Jane Boleyn: A Tudor Tale Of Intrigue & Misunderstanding – Part Three

“Jane Boleyn, like her late sister-in-law Anne, had been used as a pawn in the king’s ruthless game of politics. By the time her own life came to an end, her name had been besmirched and her mental state had deteriorated significantly. Jane’s final days were marked by a profound psychological breakdown, driven by the relentless pressures and betrayals she experienced.” – Alison Weir

In the first two parts of Jane Boleyn: A Tudor Tale Of Intrigue & Misunderstanding, I discussed the very complicated court politics and drama that ensnared the marriage of Jane and George Boleyn. They had a brilliant start as an uprising couple who had been gifted important positions at court, wealth, and two expansive mansions to make their home through the generosity of King Henry VIII. The young newlyweds had everything . The Boleyns had risen to impressive prominence.

Unfortunately their downfall was eminent. The power, wealth, and luxury they all were enjoying wouldn’t last. Anne would be accused of adultery, incest, and treason putting the light out on the Boleyn star forever. The queen and her brother George were executed leaving Jane widowed and alone. The hardship changed Jane’s life forever as she worked to regain position back at court, support herself, and wash away her tarnished reputation. Life was starting to look normal again.

Jane was finally recovering from the loss of her husband when she is given a position in Henry’s household as Queen Catherine Howard’s lady-in-waiting. Once again she is restored to live a life of a proper noble woman. This was great news for Jane or should have been but shifting allegiances once again set the stage for a dramatic downfall. This time there won’t be any reprieves or forgiveness for Jane. The whims of a tyrant king will always produce the bloodshed of others.

In today’s post, I am going to share the third and final part of my Jane Boleyn’s series. Catherine Howard is queen and is about to make life very difficult for Jane; however, is it just possible that Jane’s own choices and habit of sticking her nose where it doesn’t belong may actually be the reason for her own death? Does she finally anger Henry enough?

“Henry VIII ruled with a heavy hand, often using his power to punish anyone who challenged him. His approach to justice was marked by cruelty and a focus on removing any threats to his authority. This was evident in his treatment of individuals who fell out of favor, such as those involved in the dramatic fall of Anne Boleyn. Henry’s tyranny was not just about maintaining control but about making an example of those who opposed or displeased him. His decisions were often arbitrary, based on personal vendettas rather than legal principles. The speed with which he enacted laws and the severity of his punishments highlighted his disregard for fairness and due process, demonstrating how his reign was characterized by a brutal and capricious application of power.” – Eric Ives (The Life and Death of Anne Boleyn)


If you have not read part one or two yet of Jane Boleyn: A Tudor Tale of Intrigue & Misunderstanding then please check those out before proceeding:

Part One: Jane’s Early Life & Marriage

Part Two: The Downfall Of Anne & George Boleyn


Jane Boleyn in Tudor-era clothing, crying with tears on her face, set against a blurred, dim background.

Involvement in Catherine Howard’s Affair

Intrigues and Schemes at Henry VIII’s Court

Jane restored somewhat of a normal life by 1549 upon her return to court as a lady-in-waiting to Henry’s fifth wife Queen Catherine Howard. There was an opportunity here to move away from the scandal and reestablish her name unfortunately that is not how life played out this time. Jane’s involvement with Catherine Howard, similar to her past with Anne Boleyn, was fraught with all new risks. She was placed again at the heart of a royal scandal that would lead to tragic consequences.

Catherine Howard was still in her teenage years when she married an aging tyrannical King Henry VIII. She was woefully unprepared for the responsibilities of queenship; furthermore, Catherine’s background in an atmosphere with little supervision at her great-grandmother’s home led her to be taken advantage of by older men in her youth. All that added to her vivacious and flirtatious nature cultivated her seeking affection outside the stifling confines of her royal duties.

“Catherine Howard’s early years were characterized by a freedom and laxity that were shocking to the stricter courtiers of Henry VIII’s court. Raised in the household of her grandmother, the Dowager Duchess of Norfolk, Catherine grew up in an environment where discipline was notoriously lax and youthful flirtations were commonplace. This permissive atmosphere allowed Catherine to engage in behaviors that were considered highly inappropriate by the standards of the Tudor court. Her promiscuous behavior became well known, with numerous accounts of her intimate relationships with men, including Henry Manox, her music teacher, and Francis Dereham, with whom she was alleged to have a pre-contract of marriage. These early indiscretions, overlooked in the casual setting of her youth, would later become a perilous secret as she ascended to the role of queen.” – David Starkey (Six Wives: The Queens of Henry VIII)

Jane played a complex role that covered a lot of areas in the young queen’s life as Catherine’s lady-in-waiting. She was not just a companion but an essential confidante present in the queen’s daily activities. Jane’s experience and acumen in courtly matters made her a valuable asset to Catherine. She leaned on Jane for guidance amidst the constant pressure of court life. Jane’s duties included managing Catherine’s household, attending to her personal needs, and offering counsel.

The role Jane played extended beyond mere service into a more dangerous liaison. She was smack in the middle of the clandestine and perilous world of Catherine. Ultimately leading to both of their downfalls. Catherine’s early flirtations and youthful indiscretions made her past a ticking time bomb in the rigid, puritanical atmosphere of Henry’s court.

Jane’s Role in Catherine Howard’s Secret Meetings

As a trusted lady-in-waiting, Jane had access to the queen’s most intimate secret which included the queen expressing that she felt trapped in her marriage to the older and increasingly ill Henry. Catherine sought solace and passion in the arms of Thomas Culpepper. A charismatic and favored courtier whose role as a gentleman of the King’s Privy Chamber provided him with a ton of privilege. He was close to the king making this very dangerous. Life threatening in fact…

During Catherine’s affair with Culpepper, Jane agreed to facilitate their clandestine meetings despite knowing the gravity of the situation and its potential consequences. That decision was very unwise on Jane’s part which makes one wonder what her intentions were. Most likely she acted out of a sense of duty or misguided belief that she could protect Catherine from ever being caught. Janes’s role in the affair no matter the reason was multifaceted and risky, to say the least.

She often arranged secret nighttime meetings between Catherine and Culpepper in the queen’s private chambers. The rendezvous required clever planning with the utmost discretion so they would never be seen. Jane would ensure that the coast was clear, servants dismissed, and the doors securely locked. She stood guard outside the chamber to prevent unwelcome intrusions. Jane had to have been fully aware that discovery would mean certain death for all involved.

The queen’s room which had typically been a place of refuge and security now became the setting for these dangerous liaisons. Jane’s involvement extended to delivering messages between the lovers, using coded language, and secretive means to ensure their communication remained hidden. Many historians believe that loyalty to Catherine and her complicated past drove Jane to encourage the relationship. It didn’t matter the executioner’s axe was ever-present.

In her role as lady-in-waiting, Jane Boleyn took extraordinary measures to protect Queen Catherine Howard’s secrets. She orchestrated the logistics of the meetings with Culpepper, utilizing her deep understanding of court protocols and her access to the queen’s private quarters. Jane’s actions were not merely those of a loyal servant but of a woman acutely aware of the high stakes and potential fatal consequences. Despite the immense risk, she chose to aid the queen, reflecting her complex loyalty and perhaps her own sense of defiance against the oppressive court environment.” – Antonia Fraser (The Wives of Henry VIII}



The Final Days and Execution of Jane Boleyn

Mental Breakdown and Legal Proceedings

Catherine Howard’s downfall began with whispers that reached the ears of Archbishop Thomas Cranmer. He was wary of confronting the volatile King Henry directly so chose to leave an anonymous letter detailing the allegations. These rumors hinted at Catherine’s past indiscretions and to an ongoing affair with Thomas Culpepper. Henry ordered an immediate investigation after receiving the letter. To say he was shocked is the understatement of a lifetime. The king was furious.

The evidence against Catherine quickly unearthed Catherine’s scandalous relationship with Thomas Culpepper and her former lover Francis Dereham. Love letters and testimonies from her household staff painted a damning picture of infidelity and betrayal. When confronted, she initially denied any affair but soon confessed under immense pressure.

The gravity of Catherine’s actions became clear on November, 12th, 1541 when she was stripped of her title as queen and placed under immediate house arrest at Syon Abbey sealing the fate of not only herself but those of Dereham, Culpepper, and her accomplice in keeping the affair secret. Jane was arrested shortly after. Nothing would save her from Henry’s fury.

Jane’s role in the secret meetings between Catherine and Culpepper was unforgivable. Henry would never show mercy to her after this. Jane was taken to the Towe of London. The stress and fear of impending doom caused a severe mental breakdown. She raved incoherently and showed signs of acute distress. Guards reported that Jane alternated between bouts of hysteria and catatonic silence rendering her almost unrecognizable to those who had known her at court.

“Despite clear indications of Jane Boleyn’s mental instability, Henry VIII pressed forward with her execution by manipulating the legal system. Eric Ives, in his comprehensive study of Anne Boleyn’s life and the turbulent period surrounding her, notes that Jane’s psychological condition was a significant factor that contemporary observers recognized. However, Henry VIII, driven by his desire to consolidate power and eliminate potential threats, disregarded her mental state. The legal proceedings against Jane were marked by severe irregularities and a blatant disregard for fairness.” – Eric Ives (The Life and Death of Anne Boleyn: ‘The Most Happy)

Jane Boleyn’s Final Speech and Execution

Despite her evident breakdown, the legal proceedings against her were swift and unforgiving. Parliament passed an Act of Attainder, condemning both Catherine and Jane to death without trial. Efforts to spare her due to her mental state were futile in the face of Henry VIII’s wrath. The king’s determination to root out any perceived treachery left no room for compassion, even for a woman driven to madness by the very system she once navigated with such skill.

Jane’s tragic mental collapse and subsequent execution highlighted the brutal and unforgiving nature of Tudor justice. She was executed on February 13, 1542, at the Tower of London. The method of her execution, typical of the period, involved the use of an axe, reflecting the grim and public nature of Tudor-era capital punishment. Her final moments were marked by a somber procession to the scaffold, where she faced her end with a mix of resignation and despair.

The execution was carried out in the shadow of the Tower’s walls, a stark reminder of the ruthless political climate of Henry VIII’s reign. Jane’s death was not just the culmination of her personal tragedy but also a grim symbol of the extreme measures taken by the monarchy to eliminate perceived threats and consolidate power. Jane’s final speech:

Good Christian people, I come hither to die, and to be a true servant to the law, and therefore I will speak nothing against it. I beseech you all to pray for me, for I have been a very great sinner. I am a very great sinner; I have been so, and I am so now. Pray for me, and for my soul, and for all that I have done wrong. I have had my troubles and my trials, but I have suffered more in my heart than I have in my body. I have suffered more in my heart than I have in my body, and therefore I pray for my soul and my soul’s salvation.”


© Samantha Sebesta, Samantha James, and The Chronicles of History: Reading Into Our Past, 2024. Unauthorized use and/or duplication of this material without express and written permission from this site’s author and/or owner is strictly prohibited. Excerpts and links may be used, provided that full and clear credit is given to Samantha Sebesta with appropriate and specific direction to the original content.



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