Betwixt The Sheets: The History of Sex, Scandal & Society

Host: Kate Lister
Guest: Philippa Gregory
Episode: The Boleyn Who Betrayed Henry VIII
Date: October 10, 2025

Episode Overview

This episode of "Betwixt the Sheets" dives into the life and legacy of Jane Boleyn, Lady Rochford—sister-in-law to Anne Boleyn and a central, if often overlooked, figure in the tumultuous Tudor court. With acclaimed novelist and historian Philippa Gregory, host Kate Lister explores why Victorian and modern interpretations have cast Jane as either "mad" or "bad," and asks if there’s more to her story. The conversation weaves together scandal, survival, politics, and the dangers of living—and trying to thrive—in the shadow of Henry VIII.

Key Discussion Points & Insights

1. Jane Boleyn: The Woman Behind the Stereotypes

• Victorian and Modern Stereotyping
  • Jane is remembered as "the infamous Lady Rochford," a reputation set in Victorian times and perpetuated in modern interpretations (05:56).
  • Philippa Gregory: “She’s literally been, you know, shoehorned into two really, really typical stereotypes about women, bad or mad. And I think that she’s much more nuanced, much more complicated, much more interesting than that. And that she’s an agent of her own life.” (06:24)
• Agency vs. Circumstance
  • Gregory challenges the idea that Jane was merely a victim or a villain, suggesting she was navigating treacherous political waters with intelligence and agency.

2. Early Life and Meteoric Rise

• Background
  • Daughter of Lord Morley, a Renaissance scholar uninterested in court politics; Jane is sent to be a maid in waiting to Catherine of Aragon (08:16).
  • Marriage to George Boleyn, Anne’s brother, is arranged but unremarkable—until Anne marries Henry VIII, catapulting Jane into the royal family.
• Sudden Ascendancy
  • Jane becomes top lady in waiting to consecutive queens: Jane Seymour, Anne of Cleves, and Catherine Howard. This rise is baffling given her close relation to the disgraced Boleyns (11:32-12:17).

3. Jane as Possible Spy for Cromwell

• Unlikely Promotion After Scandal
  • Unlike other Boleyns, Jane is not disgraced after Anne and George’s executions; instead, she is promoted (12:04-12:16).
• Cromwell’s Spy Network Theory
  • Gregory posits that the only possible explanation for Jane’s survival and favor is that Thomas Cromwell used her as a spy in the Queen’s chambers—a new angle on Jane’s role at court (12:38-14:30).
  • Philippa Gregory: “He’s in the middle of setting up a huge spy administration network...I think Jane is one of these.” (13:32)

4. Jane’s Role in Court Scandals

• The Anne Boleyn Affair
  • Victorian historians blame Jane for testifying against her husband and Anne; Gregory disputes there’s contemporary evidence for this (14:56-17:05).
• Anne of Cleves’ Divorce
  • Jane provides the key statement enabling Henry’s annulment from Anne of Cleves. Gregory suggests she did so on Cromwell’s behalf, possibly benefiting both her and Anne (17:08-17:40).

5. The Katherine Howard Disaster

• No Protector After Cromwell’s Fall
  • After Cromwell’s execution, Jane loses crucial support and becomes the de facto advisor to Catherine Howard—a role fraught with risk (18:07-20:17).
• Enabling an Illicit Affair
  • Jane facilitates Queen Catherine’s secret liaisons with Thomas Culpepper, possibly thinking she could benefit if the king died and Catherine became regent (20:17, 25:32).
• The Human Side of Catherine Howard
  • Kate Lister: “I feel endlessly sorry for Katherine Howard...you just want to sit down and go, sweetheart, come on. Now, I know he’s pretty, but you can’t do this.” (23:16)

6. How It All Fell Apart

• Discovery and Betrayal
  • Catherine’s teenage affairs are exposed, leading to blackmail and investigation. Jane is eventually implicated (29:31-31:53).
• Harsh Punishments and Legal Tyranny
  • Despite legal precedent, Henry executes both Catherine and Jane via an act of attainder, bypassing trial—redefining the monarchy as a tyranny where his word is law (35:21).
  • Philippa Gregory: “Henry doesn’t have to put her on trial because Cromwell has already recreated this legal fiction...which just means the King can say, I want this person dead, signed Henry, and that’s it.” (35:22)

7. Jane’s Final Play—Feigning Madness

• Attempt to Avoid Execution
  • Jane feigns insanity to invoke Tudor law, which forbade executing the insane. For a brief period, it seems to work, as she is cared for outside the Tower (36:44-37:43).
  • Philippa Gregory: “I believe she pretends to be mad...If she can be convincing in it...she would be going, I am going to get away with this. Clever, clever, clever woman.” (37:44)
• Henry Changes the Law
  • Henry changes the law to allow execution of the insane, ensuring Jane’s death (37:45-38:08).
  • Kate Lister: “Absolute shit. Changes the entire law in order to...kill her just to get her.” (37:57)

8. On the Scaffold: The End of Jane and Catherine

• Execution Details
  • Catherine Howard is executed first, delivering a brief apology; Jane follows, kneeling in the blood-stained straw (42:10-43:23).
  • Kate Lister: “I have huge respect for that because if that had been me, I’d have got up there and just said, he was an absolute dick. I hated him. He was terrible in bed. I’ll see you all. That would have been me on the way out.” (42:30)
• Comparisons to Other Victims of Henry’s Tyranny
  • Gregory recounts the horrifying execution of Margaret Pole, drawing parallels to Henry’s increasing brutality and lack of justice (43:48-45:21).

9. Rethinking Jane Boleyn’s Legacy

• Legacy and Historical Lessons
  • Gregory hopes to redefine Jane—as a woman of agency striving to survive, rather than a mad or bad stereotype (45:55).
  • Philippa Gregory: “Maybe she was playing the card she had in a way that is absolutely admirable. Maybe she was neither a bad person as the Victorians would have, or a mad person...Maybe her legacy to us is to say, when you see tyranny coming, stand against it, because sooner or later it will come against you or the things you love.” (46:54)

Notable Quotes & Memorable Moments

• “She’s literally been shoehorned into two really, really typical stereotypes about women: bad or mad.”
  — Philippa Gregory (06:24)
• “Who’s done that? Where’s that come from? And I think the only person who could have done it would have been Henry VIII. And we know Henry VIII is not going to do that without some kind of extraordinary benefit.”
  — Philippa Gregory (12:17)
• “She says that the Queen Anne of Cleves says...the King lies beside her and sleeps all night. And in the morning he kisses her and says, good day, sweetheart. And she says, good day, my Lord.”
  — Philippa Gregory (17:10)
• “If she had pulled it off, if Katherine Howard had got pregnant by Thomas Culpepper ... she’s then the top woman of England forever.”
  — Philippa Gregory (26:46)
• “It’s not law, it’s vindictive rage...It’s narcissistic rage. I think you have to understand it in the context of a man whose vanity cannot tolerate the fact that somebody might prefer a man young enough to be a son.”
  — Philippa Gregory (34:16-35:21)
• “Henry doesn’t have to put her on trial ... the King can say, I want this person dead, signed Henry, and that’s it.”
  — Philippa Gregory (35:22)
• “I believe she pretends to be mad ... and Henry VIII changes the law, which now says you can execute a mad person.”
  — Philippa Gregory (37:44-37:53)
• “Maybe her legacy to us is to say, when you see tyranny coming, stand against it, because sooner or later it will come against you or the things you love.”
  — Philippa Gregory (46:54)

Timestamps for Key Segments

• [05:34] — Introduction to Jane Boleyn’s story and reputation
• [08:16] — Jane’s early life and rise at court
• [12:17] — Theory: Jane as a spy for Cromwell
• [14:56] — Her role in Anne Boleyn’s downfall and the Anne of Cleves divorce
• [18:07] — Cromwell’s fall and Jane’s dangerous position with Catherine Howard
• [23:16] — The Katherine Howard–Thomas Culpepper affair, Jane as enabler
• [29:31] — The unravelling: how Jane and Catherine get caught
• [35:21] — Henry’s use of tyranny, execution by attainder
• [36:44] — Jane’s attempt to escape execution through feigned madness
• [42:10] — The executions of Catherine Howard and Jane Boleyn
• [45:55] — Gregory on rethinking Jane’s legacy

Final Thoughts

An insightful, engaging episode that paints Jane Boleyn not simply as a villain or victim, but as a sharp, adaptive, and ultimately tragic figure at the heart of Henry VIII’s tyrannical court—a warning from history about the dangers of unchecked power and easy historical stereotypes.