Henry VIII and the Art of Losing Your Head

Henry VIII and the Art of Losing Your Head (Terms and Conditions Apply)

London Prat Legal & Constitutional Affairs Desk

No employee handbook in English history has ever had a shorter chapter on job security than “Serving Henry VIII.” Two wives, a chancellor, a chief minister, and countless courtiers all discovered, often with very little notice, that the King’s favour came with a distinctly limited warranty — and the returns policy involved an axe, or on lucky days, an imported French sword.

The Original At-Will Employment

Thomas More, Henry’s own Lord Chancellor and a man of famous conscience, refused to acknowledge the King’s supremacy over the church and was executed for treason in 1535 — a workplace disagreement escalated about as far as a workplace disagreement can go. Thomas Cromwell, the man who had engineered half the King’s reforms and the entire Dissolution of the Monasteries, was executed five years later on charges historians still consider flimsy at best, largely blamed for the disastrous Anne of Cleves marriage he himself had brokered. As one Kent farmer of the era supposedly muttered, “You don’t get a P45 from this King, you get a headsman.”

A Two-For-Two Record On Wives

Anne Boleyn and Catherine Howard both went to the block at the Tower of London on charges of adultery and treason, evidence for which ranged from thin to nonexistent by modern historical standards. Anne was executed on 19 May 1536, granted the small mercy of a skilled swordsman imported specially from Calais rather than the usual axeman — Henry’s version of a considerate gesture. She is said to have remarked beforehand that she had heard the executioner was very good, and that she had “a little neck.” Catherine Howard followed her to the same execution ground on Tower Green in February 1542, just six years later, making Henry the only English king to have two wives beheaded.

[Image brief: The Tower of London with a sign reading “Now Hiring — Long-Term Prospects Not Guaranteed.”]

Tower Green: A Very Exclusive Address

Executions at Tower Green were reserved for high-status prisoners, granting them privacy from the jeering crowds that gathered at the public Tower Hill site nearby, where an estimated 125 people were executed over the centuries. Being executed privately within the Tower walls was, in a grim sort of way, a status symbol — Anne Boleyn, Catherine Howard, and later the teenage Lady Jane Grey were all afforded this “privilege.” Anne was buried afterward in the Tower’s Chapel Royal of St Peter ad Vincula, alongside her brother George, who had been executed days earlier on the same conspiracy charges.

What’s often overlooked is how routine this became. Executions of nobles, once rare and scandalous events that shook the whole realm, turned into a semi-regular feature of Tudor governance by the 1530s and 1540s — a grim rhythm that historians now treat as a defining feature of the reign rather than an aberration within it.

Beyond the Six Wives: A Wider Purge

The executions extended well past Henry’s own marriages. Margaret Pole, Countess of Salisbury and one of the last surviving members of the old Plantagenet royal line, was executed in 1541 in her late 60s, reportedly on the flimsiest of treason charges connected to her son’s opposition to the King abroad. Decades later, near the very end of his reign, the poet and courtier Henry Howard, Earl of Surrey, was executed in January 1547, mere days before Henry himself died — a final, almost absent-minded flourish of the same paranoid machinery that had run through the entire reign. Jane Boleyn, Lady Rochford, who had testified against both her own husband George Boleyn in 1536 and later Catherine Howard in 1542, was ultimately executed herself alongside Catherine, having spent years as one of the court’s more dangerous double agents.

Taken together, the pattern is less “occasional royal cruelty” and more “structural feature of the regime”: once the Reformation had normalised treason charges as a political tool, and once the Dissolution had shown just how much wealth and power could be redistributed by royal decree, execution became simply one more administrative lever available to the Crown — used liberally, and often with very little actual evidence behind it.

Seven Observations on Tudor Job Security

The Tower of London had better attendance figures than most modern theatres.
Thomas Cromwell built the machine that eventually processed him.
Two wives executed is a statistic no royal HR department wants to explain.
“Treason” in Tudor England was a remarkably flexible legal term.
The imported French swordsman remains history’s most specific execution upgrade.
Job security under Henry peaked at “please don’t disagree with him.”
Nobody in the Tudor court ever really got a retirement party.

Henry VIII and the Art of Losing Your Head