Top 10 People who Loved Henry VIII and Lost their Heads

Being a friend of a monarch used to be a dangerous occupation. You could gain riches and power, but you also ran the very real risk of ending up at in the Tower of London, with your head some distance away from your body. And there was no monarch more dangerous to be around than Henry VIII. He was famous for many reasons – including the Reformation of the church – but one of the reasons he made his mark on history was the sheer number of notable people he had executed, a habit carried on by his daughter Mary. But while Mary concentrated on heretics (i.e. Protestants), Henry had a habit of turning on his friends and loyal companions – sometimes for nothing more than a theological dispute. So here’s the Top 10 friends of Henry VIII who ended up on the executioner’s block.


10. Margaret Pole (Countess of Salisbury)

There’s nothing like depending on someone and then turning on them. Margaret Pole spent many years serving the King in one capacity or another – she was lady-in-waiting to Catherine of Aragon and governess to Princess Mary. She was a loyal friend to the King’s daughter, and even offered to educate her at the her own expense after Mary was declared illegitimate. But she should have known that those kind of actions wouldn’t endear her to Henry. There was an argument with the King in 1518 over some lands, and another in 1533 when she refused to give Mary’s jewels back (Henry demanded them after stripping Mary of her title). Although she dipped back into favor every so often and was an avid supporter of the King, she was never one of his favorites.

When her son, Reginald Pole, published texts  attacking Henry’s Reformation, her position looked shaky. When Reginald – while living abroad -  helped to organize a northern Catholic uprising against the King, her fate was sealed. Frustrated at not being able to punish Reginald himself, Henry ordered that the rest of his family be arrested instead. There was very little evidence against the Countess and the tunic used as “proof” that she supported the rebels was probably fabricated. She always protested her innocence during her two and a half years in the Tower, and her cell wall was later found to have a poem inscribed on it, starting “For traitors on the block should die; I am no traitor, no, not I!“.

Innocent she may have been, but when a king decides you’re going to die, there’s no room for negotiation. She resisted death till the last, struggled as she was held down on the block. Pity the new boy who was given the task of executing her – it took a full eleven blows to finish the job.


9. Katherine Howard

Henry VIII’s fifth wife. The marriage was dubious from the start – by then Henry was old, unattractive and gouty with a leg wound from jousting that smelt repulsive. Katherine was young and beautiful and had a past that was somewhat shadowy. It’s never been proven one way or the other whether Katherine had an affair with Henry’s young groom Thomas Culpepper, but the merest suggestion of it sent Henry into a jealous rage, and he ordered both Culpepper and Katherine to be executed, along with a previous lover of hers called Francis Dereham.

The men were executed swiftly, but Katherine had to wait until a bill was passed that made it a treasonable offense for a queen to not disclose her sexual past. Once that was passed, Katherine was executed in February 1542. She went to her death with a lot more composure than Margaret Pole, and even spent time practicing how to lay her head on the block the night before her death.


8. Jane Boleyn (Lady Rochford)

A lady-in-waiting to Katherine Howard who was executed mainly for her part in covering up Katherine’s past. She too had to wait for a bill to be passed before her death as she’d gone insane while in prison and it was illegal at the time to execute a madwoman. Needless to say, Henry cleared that one up and she died on the same day as Katherine Howard.

Six years earlier, she’d been part of the death of another queen – her sister-in-law Anne Boleyn. Jane’s testimony that her husband George had been Anne’s incestuous lover sent both of them to their deaths. She stayed in favor at court for a while, as lady-in-waiting to Jane Seymour and Anne of Cleves but once again she was proof that spending time too close to Henry VIII could be a dangerous business.


7. Henry Howard (Earl of Surrey)

Here’s another example of how wrong friendship can go when it’s with Henry VIII. Henry Howard was a brave soldier and covered himself in glory during the French Wars, serving as Henry’s Lieutenant General of the King on Sea and Land. He was related to both Anne Boleyn and Katherine Howard, but kept his distance during their respective downfalls. For a while, he was indispensable to Henry as a commander and friend. So what went wrong?

Firstly, there was his habit of getting repeatedly arrested for violent behavior – including smashing Londoners’ windows in a seemingly random attack. But more importantly, there was his distinguished heritage, descended as he was from kings on both sides of his family. By this point, the King was ill and suffering from paranoid delusions and he was convinced that Surrey planned to usurp his son Edward from his throne. There was no real evidence to back this up, but Henry was taking no risks. He’d earlier executed the Earl of Buckingham for similar offenses. Henry Howard and his father were both arrested and sentenced to death, and Henry was executed in January 1547. His father survived only by being due to die on the day after King Henry himself died. His execution was postponed indefinitely, but he stayed in prison for the next six years.


6. John Fisher

The model of the pupil turning against the teacher is a well-established one in literature and film (just think of Anakin Skywalker killing Obi-wan Kenobi) and it may have all started here, with the execution of John Fisher, Bishop of Rochester, at the command of his former pupil Henry VIII.

Fisher was a Roman Catholic scholar, who was opposed to the Lutheran movement and initially, Henry supported this. He even got Fisher to preach an anti-Luther sermon outside St Paul’s Cathedral in 1526. When seeking a divorce from Catherine of Aragon, however, the protestant movement suddenly became useful to the King, who used some of their teachings to break away from Rome and establish his own church, thereby making his own decisions about who he could or could not divorce.

At that point, anti-Lutherans like Fisher became a nuisance rather than an asset. in 1534, when he refused to acknowledge Henry as the Supreme Head of the Church, he was sent to the Tower and beheaded in June 1535, on the feast of St Alban (fittingly, the first English martyr).


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