Podcast Summary: How To Fail With Elizabeth Day

Episode: Elizabeth's New Show – History’s Greatest Fails

Date: April 7, 2026

Host: Elizabeth Day
Guest Host/Co-host: Dan Jones (Historian, Author)

Episode Overview

This special crossover episode introduces “History’s Greatest Fails,” a new podcast headed by Elizabeth Day and historian Dan Jones. The episode blends Elizabeth’s signature theme—learning from personal and historical failure—with a spirited debate over Richard III: villainous Plantagenet monarch or misunderstood tragic figure? Drawing on their backgrounds as history graduates (and longtime friends), Elizabeth and Dan revisit the story, myth, and fallout of Richard III’s reign, questioning how we define failure and why some stories endure.

Key Discussion Points & Insights

1. Reconnecting Through History and Podcasting

• Elizabeth and Dan reminisce about their university days and how podcasting rekindled their friendship (00:00–01:28).
  • Notable Moment: Discovery of a photo of Elizabeth at Dan’s 21st birthday.

2. Debating the Reputation of Richard III

• Dan playfully accuses Elizabeth of being "in love" with Richard III, and Elizabeth counters that such accusations reflect the biases Ricardians often face (05:08–05:43).
  • Elizabeth (05:08): “You have accused me of being in love with Richard III, which automatically from the outset undermines my historical prerogative to put this case.”
• The debate centers on:
  • Was Richard a ruthless villain or a wrongly maligned king?
  • Did he murder the princes in the Tower?
  • Is a short, calamitous reign simply a historical “failure”?

3. Richard III: Context and Personality

• Dan sketches Richard’s background and political context (07:23–11:24).
  • Born 1452, younger brother of Edward IV.
  • Ruthless decision-making after Edward’s death placed Richard in a zero-sum political game.
  • Dan (07:23): “Richard III is actually extremely competent, but… he can’t sort of grasp the broader political implications of what he's going to do.”
  • The Woodville family, court intrigue, and the appeal of history as “reality TV.”

4. The Princes in the Tower: Failure or Brutal Necessity?

• The podcast rigorously examines the infamous case of the disappeared princes (11:24–15:07).
  • Dan argues Richard’s acts were fitting for the brutal politics of the time, calling the purported murders a “necessary political decision, but… also morally abhorrent.”
  • Elizabeth challenges the certainty, noting the lack of definitive proof—and the persistence of mystery.

5. Reframing Failure: Reputation, Legacy, and Modern Reappraisal

• Elizabeth attempts to rescue Richard from “the failure bin of history” (15:52–16:54).
  • She cites:
    • Richard’s good governance in the North.
    • Legal reforms: trial by jury, translating laws to English.
    • Progressive policies for his time.
  • Elizabeth (16:54): “He introduced trial by jury… translated a lot of laws into English so that people could understand them… speaks of such a progressive leader who existed way before his time.”
• Dan suggests that the nature of Bosworth, the “big failure,” ultimately outweighs Richard’s virtues but admits that history’s final judgment is complex.

6. Tudor Propaganda and Shakespeare’s Legacy

• Discussion pivots to how Tudor-era propaganda and Shakespeare shaped Richard’s image (18:23–24:19).
  • Dan analyzes:
    • The organic emergence of cultural narratives favoring the new Tudor dynasty.
    • Shakespeare’s use of Richard III as a familiar “evil” to grapple with moral questions, not strict historical fact.
  • Dan (22:41): “Shakespeare… isn’t in the business of making historical arguments. He’s in the business of making moral arguments.”

7. Philippa Langley and the Rediscovery of Richard III

• Elizabeth recounts the modern search and discovery of Richard’s remains by Philippa Langley (24:30–32:51).
  • Langley’s tenacity and the serendipity of finding Richard’s skeleton under a car park in Leicester.
  • Coincidental dates: Richard’s body found on August 22, the date he died, spanning 527 years.
  • Elizabeth (32:51): “Isn’t that amazing, Dan?”
  • Dan, ever the historian, points out the Julian/Gregorian calendar shift—teasing Elizabeth for her romanticism.

8. The Philosophy of Failure

• Philosophical musing on whether failure is defined by endings or by risk and how changing attitudes affect our view of the past (27:04–29:42).
  • Elizabeth asserts: “Things aren't failures simply because they end… it’s the nature of the ending.”
  • Dan links this to the current “How to Fail” ethos: learning, growth, and openness to reassessment.
  • Richard III may be “the perfect character to be reexamined, loved, [and] fetishized” in our era.

Memorable Quotes & Moments

• Elizabeth (05:08): “You’ve accused me of being in love with Richard III … from the outset undermines my historical prerogative to put this case.”
• Dan (11:24): “If he doesn’t kill those princes in the Tower, he’s insane.”
• Elizabeth (15:07): “History inflicts him with further wounds… there’s a sense of tragedy to that.”
• Dan (22:41): “Shakespeare… is in the business of making moral arguments.”
• Elizabeth (32:51): “Isn’t that amazing, Dan?”
  Dan (32:56): “Not really the same dates, though, because of the shift in the Julian Gregorian calendar.”
  Elizabeth: “You are such a buzzkill.”
• Elizabeth (29:42): “I didn’t even have something sarcastic to say after that.”

Notable Segments (with Timestamps)

• Origin of friendship and podcasting roots: 00:00–01:28
• Richard III and Tudor debate kicks off: 03:33–05:54
• Elizabeth's “Ricardian” case and Discovery magazine inspiration: 05:54–07:23
• Richard’s rise, decisions post-Edward IV: 07:23–11:24
• Princes in the Tower and political ruthlessness: 11:24–13:16
• Trial by jury and Richard’s progressive legacy: 16:05–16:54
• Tudor propaganda and the formation of narrative: 18:23–24:19
• Philippa Langley, the car park, and “serendipitous” dates: 24:30–33:24
• Philosophy of failure and changing modern attitudes: 27:04–29:42
• Preview of next episode: Failed romances in history: 33:24–34:27

Episode Tone & Language

• Friendly, teasing, and deeply engaged
• Blends academic rigor with witty repartee and personal reminiscence
• Both hosts are passionate, knowledgeable, and unafraid to poke fun (at each other and at themselves)

Closing

Dan and Elizabeth wrap up with a preview of coming topics—iconic failed romances—and promote their respective series (How To Fail, This Is History).
Elizabeth (34:42): “Let’s fail again.”
Dan: “Next time.”

For listeners new or old, this episode offers a lively, insightful, and poignant exploration of how history’s “failures” provoke debate and reflection—and why we continue to care about them centuries on.