10 Medieval Prison Breaks That Should Have Been Impossible

#MedievalHistory #PrisonBreak #History Did you know that the very first prisoner ever locked inside the Tower of London was also the very first man to escape it — climbing down a smuggled rope in 1101 after getting his guards drunk on wine he'd hidden in his own cell? Or that a single young man's escape from Constantinople in 1201 helped set the Fourth Crusade in motion — the campaign that would go on to sack the greatest Christian city on earth and bring down the Roman Empire itself? From a Welsh king's almost fairy-tale flight through Chester to the richest man in France vanishing from his cell, medieval prisoners engineered escapes so audacious that some were dismissed as legend — until the earliest sources proved they were real. This is a countdown of the 10 greatest prison breaks of the Middle Ages, spanning England, Wales, France, the Crusader states and Byzantium between 1094 and 1454: who was locked away, how they got out, and how a handful of these breakouts went on to topple kings and reshape whole kingdoms. ⏱ TIMESTAMPS 0:00 — No. 10 Scottish Rebel Escapes Chester 4:07 — No. 9 Charles The Bad 8:22 — No. 8 Hubert De Burgh 13:23 — No. 7 The Real Falstaff 18:14 — No. 6 France's Richest Man 23:42 — No. 5 The Welsh King 28:42 — No. 4 First Tower Escape 33:54 — No. 3 The Crusader Count 39:44 — No. 2 Mortimer Topples A King 46:24 — No. 1 The Escape That Sacked Constantinople 🔔 Subscribe for more forgotten history and medieval stories that never made it into your school textbook. Which of these 10 escapes do you think was the most impossible? Drop a comment and tell us which one surprised you most — and where you're watching from. #MedievalHistory #HistoryDocumentary #PrisonBreak #TowerOfLondon #MedievalEngland #HistoryFacts #Crusades #ByzantineHistory