Gone Medieval: Crusaders in Crisis – The Rebel Emperor & the Siege of Constantinople

Podcast: Gone Medieval (History Hit)
Host: Dr. Eleanor Yaniga
Guest: Dr. Tom Smith
Release Date: March 10, 2026

Episode Overview

This compelling episode of Gone Medieval explores the turbulent era of the thirteenth-century Crusades—a period of chaos, shifting alliances, and catastrophic failures. Host Dr. Eleanor Yaniga and guest Dr. Tom Smith (author of The Fifth: A History of the Epic Campaign to Conquer Egypt) guide listeners through the drama of the Fourth, Fifth, and Sixth Crusades. They reveal the increasing fragmentation of crusading ideals, egos in conflict, and the pivotal roles played by figures such as Pope Innocent III and Holy Roman Emperor Frederick II. From the notorious sack of Constantinople to the remarkable, negotiation-driven return of Jerusalem, the episode uncovers the deep fractures in Christendom and the ultimate unraveling of the crusading movement.

Key Points & Insights

Setting the Stage: After the Fall of Jerusalem

[09:00-11:35]

• The post-1187 world marks a profound shift in crusading: Instead of celebration, the West is now in supplication, desperate to recover Jerusalem after Saladin’s victory.
• The landscape has changed: Crusading activity alternates between Western kingdoms, while the Ayyubid dynasty consolidates power from Syria to Egypt.
• Quote:
  "We've gone from a 12th century, which has mostly been about supporting the Crusader states, to the 13th century, where it's about trying to regain what they've lost in 1187... The stakes have changed completely."
  —Dr. Tom Smith [10:30]

Why the 13th Century Stands Out

[11:36-13:54]

• This half-century is the most intense in the history of crusading, marked by constant campaigns—including the Fourth, Fifth, and Sixth Crusades, crusades in the Baltic and southern France, and the Children’s Crusade.
• Notable events: Siege of Constantinople (the first Christian city captured by Crusaders), invasion of Egypt as a new strategy.

The Papal Game Changer: Innocent III

[13:55-18:23]

• Pope Innocent III's reign sees the expansion and institutionalization of crusading: new taxes, broader participation (including non-combatants and women), intensified canon law.
• He is "one of our most lawyerly popes" and pioneers tax-funded crusading (Fourth Crusade's two-and-a-half percent; Fifth Crusade five percent taxes on church income).

The Catastrophe of the Fourth Crusade & the Sack of Constantinople

[18:23-43:31]

The Original Intent and Venetian Factor

• Originally aimed at attacking Alexandria, Egypt—perceived as the "breadbasket" and power source of the Muslim world.
• The Venetians build a fleet and ingenious amphibious siege weapons, with huge investment.
• Only half the expected crusader force arrives, leading to a funding crisis.

The World's Worst "Stag Do"

[20:50 and 24:22]

• The hosts use the "stag do" (bachelor party) analogy to describe the chain of mishaps:
  "It's like the world's worst stag do, where everything goes completely wrong."
  —Dr. Tom Smith [20:50]
• The crusaders are forced to attack Christian Zara to pay Venice—a key violation.

Enter Byzantium: From Regime Change to Sack

• Byzantine prince Alexios Angelos offers massive incentives for crusader help in reclaiming the throne, promising “200,000 silver marks…a standing army of 500 knights” and submission of the Orthodox Church.
• Regime change succeeds but payments dry up, leading to the fateful siege of Constantinople in April 1204.
• Memorable moment: After breaching the walls, the crusaders loot the city for three days in one of medieval Europe’s greatest disasters.

Notable Quote:
"They begin slaughtering the population, they burn more houses and they loot the city en masse for three days. So this is a really terrible outcome for the Byzantines and for the Crusaders." —Dr. Tom Smith [41:10]

Broader Impact

• Shock in Europe; undermines crusader ideology, but some pragmatists see opportunity.
• Constantinople becomes the center of the short-lived Latin Empire.

The Fifth Crusade: Egypt at the Center

[45:47-57:27]

• Inspired by the failed Fourth Crusade (which never reached Egypt), Innocent III calls for renewed action.
• The crusaders use landing craft reminiscent of D-Day to besiege Damietta, facing complex fortifications and legendary defenses, including a "chain tower" across the Nile.
• Colorful Detail:
  Oliver of Cologne invents a floating siege weapon, and another knight wields a medieval "nunchuck" made from a flail enhanced with iron.

The Epic Siege and Catastrophic Retreat

• The siege lasts 18 months. The city finally falls to starvation, opening a new crusader front in Egypt.
• Awaiting Frederick II, the crusaders, prodded by papal legate Pelagius, rashly march on Cairo at the worst possible (flood) season due to apocalyptic calculations—they believe the last Emperor and Prester John will meet in Jerusalem in 1222.
• The disastrous retreat from Mansoura:
  [57:27-65:01]
  • Crusaders, overconfident and eager not to waste their wine, drink themselves “plastered,” then botch a covert withdrawal, leading to slaughter, surrender, and the loss of Damietta.

Memorable Exchange:
"Is being French a two-edged sword? On the one hand you're really good at fortifying cities, but then on the other you just hate to see wine go to waste."
—Dr. Eleanor Yaniga [65:01]
"They're connoisseurs, basically."
—Dr. Tom Smith [65:12]

The Sixth Crusade & Frederick II: The Rebel Emperor

[65:20-82:34]

Frederick’s Unusual Crusade

• Frederick is a polymath “Wonder of the World,” more interested in learning and luxury than warfare—his initial reason for taking the cross is political leverage to be crowned Holy Roman Emperor.
• His constant delays and eventual excommunication by Pope Gregory IX set up a dramatic confrontation.
• Despite excommunication and limited troops, Frederick sails to the Holy Land, relying instead on secret negotiations with Sultan Al-Kamil.

Victory by Treaty

• The Treaty of Jaffa (Feb 1229): Bethlehem, Nazareth, a corridor to the coast, and most of Jerusalem (without the Temple Mount) return to Christian control, but Frederick cannot rebuild Jerusalem’s walls or help embattled Crusader outposts.

• His coronation in Jerusalem is a "theatrical" yet solitary act:
  "The Emperor lifts the crown and places it upon his own head. This is his city now... But this is no ordinary coronation. There is no swelling acclamation, no resplendent ceremony. No one save the Emperor's own soldiers bear witness."
  —Dr. Eleanor Yaniga [04:40]

• Frederick is pelted with tripe and offal as he departs; his conquest is legal but deeply unpopular, highlighting the increasing absurdity and fragmentation of the crusading endeavor.

Notable Quotes & Moments

• On the Fourth Crusade’s chaos:
  "Who's going to pay for the activities and the transport and where are we going to go to? ... This one goes spectacularly wrong because... no one's happy with it. And that leads to the capture and sack of the greatest Christian city in the world, Constantinople."
  —Dr. Tom Smith [21:04]

• On the fragmentation of crusading ideals:
  "Crusading has become a profoundly unstable venture, an arena for clashing egos and competing authority."
  —Dr. Eleanor Yaniga [05:32]

• On Frederick II’s character:
  "He’s just got it going on. He sort of dabbles in everything's amazing... and he's completely ruthless as well. Like, he will stop at nothing to get what he wants."
  —Dr. Tom Smith [65:37]

• On the tragic absurdity of the Fifth Crusade's end:
  "Half of the Crusade army is completely k-lied [drunk]... There's absolute chaos... burning tents, it's during the night, people are being washed away into the river and drowning... The real failure of the Crusade is determined by the waters of the Nile and also French wine, basically."
  —Dr. Tom Smith [57:27-64:00]

Timestamps for Major Segments

• [09:00] — The changed landscape after 1187 and Saladin’s victory
• [13:55] — Pope Innocent III and the expansion of crusading
• [18:23] — The launch and mishaps of the Fourth Crusade
• [29:04] — The path to the sack of Constantinople
• [45:47] — The Fifth Crusade, siege of Damietta, and Cairo campaign
• [57:27] — The catastrophic retreat and ending of the Fifth Crusade
• [65:20] — Frederick II, the Sixth Crusade, and Jerusalem retaken by treaty
• [82:34] — Reflections on fragmentation and legacies of the Crusades

Conclusion & Legacy

By the 13th century, the crusading movement was deeply fractured—no longer a unifying cause, but a theater for rivalry, personal ambition, and shifting political strategies. Pious warriors, pragmatic popes, merchant city-states, and rebel emperors all vied for power, often at the cost of Christian unity. The episode lays bare how the crusading project, once a titanic force in Christendom, unraveled under the weight of its contradictions—setting the stage for its ultimate collapse under Mongol and Mamluk incursions.

[83:01] Dr. Eleanor Yaniga:
"The movement unleashed in 1095 no longer belonged solely to popes and penitential warriors, but had become entangled in rivalries between emperors, kings and city states. The sack of Constantinople exposed deep fractures within Christendom itself, and even apparent triumphs like Frederick II’s bloodless capture of Jerusalem revealed just how fractured and precarious the crusading ideal had become."

To hear how the epic story concludes, listen to the finale episode: "The Endgame – Mongols, Mamluks, & the Twilight of the Crusader States."