Henry VIII is remembered as the king who married six women and ate his way through Europe’s livestock. But that’s the sanitized version.
Strip away the Holbein portraits and Tudor nostalgia, and you’re left with a paranoid autocrat who executed nobles based on rumors and destroyed centuries of religious heritage for cash.
He also divorced and beheaded wives with the efficiency of a production line.
Think less “glorious Tudor monarch” and more “Renaissance mob boss.”
The sheer scale and capriciousness of Henry’s crimes is outrageous. His was one of the bloodiest reigns in history.
Now, let’s tally the crimes, corpses, and close calls that followed in his wake. And I’ll tell you all the places and sites that are linked to the worst things that Henry VIII did.
Execution of the Duke of Buckingham
Edward Stafford, the 3rd Duke of Buckingham, was the first big warning sign that Henry VIII would take down anyone—title or no title—if he felt threatened.
Buckingham wasn’t just any noble. He was one of the highest-ranking men in the country and a double descendant of Edward III.
Royal blood, massive estates, piles of money. He checked every box.
And if the Tudor line ever collapsed, he was someone people could plausibly rally around. That alone made Henry uneasy.
So Henry had him charged with treason on invented offenses. The accusations? Speaking “disrespectfully” about the king and supposedly hinting he had a better claim to the throne.
There was no rebellion, no plot, no real scheme. But Tudor law made it easy. Just “imagining” the king’s death could be twisted into treason.
At trial, Buckingham was unanimously found guilty and executed on Tower Hill.
Extravagant Taxation & Forced “Gifts”
When Henry ran out of money (which was often) he didn’t tighten belts. He squeezed his subjects.
He revived the so-called “benevolences,” a cynical term for “voluntary” donations that no was allowed to refuse.
Landowners, merchants, and even clergy were strong-armed into handing over cash. Those who hesitated were threatened with treason charges. It wasn’t taxation so much as royal extortion.
He also imposed forced loans. Money the crown pretended it would pay back but never did.
Parliament barely mattered. Henry treated the kingdom like an overdraft account he never planned to settle.
War-Mongering in France
Henry also fancied himself a new Henry V and plunged England into ruinously expensive campaigns in France to boost his ego and claim territories he couldn’t hold.
The wars of 1512–1514 and 1544–1546 drained the treasury, forced new taxes, and destabilized trade. Gains were minimal and short-lived. Boulogne was about the only trophy he took, and even that didn’t last.
By the time he was done, England was financially battered, inflation was rising, and his government was melting church treasures just to cover costs.
War didn’t make England stronger. It made Henry look important while everyone else paid for it.
Treatment of Catherine of Aragon
Long before the annulment drama with Catherine of Aragon, wife #1, Henry was already chasing other women. He took mistresses like Elizabeth Blount and Mary Boleyn and even fathered an illegitimate son.
Humiliating the queen in public wasn’t technically a crime. But it showed early on how casually he’d discard loyalty when it suited him.
His marriage to Catherine lasted nearly 20 years, long by Henry’s standards. But only one child survived: their daughter Mary.
With no son to secure the Tudor line, Henry grew increasingly frustrated. Catherine suffered multiple pregnancies that ended in stillbirths or infant deaths.
Over time, Henry convinced himself the marriage was cursed or doomed from the start. A sort of divine punishment for marrying his brother’s widow.
Once Anne Boleyn came to court and caught his attention, the idea of staying with Catherine became even less appealing.
Boiling Of Richard Roose
In 1531, Henry staged one of his most sadistic public spectacles. A cook named Richard Roose, who worked in Bishop John Fisher’s household, was accused of poisoning a pot of porridge.
Fisher survived, but two others died. Rather than hang him — the standard punishment — Henry pushed Parliament to create a brand new penalty: boiling alive.
Roose was plunged into a cauldron at Smithfield while crowds watched him scream and thrash to death. No trial worthy of the name, no real evidence. Just royal theater by fire and water.
Why did Henry do it? Bother with a cook? Because his employer, the bishop, was one of the most vocal opponents of Henry’s divorce from Catherine of Aragon.
Just four years later, the bishop was imprisoned in the Tower and ultimately beheaded on Tower Hill, just days before Thomas More met the same fate.
Break with Rome
In 1533, Henry finally broke with the Pope so he could marry Anne Boleyn and try again for a male heir. A year later, the Act of Supremacy sealed the deal. Henry named himself “Supreme Head of the Church of England.”
The Pope was out. The king was now God’s English middleman.
This wasn’t a grassroots religious awakening. England had been Catholic for a thousand years, and no one was begging for a schism.
The clergy didn’t vote themselves out of Rome, and the public didn’t rise up chanting for reform. Henry didn’t guide a Reformation. He forced one through.
The break with Rome wasn’t about doctrine. It was about politics, sex, and succession. Just dressed up in religious language to make it look respectable.
Take Down of Wolsey
Cardinal Thomas Wolsey was once Henry’s top advisor. The king made him Lord Chancellor just six years into his reign.
In the church, Wolsey rose just as fast — Archbishop of York, then cardinal, then papal legate. He even imagined himself as a future pope.
But he was widely disliked. His arrogance and self-importance made him easy to resent.
Still, Henry relied on him. When the king wanted his marriage to Catherine of Aragon annulled, he expected Wolsey to deliver. But the pope refused to grant it and sided with Catherine.
That failure doomed Wolsey. Henry stripped him of his titles and seized Hampton Court Palace. He then charged Wolsey with treason for siding with Rome over the crown.
Wolsey never made it to trial. He fell ill on the journey south and died before he could be executed.
He was buried in Leicester, near Richard III, in a church once called the “sepulcher of tyrants.” I’ve never put Richard in that category, but the nickname stuck.
Execution of Thomas More
Thomas More was a brilliant Catholic scholar, writer, and statesman who stepped into Wolsey’s shoes as Henry VIII’s Lord Chancellor. He liked to call himself “the king’s good servant, but God’s first.”
Noble sentiment. Fatal in practice.
By 1532, he saw exactly where Henry was steering the ship and bailed out of office. When the Oath of Supremacy rolled around in 1534, More wouldn’t bend.
That was enough for Henry. More was hauled off to the Tower of London that same year, tried for treason on flimsy evidence, and beheaded in July 1535.
A clean death, but a loud message.
Dissolution of the Monasteries
Once Henry broke from Rome, he needed total control over his new church. Plus, he really needed cash.
England’s monasteries were wealthy, powerful, and loyal to the pope. So he wiped them out.
Between 1536 and 1540, every monastery in England was dissolved. Their lands and treasures were seized.
Some estates went straight to Henry, others were handed off to nobles to keep them loyal. Many buildings were stripped, looted, or pulled down entirely.
It wasn’t reform. It was a state-sponsored smash-and-grab. And it ended a way of life that had shaped England for centuries.
He even targeted the great shrines: Thomas Becket’s glittering tomb at Canterbury, the shrine of St. Cuthbert, and Edward the Confessor’s shrine in Westminster Abbey. All were destroyed or looted.
The human cost was massive. Thousands of monks, nuns, and lay workers were forced out with nowhere to go. The poor they once fed, housed, and treated were left adrift too.
This wasn’t reform. It was asset-stripping for cash and power.
Execution of Anne Boleyn
Henry finally married Anne in 1533 after waiting seven years. That same year, she delivered a daughter — Elizabeth — who would later become one of England’s greatest monarchs.
But for Henry, the victory was hollow. He still had no son.
Like Catherine, Anne suffered miscarriages and a stillborn son. The court began to circle.
Whispers thickened in corridors — affairs, witchcraft, incest, bad luck. Henry’s gaze slipped elsewhere, and her enemies knew it.
By 1536, it was open season. On trumped-up charges of adultery and treason, Anne was dragged to the Tower and beheaded. Another wife who couldn’t produce a male heir neatly disposed of.
Henry didn’t bother with grief. Eleven days later, he married his third wife, Jane Seymour.
Divorce of Anne of Cleves
Jane, however, died in childbirth. Her death left Henry single again, and a monarch without a wife was a monarch unfinished. The hunt resumed.
This time, he used art as his matchmaker. Hans Holbein was dispatched across Europe to paint eligible women. His portraits functioned like a 16th century dating app, swipe by courier.
The most infamous result was Anne of Cleves. Holbein’s portrait flattered her into the role of queen-to-be, and Henry agreed to the match. But when she arrived in person, he reportedly recoiled and muttered, “I like her not.”
The marriage wheezed along for six awkward months before being annulled without consummation.
Anne, no fool, didn’t fight it. She signed the papers, took the payout, and retired comfortably. The only one of his wives to leave with her head and a pension.
Execution of Thomas Cromwell
Thomas Cromwell was Henry’s iron-fisted enforcer. He interrogated Thomas More, helped bring him down, and approved the execution when More refused to back Henry’s divorce and new church.
For a while, Cromwell was untouchable. He dissolved the monasteries, funneled their wealth to the crown, and rewired England’s religious order to suit the king. But with the Tudors, loyalty always came with an expiration date.
Cromwell’s ruin came in 1540. He arranged Henry’s ill-fated marriage to Anne of Cleves and made too many enemies at court. The king who’d relied on him for a decade dropped him in an instant.
Cromwell was arrested on charges of treason and heresy, conveniently vague and politically useful. He was beheaded, condemned by the same machinery he once wielded. Another Tudor titan who rose fast and fell faster.
Execution of Margaret Pole
Margaret Pole’s brutal death in 1541 is one of the most chilling and senseless acts of Henry VIII’s reign … even by his standards.
She was the daughter of George, Duke of Clarence, brother to Kings Edward IV and Richard III. She was Plantagenet royal blood, one of the last surviving Yorkist heirs. Early on, she was trusted and even made governess to Princess Mary.
Unfortunately for her, her son, Reginald Pole, was a cardinal in Rome and openly condemned Henry’s break with the Catholic Church. Henry couldn’t reach Reginald abroad, so he took revenge on his family in England.
In 1538, Margaret was arrested. There was no trial and no real evidence. She was imprisoned in the Tower for nearly 3 years, elderly and in poor health.
She was executed in 1541. It took eleven hacks of the sword. The execution shocked even hardened courtiers. It was pure vengeance, not justice.
Execution of Catherine Howard
After divorcing wife #4, Henry was bloated, foul-tempered, and hobbling around with a festering leg ulcer. Into that thoroughly un-romantic setting walked his fifth wife, the teenage Catherine Howard.
She was lively and flirtatious, and probably saw Henry more as a rich grandfather than a husband. For a brief moment she brightened the court, and Henry swooned, dubbing her his “Rose without a Thorn.”
Then she lit the fuse on her own downfall.
Youth and impulsiveness don’t mix well with a paranoid monarch. When rumors of past and present lovers began circulating and damning evidence followed. Henry went berserk.
In 1542, Catherine followed her cousin Anne Boleyn to the scaffold at the Tower of London. She was only about nineteen.
Tried to Execute His Daughter Mary
After Henry broke with Rome, his advisors wasted no time targeting his daughter Mary. They warned him she was a threat to the succession.
She was Catholic, stubborn, and loyal to her mother’s cause. Henry responded the only way he knew how: by trying to erase her. He declared her illegitimate and entertained plans to charge her with treason.
Cromwell and his allies drafted the paperwork that could’ve sent her to the block. But Catherine Parr and Ambassador Eustace Chapuys stepped in and worked behind the scenes to save her.
Mary was forced to submit and sign humiliating documents acknowledging her father’s supremacy. She survived, barely, but only because others intervened.
Treatment of Princess Elizabeth
Henry’s angry eyes also fell on his youngest daughter, Elizabeth. After Anne Boleyn’s execution in 1536, the 2 year old became a political inconvenience overnight.
Some at court — especially conservative factions loyal to Catherine of Aragon and Princess Mary — quietly pushed for the child to be removed, erased, or allowed to die quietly out of sight.
Henry didn’t kill her. But he wiped her status clean.
Elizabeth was declared illegitimate by Act of Parliament, stripped of her title as princess, and removed from the line of succession. She was sent away from court.
For several years she lived in a kind of genteel captivity. Not in a cell exactly, but effectively exiled from public life. Dependent on the king’s moods and the factions surrounding him.
Given what happened to other relatives with Plantagenet blood, her survival was far from guaranteed. The only thing that kept Henry from disposing of her entirely was political convenience and the fact that she was, for the moment, harmless.
Catherine Paar Barely Escapes
Henry’s sixth and final wife, Catherine Parr, also barely missed the chopping block.
She was a reforming Protestant at heart, and she sometimes pushed her luck theologically. She discussed scripture with Henry, challenged his views, and surrounded herself with reform-minded ladies.
That alone made her enemies. Especially the conservative faction led by Bishop Gardiner and Thomas Wriothesley.
She was accused of undermining Henry’s authority, promoting heresy, and trying to influence him religiously.
Paranoid and in chronic pain by then, Henry signed an arrest warrant for her with the intent to interrogate and possibly try her for heresy.
Catherine got wind of the plot and staged a brilliant reversal. She played submissive, telling Henry she only debated religion to distract him from his pain and learn from his superior wisdom.
She flattered him, downplayed her intellect, and made it sound like a performance of wifely obedience. Henry’s ego swallowed it whole.
The next day, when the Lord Chancellor arrived with guards to arrest her, Henry publicly lashed out at them, pretending he’d never authorized it.
Crime Sites
Here are the key places where Henry schemed, punished, or spilled blood:
Hampton Court Palace
• Built by Wolsey, then seized by Henry.
• Hotbed of interrogations, court plotting, and marital drama.
• Catherine Howard was arrested here and tried to bolt down the gallery to reach Henry.
>>> Click here to book a half day trip to Hampton from London
Greenwich Palace
• Henry’s birthplace, as well as Mary, Elizabeth, and Edward.
• Political arrests were ordered here and courtiers dreaded morning summonses.
Whitehall Palace (York Place)
• Former Wolsey residence turned Henry’s main London base.
• Death warrants signed, council meetings held, and Anne Boleyn arrested here.
Westminster & Parliament
• Power center for the Acts of Supremacy and Treason.
• Dissolution of the Monasteries pushed through here.
• Acts of Attainder condemned Buckingham, Cromwell, and Margaret Pole without trial.
Tower of London
• Royal armory and vault for the Crown Jewels.
• Prison for fallen favorites and “traitors.”
• Execution site for Anne Boleyn, Catherine Howard, Thomas More, Cromwell, and Margaret Pole.
>>> Click here to book a Tower ticket
I hope you’ve enjoyed my guide to Henry VIII. You may find these other UK history travel guides useful:
- The Battle of Hastings
- The Battle of Lewes
- History of the War of the Roses
- History of Medieval and Tudor England
- The wives of Henry VIII
- Life of Mary Queen of Scots
- Life of Anne Boleyn
- Life of King John
- Life of Thomas Becket
- Life of Shakespeare
- Best day trips from London for history buffs
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