The Fall of Thomas More: Henry VIII’s Friend Turned Traitor?

by hans  - March 16, 2025


The fall of Thomas More is one of the most dramatic and tragic episodes of the Tudor era. Once a trusted advisor and close companion to Henry VIII, More’s steadfast loyalty to the Catholic Church ultimately led to his downfall. As the king sought to break from Rome and establish his supremacy over the Church of England, More’s refusal to compromise his beliefs sealed his fate.

His story is a cautionary tale of loyalty, power, and conviction in the face of absolute monarchy. But was he a principled martyr or a rigid idealist? This deep dive into the fall of Thomas More explores the man behind the legend and the fateful choices that led to his execution.

Rough transcript of The Fall of Thomas More: Henry VIII’s Friend Turned Traitor?

  Today, we’re going to talk about the downfall of Thomas More. There are a lot of opinions about Thomas More. Some people consider him to be a martyr. Other people think he was stubborn and doesn’t deserve to be so venerated. So we’re going to talk today about Thomas More’s relationship with Henry, how deep it went, and what went so horribly wrong. So let’s discuss.

Thomas More and Henry VIII were once the closest of companions. They were bound by a shared love of learning, theology, and sharp debate. More was no ordinary courtier. He was one of the most brilliant minds of his age, a lawyer, philosopher, and statesman whose intellect Henry both admired and respected.

They exchanged letters. They engaged in lively theological discussions. Henry invited More to spend time with him at court. He relished the company of a man whose wisdom he trusted. More, for his part, saw himself as a loyal subject, bound by duty to serve the king while staying true to his principles.

But loyalty to Henry VIII was a dangerous thing. It was expected to be absolute. Unwavering and, above all, adaptable, Henry’s needs would change and those who failed to change with them, who clung to their own beliefs rather than bending to the king’s will, were discarded, often violently. Thomas More believed an unshakable truth rooted in the authority of the Church and the Pope.

Henry, however, believed in his own supremacy. Particularly, when the Pope refused to annul his first marriage. At first, Thomas More tried to walk a careful line, staying silent rather than opposing Henry’s break with Rome outright, but silence was not enough.

In 1534, Henry demanded that all of his subjects swear an oath recognizing him as the supreme head of the Church of England. More refused. That refusal, more than anything else, sealed his fate. Henry had once called More a friend. Now, he called him a traitor, and for that, More would pay with his life. Let’s talk about Thomas More. Thomas More was not born into nobility, but his intellect, his deep religious convictions set him apart from an early age.

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Thomas More’s Early Life and Education

He was born in 1478, the son of a successful London lawyer. He received an excellent education first at St. Anthony’s School, and then he went to Oxford. It was there that he developed a passion for classical learning, philosophy, and theology, subjects that would define his life. His father insisted that he train in law, and though More followed that path, his interest remained broad.

More’s devout Catholicism wasn’t just a private matter, it shaped his entire worldview. As a young man, he actually even considered joining the priesthood. He spent time with the Carthusian monks and he adopted some of their rigorous spiritual discipline. Though he ultimately chose to pursue a legal and political career, he did remain deeply pious.

He attended mass daily. He also wore a hair shirt as an act of penance. His faith wasn’t something that he took lightly. It was the foundation of his identity. Even before Henry became king, More had ties to the royal family. He was already an esteemed, well respected lawyer and scholar when he first encountered the young Prince Henry, who was himself being raised with a humanist education that emphasized the classical learning in theology and statecraft.

More wasn’t his official tutor. That role belonged to men like John Skelton and John Skelton, Lord Mountjoy. We did an episode years ago on Tudor tutors. The tutors of the Tudors. I should go back and revisit that. Anyway, he was part of the circle of intellectuals, though, that surrounded Henry’s education.

The prince, with his sharp mind and deep interest in theology, was naturally drawn to More’s wit, wisdom, and humanist ideals. When Henry unexpectedly became the heir to the throne in 1502, after the death of his older brother, Arthur, More may have played a role in shaping the prince’s understanding of governance and philosophy.

By the time Henry ascended to the throne in 1509, Thomas More was already one of the kingdom’s most respected thinkers. It was during these early years that More’s influence was at its peak. He and Henry shared their love of learning, and More encouraged the king’s early reputation as a scholar ruler.

At this point, Henry was still a fierce defender of Catholicism. More undoubtedly would have reinforced the young king’s belief in papal authority and the importance of church doctrine. Ironically, the very beliefs that would later put them at odds when Henry sought to break from Rome. Henry often sought out More for discussions on governance, philosophy, and in 1518 he brought More into royal service as a member of his Privy Council.

From there, More’s rise was rapid. He was knighted in 1521. He became the Chancellor of the Duchy of Lancaster. In 1529, Henry made a fateful decision. Cardinal Wolsey, of course, had failed to secure the annulment of Henry’s marriage to Katherine of Aragon, and Cardinal Wolsey was on the way out, his star was fading.

More was appointed Lord Chancellor. This was the highest legal office in England. Wolsey had been that before. He was the first layman to hold the position, which showed Henry’s trust in him. But while More was loyal to the king, his greater loyalty was always going to be to the church. And as Henry’s battle with Rome escalated, More found himself in an impossible position.

Conflict with Henry VIII: The Break with Rome

Thomas More had always been a loyal subject, but his loyalty had limits. As Lord Chancellor, he was responsible for enforcing the king’s laws, but when those laws clashed with his faith, he couldn’t compromise. And Henry VIII was no longer simply a king, he was a man who was obsessed with securing his legacy.

His marriage to Katherine of Aragon had not produced a male heir, and he was convinced that his lack of sons was divine punishment. By the late 1520s, he was determined to annul his marriage and take Anne Boleyn as his queen. But the Pope, under pressure from Katherine’s nephew, Charles V, refused to grant the annulment.

More didn’t see this as a marital dispute. This was actually seen as a direct challenge to the authority of the church. Henry thought that he had the right to determine his own affairs, even if it meant breaking with Rome. More was a staunch defender of papal supremacy, and he couldn’t accept this. But, rather than openly defy the king, he chose a path of careful silence.

He didn’t speak against the annulment, but he didn’t support it either. In More’s mind, his silence should have been enough to keep him out of danger. Henry, though, saw this silence as resistance. By 1531, Henry had forced the English clergy to acknowledge him as the supreme head of the Church of England as far as the law of Christ allows.

This wasn’t yet a full break from Rome, but it was a clear step toward Henry asserting his authority over the Church. More was deeply troubled by this shift, but he was still Lord Chancellor, and he tried to get through this without openly defying the king. Then, in 1532, the tension grew when Henry pressured the clergy into accepting the submission of the clergy, which effectively placed the English church under royal control.

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This was a direct attack on papal authority, something that More could not support. In May of 1532, More resigned as Lord Chancellor. He cited ill health. In reality, he knew that he could no longer, in good conscience, serve a king who was moving toward a full break with Rome. By stepping down, he hoped to retreat from public life and avoid further conflict.

The Final Stand: Refusal to Swear the Oath

But Henry was not about to let his former friend slip away so easily. More’s quiet refusal to support the king’s religious policies didn’t go unnoticed, and his absence from Anne Boleyn’s coronation in 1533 was a bold, if silent, act of defiance. It was clear that he had chosen his side. Henry was now fully committed to asserting his authority over the church, and he could not tolerate any challenge even from a man he had once trusted.

More had tried to avoid direct confrontation, but Henry’s England had no room for neutrality. And, soon his silence would not be enough to save him. By 1534, Henry had achieved what once had seemed unthinkable. He had broken England away from the authority of Rome and declared himself the supreme head of the Church of England.

With Anne now as his queen and Katherine of Aragon cast aside, Henry was determined to solidify his power and silence any opposition. Parliament passed the Act of Succession, requiring all subjects to recognize Henry’s marriage to Anne. and accept any children that they had as legitimate heirs. But it wasn’t just a statement on succession.

This was an ideological test, a demand for total loyalty. To enforce it, Henry required his subjects to swear an oath, affirming both legitimacy of Anne’s children and his supremacy over the church. The wording was carefully crafted. Swearing the oath meant acknowledging that the Pope had no authority in England.

This was an outright rejection of Rome, and he was making his subjects agree to it. This was where More, who had spent years walking the tightrope between loyalty to the king and loyalty to his faith, could no longer maneuver. When called on to take the oath in April 1534, Thomas More refused. He didn’t openly condemn Henry or his new marriage, but neither would he swear to something that denied the Pope’s authority.

His legal training made him cautious. He avoided outright treasonous speech, knowing that he could be imprisoned or executed Henry’s supremacy. Instead, he simply stayed silent. believing that his lack of affirmation should not be treated as a rebellion. But Henry, of course, saw things quite differently.

Imprisonment and Trial

Silence to him was defiance. If More, one of the most respected legal minds in England, refused the oath, what would stop others from questioning Henry’s authority? More’s refusal was dangerous. It set a precedent. It showed that loyalty to Rome could still exist in England. And on April 17, 1534, Thomas More was arrested and taken to the Tower of London.

At first, he was treated with some leniency. He was allowed visits from his family and access to books. But, as the months passed, his condition worsened. Henry and his ministers, particularly Thomas Cromwell, were determined to break him. More’s family pleaded with him to take the oath, to say the words that could save his life.

But Henry himself may have still hoped for More’s submission. He had once admired the man, and executing him would be a public stain on his reign. But More would not yield. He had given everything in service to Henry, his wisdom, his loyalty, his legal expertise. But he would not give up his conscience.

And for that, he would pay the ultimate price. Locked away in the Tower of London, Thomas More found himself in a grim but strangely familiar position. He had prosecuted men for heresy, seen others sent to their deaths for defying the Church, and now he was the one awaiting a fate decided by a king who had once called him a friend.

But if Henry thought imprisonment would break More’s will, he underestimated the depth of his resolve. Like we said, at first, his imprisonment wasn’t harsh. He was allowed books. He had writing materials. His daughter also visited him, and she pleaded with him to take the oath. He had no illusions about what lay ahead, but he still refused to outright denounce the king.

Instead, he carefully crafted his words, staying just within the legal boundaries to avoid outright treason while holding firm to his principles. More’s letters from the tower reveal his state of mind. He was calm, he was feeling deeply religious, and even slightly, darkly humorous at times. Writing to Margaret, he reassured her that he was at peace with his decision.

And he urged her not to grieve. His faith remained unshaken, and if anything, it seemed to strengthen as his imprisonment stretched on. Meanwhile, Henry VIII hesitated. More’s execution wasn’t a decision that he took lightly. Unlike Anne Boleyn or other perceived enemies, More had been a trusted advisor, an intellectual equal, a man that Henry had genuinely admired.

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The King had hoped that More’s imprisonment alone would be enough to force his submission, that he would bend rather than break. Over the course of months, Henry sent envoys to persuade More, offering him multiple chances to swear the oath in private without public humiliation. Each time, More refused.

In June of 1535, Bishop John Fisher, More’s fellow prisoner and a similarly steadfast opponent of Henry’s policies was executed. Fisher’s death was a warning, a signal that Henry’s patience was wearing thin. The king had once been reluctant to execute a cardinal of the church, just as he hesitated to execute More.

But once that first domino fell, the next would soon follow. More knew Fisher’s fate was a harbinger of his own. If Henry was willing to send a bishop to the scaffold, there would be no mercy for him. But he still would not yield. His silence, once his greatest defense, had become his death sentence. The trap had closed, and soon, More would face the final reckoning.

More was brought to trial on July 1, 1535 at Westminster Hall before a jury packed with Boleyn’s father, brother and uncle. The proceedings, of course, were a mere formality. The verdict had already been decided. The main charge was treason. More was accused of denying the king’s supremacy over the church.

But proving this was difficult. More had said nothing that could be used against him. Enter Richard Rich, one of Cromwell’s most ambitious allies. Rich took the stand and testified that during a private conversation in the Tower, More had stated that Parliament had no authority to make Henry the head of the church.

More immediately denied this, declaring that Rich’s testimony was a blatant lie, adding, with biting sarcasm, that he would never have shared such a thought with a man of Rich’s character. But, of course, truth mattered little in a trial where the outcome was already written. Rich’s perjury was enough. The jury, likely under immense pressure, found More guilty of treason.

With the verdict decided, More finally broke his silence. Since he was condemned regardless, he spoke openly at last. No king, he declared, could rightfully claim to be the head of the church. That authority belonged to the Pope alone. He had remained silent not out of uncertainty, but out of prudence. Now, with nothing left to lose, he made his opinion clear.

Execution and Legacy

The sentence was death by hanging, drawing, and quartering, the most brutal punishment for traitors. But Henry, perhaps already uneasy about executing a man he had once held in such high esteem who was loved around the world, commuted the sentence to beheading. Even at the end, More’s execution was made to look like an act of reluctant necessity rather than outright vengeance.

His fate was set. In a matter of days, Thomas More would walk to the scaffold. On the morning of July 6, 1535, Thomas More was led from the Tower of London to Tower Hill, where his execution would take place. The streets were lined with spectators. Some came to mourn, others simply to witness the fall of a man who once was so close to the king.

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More was composed and he walked with dignity even as he approached his final moments. According to reports, when he climbed the scaffold, he reassured the executioner, telling him not to fear his task. In a final act of defiant wit, he adjusted his beard a bit before laying his head on the block. He remarked “This hath not offended the king.”

Moments later, with a single stroke of the axe, Thomas More was dead. His execution sent shockwaves through Europe. Charles V, Holy Roman Emperor, was said to be appalled, lamenting that Henry had executed the only man in England worthy of the name of a statesman. Erasmus, More’s longtime friend, mourned the loss deeply, writing that England had killed her wisest man.

The Catholic Church, which had already begun to see More as a symbol of resistance against Henry’s break with Rome, would later canonize him as a saint. But did More see himself as a martyr? He never actively sought death, and he spent much of his time in the Tower trying to walk this tightrope of the legal pitfalls that might condemn him.

Yet when the end became inevitable, he embraced it with the resolve of a man who believed he was dying for his faith. In his final speech, he declared, “I die the king’s good servant, but God’s first.” To the Catholic world, this was proof of his sanctity. To Henry, it was the ultimate defiance. More’s body was buried in an unmarked grave, but his severed head was displayed on London Bridge, a grim warning to others who would challenge the king’s supremacy.

Later, his devoted daughter, Margaret Roper, recovered it and preserved it as a relic. Even in death, More remained a powerful symbol of resistance. Thomas More remains one of history’s most complex figures. To some, he is a saint and a martyr, a man who died for his principles. To others, he was a rigid idealist, unwilling to bend, even when his life was at stake.

His legacy is further complicated by his earlier role as a persecutor of heretics. He was not simply a victim of oppression, but he was also a man willing to enforce his own strict beliefs on others. But regardless of how he is judged, his influence is enduring. His writings, particularly Utopia, are widely studied.

His steadfast resistance to Henry’s religious policies has cemented him as one of the most famous figures of the Reformation, and in 1935 he was finally canonized as a saint, officially recognized as a defender of the faith. In the end, his story was not just a story of a friendship turned fatal, it was a warning of the dangers of unchecked power and the price of unwavering conviction.

We will leave it there for now. Thomas More. What do you think about him? Let me know. Leave me a comment wherever you’re listening to this. I would love to know. I personally have mixed opinions about him. I don’t love how he persecuted others for their beliefs, and he surely shouldn’t have been surprised that came back to haunt him then, given that he had done it himself. Life and people are complicated and we don’t always have to understand them or agree with them to appreciate their story and have empathy.

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