He was the smartest man in the room. Usually, people like that are insufferable, but Saint Sir Thomas More was different. He cracked jokes while facing the executioner's axe. He was a high-powered lawyer who wore a scratchy hair shirt under his silk robes. He was basically the 16th-century version of a tech disruptor, but for law and theology.
Most people know him from the play A Man for All Seasons. They see this noble, stoic figure standing up to a grumpy King Henry VIII. That's part of it, sure. But the real Thomas More was messier. He was a guy who loved his kids, wrote a book about a fictional island called Utopia that people still argue about today, and eventually chose to lose his head rather than say something he didn't believe.
It’s easy to look back and think, "Oh, it was just a different time." But More’s dilemma is surprisingly modern. It’s about where you draw the line between your job and your soul.
The Rise of a Tudor Powerhouse
Thomas More wasn't born into the inner circle. His dad was a judge, so he grew up with law in his blood, but he had to work for his status. He was a prodigy. By his twenties, he was already a respected lawyer and a member of Parliament.
He almost didn't become a lawyer, though. For a while, he lived near a monastery and seriously considered becoming a monk. He liked the silence. He liked the discipline. But he also liked the idea of a family, so he chose the world over the cloister. He ended up marrying Jane Colt and, after she died young, he married Alice Middleton.
His house in Chelsea was a literal hub for the European intelligentsia. The great scholar Erasmus was his best friend. They’d sit around and roast the corruption in the Church, even though they were both devout Catholics. It was a weird, vibrant time to be alive. The Renaissance was hitting England, and More was right at the center of the blast zone.
Henry VIII loved him. At first, anyway. Henry was young, athletic, and obsessed with being seen as an intellectual. He’d keep More late at night just to talk about astronomy or divinity. More was eventually named Lord Chancellor in 1529, which was basically the highest office in the land. He was the King's right-hand man.
When the Great Matter Went South
Then came the divorce. Well, the "annulment" if we’re being technical. Henry wanted out of his marriage to Catherine of Aragon because she hadn't produced a male heir. He wanted to marry Anne Boleyn. The Pope said no.
This created a massive legal and spiritual bottleneck. Henry decided that if the Pope wouldn't give him what he wanted, he’d just start his own church. The Church of England. And as King, he’d be the Supreme Head.
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For Saint Sir Thomas More, this was a hard pass.
He didn't scream or start a rebellion. He just... went quiet. He resigned his post as Chancellor, claiming he was sick. He tried to disappear into private life. But in the Tudor court, silence was considered a form of loud, obnoxious protest.
The Trial and the Tower
In 1534, the government passed the Act of Supremacy. You had to take an oath acknowledging Henry as the head of the Church. More refused.
He didn't refuse because he hated Henry. He refused because he believed that the unity of the Church was more important than the ego of a king. He was a legalist to his core. He told the investigators that as long as he didn't speak against the King, they couldn't legally kill him for his thoughts.
He spent over a year in the Tower of London. If you visit today, you can see where he was kept. It wasn't a dungeon, but it wasn't a hotel. His health failed. His wife, Alice, visited him and basically told him he was being an idiot. She couldn't understand why he'd trade a comfortable house in Chelsea for a cold cell just for a "scruple."
"Is not this house as near heaven as my own?" he famously asked her.
The trial was a sham. A man named Richard Rich—who More had once tried to help—gave false testimony, claiming More had spoken the words of treason. More’s response was legendary. He basically told Rich that he was sorry Rich had committed perjury, especially since Rich had done it for the sake of becoming Solicitor General for Wales. "In good faith, Master Rich, I am sorrier for your perjury than for my own peril," More said.
The Complicated Legacy of Utopia
We can't talk about More without talking about Utopia. He wrote it in 1516, and it’s one of the most misunderstood books in history. He invented the word. In Greek, it’s a pun: it can mean "good place" or "no place."
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In the book, he describes an island where there’s no private property, everyone works six hours a day, and there's religious tolerance. Some people think More was a secret socialist. Others think the whole thing was a giant satire.
Honestly? It was probably a bit of both. He was pointing out how absurd and greedy European politics had become. But he also knew that humans are fundamentally flawed. You can’t build a perfect society with imperfect people.
Critics often point to More's darker side. When he was Chancellor, he was involved in the prosecution of heretics. Some were burned at the stake. This is the part of the story that doesn't make it into the glossy movies. It’s the nuance that makes him human. He was a man of his time, and in the 1500s, heresy wasn't just a difference of opinion—it was seen as a spiritual plague that would destroy society. He was trying to "save" the world, even if his methods were brutal by our standards.
The Execution
On July 6, 1535, he was led to Tower Hill. He was weak and his beard was long. Even at the end, he was funny. He asked the lieutenant for help getting up the rickety wooden steps of the scaffold, saying, "I pray you, Master Lieutenant, see me safe up, and for my coming down let me shift for myself."
His final words on the scaffold were: "The King's good servant, but God's first."
He was beheaded with a single stroke. His head was put on a spike on London Bridge for a month until his daughter, Margaret Roper, bribed someone to let her take it down. She reportedly kept it for the rest of her life.
Why We Still Care
So, why does a lawyer from 500 years ago matter?
Because we live in an era of "groupthink." We live in a world where it’s very easy to just say whatever the crowd wants you to say to keep your job or your social standing. More represents the "inner check."
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He wasn't a rebel for the sake of being a rebel. He actually liked being part of the system. He liked his wealth and his influence. But he had a core that was non-negotiable.
The Catholic Church canonized him as a saint in 1935. Even the Soviet Union, weirdly enough, honored him for the communist ideas they thought they saw in Utopia. He’s a Rorschach test for history.
How to Apply the "More Mindset" Today
If you're looking for a way to channel some of that Saint Sir Thomas More energy, it doesn't mean you have to go out and get martyred. It’s about intellectual honesty.
- Identify your "Non-Negotiables." Most of us drift through life agreeing with whoever is loudest. Take ten minutes and write down three things you would never compromise on, even if it cost you a promotion.
- Read deeply. More was a humanist. He read the classics. He looked at the long arc of history, not just the "trending" topics of 1520.
- Use humor as a shield. When things get tense, a well-timed joke can preserve your humanity. More used wit to keep his dignity when he had nothing else left.
- Understand the "Other Side." More was friends with people he disagreed with—at least until politics made that impossible. He engaged with the best ideas of his time.
More’s life wasn't a clean, perfect narrative. It was full of contradictions. He was a champion of liberty who persecuted dissenters. He was a wealthy politician who wore a hair shirt. But in the end, he proved that a single human conscience is more powerful than the decree of a king.
That’s a heavy thought to carry. But it’s one worth remembering next time you're tempted to say something you don't believe just to get along.
If you want to dive deeper into the primary sources, start with his letters to his daughter Margaret from the Tower. They are heartbreaking, funny, and deeply human. You can find them in most collections of his "Last Letters." They give you a much better sense of the man than any textbook ever could.
Check out the National Portrait Gallery's archives for the Hans Holbein the Younger portrait of More. It's famous for a reason. You can see the stubble on his face and the intensity in his eyes. It’s the face of a man who knew exactly what he was doing, and exactly what it was going to cost him.