Why Henry VIII's Closest Friend Was Boiled in Public — The Thomas More Case

Added: 2026-05-24

[00:00:00]If I had to name the exact moment Henry the VIII stopped being my king and started being my executioner, I would tell you it was not in the Tower. It was not at the trial. It was in the garden, a summer afternoon in Chelsea. The king unannounced at the gate as he sometimes was. Dinner together, laughter, wine.

[00:00:22]And then afterward the two of us walking by the river and Henry with his arm around my neck, his enormous jewel-ringed arm, the arm that could have belonged to a blacksmith if God had not made him a king.

[00:00:34]And he talked about nothing in particular.

[00:00:37]Birds, a theological joke, the smell of the garden after rain.

[00:00:44]William Roper, my son-in-law, watched from a window.

[00:00:49]Afterward, he told me he had never seen the king do that with any man except Cardinal Wolsey.

[00:00:57]He seemed to think I should feel honored. I told him, "Son Roper, I may tell thee I have no cause to be proud thereof. For if my head would win him a castle in France, it should not fail to go off."

[00:01:12]That was 1523.

[00:01:14]I had 12 years left to live.

[00:01:17]And I had already understood something that would take England another century to fully name, that the friendship of a king is a trap dressed as a privilege.

[00:01:27]Welcome to Untold Tortures.

[00:01:30]My name is not important. The story is.

[00:01:34]And the story of Thomas More is one of the strangest, most heartbreaking, and most politically relevant executions in English history because this is not the story of a rebel. It is not the story of a traitor. It is the story of the man Henry VIII loved most and what Henry VIII did to him anyway.

[00:01:54]Let us begin where all things in this story begin with a document. More spent his entire life surrounded by documents.

[00:02:04]Born on the 7th of February, 1478, in Milk Street in the city of London, the son of a lawyer, Thomas More was a creature of paper and ink from the moment he could hold a quill. His father, Sir John More, sent him at 13 to serve in the household of Archbishop Morton, the Lord Chancellor of England, where the boy waited at tables and listened to the conversations of powerful men and was described by the Archbishop himself as remarkable.

[00:02:34]From there, Oxford, then Lincoln's Inn, then a career so dazzling that even Erasmus of Rotterdam, the most celebrated intellectual in Europe, made the journey to England largely to spend time with him.

[00:02:48]Erasmus wrote in a letter to their mutual friend Ulrich von Hutten in 1519 that Thomas More was, in his estimation, born for friendship. Those were his exact words, natus ad amicitiam, born for it. He described a man who could extract delight from the dullest people and situations, whose family affections were warm yet unobtrusive, who gave freely and gladly and expected nothing in return.

[00:03:19]And it was true.

[00:03:21]By every account that survives, from the biographies of his son-in-law William Roper, from the diplomatic dispatches of the Imperial Ambassador Eustace Chapuys, from More's own letters held in the British Library, Thomas More was the kind of man who made everyone around him feel that they were the most interesting person in the room, including the king.

[00:03:44]The first meeting between Thomas More and the future Henry the VIII happened in 1499.

[00:03:50]More was 21 years old, a law student still finding his way.

[00:03:56]The future king was eight.

[00:03:58]Erasmus was visiting England, staying with Lord Mountjoy, a courtier who had once been his student in Paris.

[00:04:06]Mountjoy suggested a visit to nearby Eltham Palace, where the young Prince Henry lived with his sisters.

[00:04:14]More came along. He and a friend, Edward Arnold, presented the boy prince with some verses they had composed. The golden-haired child, clever, alert, already performing for visitors, received them well.

[00:04:29]That was the seed. A gifted young lawyer presenting poetry to a prince who was not yet expected to become king.

[00:04:37]Henry's older brother Arthur was still alive.

[00:04:40]Henry was the spare, the scholar, the one being educated for the church.

[00:04:45]Nobody yet suspected that Arthur would be dead within three years, and that the spare would become the most consequential monarch England had ever produced.

[00:04:55]By the time Henry VIII came to the throne in 1509, More had become famous.

[00:05:01]His legal practice was flourishing. He was serving as undersheriff of the city of London, effectively the city's chief legal officer.

[00:05:10]And his reputation for fairness was so complete that he was described by contemporaries as the general patron of the poor, a judge who refused bribes from wealthy clients who gave free counsel to widows and orphans, who was known to return gifts in kind when he judged he should not accept them.

[00:05:30]And Henry, the new king, wanted him.

[00:05:34]There was something intoxicating about the early years of Henry VIII.

[00:05:39]You have to understand that to understand what More walked into.

[00:05:43]Henry was 17 when he took the throne.

[00:05:46]He was over 6 ft tall.

[00:05:48]He was an athlete, a scholar, a musician who played the lute and the recorder, and had composed actual songs, at least two of which survived today.

[00:05:59]He spoke Latin, French, and Spanish.

[00:06:02]He had read theology seriously enough to engage with humanist debate.

[00:06:07]He had the physical presence of a tournament champion and the intellectual appetite of a Renaissance prince, and his subjects rejoiced.

[00:06:16]When the news of Henry VII's death spread through London, the humanist scholar Lord Mountjoy wrote to Erasmus in Italy and could barely contain himself.

[00:06:27]Our king does not desire gold or gems or precious metals, but virtue, >> [music] >> glory, immortality.

[00:06:35]That was the mood of 1509, a new age, a new kind of king.

[00:06:40]Thomas More was 31 when Henry came to the throne.

[00:06:44]He looked at this young golden king and felt, perhaps for the first time in his life, that the world he had imagined in books, a world where learning and virtue could actually govern, might be real.

[00:06:57]By 1517, Henry had recruited More into his service as a secretary and personal advisor.

[00:07:03]By 1521, More had been knighted. By 1523, he was elected Speaker of the House of Commons.

[00:07:11]By 1529, when Cardinal Wolsey fell from power, Henry made Thomas More his Lord Chancellor, the highest legal office in England, and the first time in the kingdom's history that the position had been held by a layman, rather than a churchman.

[00:07:28]Henry came to Chelsea unannounced. He walked arm in arm through the garden. He laughed at More's jokes, and More laughed at his.

[00:07:37]He so monopolized More's time that More could not get leave to visit his own family more than once a month.

[00:07:44]It was the greatest friendship of two of the most brilliant minds in Tudor England.

[00:07:49]And More already knew it was going to kill him.

[00:07:54]You need to understand what More was.

[00:07:57]Not the saint. They would not make him one until 1935.

[00:08:02]Not the movie version from A Man for All Seasons. The actual man. He was complicated. He was genuinely, thoroughly complicated in ways that his hagiographers have spent five centuries trying to smooth over.

[00:08:16]He wrote Utopia, one of the strangest, most radical political books of the 16th century.

[00:08:23]A satirical portrait of an ideal island society that imagined religious tolerance, six-hour workdays, communal land ownership, and universal education for women at a moment when none of those things existed anywhere in Europe.

[00:08:39]He coined the word Utopia himself from the Greek outopos, meaning no place.

[00:08:46]He knew the world he described could not exist. That was the joke. And the tragedy. He believed passionately in the education of women. His own daughters, including his beloved Margaret, were educated in Latin, Greek, logic, philosophy, and music to a standard that astonished male scholars who encountered them.

[00:09:08]Erasmus credited More's example with changing his own views on female education.

[00:09:14]Margaret More, who became Margaret Roper upon her marriage, was considered one of the finest Latin translators in England.

[00:09:22]She published a translation of Erasmus at 19.

[00:09:25]He was funny.

[00:09:27]Genuinely, naturally funny.

[00:09:30]With the dry wit of a man who had spent a lifetime watching powerful people make fools of themselves and had learned to find it entertaining rather than despairing.

[00:09:40]And he could also be pitiless.

[00:09:42]As Lord Chancellor, he pursued Protestant heretics with a ferocity that has horrified his admirers for centuries.

[00:09:50]He had men imprisoned and interrogated.

[00:09:53]He was present at and may have encouraged the burning of books.

[00:09:57]Whether he personally participated in the torture of prisoners in his house is debated by historians.

[00:10:04]His Catholic admirers have strenuously denied it.

[00:10:07]And the evidence is not conclusive. But his written attacks on Protestant reformers were vicious, crude, and deliberately cruel.

[00:10:16]He called Martin Luther things that would not be appropriate to repeat at a family dinner.

[00:10:22]He was a man who believed in a certain order of the world, a Catholic papally governed order.

[00:10:29]With such absolute conviction that he was willing both to impose it on others and to die for it himself.

[00:10:36]This is the man Henry the VIII murdered.

[00:10:40]Now we need to talk about a woman.

[00:10:43]Because without her, this story ends differently.

[00:10:48]Anne Boleyn entered Henry the VIII's serious attention somewhere around 1526.

[00:10:55]She was not the first royal mistress.

[00:10:57]Her own sister Mary had occupied that role before her.

[00:11:01]But she was different in a way that still reverberates through English history.

[00:11:07]Anne refused to be a mistress.

[00:11:09]She wanted to be queen.

[00:11:11]Henry the VIII was already married.

[00:11:14]He had been married to Catherine of Aragon for 17 years.

[00:11:19]And Catherine had given him one surviving child, a daughter Mary, and no surviving sons.

[00:11:26]Henry wanted an annulment.

[00:11:28]He had convinced himself, perhaps sincerely, that his marriage to Catherine violated the biblical prohibition on marrying a brother's widow, since Catherine had briefly been married to Henry's brother Arthur before Arthur's death in 1502.

[00:11:44]He sent his case to Rome.

[00:11:46]Pope Clement VII, in a position of great difficulty, since Catherine's nephew was the Holy Roman Emperor Charles V, who was essentially his military protector, declined to grant it.

[00:11:59]For years, Henry maneuvered. For years, Wolsey tried and failed. For years, the divorce, the great matter, as it was being called, went nowhere.

[00:12:11]And Thomas More watched all of this with a quiet, gathering dread. He had not said a word against the king's position.

[00:12:19]He was careful. He was precise.

[00:12:22]He resigned the Lord Chancellorship in 1532, citing his health, which was not entirely untrue, but everyone understood the real reason.

[00:12:32]He would not endorse the break with Rome.

[00:12:35]He would not endorse the annulment. He would not say it publicly, but he would not say otherwise, either.

[00:12:42]He went home to Chelsea.

[00:12:44]He lived quietly.

[00:12:46]He stopped attending public events.

[00:12:48]He reduced his household. His fortune had diminished since leaving office, and he was genuinely struggling financially.

[00:12:56]He read. He wrote. He walked in the garden where Henry had once walked beside him.

[00:13:02]He thought that silence might be enough.

[00:13:04]It was not.

[00:13:07]In March 1534, Parliament passed the Act of Succession.

[00:13:12]The act established that Henry's marriage to Catherine was void, that his marriage to Anne Boleyn was legitimate, and that their children, beginning with the infant Princess Elizabeth, were the legitimate heirs to the throne.

[00:13:25]Every adult in England was required to swear an oath to this effect. More was summoned to Lambeth Palace on the 13th of April, 1534.

[00:13:36]He was presented with the oath and asked to sign it. He refused. He sat for an hour in the garden of Lambeth Palace watching other men go in and come out, watching them sign, watching them accommodate themselves to the new world.

[00:13:51]"He could see them through a window." He later wrote to Margaret. He prayed. He thought. He waited. Then he went back inside and said very quietly that he could not in good conscience swear to the oath as written.

[00:14:05]He was not immediately violent or dramatic about it. He was careful and lawyerly. He said he would swear to the succession, to the legitimacy of Princess Elizabeth, but he could not swear to the broader preamble, which implicitly denied papal authority.

[00:14:21]He offered an alternative. It was rejected.

[00:14:24]On the 17th of April, 1534, Thomas More was committed to the Tower of London. He was 56 years old. He had a stomach complaint that had troubled him for years. He had a beard he had not trimmed since he heard about the bill against him as a sign of mourning for the world he was losing. His goods were already being inventoried by royal officers.

[00:14:46]He was not yet sentenced. He was not yet charged. He was being held as a form of persuasion. They held him for 14 months.

[00:14:55]If you've stayed with this story this far, you already know this isn't the history they hand you in school.

[00:15:01]This is the version where the king who walked arm in arm with his closest friend spent 14 months trying to break that friend by inches. Subscribe now because what comes next is where the mask comes off completely.

[00:15:15]During those 14 months in the Bell Tower, More wrote.

[00:15:20]He wrote to Margaret constantly.

[00:15:22]His letters to her, several of which survive in the British Library, are among the most extraordinary documents of the Tudor period. He was witty in them. He was affectionate. He wrote about the books he was reading, the progress of his meditations, the prayers he was saying. He was also watched. Everything he wrote was seen.

[00:15:42]He knew this. He wrote with the knowledge that his jailers read every word. And he still managed to say what he meant.

[00:15:50]He wrote, "I have more cause to pity them than to be angry with them."

[00:15:54]He was talking about the men who imprisoned him.

[00:15:57]The pressure on him was systematic and relentless. He was visited repeatedly by members of the Privy Council, the Duke of Norfolk, Thomas Cromwell, Archbishop Cranmer, who urged him in turn to swear, to give the king what he needed, to stop this foolishness, to think of his family, to think of his position, to think of his life.

[00:16:21]His wife Alice visited him in the Tower and famously asked him what the point was of sitting in a stinking cell when he had a fine house in Chelsea with a library and a garden and children and every comfort.

[00:16:33]He loved Alice.

[00:16:34]His relationship with her was complicated. He had married her quickly after his first wife Jane died. And Erasmus, with characteristic unkindness, described her as lacking sexual attractions, which More had chosen for reasons of practicality.

[00:16:51]But, she was real to him.

[00:16:53]And he wrote about her with warmth. And her question must have landed somewhere.

[00:16:58]He told her in effect that the difference between sitting in his cell for a year and being in the Tower for a shorter time and then dying was this, that one ending involved his soul intact and the other did not. He could not sign.

[00:17:13]By the spring of 1535, Henry needed this to end.

[00:17:17]More's silence was becoming an embarrassment.

[00:17:21]More had been careful, scrupulously, legally careful never to say out loud that he denied Henry's supremacy over the church.

[00:17:30]Silence was not legally treason.

[00:17:32]Under English law as it then stood, silence was technically consent.

[00:17:38]Thomas Cromwell, the King's secretary and the architect of the break with Rome, understood the problem. He needed More to say something. He needed a word, a sentence, anything that could be called denial. He sent a man to the Bell Tower. The man's name was Richard Rich.

[00:17:58]He was 35 years old and he was the Solicitor General and by every account of the period, he was one of the most thoroughly disreputable men in Tudor England. Which, given the competition, is saying something. Rich came to More's cell in June of 1535, ostensibly to collect More's books and writing materials. The books were being confiscated. While the books were being packed, Rich and More talked. They exchanged what More later described as a philosophical hypothetical, a game of suppositions, the kind of intellectual exercise that More had spent his whole life playing with scholars and students.

[00:18:39]Suppose the Parliament were to pass a law declaring God not to be God.

[00:18:44]Would that law be binding? It was the kind of thing More had discussed a thousand times with Erasmus, with Colet, with his own children over dinner. Rich remembered it differently. He remembered it as More making a direct declaration that Parliament had no power to make the King head of the church.

[00:19:03]On the 1st of July, 1535, Thomas More stood trial for high treason in Westminster Hall.

[00:19:11]The same hall where he had sat as a judge.

[00:19:15]He was weak from 14 months of imprisonment.

[00:19:19]He had difficulty standing.

[00:19:21]He listened to the charges, four counts, the last and most serious being his alleged conversation with Richard Rich.

[00:19:30]When Rich took the stand and gave his testimony, More's response was measured, precise, and devastating. He called Rich a perjurer to his face. He asked the court to consider whether it was remotely plausible that he, Thomas More, who had held his tongue for over a year in the face of all pressure, would have chosen to confide a treasonous declaration to a man whose reputation for honesty was, to put it mildly, not established. He said, addressing Rich directly, "In good faith, Mr. Rich, I am more concerned for your perjury than my own danger."

[00:20:08]The jury deliberated for 15 minutes.

[00:20:11]The verdict was guilty. The sentence was read, to be hanged, drawn, and quartered. Henry, in his mercy, commuted this to beheading.

[00:20:21]Let us stop here for a moment, because the irony is almost impossible to look at directly.

[00:20:28]Henry VIII was about to execute the man who had helped him write the theological arguments that justified his authority over the Church of England.

[00:20:37]More had assisted in drafting the royal response to Martin Luther.

[00:20:41]He had served as Henry's secretary, his speaker, his chancellor.

[00:20:46]He had been Henry's closest intellectual companion for over two decades.

[00:20:51]And Henry did it anyway.

[00:20:54]On the night before his execution, More sent Margaret his hair shirt, a garment of rough fabric worn against the skin as a private act of penance, a secret he had kept his entire public life, hidden under his fine robes and his legal gowns, the private discipline of a man who believed in suffering the flesh to free the soul.

[00:21:14]He sent it to her so that no one would see it on the scaffold, so that only she would know.

[00:21:21]He wrote to her with a piece of charcoal, since they had taken his pen.

[00:21:25]"I long to go to God."

[00:21:28]The morning of the 6th of July, 1535, was warm.

[00:21:32]Henry the 8th was hunting at Reading.

[00:21:36]More was led from the bell tower to the scaffold on Tower Hill.

[00:21:40]The crowd was smaller than usual.

[00:21:43]Henry had been careful about this, worried about what the crowd's mood might be.

[00:21:49]More looked at them anyway and smiled.

[00:21:52]He asked the Lieutenant of the Tower for help climbing the rickety scaffold steps.

[00:21:57]"I pray you, Master Lieutenant, see me safe up, and for my coming down, let me shift for myself."

[00:22:06]Even then, even then he was funny. He spoke briefly. He declared himself the king's good servant, but God's first.

[00:22:14]Then he knelt at the block, carefully moved his long gray beard out of the way. It had grown untrimmed for 14 months, and said that his beard had never committed treason, and deserved not to be cut.

[00:22:27]The chronicler, Charles Wriothesley, writing in the same year, recorded the death in nine words. "His head was stricken from his shoulders and had no more harm." He was buried in the Chapel of St. Peter ad Vincula, inside the Tower.

[00:22:43]Unmarked grave, no ceremony. The headless body of the man who had been the king's closest friend, thrown into the ground without a stone.

[00:22:53]His head was boiled, as was the custom, to preserve it, and placed on a spike on London Bridge, where it joined the head of John Fisher, the elderly Bishop of Rochester, who had been executed two weeks before for the same refusal.

[00:23:09]Now we get to the part the official record does not especially want to discuss.

[00:23:16]Margaret Roper, 30 years old, Thomas More's oldest daughter, the woman he had educated to a standard that astonished Europe, watched her father's head go up on London Bridge.

[00:23:29]And she waited.

[00:23:30]According to the historian Thomas Stapleton, writing in the 1580s and drawing on eyewitness accounts, Margaret watched that bridge with the patience of someone who understood that she would only have one opportunity. The head was due to be taken down after about a month as a new head would need the pole.

[00:23:49]When it was taken down, the executioner's officer would throw it into the Thames.

[00:23:55]Margaret had already bribed the officer.

[00:23:58]She obtained her father's head. She smuggled it home. She was questioned by the King's Council about this. She had technically stolen state property, but was released without punishment. Perhaps because even Henry VIII's government thought there were limits to what could justifiably be done to a woman who retrieved her father's skull from a bridge. She preserved it in spices. She kept it in a lead casket. She carried it with her for the remaining 9 years of her life.

[00:24:28]When she died in 1544, she was buried with it in the Roper family vault under the chapel of St. Dunstan's Church in Canterbury.

[00:24:38]The vault was last opened in 1978 and again in 1997.

[00:24:44]The skull is still there. It has deteriorated, exposed to damp air, possibly disturbed by vandalism in the 19th century.

[00:24:54]There are currently ongoing discussions about preserving it as the 500th anniversary of Moore's death approaches in 2035.

[00:25:03]500 years later, the head of Henry VIII's closest friend is slowly falling apart in an Anglican church in Kent in a vault sealed with a floor plaque that reads, "Beneath this floor is the vault of the Roper family in which is interred the head of Sir Thomas More of illustrious memory, sometime Lord Chancellor of England, beheaded on Tower Hill 6th July 1535."

[00:25:30]There is something worth sitting with here, a connection that does not stay in the past.

[00:25:36]Richard Rich, the man who lied to put More on the scaffold, lived until 1567.

[00:25:43]He was pardoned, rewarded, elevated.

[00:25:47]He died in his bed as the first Baron Rich, wealthy and powerful and comfortable, one of the most successful men of the Tudor age.

[00:25:57]Thomas Cromwell, who orchestrated the case, was executed by Henry VIII himself 5 years later in 1540, not for this, but for political failures of a different kind.

[00:26:11]Henry VIII died in 1547 in agony from what was likely a combination of septic infection, possible syphilis, diabetes-related complications, and liver failure.

[00:26:24]His body began to decompose before burial.

[00:26:27]In 1813, his coffin at Windsor was found to have leaked.

[00:26:33]The man who walked arm-in-arm in a Chelsea garden and told his friend he was the most singularly favored subject in the realm outlasted none of his choices.

[00:26:44]His church, the Church of England, exists today because he refused to accept Rome's authority.

[00:26:51]His daughter Elizabeth would become one of the greatest monarchs in English history.

[00:26:56]His son Edward would die at 15.

[00:26:59]His first queen, Catherine, died alone and unrecognized, stripped of her title.

[00:27:05]His closest friend's head rots in a church in Canterbury.

[00:27:09]What do we do with this?

[00:27:11]The uncomfortable question about Thomas More.

[00:27:14]The question that separates historians, that separates his Catholic admirers from his secular critics, that has divided writers for centuries, is whether he deserves our sympathy.

[00:27:26]He died for a principle. Yes, but he also persecuted others for their principles.

[00:27:32]He killed men for their faith, men who were doing in their Protestant context exactly what he was doing in his Catholic one, refusing to compromise their conscience.

[00:27:44]He believed in the education of women with a passion that was radical for his era.

[00:27:49]He also believed that heretics deserved to burn.

[00:27:53]He was funny, warm, [music] brilliant, devoted to his daughter, capable of making friends with anyone, and capable of being savagely cruel to people he considered wrong about God. He was human, fully, uncomplicatedly, contradictorily human. And the king he served had him killed not for any of the complicated things, not for his persecution of Protestants, not for his conservatism, not for anything he actually did. He was killed for staying quiet, for not signing the paper, for the one document in a life built on documents that he refused to authorize with his name.

[00:28:32]The man who coined the word Utopia, no place, died to preserve a world that no longer existed under a king who no longer was who he had believed him to be, in defense of a church that England had decided it no longer needed. He was a saint, they would say 400 years later, patron of statesmen and politicians, the universal man of the Northern Renaissance, a man for all seasons.

[00:28:58]He was also a flawed, brilliant, frightened 57-year-old with a gray beard and a bad stomach sitting in a cell by the river writing letters to his daughter with a piece of charcoal holding the one thing he had never sold and refusing to let go of it.

[00:29:15]That might be enough.

[00:29:17]That might be everything.

[00:29:19]If this story has cut something loose in you, if you think the versions we hand down in textbooks deserve to be cracked open and looked at honestly, subscribe to this channel. We do not simplify. We do not sanctify. We find the human being inside the historical figure and ask what it cost them to be who they were.

[00:29:39]The next story comes from a different century and a different kind of silence, but the question is the same. What do you hold on to when everything else is taken?