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Henry VIII’s Most Brutal Executions

Charlotte Bond
Painting of Henry VIII (Photo Credit: Imagno/Getty Images)

Henry VIII is perhaps the best-known English king in history. People remember him for the number of his wives, his sweeping religious reforms, and his habit of executing those who disagreed with him.

In some cases, Henry’s own personal feelings urged him towards a particularly brutal or ignoble death for his enemies. Below are eight Tudor executions that show Henry at his most unpleasant and vengeful.

Richard Roose, died April 1532

Richard Roose was the cook for John Fisher, the Bishop of Rochester. When Fisher held a dinner party, Roose served up a porridge which was eaten by the guests and two beggars who came to the door. The guests were seriously ill and the beggars died. Fisher was unaffected since he didn’t eat the porridge or anything else that day.

Having been arrested on suspicion of poisoning, Roose was tortured until he confessed that he had added a white powder to the porridge. It had been given to him by a stranger, and Roose had naively assumed that it was a laxative, something that would incapacitate people for a prank, not kill them.

Henry had a mortal fear of poisoners and so put forward an act of parliament that made poison a treasonous offense, the punishment for which was death by boiling. Since the act had a retrospective effect, it meant that Roose had to face such an unpleasant fate.

Roose was given no trial and no opportunity to defend himself. The King merely sentenced him to death after “a lengthy speech expounding his [the King’s] love of justice and his zeal to protect his subjects and to maintain good order in the realm.”

On the day of his execution, Roose was tied up in chains then repeatedly lowered into and lifted out of a vat of boiling liquid until he was dead.

illustration of death by boiling

Illustration of a death by boiling. Holy Eulampia and her brother are boiled alive in oil and the Martyrdom of Saint Rufina Rome, Jan Luyken, Barent Visscher, Jacobus van Hardenberg, 1700. (Photo Credit: Sepia Times/Universal Images Group via Getty Images)

Historian G. W. Bernard has speculated that Henry’s extraordinary reaction to this attempted poisoning might indicate a guilty conscience and hint at the fact he either had a hand in the poisoning attempt or at least knew about it.

Pilgrimage of Grace, October 1537

In October 1536, parts of Northern England rose up in revolt against Henry and the religious upheavals he was implementing.

Under the leadership of Robert Aske, the rebellion had some success. With 30,000-40,000 men under his command, Thomas Howard (the Duke of Norfolk) and George Talbot (the Earl of Shrewsbury) were forced to negotiate near Doncaster. With a promise of pardons all around and a Parliament to be assembled in York, Aske sent his rebels home, all feeling pleased that the King had seen their side of the argument.

However, the King never intended to keep his promises, and when a new uprising took place (one not authorized by Aske and his associates), the Duke of Norfolk quickly suppressed it and the leaders of the Pilgrimage of Grace were arrested.

In all, 216 rebels were executed, including lords, knights, and abbots. Some were hanged, others beheaded. The unfortunate Thomas Moigne, the MP for Lincoln, suffered the worst death, being hanged, drawn, and quartered. Robert Aske was hanged in chains, his body placed in a gibbet as a warning to others.

Sean Bean as Robert Aske

Sean Bean as Robert Aske in ‘Henry VIII,’ 2003 (Photo Credit: Granada Television for ITV)

Thomas Cromwell, died July 1540

Thomas Cromwell rose to favor when he helped secure Henry a divorce from his first wife, Catherine of Aragon. He had a turbulent relationship with Anne Boleyn, but he survived her downfall, with some commentators suggesting he might have had a part in engineering it.

However, his own downfall was imminent after he arranged a marriage for Henry with Anne of Cleves, whom the King did not like at all. Henry had seen a flattering portrait of Anne (depicted below), but her actual appearance repulsed him and he declared he couldn’t consummate the union.

Drawing of Anne of Cleves

Anne of Cleves’, (1515-1557), 1830. Anne of Cleves (1515-1557) Queen of England from 6 January to 9 July 1540 as the fourth wife of King Henry VIII. From “Biographical Illustrations”, by Alfred Howard. [Thomas Tegg, R. Griffin and Co., J. Cumming, London, Glasgow and Dublin, 1830]. Artist Unknown. (Photo Credit: The Print Collector via Getty Images)

It was powerful enemies like the Duke of Norfolk and Stephen Gardiner, the Bishop of Winchester, who plotted Cromwell’s downfall. The Duke of Norfolk was particularly keen that his niece, Catherine Howard, should become queen in place of Anne of Cleves. The King was very much taken with Catherine and ensured that Cromwell was arrested at a council meeting on June 10, 1540.

Imprisoned in the Tower of London, Cromwell was stripped of his wealth and titles, and it was decreed the man who’d become Chancellor should now only be known as “Thomas Cromwell, cloth carder.” While the list of his offenses was long, everyone knew that Cromwell’s death was Henry’s revenge for the unwanted marriage.

In some versions, Cromwell’s enemies ensured that his executioner was either drunk or sufficiently inexperienced that he botched the job, taking several blows to sever Cromwell’s head from his body. If true, this would have been a final indignity for a once-proud man.

Illustration of Thomas Cromwell

Thomas Cromwell (Photo Credit: ullstein bild/ullstein bild via Getty Images)

Margaret Pole, died May 1541

When she was imprisoned in the Tower, Margaret Pole was 67 years old and considered an old woman by Tudor standards. When her son, Reginald Pole, was marked as a traitor, Margaret wrote to him, reproving him for his folly. However, Reginald continued with his criticisms of Henry’s actions and policies, and since Reginald was out of Henry’s reach in Padua, it was his family in England that paid the price.

A search of Margaret’s home produced evidence suggesting she still supported the Catholic faith, something that Henry had ruled unlawful. She was sentenced to death at the King’s pleasure, and she ended up sitting in the Tower for two and a half years with the threat of execution hanging over her.

When she was told she would die that day, she refused to believe it or come quietly. She said beheading was for traitors and she was no traitor. When she refused to put her head on the block, her jailers had to force her down onto it. Even then, she twisted her neck this way and that way in protest.

To make it even worse, Margaret’s executioner was inexperienced, and reports suggest it took eleven blows of the axe before she was dead. The Imperial ambassador, Eustace Chapuys, witnessed the execution and he wrote that the execution was “a wretched and blundering youth who literally hacked her head and shoulders to pieces in the most pitiful manner.”

Margaret Pole

Margaret Pole, Countess of Salisbury, 14.8.1473 – 27.5.1541, English noblewoman, death, execution in the Tower of London, copper engraving, Review of Fox’s Book of Martyrs by William Andrews, 1826 (Photo Credit: Public Domain)

Thomas Culpepper as compared to Francis Dereham, December 1541

While Henry might have initially been pleased to be married to a young and flirtatious Catherine Howard in place of Anne of Cleves, his happiness was not to last when she conducted an affair with Thomas Culpepper, one of Henry’s favorite courtiers.

Francis Dereham was also caught up in the controversy, although with a charge of sleeping with Catherine before she was married to the King.

Both men were sentenced to death, and both petitioned Henry to have their traitor’s death commuted to beheading. Even though Culpeper’s crimes were arguably greater than Dereham’s (since he’d slept with Catherine while she was queen), his request was granted but Dereham’s was not.

On December 10, 1541, both men were executed. A report at the time described the scene: “Culpeper and Dereham were drawn from the Tower of London to Tyburn, and there Culpeper, after an exhortation made to the people to pray for him, he standing on the ground by the gallows, kneeled down and had his head stricken off; and then Dereham was hanged, membered, bowelled, headed, and quartered [and both] their heads set on London Bridge.”

handwritten letter

Letter from Catherine Howard to Thomas Culpepper (Photo Credit: Catherine Howard, Public Domain)

Jane Boleyn, died February 1542

Another courtier to be swept up in Catherine Howard’s disgrace was Jane Boleyn, Viscountess Rochford.

Jane had managed to survive the scandal that had seen her husband, George Boleyn, beheaded for incest with his sister, Anne Boleyn. She returned to court where she served Jane Seymour, Anne of Cleves, and Catherine Howard when they were all queen. When Catherine was accused of adultery, Jane was implicated as an accessory, and she was taken to the Tower of London and interrogated (although not tortured). This treatment led to her having a nervous breakdown and being declared insane at the beginning of 1542. The law at the time meant that people declared insane could not stand trial.

However, with her name linked to both Catherine Howard’s and Anne Boleyn’s disgraces, Henry was determined that Jane should be punished. As such, he overturned the law and made an exception that when a person was accused of high treason, they could be tried and executed.

Both Jane Boleyn and Catherine Howard were executed on February 13, 1542. Their bodies were buried at the Tower of London, close to where the bodies of Anne and George Boleyn had been laid, a stark reminder that no one could outrun Henry’s vengeance forever.

actress playing Jane Boleyn

Joanne King portrays Jane Boleyn, Viscountess Rochford, in 2007’s ‘The Tudors’ (Photo Credit: Sony Pictures Television, Showtime, MovieStillsDB)

Anne Askew, July 1546

A relative of Robert Aske, Anne was one of only two women to have been tortured at the Tower of London and burnt at the stake.

Anne drew attention to herself by preaching as a Protestant in London. An attempt to transport her to Lincolnshire and keep her there failed, and she soon escaped and returned to London to continue her sermons. After several brushes with the law, Anne was arrested for a third time in May 1546 and taken to the Tower of London.

She was placed on the rack in the hope that she would give up other Protestant names to her torturers, but she did not. When she was taken to her place of execution in Smithfield, London, she had to be carried in a chair because she was so crippled by her torture.

At the stake beside her were three other Protestants. An unknown sympathizer had slipped bags of gunpowder to all of them which ignited in the flames. The four were blown up and thus saved from the agonizing death of being burned alive.

Martydorm of Anne Askew

“Martydorm of Anne Askew”. “Book of Martyrs”, John Foxe (1869). (Photo Credit: Unknown author, Public Domain)

Anne Boleyn, died May 1536

Virtually everyone knows the life and fate of Anne Boleyn, and while she had a swifter and more merciful death than those listed above, she makes this list because the King’s mercy might actually have been his usual cruelty in disguise.

When Anne Boleyn knew that she was going to die, she asked for a French swordsman to be summoned to execute her. Being beheaded by a sword was swifter and cleaner than beheading by an ax. As a sign of mercy, Henry agreed.

Anne de Boleyn at the Tower of London

Anne de Boleyn at the Tower of London, in the first moments of her arrest (Photo Credit: Édouard Cibot – Musée Rolin, Autun, France, Public Domain)

More from us: Six Mysteries About Anne Boleyn (Or Should That Be Nan Bullen?)

However, the man chosen to behead the queen was an expert swordsman from Saint-Omer in France. It was necessary to order him from France and then allow time for him to cross the Channel. The Anne Boleyn Files and other sources point out that if the swordsman was to be there for the planned execution date of May 18, 1536, then he needed to be ordered on the 12th or 13th of May, perhaps even as early as the 9th or 10th.

But Anne’s trial only happened on May 15, 1536 – meaning that Henry must have ordered the headsman even before the trial took place, suggesting that Anne’s fate was already sealed even before she had a chance to defend herself.