10 Bizarre Crusades: Conflicts That Shook the Church

by Marcus Ribeiro

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

Illustration of the Crusade Against Markward – part of 10 bizarre crusades

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

Illustration of Humbert’s Crusade – part of 10 bizarre crusades

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.

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8 The Battle Of Nicopolis

Illustration of the Battle of Nicopolis – part of 10 bizarre crusades

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

Illustration of the Stedinger Crusade – part of 10 bizarre crusades

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

Illustration of the Anti‑Colonna Crusade – part of 10 bizarre crusades

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.

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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

Illustration of the Italian Crusades – part of 10 bizarre 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

Illustration of the Aragonese Crusades – part of 10 bizarre 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

Illustration of the Trade Crusade Of Alexandria – part of 10 bizarre crusades

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.

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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

Illustration of the Contra‑Catalan Company Crusade – part of 10 bizarre crusades

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

Illustration of the Waldensian Crusade – part of 10 bizarre crusades

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.

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