After Dark: Myths, Misdeeds & the Paranormal

Episode Title: Who Was Medieval Europe's Most Evil Monarch?
Host: History Hit
Date: November 27, 2025
Guests: Anthony Delaney, Maddy Pelling, Eleanor Yanaga

Episode Overview

In this episode, hosts Anthony Delaney and Maddy Pelling delve into the dark side of medieval European monarchy to answer a ghoulish question: Who was the most evil medieval monarch? With historian and “Gone Medieval” host Eleanor Yanaga as their guest, they explore the notorious reigns of Vlad the Impaler, Pedro the Cruel, Isabella the “She Wolf” of France, and Richard the Lionheart. Through vivid stories, heart-stopping legends, and controversial scores, the team debates which ruler truly stands out as the vilest of them all. The episode is darkly witty, irreverent, and loaded with juicy historical tidbits.

Key Discussion Points & Insights

1. The Contenders: Setting the Scene

• The hosts and Yanaga set out to evaluate four infamous monarchs—Pedro the Cruel, Richard the Lionheart, Isabella the She Wolf of France, and Vlad the Impaler—for their misdeeds and legacies.
• Eleanor Yanaga highlights that being the "worst" monarch can mean anything from being a "total psychopath and serial killer" to being a cunning, vindictive schemer. (04:52)

Notable Quote:

• "There's a lot of different ways to be a dickhead when it's gonna come to medieval monarchy."
  — Eleanor Yanaga (05:28)

2. Pedro the Cruel: Revenge, Romance, and Cadaver Queens (05:41–15:58)

• Background: Pedro I of Portugal, aka Pedro the Cruel, is introduced as a lesser-known but suitably dramatic figure. His infamous vendettas and personal revenge set him apart.
• Romantic Drama: Married for political alliance to Blanche of Bourbon, Pedro instead becomes obsessed with Ines, a lady-in-waiting. When his father has Ines murdered—possibly with the involvement of Pedro's half-brother—Pedro's rage is unleashed.
• Revenge: Upon becoming king, Pedro exacts bloody revenge by allegedly tearing out the hearts of Ines' murderers with his own hands. Whether this is fact or chronicler's embellishment is debated, but the symbolism remains powerful.
• Gothic Legend: Chroniclers claim Pedro had Ines’ body exhumed, crowned, and forced the court to pay homage. Yanaga notes it's probably untrue but indicative of his reputation.
• Reflection: The group reflects that, although Pedro’s vengeance was horrific, his violence stemmed from grief and personal vendetta, giving him a twisted romantic edge rather than pure villainy. His gestures were both poetic and macabre.

Memorable Quotes:

• "He does kind of like straight up serial killer violence, you know, but it is revenge, you know...it's giving Mandy, right?"
  — Eleanor Yanaga (14:32)
• "If I die and someone doesn't cut out someone else's heart for me, I'm not interested. Like 100%. I'm on board."
  — Host 1 (52:22)

Timestamps:

• Political backdrop & family drama: 05:45–10:34
• Legendary revenge and aftermath: 10:34–15:58

3. Richard the Lionheart: Crusader, Tax-Leech, and Assassin Hireling (16:12–25:31)

• Decorated Reputation: Known as a heroic English monarch, Richard’s legacy is sharply challenged by Yanaga, who calls him "the Wario of Pedro the Cruel."
• Absentee King: Richard barely visits England (only four times), doesn’t speak English, and views the realm as a “bank account” to finance his war efforts.
• Oppressive Taxes: He institutes the “Saladin Tithe,” an oppressive tax (25% of all property) to fund his crusades, sells public offices, and plunders the populace.
• Crusade Atrocities: On the Third Crusade, Richard besieges Christian kingdoms en route, executes (possibly 2,700+) Muslim prisoners at Acre, and is widely suspected of orchestrating the assassination of Conrad, King of Jerusalem.
• Europe-Wide Infamy: Detained in Europe upon his return, his ransom nearly bankrupts England. He is generally despised on the continent.
• Legacy Debunked: Richard is idolized in later English legends only as an absentee; his myth grows precisely because of his absence and the nation’s subsequent longing.

Memorable Quotes:

• "He does not care about this country at all whatsoever... He’s got no interest in England as anything other than a bank account."
  — Eleanor Yanaga (17:02)
• "The only good thing about Richard the Lionheart is his at least bisexuality... a flexible king, very close with his boys, et cetera."
  — Eleanor Yanaga (17:27)
• "His mom, like, basically bankrupts the country, gets all this money out. They let him out. People hate Richard so much that when he's let out...he writes...'the devil is loose. Look to yourself.' "
  — Eleanor Yanaga (24:33)

Timestamps:

• Deconstructing the myth: 16:12–20:53
• Crusade atrocities & European view: 20:53–25:31

4. Isabella the She-Wolf of France: Queen, Usurper, Survivor (29:05–36:40)

• Introduction: Isabella is framed as messy but fascinating—a French princess who marries Edward II of England.
• Marital Turmoil: Edward II’s open favoritism for his male lovers leads Isabella to political exile and eventual rebellion, aided by her own lover, Roger Mortimer.
• Coup and Retribution: Isabella together with Mortimer overthrows Edward II. The king is either murdered or conveniently dies in prison; legends of a red-hot poker are likely symbolic.
• Ruling with Her Lover: Isabella effectively rules England with Mortimer until her son, Edward III, takes over, executing Mortimer and sending Isabella into comfortable semi-exile.
• Schemer and Powerbroker: Isabella’s scheming embroils her in scandal, including the infamous “Tour de Nesle” affair, indicting sisters-in-law of adultery, which has major dynastic consequences.
• Legend and Legacy: Known as the “She Wolf” in her own lifetime, her notoriety was immediate. Despite her ruthless actions, she lived out her days in luxury and maintained a complex relationship with her son.

Memorable Quotes:

• "Isabella, the She Wolf of France—you know, they're trying to say it as like brackets. Derogatory. I'm like brackets. Positive."
  — Eleanor Yanaga (29:23)
• "I love her because...she notices everything. She's incredibly smart. And she will call you out. Right. And I love that for her."
  — Eleanor Yanaga (35:50)

Timestamps:

• Isabella’s background and takeover: 29:05–33:13
• The Tour de Nesle Affair: 34:23–35:05
• Marks out of 10 and historical consequences: 36:40–37:32

5. Vlad the Impaler: Horror & National Hero (37:32–49:17)

• Bloody Infamy: Vlad, Prince of Wallachia, is the archetype of brutality; impaling thousands on stakes and terrorizing the region.
• War on All Sides: He slaughtered local German (Saxon) settlers as well as Ottoman envoys, sometimes using their deaths to send horrifying political messages. His reign was marked by betrayal and shifting alliances.
• Innovation in Fear: Impalement was not standard practice; Vlad popularized it as a unique form of terror, often publicly displayed.
• Transgressive Atrocities: He is accused in legend of massacring beggars and even his own people, transcending the accepted, brutal norms of medieval warfare.
• Monstrous Legacy: Despite (or because of) these atrocities, Vlad remains a folk hero in modern Romania for defending his land from foreign control. European contemporaries, however, saw him as beyond the pale.
• From Vlad to Dracula: Vlad’s reputation would be cemented and mythologized by Bram Stoker’s “Dracula”—a literary transformation that, while loosely based on the real figure, ensured historical immortality.

Memorable Quotes:

• "He’s an innovator...he really is able to, like, go for it with these guys."
  — Eleanor Yanaga on impalement (41:06)
• "The idea here is that these guys might have been alive. It's a real slow one."
  — Eleanor Yanaga on impalement (42:16)
• "Ask anyone else in Europe and they're like, that man is a monster. He's an awful person. And I think that we don't talk about it enough. So yeah, screw that guy."
  — Eleanor Yanaga on Richard, letting Vlad win (25:30)

Timestamps:

• Atrocities and impalement: 37:32–44:31
• Myths about beggars and breaking the king’s moral code: 45:12–47:48
• Vlad in literature and history: 49:17–51:06

Final Rankings & Reflections (51:41–53:28)

Eleanor Yanaga’s Final Ranking:

1. Vlad the Impaler (most evil due to sheer body count and inventive cruelty)
2. Richard the Lionheart (“statistically and spiritually, a true villain”)
3. Isabella (brutal but less bloody)
4. Pedro the Cruel (his misdeeds most “romantic” and personal)

Hosts agree: Vlad tops the list as the worst, though Richard is a close second in their loathing. Isabella is a messy but fascinating power-player, while Pedro’s crimes read more as operatic tragedy.

Memorable Finale Quotes:

• "I think that we have to go with Vlad. I want it to be Richard just because I hate him so much. But I think the kill count is just too high."
  — Eleanor Yanaga (51:48)
• "If I die and someone doesn't cut out someone else's heart for me, I'm not interested. Like 100%. I'm on board."
  — Host 1 (52:22)

Notable and Amusing Moments

• Hosts' Lively Banter: The episode is full of playful asides, hyperbolic sympathy for Pedro, exasperation with Richard, and outright admiration for Isabella's scheming.
• Team Pedro’s Heart-Tearing Fandom: Several times, the hosts (especially Host 1) gleefully support Pedro’s violent romantic revenge as justifiable.
• Red-Hot Poker Lore: The myth of Edward II’s demise by red-hot poker is dissected for its symbolism and its gruesome place in the medieval imagination.
• Hosts’ Scores and Fantasies: The team scores each monarch on an “evil” scale, and imagines themselves in similar positions, with tongue-in-cheek asides about personal revenge and relationship standards.

Timestamps for Main Segments

• Pedro the Cruel: 05:41–15:58
• Richard the Lionheart: 16:12–25:31
• Isabella, She-Wolf of France: 29:05–37:32
• Vlad the Impaler: 37:32–51:41
• Final Rankings & Reflections: 51:41–53:28

Overall Tone and Takeaway

The episode is wickedly funny, irreverent, and thoroughly researched. Hosts combine grisly medieval lore with modern sensibilities, questioning not only why these monarchs behaved as they did, but why we are still fascinated by their legends. Eleanor Yanaga’s insightful, often hilarious commentary anchors the show, and her perspective reframes familiar histories, debunking myths and revealing new angles on villainy.

Who was the most evil monarch?
Vlad the Impaler emerges as the undisputed "champion" for his unprecedented cruelty and kill count, but all four leave an indelible (if unnerving) mark on European history.

Event details, ad reads, and outros have been omitted to focus on historical content.