Gone Medieval – "Tower of London: Medieval Prison"

Host: Matt Lewis
Guest Host: Eleanor Janega
Special Guest: Tom Horton (comedian, former Tower resident)
Release Date: January 9, 2026

Episode Overview

This episode delves into the Tower of London’s long history as a medieval prison. Hosts Matt Lewis and Eleanor Janega journey inside the Tower after hours, exploring its stories of confinement, daring escapes, infamous deaths, legends, and everyday realities for both high-status and ordinary prisoners. They bring the history to life by visiting key locations, discussing famous cases from Ranulph Flambard to the Princes in the Tower, and conclude with a candid conversation with comedian Tom Horton, who lived in the Tower as a modern resident.

Key Discussion Points and Insights

Setting the Scene: The Tower by Night (00:39–02:54)

• Atmosphere: Hosts arrive at the Tower after closing, describing its imposing appearance lit against the night sky—a blend of awe and foreboding.

  • “We stood right outside the immense White Tower...the white stone sort of glowing against the darkness of the sky. Oh, it’s so atmospheric.” – Matt (01:14)

• Dual Role: The Tower’s aforementioned palace function is acknowledged, then focus turns to its history as a site of imprisonment.

Early Prisoners and Escapes (03:14–12:57)

Construction and Norman Origins (03:28–04:59)

• The White Tower, built by William the Conqueror, symbolized Norman dominance, constructed with stones imported from Caen, Normandy, to emphasize the connection.

Ranulph Flambard: The First Famous Prisoner and Hollywood-Worthy Escape (05:10–08:59)

• Flambard, imprisoned after William II’s death, escapes ingeniously by smuggling a rope in a wine barrel, getting his guards drunk, and climbing to freedom.
  • “He has a barrel of wine brought in...and in the barrel of wine, he’s hidden a rope. And he proceeds to get his guards just blinding drunk...and then after they all pass out drunk, he takes the rope and scales out of the White Tower.” – Eleanor (07:52)

Roger Mortimer: Treason, Intrigue, and Another Escape (09:21–12:57)

• Mortimer and his uncle Roger, convicted of treason against Edward II, escape using a rope ladder and poisoned wine, aided by sympathetic insiders.
  • “It’s very daring...he gets through the kitchens, uses a rope ladder...and they get into a boat that’s waiting for them in the river.” – Matt (11:58)
  • These stories highlight the relative comfort and privilege of noble prisoners—and the Tower’s less-than-flawless record as a prison in its early centuries.

The Tower's Architecture and Prison Conditions (14:00–17:27)

• Garden (Later, Bloody) Tower: Originated as accommodations for elite guests and later repurposed as prison quarters.
• Descriptions of the imposing doors, portcullis, and tight spiral staircases set a physical context for incarceration.
• Higher status prisoners lived in surprisingly genteel conditions compared to modern dungeon stereotypes.
  • “As far as London property goes...it would be way, way, way too much, you know, but it is larger ceilings...15 foot ceilings. Nice bit of wood. Nice windows with a good view.” – Eleanor (16:44)

Notorious Inmates & Legends (17:27–34:00)

Henry VI and the Bloody Tower (17:27–21:26)

• Imprisonment, uncertain death, and Yorkist/Tudor propaganda.
• Dying “of pure melancholy” is dismissed by Eleanor—conditions, health and simple “bad luck” were more likely.
  • “I don’t necessarily believe that Henry VI dies because his heart is broken, but...if you’re in a melancholic position while you are imprisoned in a dungeon, it is just easier to not make it back, not rally.” – Eleanor (19:31)

George, Duke of Clarence: Fact and Fiction (22:23–27:48)

• Story of his supposed execution by drowning in a barrel of Malmsey wine is discussed and debunked as likely myth, but it endures thanks to family legend and its dark humor.
  • “The story of George instead is that George ends up being drowned inside—stop me if you’ve heard this one—a barrel of wine.” – Eleanor (23:50)
  • “Drowning is not a good way to go...but we Stan. We Stan a petty guy, you know.” – Eleanor (26:52)

The Princes in the Tower: Royal Victims, Enduring Mysteries (27:48–32:05)

• The tragic story and historical debate over Edward V and Richard. The absence of records is interpreted both as evidence of cover-up and as normal for the period.
  • "It’s the same problem that we have with George, isn’t it? Because since they are royal...who knows what happened?" – Eleanor (28:10)
  • The legend of ghostly child apparitions is mentioned with skeptical affection.

Political Prisoners, Executions, and Medieval Justice (32:46–38:14)

• The Tower was reserved for high-profile political prisoners—useful for both spectacle and demonstration of royal power.
• “Being brought to the Tower is a big and specific political display. This is a seat of royal power and a seat of royal power in London.” – Eleanor (32:48)
• William Wallace: Brief biography, dramatic trial, and brutal execution signals the Tower's use for punishing threats to royal authority. (34:46–36:08)
• William de la Pole: The longest-serving prisoner (37 years), left to languish in relative comfort but clear suffering.
  • “However comfortable it might be, 37 years of your freedom being restricted, even if you’re in the comfortable apartments...is nobody’s idea of fun, is it?” – Matt (37:54)

Who Would You Save? Ethical Dilemmas (39:24–41:42)

• Matt and Eleanor each choose which prisoner they would save:
  • Eleanor: Anne Boleyn—wronged by Henry VIII, her death setting a grim precedent.
  • Matt: Henry VI—a tragic figure undone more by fate than personal crime.
  • “Oh, now it’s illegal for women to have hobbies...she really did nothing wrong.” – Eleanor (39:47)
• Eleanor also makes a heartfelt plea for the Tower's non-human inmates, especially the menagerie animals.

The Tower as a Home: Interview with Tom Horton (42:11–55:00)

Living in History (42:11–45:22)

• Tom explains his residency (by virtue of his father’s role as Constable):
  • Lived in the Queen's House (now King's House), a Tudor building with layers of significant history—including the room where Guy Fawkes was interrogated.

Ghosts, Legends, and Bizarre Modern Realities (45:22–51:52)

• Tom’s bedroom: Once a cell that allegedly housed Arabella Stewart, whose ghostly portrait tormented him until he rehung it out of superstition.
  • “I took the painting down. I then became really ill and started vomiting green bile…and it was only when I put the painting back up that I got better. So in many ways, I think that was her ghost who was not wanting me to find love, as she couldn’t either.” – Tom (47:49)
• The supernatural is a constant subject among Tower residents—the infamous "ghost bear" and the ever-present sense of history’s weight.

Community and Perspective (51:52–53:47)

• Unique sense of village life and heritage among the 130 residents within the Tower walls.
• The evolution of the community and the Tower itself serves as a reminder that history is ongoing.
  • “History isn’t just in the past. It’s a constant thing that keeps on going.” – Tom (53:25)

The Tower's Legacy (55:14–End)

• The Tower has been a symbol of royal authority and a site of power struggles, execution, imprisonment, and transformation for over 900 years.
• Its roles as fortress, palace, prison, and home overlap, reflecting England’s turbulent story.
  • “The Tower of London represented a fierce authority from the very moment that it was built...It’s a site of refuge, yes, but also of imprisonment and political executions.” – Matt (55:14)

Notable Quotes & Memorable Moments

• On the architectural message:

  • “He’s making this direct connection. He’s saying, this is now a part of Normandy...guess what, there’s a bit of Normandy right here.” – Eleanor (04:22)

• On infamous escapes:

  • “Hollywood, please make a movie about this.” – Eleanor (07:52)

• On the reality for most prisoners:

  • “We’ve had two examples of the tower being a rubbish prison, but maybe we could go inside and think a bit about some people who weren’t quite so lucky.” – Matt (13:29)

• On tragic royal kids:

  • “We are quite possibly standing on the spots where a 12-year-old and a 9-year-old boy stood 500 years ago. And whatever happened to them, they’re confused, they’re scared. They’ve lost their dad, their mom has fled into sanctuary, their future has been turned upside down.” – Matt (30:51)

• On the enduring allure of the Tower:

  • “You can’t not be overwhelmed…and with the White Tower standing up...the place they had the beheadings. You can hear the ravens. Yeah, I mean you can’t not be taken by it.” – Tom (49:27)

Timestamps for Important Segments

• Tower as Palace vs. Prison – Introduction: 00:39–03:22
• Ranulph Flambard and the Wine Escape: 05:10–08:59
• Roger Mortimer’s Daring Breakout: 09:21–12:57
• Touring the Bloody Tower: 14:00–17:27
• Henry VI & the Death of Kings: 17:27–21:26
• Clarence and the Barrel of Malmsey: 22:23–27:48
• Princes in the Tower - Legends and Realities: 27:48–32:05
• Political Prisoners & Medieval Justice: 32:46–38:14
• Longest Serving Prisoner (William de la Pole): 37:54–38:14
• Who Would You Save?: 39:24–41:42
• Tom Horton Interview (Tower as Home): 42:11–55:00
• Tower’s Role Through History/Closing Thoughts: 55:14–end

Tone & Style

• Richly descriptive, humorous, affectionate for history’s quirks and mysteries, with gentle myth-busting and a running warmth of camaraderie between hosts.
• A mix of light-hearted banter (“We Stan a petty guy, you know.” – Eleanor, 26:52) and poignant reflection on the fates of prisoners past.

Useful for Listeners Who Haven’t Heard the Episode

This summary captures the spirit, key content, most compelling stories, and insightful moments from the episode. It explores the Tower not just as a building, but as a site layered with legend, trauma, and ongoing life—shedding new light on its evolution from fortress and palace to feared dungeon and even modern residence, all while debunking popular myths and highlighting the humanity (and sometimes pettiness) of its many inmates.