Get Out of Jail Free Cards: The Many Annulments of Henry VIII (Guest Post)

By Jillianne Hamilton

Everyone knows Henry VIII was unlucky in love. Not nearly as unlucky as many of his wives, of course, but Henry would certainly have considered himself the most unfortunate man in England when it came to his married life.

The excuses he used to get out of his marriage varied from wife to wife. But he and his advisors were able to come up with excuses that never put the king at fault. Ever.

His first marriage was the most complicated to end because of a few factors. Henry’s marriage to Catherine of Aragon, daughter to Fernando and Isabel of Spain, was permitted in the first place because of a special dispensation written up by Pope Julius II. Catherine had previously been married to Henry’s older brother, Prince Arthur, the young man everyone assumed would be the next king of England. However, fate intervened and he died of illness a few months into the marriage.

So what was the problem? The Bible states that if a man marries his brother’s widow, it is sinful, bordering on incest. The punishment of this union would be childless. Julius II, God’s spokesperson on earth at the time, said it was fine so Catherine’s marriage to the newly created King Henry went on as planned. However, after years of unsuccessful pregnancies, no male heir showed up and Henry decided Julius had been wrong to allow the marriage to go further. God was not pleased with his choice of wife and this was his punishment.

After years of fighting with papal delegates sent from Rome, and with the new pope, Clement VII, Henry took matters into his own hands and cut ties with the traditional Catholic Church, making himself Supreme Head of the Church of England. Finally, with this move, Henry’s marriage to Catherine was decreed to be invalid and his marriage to his second wife was named valid.

Of course, we all know his second wife, Anne Boleyn, was not meant long for this world. Henry, once again, had his marriage dissolved quickly and easily. Days before Anne’s sad end, her marriage to the king was ended but the reason for it was not given on official court documents but it was likely because of Anne’s pre-contract to Henry Percy or because of the king’s relationship with Mary, Anne’s older sister.

The pope had previously given a dispensation stating that Henry could marry Anne (once Catherine had passed away, of course), even though Henry admitted to having a sexual relationship with Anne’s sister. It was basically the exact same situation as Catherine and Arthur except there was no marriage. Again, it was probably decided the pope was wrong to give that dispensation in the first place. Again, God was displeased with his marriage and was punishing him by not giving him a son. Again, the marriage wasn’t ended by divorce, it was annulled. It was like it had never happened. Again, Henry was free to take another wife.

New reasons for dissolving marriages came into play for Henry’s fourth wife, Anne of Cleves. Henry and Anne slept in the same bed at least a few times but never had sex. Henry tried, but it just didn’t happen. Again, Henry and his advisors found ways out of the marriage without calling into question Henry’s manhood. The marriage was eventually ended on the grounds of non-consummation (because Henry found Anne so unattractive) and pre-contract. Anne had previously been betrothed to Francis, the son and heir of the Duke of Lorraine back in Germany. However, the pre-contract had ended years before Anne’s arrival in England.

The annulment of Henry’s union to Anne of Cleves as not the last time pre-contract would be used as a way of saying a marriage had never happened because it wasn’t legal. During the catastrophic downfall of Katheryn Howard, Henry’s fifth wife, whispers and rumors about the young, vivacious queen reached the ears of Archbishop Cranmer. Cranmer investigated these rumors and interviewed Francis Dereham, a former lover of Katheryn’s. Dereham claimed they had agreed to marry but there is little evidence that suggests Katheryn made such an agreement. Still, pre-contract was once again used to annul the marriage, soon before Katheryn was sent to the executioner’s block.

However, if she really was pre-contracted to Dereham, then Katheryn hadn’t actually been unfaithful to the king with Thomas Culpepper. She’d been unfaithful to Dereham. But reason and logic weren’t really part of the equation at that point, as Henry was so heartbroken and angry, he considered ending Katheryn’s life by his own hand.

Getting rid of wives became infinitely easier for Henry once he named himself Supreme Head of the Church even though many of his excuses weren’t religion based at all. If pre-contract, non-consummation and Bible passages weren’t available excuses, I’m sure Henry’s advisors would have come up with other ways of getting Henry out of his unfortunate situation.

Jillianne Hamilton is the author of The Lazy Historian’s Guide to the Wives of Henry VIII, now available on paperback and ebook. Check out her blog, The Lazy Historian, for more information.

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The Differences in the Wives of Henry VIII

Raised as the second son, or “spare”, Henry Tudor, Duke of York was never intended to be King of England. When his older brother Arthur, Prince of Wales died unexpectedly in 1502 Henry was thrust into the spotlight as heir to the throne of England. His training began immediately and Henry despised the fact that his father controlled everything around him. He went from being raised with his sisters to being separated from the world.

When there were discussions by Henry VII and the parents of Katherine of Aragon to arrange a marriage between Henry and his widowed sister-in-law Henry appeared excited to marry his deceased brother’s wife. She was a beauty afterall and Henry was used to getting what he wanted.



Prior to the death of Henry VII the king had decided against the marriage of his son with the dowager Princess of Wales after a dispute with her parents over the dowry she was to bring to her marriage to the now deceased Arthur. Henry would not marry Katherine  of Aragon after all.

Things changed when King Henry VII died in 1509 and his son Henry was declared King Henry VIII. The new king declared he was to marry Katherine and the couple were jointly crowned. Katherine was as happy to marry Henry as he was to marry her. She was raised to be queen and had expected for many years to be Queen of England.

When we look at the following wives of Henry VIII things look a little differently – many had never expected to be queen or had a true desire to marry the king from the start. Anne Boleyn and Kateryn Parr had both realized that Henry wished to marry them and there was nothing they could do about it – you couldn’t say no to the king.

Here is a fun look at the six queens of Henry VIII and their differences. I don’t usually write pieces like this so I hope you enjoy the humor in the titles.

katherine of aragon – raised to be a queen

Katherine of Aragon was the Spanish infanta, daughter of the Catholic Monarchs, Ferdinand II of Aragon and Isabella I of Castile.  She was raised to be a queen consort. To know her role as a woman, be the most pious queen and show her bravery.

Blamed for not providing her husband with a surviving son, Katherine would give birth (or miscarry) several babies but only their daughter Mary survived to adulthood.

Katherine of Aragon, NPG

When Katherine realized her husband, the king, was interested in Anne Boleyn she did not believe their relationship was serious. She had faith and confidence in the fact that Henry would come back to her. When he didn’t she fought with all her mother’s grace to against divorce proceedings.

Henry and Katherine’s daughter Princess Mary was the king’s ‘Pearl of the Realm’. Mary unfortunately suffered the consequences by taking the same stance as her mother. They would not surrender.

Katherine of Aragon would go on to carry the love of her supporters with her. She spent time praying for a better outcome to her cause. Around every corner Katherine’s end would draw near. She died, nearly alone, in January 1536 at Kimboltan Castle. Henry was free of his first wife for good and Anne Boleyn was without a doubt his queen.

After her death their daughter Mary was declared a bastard and removed from the line of succession for many years.

anne boleyn – reluctant, triumphant and ill-fated

Anne Boleyn was the English born daughter of Sir Thomas Boleyn and Elizabeth Howard. Anne grew up at Hever Castle with her older sister Mary and younger brother George.

Anne was not raised to be queen – but she had a great upbringing being educated at the court of Margaret of Austria in Mechelen, learning to speak French fluently among many other skills.

Through Elizabeth Howard Anne came from the powerful noble Howard family led by the Duke of Norfolk. Her father Thomas Boleyn climbed up in the ranks within the inner circle of Henry VIII; Her brother George became Lord Rochford and the Boleyns prospered during Anne’s reign.

Anne Boleyn



Anne Boleyn believed she would give the king the strong son he so desired. In 1533 she gave birth to Princess Elizabeth (future Elizabeth I), but the king believed boys would follow. Unfortunately they would not survive.

Henry VIII eventually tired of Anne Boleyn, he had learned from his divorce with Katherine and made sure this time things would go much smoother and quicker for him. Anne Boleyn, like Katherine of Aragon, had a daughter whose rights were at risk during the downfall of her mother. Anne, like Katherine, did everything she could to fight for her daughter’s rights.

Anne Boleyn was executed on the 19th of May 1536. Her daughter Elizabeth was declared a bastard and removed from the line of succession for many years.

jane seymour – silent but deadly

Jane Seymour, like her predecessor, Anne Boleyn, was English. She was born to Sir John Seymour and Margery Wentworth and most likely grew up at Wolf Hall with her siblings: Edward, Henry, Thomas, Elizabeth and Dorothy. The Seymours were not considered royalty but they were what could be considered of noble birth. They had been around for generations.

Jane Seymour caught the eye of King Henry VIII while serving in the household of Queen Anne Boleyn. It is believed that Henry was attracted to Jane because she was the complete opposite of Anne. Jane also knew well how to play the game with Henry – telling him she could not be his mistress, for her own honor.

Jane Seymour

Ten days after the execution of Anne Boleyn, Jane became the third queen consort of Henry VIII. We don’t know what feelings, if any, Jane had for Henry but what we do know is that she finally presented the king with the surviving male heir he so desperately wanted.

Jane Seymour died twelve days after the long delivery of her son Edward on the 24th of October 1537.

anne of cleves – naive

Anne of Cleves was the daughter of John III, Duke of Cleves and Maria of Jülich-Berg.

After Henry VIII’s marriage to Katherine of Aragon, which was his choice yet still a political match, he moved to Anne Boleyn, who was a love match, followed by Jane Seymour who was also a love match. When it came time to find a fourth queen it became imperative once again to marry for political reasons – this is why Anne of Cleves became a candidate and eventually wife of the King of England.

Anne of Cleves



Unfortunately the marriage alliance would not be a success for Henry. The king did not wish to marry Anne, he was upset for multiple reasons but most believe it’s because she did not recognize him when he was in disguise to greet her at Dover. This bruised the overweight king’s ego and he began to say things like, “I like her not!” and by saying such blasphemous things like her breasts were loose and she was no virgin.

Anne and Henry were only married for six months but Anne had learned from Henry’s prior relationships. When the time came she willfully accepted his offer of annulment/divorce and became the “king’s sister”. Anne outlived Henry VIII and all of his wives, including his last, Katherine Parr.

katheryn howard – outgoing and provocative

Katheryn Howard was the daughter of Edmund Howard and Joyce Culpeper – Edmund Howard was the son of Thomas Howard, 2nd Duke of Norfolk and younger brother of Thomas Howard, 3rd Duke of Norfolk. In a nutshell, Katheryn Howard came from the prestigious Howard family. Unfortunately, not long after the death of her mother (at about age five) Katheryn was sent to live with her step-grandmother the dowager Duchess of Norfolk, Agnes Tilney. Tilney had many wards under her roof but also seen often at court. With the dowager duchess being away at court so often it appears that she had little direct involvement in the upbringing and education of her wards.

On the 28th of July 1540, Katheryn Howard became Henry VIII’s fifth queen consort during a secret ceremony at Oatlands Palace. Their nuptials were kept secret for ten days before returning to the insanity of court life. The king, who was infatuated with his new bride, wanted to spend quality time alone with her before returning to his courtly duties.

Katherine Howard

In Katheryn, Henry found what represented the qualities that he admired most in a woman: Beauty, charm, a pleasant disposition, obedience and virtue. All of which were much like his mother, Elizabeth of York…unfortunately Katheryn Howard was not the virtuous wife Henry had hoped for.

Katheryn Howard’s “loose” past with the dowager duchess and with her poor decision making while queen, particularly when it came to Dereham and Culpeper, ultimately led to her downfall.

On 10 February 1542 Queen Katheryn Howard entered the Tower and three days later she was executed.

kateryn parr – the perfect queen

Kateryn Parr was born in 1512 to Sir Thomas Parr and Maud Green.

Kateryn is usually seen as the Queen who came from nowhere, a nobody. Actually, Katherine was the daughter of a substantial northern knightly family who – like the Boleyn’s – had gone up in the world due to royal favor and advantageous marriages. According to David Starkey, Katherine was most likely better educated than Anne Boleyn and her lineage was better than the Boleyns. –TudorQueen6.com

Henry VIII set his eyes on Kateryn Parr while she was in the household of his daughter, Lady Mary. Around the same time Kateryn had become a widow after the death of her second husband, Lord Latimer. Kateryn and Thomas Seymour had fallen in love and were hoping to marry when Henry swooped in and proposed to her. She could not refuse the King and believed it was God’s doing for her to become queen consort.

Katherine Parr

Kateryn married Henry VIII on the 12th July 1543, at Hampton Court Palace. She had never imagined being queen – Henry was her third husband.

Kateryn was exactly what Henry VIII needed. She was great with his children and knew much better than previous wives (for the most part) when to speak and when not to.

Kateryn did not marry for love with her first three marriages, but she did find love in the children of her husbands – Katherine was a marvelous step-mother.

It wasn’t until she married Thomas Seymour that she finally found love and was blessed with a daughter, Mary Seymour.

Kateryn Parr died on the 5th of September 1548, only days after giving birth to her daughter, Mary.

Here is my podcast on the same subject:

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