing a gruesome death on a latrine, Philip ordered a retreat across the mountains. The Aragonese seized the opportunity, ambushing the weakened French forces in a mountain pass and slaughtering many. Philip managed to secure safe passage to Perpignan, where he soon died, marking a disastrous end to the Aragonese crusade.

3 The Trade Crusade Of Alexandria

Peter de Lusignan, the king of Cyprus and the last ruler of a major crusader state, spent the 1360s traversing Europe in search of backing for a crusade against Egypt. With papal approval and fleets from both Venice and Genoa, he launched an assault on Alexandria in 1365.

While the proclaimed aim was the conquest of Egypt—a goal that strained credulity given the limited resources—modern scholars argue that Peter’s true motive was economic. By devastating Alexandria, he hoped to divert trade routes back through Cyprus, thereby undermining the thriving Mediterranean commerce that bypassed his island.

After seizing and looting the city, the crusaders withdrew at the first sign of a massive Egyptian army approaching. Both Venice and Genoa later issued formal apologies for their participation, underscoring the dubious nature of the venture.

2 The Contra‑Catalan Company Crusade

In 1303, the Byzantine Empire hired the mercenary Catalan Company, led by the former pirate Roger de Flor. Their tenure was marked by a series of betrayals, including the murder of Roger and a failed siege of Constantinople. By 1311, the Company had crossed into Greece, defeating Duke Walter of Athens and seizing his duchy.

Although the Catalans had previously taken Athens after the Fourth Crusade, Walter’s relatives appealed to the Pope, arguing that the mercenaries had usurped legitimate rule and were overly friendly with the Turks. Responding to these complaints, Pope declared a crusade against the Catalans in 1330.

The papal crusade never garnered widespread support, allowing the Catalan Company to retain control of Athens for another half‑century, demonstrating the limited effectiveness of papal authority when confronted with entrenched mercenary power.

1 The Waldensian Crusade

The Waldensian Crusade stands as perhaps the final crusade of the medieval era, a modest and largely ineffective campaign against the Waldenses—a Christian sect that championed poverty and had been condemned as heretical since the twelfth century. By the late fifteenth century, Waldensian communities persisted in southern France and northern Italy.

In 1487, Pope Innocent VIII issued a crusade targeting the Waldenses in the Dauphiné region. The sect retreated into the Alpine mountains, where they mounted a stubborn resistance, leading crusader forces to assault fortified caves in a series of brutal engagements.

Historian Peter Lock later described the effort as a “small‑scale event … characterized by violence and rapine and achieved nothing,” underscoring how this final anti‑heretical crusade failed to produce any lasting religious or political change.

When you think of crusades, you probably picture knights storming Jerusalem or battling pagans in the Baltic. Yet the medieval papacy launched a whole parade of oddball holy wars that most people have never heard of. In this roundup we spotlight the 10 bizarre crusades that slipped through the cracks of history, each a mix of politics, ambition, and outright madness.

Why These 10 Bizarre Crusades Still Matter

10 The Crusade Against Markward

The saga begins with a straight‑up political showdown: Pope Innocent III declared a crusade against Markward of Annweiler, a German noble who had seized Sicily after Emperor Henry VI’s death. Markward claimed the late emperor’s will named him regent, a move that infuriated the pope, who suddenly framed the dispute as a holy war.

What makes this episode bizarre is that Markward was a faithful Christian who had actually fought in the Third Crusade. Still, the papacy raised a crusader army under Walter of Brienne, hoping to wrest control of the island. The whole affair was unpopular, as many saw it as a power grab rather than a fight against heresy.

Before any grand battle could unfold, Markward died of an unexpected illness, ending the conflict without a single clash. Though anticlimactic, the episode set a precedent for future crusades that were driven more by politics than piety.

9 Humbert’s Crusade

In 1343 Pope Clement VI mounted a joint Venetian‑Hospitaller expedition to capture the Turkish port of Smyrna. The mission flopped spectacularly, prompting the pope to issue a broader call for a crusade against the city. Only one eager soul answered: Humbert, the impulsive Dauphin of Viennois.

Humbert was swiftly appointed commander and set sail with roughly nine hundred men. En route, his tiny fleet was ambushed by the Genoese, who feared he might target the nearby island of Chios. The skirmish left his force rattled but still determined.

When Humbert finally reached Smyrna in 1346, he discovered the original expedition had dissolved into a brawl between Hospitallers and Venetians. Disillusioned, he packed up his troops and headed home, leaving the crusade to fade into obscurity.

8 The Battle Of Nicopolis

When the Ottoman Turks pushed into Europe, the Kingdom of Hungary cried out for a crusade. Even though the papacy was split between Rome and Avignon, both popes agreed to sanction a massive expedition against the Muslim advance.

The war‑break halted the Hundred Years’ War, freeing up a wave of young French and Burgundian nobles eager to prove themselves. The 24‑year‑old son of the Duke of Burgundy was elected leader, turning the campaign into a flamboyant contest of who could outfit the most glittering retinue.

Reaching the Balkans in 1396, the crusaders clashed with Sultan Bayezid I—known as Bayezid the Thunderbolt—at Nicopolis. While the Hungarians urged caution, the western knights charged head‑first up a steep hill toward a fortified position. The reckless assault ended in slaughter, crushing the crusade in a single, disastrous blow.

7 The Stedinger Crusade

The Stedinger were a band of independent peasants from northern Germany who flat‑out refused to pay tithes or perform unpaid labor for the Archbishop of Bremen. After they repelled the archbishop’s first army in 1229, the bishop escalated the conflict by branding the peasants heretical.

Archbishop Gregory IX appealed to Pope Innocent III, who proclaimed a crusade against the Stedinger in 1232. Though the peasants were not doctrinally heretical, they had simply resisted feudal taxes. The papal bull promised full indulgences to anyone who fought them.

The Stedinger managed a single victory against a crusader force but were ultimately overwhelmed when a fresh papal army crushed them in 1234, ending the short‑lived crusade against the stubborn farmers.

6 The Anti‑Colonna Crusade

Late‑13th‑century Rome was a battlefield of noble families: the Orsini, the Caetani, and the Colonna. In 1294 the Orsini and Caetani teamed up to elect Benedetto Caetani as Pope Boniface VIII, enraging the Colonna, who looted the papal treasury two years later.

Pope Boniface responded by kidnapping the Colonna cardinals Giacomo and Pietro, forcing the family to return the stolen loot. Even after the money was handed back, the Colonna felt betrayed and launched a series of attacks on the papal household.

Accusing the pope of heresy and murder, the Colonna were formally excommunicated, and a crusade was declared against them. After being driven out of Rome, they allied with the French king to assault the pope at Anagni. The French halted Sciarra Colonna from beating the pontiff to death, but Boniface died days later, effectively ending the anti‑Colonna crusade.

5 The Italian Crusades

Even after the anti‑Colonna crusade fizzled, the papacy kept meddling in Italian politics, repeatedly declaring crusades against rival city‑states throughout the 14th century. In 1309 a dispute over Ferrara sparked a papal crusade against Venice, though the Venetians backed down before any fighting began.

In 1317 the pope launched yet another crusade targeting the Estensi of Ferrara, the Visconti of Milan, and even Frederick of Montefeltro. The conflict dragged on for years, expanding in 1324 to include Mantua and again in 1327 to confront Emperor Louis IV.

Later, in 1355 a crusade was declared against several noble families of Romagna, which Cardinal Gil Albornoz subdued over two years. Another papal crusade against the Visconti followed in 1363. Though fought mainly by mercenaries, participants received full indulgences and the usual crusader privileges.

4 The Aragonese Crusades

Pope Martin IV, effectively a puppet of the French royal house, became embroiled in a fight with King Peter III of Aragon, who had invaded Sicily. The pope excommunicated Peter and demanded he hand over the Aragonese crown to a French prince.

When Peter refused, Martin declared a crusade against Aragon. The French king Philip III marched across the Pyrenees, besieging Girona, but the Aragonese navy cut off the French supply lines. A dysentery outbreak ravaged the French camp, even striking the king himself.

Terrified of dying on a latrine, Philip ordered a retreat across the mountains. The Aragonese ambushed the exhausted troops in a narrow pass, slaughtering many. Philip escaped to Perpignan, where he soon died, bringing the Aragonese crusade to a grim close.

3 The Trade Crusade Of Alexandria

Peter de Lusignan, king of Cyprus and the last ruler of a major crusader state, spent the 1360s canvassing Europe for support to launch a crusade against Egypt. With papal backing and fleets from Venice and Genoa, he set his sights on Alexandria in 1365.

Peter’s stated aim was to conquer Egypt—a wildly ambitious goal given his limited resources. Modern scholars suspect his true motivation was economic: Italian merchants were bypassing Cyprus by buying directly from Alexandria, and Peter hoped to redirect trade through his island by devastating the Egyptian port.

After seizing and pillaging Alexandria, the crusaders withdrew at the sound of the approaching Egyptian army. Both Venice and Genoa later issued full apologies for their participation, acknowledging the disastrous nature of the venture.

2 The Contra‑Catalan Company Crusade

In 1303 the Byzantine emperor hired the Catalan Company, a band of mercenaries led by the ex‑pirate Roger de Flor. Their tenure was marked by betrayals, including the murder of Roger and a botched siege of Constantinople.

By 1311 the Company had crossed into Greece, defeating Duke Walter of Athens and seizing his duchy. Although the Catalans had previously taken Athens after the Fourth Crusade, Walter’s heirs appealed to the pope, claiming the mercenaries usurped their rightful lands.

Pope declared a crusade against the Catalans in 1330, accusing them of over‑friendly ties to the Turks. The crusade failed to garner popular support, and the Catalan Company continued to rule Athens for another half‑century.

1 The Waldensian Crusade

The final and perhaps most obscure crusade of the Middle Ages was waged against the Waldensians, a Christian sect emphasizing poverty. Declared heretical in the 12th century, the Waldensians persisted in southern France and northern Italy well into the late 1400s.

In 1487 Pope Innocent VIII launched a crusade against them in the Dauphiné. The Waldensians retreated into the Alpine caves, where they fought a series of brutal assaults by crusader forces. Historian Peter Lock summed up the campaign as a small‑scale, violent episode that achieved nothing of lasting significance.

Despite the ferocity of the attacks, the Waldensian movement survived, illustrating how even a waning papacy could still muster a crusade against dissenting believers.