Top 10 Heads That Rolled During the Reign of Henry VIII

By: Julia Layton  | 
Royalty Image Gallery Henry VIII presided over England for 36 bloody years. See more pictures of royalty.
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Key Takeaways
  • During Henry VIII's reign, tens of thousands of English subjects were executed, with notable figures like Edmund Dudley and Richard Empson losing their heads in 1510.
  • Royal lineage posed a threat to Henry VIII, leading to the execution of Edmund de la Pole in 1513 and Edward Stafford in 1521.
  • Religious and political opposition resulted in the beheadings of individuals like Elizabeth Barton in 1534, John Fisher in 1535, and Thomas Cromwell in 1540.

During the reign of Henry VIII, between 1509 and 1547, a­n estimated 57,000 [source: The Tudors] and 7­2,000 [source: Historic Royal Palac­es] English subjects lost their heads. It was a violent time in history, but Henry VIII may have been particularly bloodthirsty, executing tens of thousands during his 36-year reign. By comparison, the daughter who succeeded him on the throne, who came to be called "Bloody Mary," killed fewer than 300 people during her six years as queen.

Perhaps one of the primary reasons for Henry VIII's notoriety is not the sheer volume of killings but, instead, the controversy surrounding them. Henry VIII presided over the English Reformation, a period of great change characterized by England's break from the Catholic Church. The trouble started when Henry married his older brother's widow, Catherine of Aragon, a member of the Spanish royal family.


After years of marriage, Henry wanted to divorce Catherine. She had suffered through several still births and a handful of infant deaths and hadn't borne a son. Henry became obsessed with producing an heir to carry on the Tudor family lineage, and he finally convinced himself that his marriage to Catherine had been a sin in the eyes of God. He even believed the union's sin was the reason why his legitimate male children kept dying. So he set about obtaining an annulment from the church based on the edict stating that a man can never marry his brother's wife. The problem was, it was the pope who had sanctioned the marriage in the first place, on the basis of Catherine's oath that her marriage to Henry's brother was never consummated.

­What ensued was a political and religious fiasco. In the end, Henry cast out the Catholic Church and established himself as the head of the Church of England, God's representative on Earth. He divorced Cath­erine and married his mistress, Anne Boleyn, in the hopes of getting a son. In the process of achieving this single goal, Henry ordered the beheadings of some of the top political minds of the day, a few cardinals of the Church, at least one nun, a couple of his six wives, and countless members of the royal court who questioned the purity of his motives.

Of course, with tens of thousands of heads rolling, people were executed for a wide variety of crimes. In this article, we'll look at ten of the most significant executions of Henry's reign, beginning with the beheadings he ordered immediately upon securing the throne. As one of his first acts as king, Henry ordered the executions of two of his father's top advisors, the notorious Dudley and Empson.

10. Edmund Dudley and Richard Empson

Henry VIII established his reputation as a people's king by executing Richard Empson (L) and Edmund Dudley (R), who had been on his father's (C) council.
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Executed 1510

Henry VIII's father, Henry VII, wasn't a very popular king. The primary goal of his government was to amass riches in order to solidify the ultimate power of the monarchy. In achieving this end, his financial council essentially stole money from subjects under the pretext of various taxes and fees. Two of the most powerful men on this council were Edmund Dudley and Sir Richard Empson. These two men became symbols of the financial looting that infused the rule of Henry VII.

The people of England despised these men who were held responsible for Henry VII's policies. Immediately upon the death of Henry VII and succession of Henry VIII, the new king made a move to secure his popularity and his image as a king of the people. He found shaky evidence that Dudley and Empson had been embezzling money, his court found them guilty and Henry had them beheaded. They died in public executions in 1510.


While Henry VIII began his reign as a popular monarch, he wasn't without his powerful political enemies. The next two men on the list died because they were of royal lineage and could assert reasonable claims to Henry's throne.


9. Edmund de la Pole

Edmund de la Pole had a fairly legitimate claim to the throne: He was the nephew and heir of King Richard III. Richard died at Bosworth Field at the hands of Henry Tudor who later became Henry VII.
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Exec­uted 1513

King Richard III, Henry VII's pred­ecessor, was a member of England's York family. Henry Tudor, of important royal lineage on his mother's side, led a battle against the king in 1485 to take the throne. Richard III died on the battlefield, and Henry Tudor became King Henry VII.

Edmund de la Pole was of York family lineage on his mother's side: His mother was Richard III's sister. As King Richard III had died without an heir, the crown would've landed with the de la Poles if Henry VII hadn't claimed the throne -- Richard had named his nephew Edmund as his successor.


As a legitimate threat to the Tudor monarchy, de la Pole would've been in danger even if he hadn't taken the step to try to overthrow Henry VII. He left England for the Netherlands, where he temporarily gained the support of the emperor Maximilian in his quest to reclaim the thrown. But Henry VII ended up making a deal with the emperor, and Maximilian withdrew his support. Upon returning to England, de la Pole found himself branded a traitor.

In order to save his own life, de la Pole turned himself in to Henry VII's son, Prince Henry, who promised to merely imprison him. He kept his promise until he succeeded his father on the throne. To protect himself as king, Henry VIII ordered de la Pole beheaded in 1513.

But that wasn't the end of the Yorks. Henry VIII faced serious opposition from another man, a popular noble and powerful politician. Edward Stafford, Duke of Buckingham, sealed his fate when he spoke too much of his claim to the English throne.


8. Edward Stafford

Edward Stafford carried Henry's crown at the coronation of the king and his queen, Catherine of Aragon.
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Executed 1521­

Ed­ward Stafford was of royal blood, a descendant of King Edward III. He was powerful in Henry VIII's court, he bore the crown at Henry's coronation and he was popular with the people. Stafford also won a battle against Cornish rebels in the English countryside in 1497 [source: Luminarium] and was considered to be a great military leader. Henry VIII was not.


However, stirrings at court ended his friendship with Henry when people began to whisper about Stafford's claim to the throne. The king put Stafford on the sidelines, and Stafford fought back. He became the central figure around which many marginalized nobles gathered, and he came to be a voice of opposition against the king.

Stafford may have been simply ignored, or imprisoned, had it not been for a rumor that surfaced in 1521. People said Stafford was speaking about the king's death. Some claimed they'd heard Stafford describe visions of Henry's demise. Henry's top advisor at the time, the powerful Cardinal Wolsey, hated Stafford and encouraged the king to take the accusations seriously.

After questioning witnesses himself, Henry must have been convinced by the accusations because he had Stafford beheaded for treason that year. Henry VIII never faced another serious claim to his throne.

Threats to his policies, though, persisted throughout his reign. They became common practice once he started his quest to annul his marriage to Catherine of Aragon. One source of significant protest came from an unlikely source, a young servant who claimed to have supernatural insight. Henry didn't care for her mystical visions.

7. Elizabeth Barton

Elizabeth Barton had visions that it was against God's will for Henry to marry Anne Boleyn. He put an end to her mysticism.
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­Executed 1534

Elizabeth Barton was a young, lowly servant when she first made a name for herself as a mystic. At the age of nineteen, she got sick, and in her illness, she began to have visions. In 1525, with Henry VIII's pursuit to gain permission from the pope to marry Anne Boleyn in full swing, Barton's visions became supernatural evidence of God's will: Henry was not to marry Anne.

Some people thought she was simply crazy, others believed her visions were a result of her illness, and still others believed she was a conduit for God. Her master, the Archbishop of Canterbury, fell into the latter group. He got Barton into a convent, where she became a nun and so attained a degree of legitimacy. Over the course of the next 10 years, her visions became bolder and increasingly threatening to Henry's assertion that his desire to divorce Catherine was based on legitimate religious principal.


Barton's visions about the consequences of the king's pursuit eventually became so ominous that they were considered treasonous. She was arrested, and under intense interrogation, she confessed to having faked everything. She was beheaded in 1534. No consensus was ever reached on whether her visions were divinely inspired or the result of a troubled mind. To this day, the Catholic Church gives some credence to Barton's apparent mysticism [source: Catholic Encyclopedia].

Barton is just one of the many insistent Catholics who lost their heads to Henry VIII's pursuit of a divorce. Cardinal John Fisher became a martyr and a saint when he refused to support the Supremacy Act that made Henry VIII the head of the church and the Act of Succession that made Anne Boleyn the legitimate queen of England.


6. John Fisher

John Fisher denied Henry VIII's supremacy but was later canonized for his staunchness.
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Executed 1535

Henry VIII and Cardinal Wolsey went to John Fisher when they first came up with the idea of annulling the king's marriage. Fisher was a priest, a cardinal and confessor to Henry VII's mother before her death. He founded St. John's College at Cambridge. He was widely respected in Europe as a theologian after publishing works decrying Luther's movement to reform the Catholic Church. When Henry and Wolsey approached him for advice, he was clear: An annulment would go against the will of God.

They proceeded anyway, and Fisher never relented in his opposition. He openly defended Catherine, making great trouble for Henry. When the Supremacy Act passed in 1534, Fisher, with Sir Thomas More (keep reading) at his side, refused to take the required oath because it was a repudiation of papal authority. They were sent to the Tower of London, the city's prison, where they waited to find out what Henry would do with them. It was after this that the pope made Fisher a cardinal. Henry took this as a slap in the face, and Fisher's fate was sealed.


Fisher was dragged in front of the king's council many times during his imprisonment, and he always refused to speak about the Supremacy Act. Finally, under the guise of questioning Fisher about the act off the record, Henry's lead council got Fisher to say that Henry could never be supreme ruler of the church. The recently passed Supremacy and Treason Act made denying the king's supremacy an act of treason. Cardinal John Fisher was beheaded in 1535. The Catholic Church made him a saint 400 years later.

The Supremacy Act that annulled Henry's marriage opened the door for him to indulge his every marital desire. He married five more women after Catherine. He had his second and fifth wives beheaded. Catherine Howard was wife number five, and her crime was far less political than Fisher's.

5. Catherine Howard

Catherine Howard was executed for being unchaste. Her portrait is from a painting by Hans Holbein the Younger, engraved by Francesco Bartolozzi.
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Executed 1542

Henry VIII married Catherine Howard after he annulled his fourth marriage to Anne of Cleves. Henry never liked Anne of Cleves -- it was a politically motivated marriage arranged by Thomas Cromwell, and she was apparently homely. Cromwell paid for his poor judgment with his career. Henry married Catherine about two weeks after Anne was out of the picture. The Howards were a powerful family in Henry's court, with influence and high standing. Catherine seemed a good fit, and it took two years for Catherine's sordid past to catch up with her.

As things so often happened at court, it started with a rumor. This one, though, was true. It seemed Catherine Howard had had lovers before Henry. The king didn't know this when he married her, and he was humiliated when the truth came out. To make matters worse, the queen had appointed one of her pre-marital lovers to be her secretary. Rumor had it the affair continued after her marriage to the king.


The adultery aspect of the charge was never proven, but it didn't matter. Upon learning that he had married a nonvirgin, Henry had Parliament pass an act declaring it treasonous for an unchaste woman to marry the king. Catherine Howard was promptly beheaded for treason.

Henry also had Catherine's uncle beheaded, but for entirely different reasons. Henry Howard was the victim of courtly lies, the result of a power struggle between two of the court's most powerful families, the Howards and the Seymours.

4. Henry Howard

Henry Howard was executed for treason on trumped up charges. He helped introduce the sonnet to England.
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Executed 1547

Henry's court was a place of constant positioning for the king's favor. Henry's hangers-on were always vying for power, and Henry Howard, Earl of Surrey, lost his life when the Seymours felt threatened.

Jane Seymour was Henry's third wife. She died soon after they married, but delivering Henry a legitimate male heir helped maintain the Seymours' power. But the Howards, too, had the king's ear. Henry Howard's father had been entrusted with the upbringing of Henrys VIII's illegitimate son by Elizabeth Blount. One sign of favor at court was an allegiance by royal marriage, and there was talk of two possible suitors for Henry's young daughter, princess Mary. One was a Seymour, Jane's brother; the other was Henry Howard. This set the stage for a battle.


The Seymours told the king that Howard had quietly supported the Catholics in a rebellion against the Supremacy Act in 1536. Howard had actually fought against the rebels, but the accusation still landed him in prison for two years. After he got out, he started making trouble for the Seymours, trying to block a marriage between his sister and one of the Seymours and making various accusations questioning the Seymours' loyalty to the king.

The Seymours struck their final blow: They again accused Howard of supporting the Catholics, but this time, they made his sister testify against him. She admitted on the stand that her brother was, in fact, a devoted Catholic. This was seen as a rejection of the king's supremacy. The Seymours combined this testimony with the fact that Henry Howard's father had had a claim to the throne before Henry VIII became king (though he never fought for it), and they convinced the king, who was by that time very ill, that the Howards intended to usurp the throne.

Henry Howard, Earl of Surrey, was beheaded in 1547, the same year the king died. It was Henry VIII's last execution. Howard had written volumes of poetry while imprisoned, and ended up creating the form that eventually came to be called the Shakespearean sonnet [source: Britannica].

The Howards and the Seymours were powerful, but they were nothing compared to Thomas Cromwell, the king's chief advisor during the successful break from the Catholic Church. Cromwell had the king's ear for eight years -- a long time in the world of Henry VIII. He lost his head only after he succeeded where all others had failed.

3. Thomas Cromwell

Thomas Cromwell's poor match-making skills set him on the path to beheading.
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Executed 1540

Thomas Cromwell served as the king's main advisor from 1532 to 1540. He was the one who finally succeeded in getting the king his divorce. It's possible that Cromwell was the mastermind behind the whole English Reformation [source: Britannica].

Cromwell took over after Cardinal Wolsey's fall from grace. Cromwell was a politician, brought up from Parliament to serve the king. He came to full power when he figured out a way to annul Henry's marriage to Catherine without the pope's permission: Remove the pope's power from England. Cromwell succeeded in getting Parliament to pass the Act of Supremacy that made Henry the head of the church. He disbanded monasteries and did away with the taxes paid to Rome. He effectively removed Catholicism from England, establishing England as a sovereign state.


With Cromwell's adept maneuvering, the king was able to leave Catherine and marry Anne Boleyn. Had the marriage not imploded, Cromwell may have kept his position. But as it turned out, he made a big mistake: After the death of Henry's third wife Jane Seymour, Cromwell convinced Henry to marry Anne of Cleves, of German royal lineage, for political reasons. Henry couldn't stand Anne, and he had the marriage annulled almost immediately. That was the beginning of Crowell's end.

The bad marriage separated Cromwell from the king, and Cromwell's enemies (he was a politician so he had many) set to work. While working to remove the influence of Roman Catholicism from England, Cromwell had occasionally aligned himself with the Lutherans, who were calling for reform in the Catholic Church. The Lutherans were considered heretics, and Henry had published papers denouncing them. Even after the break from the Church, Lutheranism was against English law. After Cromwell lost the king's support, his enemies used this connection to the Lutherans to convince the king that Cromwell was a heretic.

Thomas Cromwell was beheaded for heresy in 1540. He never received a trial.

Cromwell was a powerful man during the reign of Henry VIII. But the next execution on the list did away with one of the most noted individuals in all of English history: Thomas More.


2. Sir Thomas More

Thomas More was a statesman, writer and Catholic martyr who refused to swear to the Acts of Supremacy and Succession.
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Executed 1535

Thomas More was a noted humanist, lawyer, theologian, historian, philosopher, statesman and devout Catholic. He wrote "Utopia," a famous work of humanist principles that was read by every learned member of English society, and is still part of the cannon in universities. Shakespeare based his play "Richard III" on More's book "History of King Richard III." This accomplished and respected man became one of Henry VIII's advisors in 1518.

Leading up to the Supremacy Act of 1534, More tried to support the king as much as he could without betraying his religious beliefs. On at least one occasion, he was the king's spokesman in Parliament regarding the break from the Church. He did not, ultimately, stand in Henry's way, but he stayed true to his convictions. He didn't attend the coronation of Anne Boleyn, and he refused to swear to the Acts of Supremacy and Succession. The former offense angered the king, but the latter was an act of treason.


More's fall was swift. He was charged with conspiring with Elizabeth Barton, the nun whose visions so incensed the king. But a letter turned up that absolved him: He had written to Barton telling her to stay out of the king's business. When called on to swear to the Supremacy Act, More allowed that Henry was the supreme leader of the church but said he couldn't take the actual oath because it included a statement against the pope. More was taken to the Tower of London. He didn't much mind it, the prison life suiting his asceticism [source: Britannica]. In 1535, he was beheaded for treason. His head sat on display on London Bridge for a month after his death [source: Catholic Encyclopedia].

While imprisoned, More wrote the book "A Dialogue of Comfort Against Tribulation," viewed as a masterpiece of religious literature [source: Britannica]. More was canonized by the Catholic Church in 1935, the same year as John Fisher.

Finally, we get to one of the most ironic executions of Henry's reign. Anne Boleyn died by the same law that allowed her to become queen.


1. Anne Boleyn

After failing to produce a male heir, Anne Boleyn was accused of adultery and executed. She was, however, one of the most influential queen consorts in history.
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Executed 1536

Anne Boleyn was a young lady-in-waiting to the queen when Henry first noticed her. He was married to Catherine of Aragon at the time, and displeased with his lack of a male heir. The Boleyn family pushed Anne to exploit his attention. The rest is history.

Anne most likely would've been a mere mistress were it not for the legitimate heir factor and her own ambitions: She was determined to be queen. That, and Henry VIII actually fell in love with her. His divorce from Catherine slowly became more about marrying Anne than about having a son. In 1527, Henry started speaking quietly about getting rid of Catherine. In 1534, he granted himself the annulment, but he had actually married Anne the year before.

Anne was not well liked in Henry's court, especially after she became queen and she soon lost the king's love. She didn't give him a son in their first few years of marriage (although she did produce a daughter), and another young lady-in-waiting soon caught Henry's attention. He wanted to marry Jane Seymour. In his quest to marry Anne, and in satisfying her desire to be queen, Henry had already succeeded in making himself the sole decision maker in matters of marriage and divorce. There was nothing to stand in the way when he fell out of love with Anne.

Of course, he needed a good reason for the divorce so he wouldn't lose the support of the people (any more than he already had). Thomas Cromwell produced one: Anne had committed adultery with several men, including her brother. The charge was almost certainly false. There was no evidence to support it. But Cromwell was in charge of the court, and she was found guilty. Anne Boleyn was beheaded in 1536, two years after the king removed the pope's influence from England so their marriage would be legitimate. Her daughter became Queen Elizabeth I.

While Henry VIII held the throne, England went through changes that would eventually lead to the creation of modern sovereignty -- a nation not beholden to the church -- though Henry never intended it. He was a walking contradiction, a devoted Catholic who rejected the Pope and founded his own religion; a king of the people and an educated humanist who executed tens of thousands of subjects. In the end, Henry VIII produced one male heir, Prince Edward, his son by Jane Seymour. Edward took the throne when his father died; he was 10 years old. He died of illness five years later, passing the crown to Henry's daughter by Catherine of Aragon, Princess Mary. Queen Mary's primary objective became reinstating Catholicism in England. She failed in her quest, though she burned hundreds of people at the stake in the process. Elizabeth I succeed her older sister and reigned for 45 years.

For more information on Henry VIII, the Tudors, and English royalty, head to the links page.

Frequently Asked Questions

How did Henry VIII's marriages influence his political decisions?
Henry's marriages, particularly his desire for a male heir, led to significant political and religious upheavals, including the English Reformation and the establishment of the Church of England.
What was the role of Thomas Cromwell in Henry VIII's reign?
Thomas Cromwell was instrumental in facilitating Henry's divorce from Catherine of Aragon and the subsequent establishment of the Church of England, serving as Henry's chief advisor.

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More Great Links

  • Anne Boleyn.
  • Catherine Howard.
  • Edmund de la Pole.
  • Edmund Dudley.
  • Edward Stafford, 3rd Duke of Buckingham.
  • Elizabeth Barton. The Catholic Encyclopedia.
  • Elizabeth Barton. Encyclopedia Britannica.
  • Henry Howard, Earl of Surrey.
  • Henry VII. Tudor
  • Henry VIII. Historic Royal Palaces.
  • Kings of England. UK & Ireland Genealogy.
  • Saint John Fisher.
  • Sir Richard Empson.
  • Thomas Cromwell, earl of Essex.
  • Sir Thomas More.
  • The -mary.htm