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Did Henry VIII Regret Executing Anne Boleyn? Some Historians Think So

When Henry VIII passed away in 1547 at age 55, he left behind a few children and a famously bloodstained history of failed marriages. To be fair, not all six of his couplings culminated in calamity. He stayed close friends with Anne of Cleves, for example, following their divorce in 1540; and his union with Catherine Parr only ended because he died.

But the Tudor ruler’s relationship with Anne Boleyn was dramatic from start to finish. Henry had become infatuated with Anne during her stint as a lady-in-waiting to his first wife, Catherine of Aragon, in the mid-1520s. All but one of Catherine and Henry’s children—the future Queen Mary I—died in infancy or earlier, and it began to seem highly unlikely that they’d succeed in producing a healthy male heir. So in 1527, hoping for better luck with Anne, Henry sought an annulment from Catherine on the grounds that because she’d previously been married to his (now-deceased) brother, his own union with her was invalid. Catherine’s childbearing difficulties could even have been the result of their unholy matrimony, if a certain Bible verse was to be believed.

Whatever Pope Clement VII’s personal feelings about the cogency of that argument, they took a backseat to the international affairs at play when the claim came in; namely, that Charles V—Holy Roman Emperor, King of Spain, and Catherine’s nephew—was in the process of taking over Rome. With that situation coloring his decision, the pope denied the annulment request and instead informed Henry that he’d be excommunicated should he marry Anne anyway.

In 1533, Henry VIII married Anne anyway, breaking away from the Catholic Church and changing the course of British history in the process.

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An 1848 painting by Henry Nelson O’Neil of Catherine of Aragon appealing to Henry VIII in front of a crowd. / Heritage Images/GettyImages

Unfortunately, Henry and Anne’s honeymoon phase was short-lived. After three years of marriage, Anne, too, had failed to produce a surviving male heir (though she had given birth to the future Queen Elizabeth I). Possibly encouraged by advisors keen to oust Anne, Henry VIII began to believe that she had been unfaithful to him. In 1536, she was imprisoned in the Tower of London on charges of adultery and treason, found guilty, and beheaded on May 19. Anne’s self-made widower quickly wed one of her ladies-in-waiting, Jane Seymour—already his mistress—and seemingly put his second wife out of his mind for good.

But if ever there were a time for Henry VIII to express remorse over the downfall of Anne Boleyn, it probably would have been on his deathbed. And there is some evidence suggesting he did just that. 

In 1575, French explorer and Franciscan friar André Thevet published a sweeping world history called La Cosmographie Universelle, which included a brief account of Henry’s death.

“Several English gentlemen have assured me that he had fine repentance of the offenses committed by him, being at the point of death: & among other things, of the injustice & crime committed against the said Queen Anne Boleyn, falsely vanquished & accused of what was imposed on her,” Thevet wrote, translated from French.

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An illustration of André Thevet circa 1550. / RareMaps.com, Wikimedia Commons // Public Domain

Though Thevet didn’t mention any contacts by name, 16th-century Protestant historian John Foxe supported the assertion that Henry VIII did indeed do some repenting during his final hours. In his book Actes and Monuments (also known as the Book of Martyrs), Foxe explained that as Henry VIII’s health deteriorated, Privy Councillor Sir Anthony Denny bravely broke the news to the king that he’d likely die soon—a task nobody else had wanted to do. Denny then “exhorted him to prepare himself to death, calling himself to remembrance of his former life, and to call upon God in Christ betimes for grace and mercy, as becometh every good Christian man to do” [PDF]. According to Foxe, the ailing monarch then proceeded to “consider his life past.”

“‘Yet,’ said he, ‘is the mercy of Christ able to pardon me all my sins, though they were greater than they be,’” Foxe wrote.

If Henry discussed Anne at any point during his demise, Denny or some other attendant could have easily heard it. “Doctors, close assistants who provided personal care, etc. Even possibly spiritual advisors (additional to [Archbishop of Canterbury Thomas] Cranmer) with whom he’d become close over the years,” historian Sandra Vasoli, author of Anne Boleyn’s Letter from the Tower, tells Mental Floss. “I’m sure, as well, that since he was lying there knowing he wasn’t getting better, there must have been conversations about his life’s reflection. Did word get around about any statements Henry made about life regrets? Did he, in a personal moment, unburden himself to one of the doctors or friends who attended him? Of course that is very possible, even probable.”

But Vasoli doesn’t think “several English gentlemen” implies that Henry VIII’s deathbed regret over Anne’s execution was just a rumor Thevet picked up somewhere. “Hey, people talk, but Anne was a sore subject—and not one to be bandied about lightly,” she explains. Moreover, being a well-connected writer from a respected religious order, Thevet likely had better sources for his cosmography than the grapevine. Vasoli thinks he could even have spent time in the friary at Greenwich Palace, where Henry was born and lived for years.

Though the news of Henry VIII’s purported remorse hardly became common knowledge after La Cosmographie Universelle was published, more than one historian alluded to it in later years. Among them was White Kennett, an early 18th-century English antiquarian and bishop who mentioned it in his own papers, which Vasoli came across during her own research. Agnes Strickland also brought it up in a volume of her 1840s series Lives of the Queens of England

In Strickland’s opinion, the fact that the Franciscans as a whole “had suffered so much for their [steadfast] support” of Catherine of Aragon over Anne Boleyn lent credence to Thevet’s claim. Since he had tacitly gone against the party line by writing “a testimony in favor” of her, his statement “ought to be regarded as impartial history.”

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An 18th-century illustration of the once happy couple. / Hulton Archive/Getty Images

It’s also not difficult to imagine that Henry VIII would have truly felt sorry for killing someone he once held so dear. He had, after all, written her more than a dozen love letters (not to mention that whole business of wrenching the Church of England from Roman Catholic authority in order to be with her).

“I think Henry was an enormously complex man with widely veering emotions and impulses. I absolutely know that he had adored Anne, and that she loved him back with an incredibly strong connection. Theirs was without doubt a passionate, brilliant, emotional affair,” Vasoli says. As death loomed, he may have revisited their romance and lamented his own role in rather rashly snuffing it—and Anne’s life—out. So while Vasoli admits that “nothing is certain here, by any means,” she, for one, believes that Thevet’s report rings true.

“Yes, I think Henry had great grief over his rapid execution of Anne, who, I feel certain, was the love of his life,” she says.