After Dark: Myths, Misdeeds & the Paranormal

Episode: Who Was The Ultimate Tudor Traitor?

Hosts: Anthony Delaney & Maddy Pelling
Guest: Philippa Gregory (historian & author)
Release date: October 9, 2025

Episode Overview

This episode dives into the life and legacy of Jane Boleyn, Lady Rochford—often vilified as the "ultimate Tudor traitor." Hosts Anthony and Maddy are joined by renowned historian and author Philippa Gregory to unpick the myths and realities around Jane's alleged betrayals, her tumultuous court life, and her strategic maneuvering for survival in Henry VIII's perilous, power-hungry court. Drawing from Gregory’s new book, The Boleyn Traitor, the discussion explores how history (and historical fiction) has interpreted one of the Tudor period’s most enigmatic—and maligned—female figures.

Key Discussion Points & Insights

1. The Fascination with the Tudors

[06:39]

• Gregory explains the enduring attraction to Tudor history as stemming from its political turbulence, consolidation of royal power, and the rise (and tyranny) of Henry VIII.
• Society’s current fascination with "strong male leaders" mirrors the gravitation toward the tragic, powerful figures of the Tudor era.
• "That's really the start of tyranny… and it's extraordinary to look at it now, when countries are embracing the idea of a strong male leader." – Philippa Gregory [07:20]

2. Jane Boleyn: Her Rise and Reputation

[09:15]

• Jane Parker (later Lady Rochford), daughter of Lord Morley, began as an upper aristocrat but not at the heart of court power.
• Her marriage to George Boleyn thrust her into proximity with royal drama when Anne Boleyn became queen.
• Jane’s ability to survive the fall of the Boleyns and even be promoted at court raises questions about her political skill and alliances.
• Gregory disputes the long-held belief that Jane was responsible for the downfall of her husband (George) and Anne Boleyn.

3. The Sources of Jane's Infamy: Victorian & Modern Interpretations

[13:36]

• Victorian historians painted Jane as a treacherous, jealous woman, responsible for bringing down Anne and George.
• Later historical analysis constructed Jane as a sexual voyeur or simply "mad."
• Gregory challenges all these narratives:
  • "The idea that she is, in fact mad, I think, completely ignores the fact that at the time… there is no death penalty on people who are recognized as mad. So it's a completely rational way of saving her own life…" – Philippa Gregory [16:13]
• Modern historians and fiction writers are urged to bring nuance, recognizing Jane's survival strategies over reductive stereotypes.

4. The Alleged Betrayal: Did Jane's Testimony Doom Anne and George?

[17:02]

• The idea that Jane betrayed Anne and George finds little support in primary sources.
• The "betrayal" narrative was shaped by Victorian priorities and anxieties, eager to exonerate Anne by crafting a female antagonist.
• "It's very, very good for the Victorian historians to say it's his wife. Horrible Jane. Another woman, probably jealous." – Philippa Gregory [19:20]

5. Thomas Cromwell’s Influence and Jane’s Court Survival

[22:10]

• Gregory presents the theory that Jane’s continued ascent and protection after her husband's execution were likely due to Thomas Cromwell.
• Jane was repeatedly placed in positions of influence in the courts of successive queens, suggesting powerful backing.
• Cromwell may have used Jane for intelligence and managing delicate matters, such as the annulment of Henry’s marriage to Anne of Cleves.

6. Women as Power Brokers in the Tudor Court

[25:48]

• Women's roles as career courtiers, particularly as ladies-in-waiting, are underappreciated in historical study.
• Jane’s continuous court appointments despite her family’s downfall challenge the notion that only men held political power.
• Jane had both motive and means to continue at court and may have actively chosen to remain entrenched in royal service.

7. Jane’s Downfall: The Catherine Howard Affair

[31:34]

• The loss of Cromwell as her patron left Jane exposed.
• Jane was implicated in arranging meetings between Queen Catherine Howard and Thomas Culpepper.
• Gregory speculates Jane's pragmatic rationale: facilitating conception to secure Catherine’s position, with the hope it would result in influence and stability.
• "If it had worked, it would have been an extraordinary power play… She could have married Thomas Culpepper then and her son would [be] King of England. It's not a stupid thing to do in the circumstances…" – Philippa Gregory [34:07]

8. The End: Madness, Survival, and Execution

[36:43]

• Facing execution, Jane may have feigned madness because Tudor law prohibited the execution of the insane.
• Henry VIII, in an act of personal vindictiveness, changed the law so Jane could be executed.
• "It's classic tyrant behavior that tyrants use the law for their personal vindictiveness… and it's one of the real kind of warning signs that you've gone beyond having a bit of a narcissist running the country, you've stepped into tyrant territory." – Philippa Gregory [38:25]
• The segment draws modern parallels to contemporary power abuses by strongmen.

9. Unpacking Misogynist Tropes in History

[42:26]

• The conversation reflects on how stereotypes—virgin, wife, adulteress, hag—have enabled historians to erase women’s agency.
• Jane is shown as a survivor and strategist, rather than a passive or irrational figure.
• "There are, you know, sluts. But there's no stereotype of a scholar, there's no stereotype of an artist, there's no stereotype of female genius…" – Philippa Gregory [43:04]

10. The Craft of Historical Fiction & Gregory’s Process

[46:21]

• Gregory shares her writing approach: the importance of historical research, channeling obsession for her characters, and ignoring external expectations during the creative phase.
• Distinction between the immersive act of writing and the public phase of publishing and promotion.
• "When you are starting a novel, the last thing you can do is think about the readers… By the time I sit down to write, I've done something like a year of research on this character. I am just desperate to start telling her story…" – Philippa Gregory [46:21]

Notable Quotes & Memorable Moments

• "It's a sort of a Christmas Eve with a little bit of Halloween thrown in." — Philippa Gregory on the anticipation of a new book release [05:35]
• "She's a bad woman, end of story… She's obsessively addicted to sex, so much so that her particular kink is sex done by queens of England. Very, very particular and very high risk." – Philippa Gregory, satirizing the extremes of historical interpretation [15:46]
• "Most of the time people want to stay in. If they can get back, they do. And she has this extraordinary opportunity." – Philippa Gregory on court survival [27:26]
• "You don't get to be lady-in-waiting to the Queen of England because people like you… it's got to be Cromwell." — Philippa Gregory [29:03]
• "In Henry and all tyrants… it just gets worse." — Philippa Gregory [30:45]
• "If you remove that element of her personality and who she was, some of her behavior and the places we find her in are sort of inexplicable, really, aren't they?" — Maddy Pelling, on Jane’s motivation [44:47]
• "I am in love with my work. I just want to be with it all day." — Philippa Gregory on writing [46:53]

Important Segment Timestamps

• 00:00–01:26 – Podcast opening, ad breaks (skip)
• 01:43 – Introduction to Jane Boleyn and her notorious historical reputation
• 04:38 – Introduction of guest Philippa Gregory and her upcoming book
• 06:39–09:15 – What draws us to the Tudor period, and why the Boleyns fascinate
• 09:15–13:36 – Jane’s background, the Boleyn rise, and interpreting Jane's actions
• 13:36–17:02 – How historians have shaped Jane's image
• 17:02–19:20 – Disputing Jane’s supposed betrayal
• 22:10–25:48 – The Cromwell theory and Jane's roles with three queens
• 25:48–31:05 – Women as courtiers and strategists; career motivations
• 31:34–36:43 – The Catherine Howard affair and Jane’s fatal miscalculation
• 36:43–38:25 – Jane’s final strategy and execution, Henry’s law change
• 42:26–44:56 – Stereotypes and absence of women’s agency in history
• 46:21–48:55 – Gregory’s fiction process and relationship to her readers

Conclusion

This episode expertly dismantles the myths surrounding Jane Boleyn, Lady Rochford—moving beyond her infamy as a Tudor traitor. Through historical scholarship and informed speculation, Philippa Gregory, with hosts Anthony and Maddy, invites listeners to reconsider Jane as a shrewd survivor and a shadow power in the Tudor court, caught in the machinations of a dangerous regime. The discussion not only reclaims Jane’s agency but highlights the broader erasure of women’s complex roles in history, making the episode a must-listen for Tudor enthusiasts, feminists, and fans of historical fiction alike.