Henry VIII’s betrayals and executions defined one of the bloodiest reigns in English history. From trusted advisors to beloved queens, no one was safe from the axe once they fell out of favor with the king. This post explores some of the most shocking downfalls during Henry’s rule—including Anne Boleyn, Thomas Cromwell, Cardinal Wolsey, Margaret Pole, and Thomas More—and asks a haunting question: did Henry VIII ever regret these ruthless decisions?
As we revisit these infamous moments of betrayal and brutality, we’ll examine whether the king’s legacy was shaped not only by his thirst for power—but also by any trace of remorse that may have lingered behind the crown.
Did Henry VIII Ever Regret the Executions of Anne Boleyn, Cromwell, or Thomas More?
So today we’re going to talk about some of Henry VIII’s most brutal executions and punishments—because I count Wolsey in this list as well. Then we’ll talk about whether Henry ever regretted some of these downfalls, because evidence shows he might have. Of course, he never actually blamed himself—he blamed others for what happened, claiming he’d been given bad advice, etc., etc.
We’re going to look at four of the most brutal executions—the ones that really stain Henry’s legacy. I mean, there are a lot of them, but we’re going to pick four. And like I said, I’m including Wolsey, even though he wasn’t executed, because his downfall was so swift, and he probably would have been executed if he had lived to be tried. Then we’ll talk about whether Henry ever regretted them.
So, Henry VIII’s reign is remembered as a bloody one. Heads rolled at an alarming pace, and few—even among his closest friends and advisors—were truly safe. But once the dust settled and the scaffolds were cleared, did Henry ever regret the brutal falls he orchestrated? Was there even a glimmer of remorse behind the crown?
Today, we’ll talk about the aftermath of some of Henry’s most shocking betrayals:
- The downfall of his second queen, Anne Boleyn
- The execution of his right-hand man, Thomas Cromwell
- The long fall of Cardinal Wolsey
- And the horrifying death of Margaret Pole, an elderly noblewoman whose execution shocked even the most hardened courtier
Let’s start with Anne Boleyn. Anne Boleyn was the woman for whom Henry had broken England apart—the dazzling queen who had once been the center of his universe. But by 1536, she was fighting for her life against a tide of false accusations: adultery, incest, and treason. Her trial was a farce. Her execution was swift.
In the immediate aftermath, Henry wasted no time mourning. Just days after Anne’s death, he was seen parading on the Thames in a barge, openly celebrating with the ladies of the court. Preparations for his marriage to Jane Seymour were underway almost before Anne’s body had cooled.
Outwardly, it looked like Henry had brushed her aside without a second thought. But there are hints that her death left a deeper mark. His moods reportedly grew darker over the summer. Courtiers noticed an increasing irritability and a hardening of his already suspicious nature. He rarely spoke of Anne, and when he did, it was to blame her for her own downfall. If there was any regret there, it wasn’t the kind that softened him—it was the kind that twisted itself into bitterness and paranoia.
What about Thomas Cromwell? When Henry broke apart the old England, Cromwell had been his architect—the man who helped build the new England out of the rubble of the old one.
For years, Cromwell had been indispensable, clearing the way for Henry’s ambitions through diplomacy, legislation, and, when necessary, a few carefully arranged executions. It was Cromwell who had overseen Anne’s downfall, and yet, just four years later, Cromwell himself would fall victim to the same brutal machinery.
Cromwell’s biggest mistake was arranging Henry’s disastrous marriage to Anne of Cleves—a political match that Henry found personally unbearable. Enemies at court seized on the opportunity, and Cromwell was arrested, imprisoned, and executed within months.
Now, in this case, there actually is strong evidence that Henry did regret what he had done. The Spanish ambassador Eustace Chapuys reported that Henry called Cromwell “the most faithful servant he ever had.” He blamed others—especially the Duke of Norfolk and Stephen Gardiner—for poisoning his mind against Cromwell.
Afterwards, Henry reportedly ordered Cromwell’s portrait hidden away because he couldn’t bear to look at it. It’s one of the few instances where Henry’s guilt seems to have broken through his usual justifications. But, as always with Henry, the realization came too late to save anyone.
Now let’s talk about Cardinal Wolsey. Long before Anne Boleyn or Thomas Cromwell, there was Thomas Wolsey—the brilliant, ambitious cleric who served as Henry’s chief minister for nearly two decades.
Wolsey had shaped Henry’s early reign, securing alliances, negotiating treaties, managing the court. But when he failed to deliver the King’s annulment from Katherine of Aragon, his enemies closed in. In 1529, Wolsey was stripped of his office and titles. Two years later, he was summoned to London to face charges of treason. He died on the road at Leicester Abbey, likely of illness, but few doubted that had he actually made it to London, the block would have awaited him.
Henry’s reaction to Wolsey’s death was complex. On one hand, he raged against Wolsey’s betrayal. On the other, he was reportedly somber at the news, musing that Wolsey had served him well—until he didn’t. If Henry felt regret here, it seems to have been brief, quickly swallowed up by the narrative that Wolsey had simply failed him.
Finally, the most brutal execution of them all was Margaret Pole. Few executions during Henry’s reign were as shocking or grotesque as that of Margaret Pole. She was the Countess of Salisbury in her own right and a niece of Edward IV, which meant Margaret carried royal blood—making her a permanent thorn in Henry’s side as he grew more paranoid about threats to his dynasty.
In 1541, after years of tenuous imprisonment in the Tower, she was abruptly sentenced to death without a formal trial. Her execution was a horror. The inexperienced headsman missed the mark repeatedly, hacking her to death in a gruesome, drawn-out scene that horrified witnesses. She even reportedly tried to run away, saying that she wasn’t going to simply put her head on the block. The executioner chased her, and she was in her sixties at the time—it was a horrific and chaotic scene.
There is no record that Henry expressed any regret over Margaret’s death. In fact, it’s unclear whether he ever dwelled on it at all. Foreign observers, however, were appalled, and Margaret’s execution further darkened Henry’s reputation across Europe.
If he ever had second thoughts, they never made it into the historical record. More likely, by this stage of his reign, he was too far gone—isolated, suspicious, and convinced that bloodshed was the only sure path to security.
Speaking of executions that shocked Europe, I’m going to throw in an extra one here: Thomas More. Thomas More wasn’t just Henry’s Lord Chancellor. He had once been a beloved courtier, an intellectual companion, a trusted friend—almost a father figure.
Early in his reign, More had helped nurture the King’s humanist image. He encouraged him in his studies and praised his mind. Their relationship was deeply personal, which made More’s refusal to accept Henry’s supremacy over the Church all the more devastating.
More’s execution in 1535 was carefully staged. He was charged with treason for his silence, not for any public rebellion, and he was beheaded at the Tower. His final words were a masterclass in quiet defiance. He died, he said, “The King’s good servant, but God’s first.”
As for Henry, there’s little evidence that he openly regretted More’s death. If anything, he seemed to have convinced himself that More’s stubbornness had left him no choice. But the shadow of More’s martyrdom lingered, and abroad, Henry’s reputation suffered badly. If Henry ever felt any private sorrow for sending an old friend to the scaffold, he kept it buried deep—another hard scar on a reign increasingly defined by the blood of the once beloved.
So, did Henry ever regret any of the blood on his hands? In Thomas Cromwell’s case, this is unique—because he almost certainly did. But it was too late to undo it. With Anne Boleyn and Cardinal Wolsey, perhaps there was a passing shadow of regret, but it quickly hardened into blame or bitterness. With Margaret Pole, there’s not a shred of evidence that he felt anything at all. And with Thomas More, he seemed to justify the whole thing, insisting that More had brought it on himself.
So if Henry ever regretted anything, it wasn’t the cruelty—it was losing the people who once served his ambitions, and losing pieces of himself along the way. There we go—a little reflection on some of the worst downfalls of Henry’s reign, and whether he ever regretted them. Interestingly, with Cromwell, he did. But with the others? Not so much.
Related links:
Anne Boleyn’s Final Hours
David Crowther on Thomas Cromwell
Episode 180: Cardinal Wolsey
Episode 081: Tudor Times on Margaret Pole
The Fall of Thomas More: Henry VIII’s Friend Turned Traitor?
Heather Teysko is the creator, writer, and producer of The Renaissance English History Podcast, the original Tudor history podcast, started in 2009. She's been writing about history online for over 25 years, since her first site on Colonial American history became number one in history on Yahoo in 1998. In 2019 she created Tudorcon, which is now a yearly event, in addition to writing books, and running TudorFair.com - a whimsical Tudor Merch shop.
She has been passionate about Tudor England since she first read Alison Weir's The Six Wives of Henry VIII 30 years ago, and subsequently moved to London after college to spend her time immersed in Tudor history (how exciting when she got to interview Alison for the first time!). In addition to history, she is passionate about travel, and has lived in 3 countries and 4 states (not counting her perpetual state of confusion), and her family (who help her host her YouTube channel occasionally).
