Henry VIII’s Painter Hid Symbols In His Art – And One May Identify The King’s Fourth Wife

The guy responsible? You may have heard of him: a certain Hans Holbein. He’s widely considered to be one of history’s most accomplished portraitists. Henry VIII noticed that talent, too, and so he hired the German to be his court painter.

Holbein was obviously tasked with painting a portrait of the king himself. But aside from that, he was also asked to work on portraits of people close to the king. And it was one of these pieces – from 1540 – that captured Moyle’s professional attention centuries later.

Moyle is aware of Holbein’s unique techniques, so she knows that his work often says more than you’d see at a glance. In other words, his paintings sometimes contain hidden messages or signs. Everything he created was meticulous, and no detail was incidental. Yep, it all mattered and told a story.

With that in mind, Moyle couldn’t help but notice something about Holbein’s work from 1540. On the surface, the portrait depicts one of Henry’s wives, but the expert got the impression that there was more to the piece. So, she started to investigate. And what she found totally defies traditional wisdom.

Holbein had actually come from an artistic family. In fact, it was his father who had taught him to paint. And the German spent much of his adult life traveling around Europe for work. Eventually, that brought him into contact with a king.

And if you’ve seen any of Holbein’s most famous artworks, they’ll likely have been produced when he was living in England. He settled there permanently in 1532 and rose to become one of the country’s most prominent artists. Then he got his most important job yet.

Yep, at some point, Holbein became the official painter of the royal court. The record on precisely when this happened is a little patchy, but it’s thought to have occurred around 1536 or maybe a little earlier. In any case, that brought him into the realm of Henry VIII – sometimes a dangerous place to be.

Yes, we’re talking about that Henry VIII – the one with six wives and a bit of a bloodlust. Across 37 years, he sat on the English throne and had a profound and long-lasting impact on the country. It’s his personal life we most remember him for, though. And there’s a hint at this contained within the Holbein painting.

Henry was crowned king while he was only 17. Then, just over a month later, he tied the knot with Catherine of Aragon – the first of many wives to come. With her, the king had three boys and three girls, but only Mary would survive into adulthood. This spelled doom for Catherine.

Henry was frustrated that Catherine hadn’t given him a surviving heir, so his attention turned elsewhere. He sought permission from the Pope to divorce Catherine, but his request was denied. Ignoring the Catholic Church’s stance, Henry divorced her anyway and went on to found the Church of England. He then married his second wife Anne Boleyn in 1533. Yes, Holbein was coming into the middle of this right royal mess...

When Henry’s marriage failed to bring him a male heir, though, he tried to break it off. And yet again, it was curtains for his wife. He accused Anne of adultery and other crimes and received an annulment. These accusations against his wife were probably made up, but Anne was beheaded nonetheless.

Henry moved on pretty quickly, tying the knot for the third time mere days later. This latest marriage was to Jane Seymour, who actually did give birth to a male heir. Jane was the mother of the future king Edward VI, but she passed away weeks after the birth of her child. That tragedy may have left Henry shaken, but it’s not Jane who seems to be featured in that Holbein portrait.

Henry didn’t marry again for a couple of years after Jane’s death, but he was eventually advised to seek another wife. For political reasons, the king was pushed to tie the knot with one of two sisters from the German aristocracy. Then, after the royal was shown paintings of each woman, he chose to marry Anne of Cleves. The only issue? When the two finally met, the king angrily claimed that Anne was less attractive than in her portrait. Their marriage was annulled after just a few days – but it wouldn’t be the end of the connection between Henry and Anne.

Henry went on regardless, wedding a then-19-year-old Catherine Howard. But like Anne Boleyn before her, Catherine met a gruesome end after the marriage. The English monarch also accused her of adultery, and she was beheaded in 1542. Turns out Henry was a very hard man to please!

Finally, in 1543, Henry married the woman who would turn out to be the last of his six wives. Catherine Parr was arguably the most influential of all the king’s spouses, with some historians claiming that she altered the very culture of English royalty. She helped to repair broken relationships within the Tudor court and supported her husband during his war against France. It was a happy ending of a sort.

Henry passed away four years after his and Catherine’s wedding, and Catherine herself died a year after that. But although Henry’s turbulent reign as king came to its natural end, the man – and his six wives – still intrigue us today. He certainly intrigued Franny Moyle, anyway.

And Henry may have intrigued Holbein, too. As the official portraitist to the king, he created plenty of miniature versions of him in paint. Yep, small portraits were very popular during Henry and Holbein’s era. But why, exactly?

Well, these tiny works of art were small enough for people to carry around. This was an important feature at the time – particularly among members of the aristocracy, who were prone to having dramatic trysts and relationships. And thanks to Franny Moyle, one particular portrait miniature has captured historians’ attention.

The piece in question was created by Holbein back in 1540, and it’s a treasured work from one of history’s best portrait painters. And for a long time, we assumed that the miniature was presumed to depict Henry’s fifth wife Catherine Howard. Now, though, Moyle has put forward another theory.

Moyle argues that the woman depicted isn’t Catherine at all, but rather Henry’s fourth wife Anne of Cleves. It’s a gripping hypothesis for art historians. And the way Moyle came to this conclusion is even more interesting.

Holbein has a reputation for including hidden signs and symbols in his work. And while the untrained eye won’t spot them, they’re very revealing to an expert like Moyle. So, what was it about this piece from 1540 that jumped out at the art historian?

Well, the telling detail wasn’t actually a feature of the painting itself. Instead, it was all about the manner in which the work was displayed. Basically, the miniature was mounted to a playing card. And given Holbein’s reputation, Moyle couldn’t ignore the potential significance of this.

After all, another of Holbein’s portrait miniatures was also mounted on a playing card – one showing the ace of spades. This work depicted Thomas Cromwell, who was an important figure within Henry VIII’s court. And he had a reputation for speaking in blunt, plain terms. You could say that he was the type to “call a spade a spade,” as the famous expression goes.

Given Holbein’s love for a visual pun, then, it seems no accident that he decided to mount his depiction of Cromwell onto an ace of spades card. And Moyle has argued that the artist did something similar for the 1540 miniature once thought to depict Catherine Howard.

The 1540 piece was mounted to a card bearing the four of diamonds. And Moyle sees this as significant. Based on what she knows about Holbein, she thinks that the artist chose this specific card because his subject was Henry VIII’s fourth wife. She, of course, was Anne of Cleves – not Catherine Howard. But do we know this for sure?

Both Catherine and Anne married Henry in 1540 – the very year that this miniature was created by Holbein. That makes the two women equally as likely to be depicted in the artwork. And there are other details in the painting that make it difficult to decipher between the two ladies. That jewelry could belong to either one of them.

On the surface, the pendant in the artwork looks like something once owned by Jane Seymour – the third of Henry’s wives. But in May 2021 Moyle told The Observer, “When Henry got rid of one wife, he was in the habit of handing down their belongings to their successors.” Again, this could mean the woman in the miniature is either Catherine or Anne. So, how can Moyle be so sure that it’s Anne?

Well, there are details in the painting that support Moyle’s theory. For one thing, the woman in the miniature doesn’t appear to be terribly young. Catherine was still a teenager when she tied the knot with Henry, while Anne was an adult well into her twenties.

But perhaps Moyle’s most convincing argument comes from looking at another one of Holbein’s paintings. In 1539 he produced a portrait that unquestionably depicted Anne of Cleves, and Moyle thinks this depicts the very same person in the miniature. As she remarked to The Observer, “They’re the same woman. She has this soporific expression in both paintings.”

When Holbein captured Anne’s likeness for the original piece, the artist depicted his subject wearing clothes from Germany. Henry didn’t like this style, though, and generally found Anne to be unattractive. One person close to the king is supposed to have said, “He was not pleased with her in that German dress.”

So, Moyle believes that Anne would have wanted a new portrait to be produced. In this fresh artwork, she would dress in clothes that were more acceptable to English sensibilities at the time. Henry may then find her more attractive when he looked at the miniature and saw her wearing something more to his taste.

Moyle explained to The Observer, “So, I think there’s a good reason why, in early 1540 [Anne] – or Thomas Cromwell, perhaps, who was very pro the marriage – might suggest Holbein paint her again so that, in the little miniature that Henry had in his pocket, he could see a version of Anne that was more appealing.”

As Moyle understands it, either Anne or somebody else with an interest in her marriage tried to charm Henry. The thinking behind such a move, presumably, was to convince the king that the marriage was worthwhile. But they failed, as he was soon embarking on his next union with Catherine Howard.

If Moyle’s theory about the portrait miniature is right, though, why did people think it was Catherine Howard for so long? Well, one potential reason for the misunderstanding could be that nobody actually knows what Catherine looked like. No official portraits of her have ever conclusively been found.

Catherine was only married to Henry for a short period of time, so maybe she never had the opportunity to pose for a portrait. On the other hand, a picture may have once existed – only to be destroyed after Henry had Catherine executed.

The whole saga is just another messy, confusing footnote in the story of Henry and his royal court. It seems that everyone close to him was affected by the king’s conduct! Even Holbein didn’t escape without a little trouble of his own.

In a conversation with the Radio Times, Moyle argued that Holbein fell out of favor with Henry after the furor surrounding Anne’s initial portrait. Eventually, though, he managed to get back into the king’s good books. And for that, the artist could apparently thank his extraordinary talent.

Moyle said, “It takes about a year for his work to pick up again after that incident... Holbein gets off through a mixture of brilliance and charm. I can only suggest that it was because of his talent, and the king’s personal love of him, that the king didn’t want to lose him.”

Holbein ultimately produced a huge number of works for Henry, depicting the king along with members of his inner circle. And by the time he passed away in 1543, his legacy was assured – even if there’s a great deal of controversy surrounding that painting.

Holbein got off lightly, in fact. Henry had a habit of beheading people, after all! Falling out of favor with the king often meant death, and he wasn’t afraid to use that even against his wives if he had to. But whatever you think you know about Henry and his bloodlust, the truth is far more terrible.

By the time Henry died, his reputation was unenviable to say the least. And he’s gone down in history as one of the most ruthless and murderous of monarchs ever to sit on a throne. Henry's killing sprees included family members and close associates – sometimes of many years standing. Then there were the untold numbers of people who were put to death for resisting his religious reforms.

And many of the people who were executed at Henry's behest died anything but quick deaths. In 16th-century England, judicial punishment for things like heresy, witchcraft and treason were extraordinarily barbaric. Monks in particular were often subjected to brutal penalties if they disagreed with Henry’s religious reforms.

The king had broken with the Pope in Rome and declared his own supremacy over the English church. Though many of his people refused to accept this, and they were sorely persecuted for their dissent. For now, let’s consider some extreme examples of the many holy men who were barbarously treated for their beliefs.

Two monks from the Carthusian monastery in London – James Walworth and John Rochester – were condemned on false charges of treason. The court sentenced them to be hung in chains from the walls of York Castle. And they were left there until they died. Many other monks were hung, drawn and quartered or died in chains in filthy, disease-ridden dungeons. Yet the Roman church regarded many of these unfortunates – including Rochester and Walworth – as martyrs and sanctified them.

But it had not always been thus with Henry. The king was a mere youth of 17 when he ascended to the throne in 1509 after the death of his father: Henry VII. In fact, he had not expected to take on the role until his elder brother Arthur – who would have succeeded – died in 1502. The young Henry is said to have been an accomplished scholar and a keen sportsman and hunter.

When Henry was crowned he was a strapping youth – six feet tall and athletically built. He was also a talented musician and a keen follower of the arts. The people of England were happy to see this handsome young man ascend the throne and the early years of his reign were not marred by the terror and brutality he is now famous for. Yep, that was to come later.

But early in Henry’s reign, he displayed an example of the ruthlessness he was all too capable of. Just two days after the new king took the crown, he had two of his father’s principal ministers executed. He clearly planned to start his rule with a clean slate. But that grimness aside, there was something to celebrate: a royal wedding.

Six weeks into his reign, Henry married his brother Arthur’s widow: Catherine of Aragon. She was the daughter of the Spanish royal couple King Ferdinand II and Queen Isabella. Born in 1485 Catherine had married Arthur in 1501, the year before he died aged just 15. When her husband died, Catherine was betrothed to Henry – then still only a lad of ten.

In fact, it’s possible to trace much of the horror of Henry’s later reign to his marriage to Catherine. So what happened? Well, the central problem with the marriage was a common one among royalty during the Middle Ages. At all costs, the king had to have a male heir. He and Catherine did indeed have six children. But it was a time when infant mortality was a sad fact of life.

Sadly, almost all of Catherine’s pregnancies all ended in miscarriage or stillbirth. There was only one survivor – a daughter called Mary Tudor. By 1527 Catherine had now past the most likely years of bearing a healthy child, and Henry decided that he’d had enough. He wanted a divorce so that he could remarry and try afresh to produce a male heir.

Yet there were two major obstacles to Henry’s desire. These were his wife, of course, and the Pope in Rome – Clement VII. Divorce was forbidden by the laws of the Roman Catholic Church. It could only be allowed with a specific dispensation from Rome. And Pope Clement VII refused to grant this. Then there was Catherine, who also wouldn’t grant the king’s wish.

But how did Henry deal with the authority of the Roman Catholic Church? Cunningly, he declared that its writ did not extend to the Church of England. So he had no need of Clement’s permission to divorce. As for Catherine, Henry had his own way of dealing with her stubborn refusal to accept an annulment of their 25-year-long marriage. He made her a virtual prisoner at Kimbolton Castle in the county of Huntingdonshire. Sadly, she died there in 1536.

In 1533 Henry wedded his second wife – Anne Boleyn – in secret. After the marriage, he got the Archbishop of Canterbury to declare his union with Catherine over – thus legitimizing his status with Anne. Then, the king went even further. Now, with the support of Parliament, he declared himself head of the English church in place of the pope.

But many of Henry’s subjects were strongly opposed to this break with Rome. As we’ve seen, in particular many monks adamantly rejected this move. And opposition to the king’s will on this matter was a dangerous path to tread. It would, over the years, lead to a horrifying amount of bloodshed as Henry crushed anyone who set themselves in defiance of their monarch. He also dismantled the network of monasteries across England.

Just how opposed many English people were to Henry’s usurpation of the Roman Catholic Church became evident enough in 1536. That year saw an uprising in the north of England known as the Pilgrimage of Grace. Led by a Londoner called Robert Aske, as many as 40,000 people took up arms against their monarch.

And Henry’s response was entirely in character. He deputized the Duke of Norfolk to crush the rebels who had seized the northern city of York. Robert and his followers had demanded that England should revert to papal authority. Norfolk made some ambiguous promises and offered a comprehensive pardon. But it was a ruse which the rebels swallowed. They dispersed and Norfolk and his men were able to arrest and punish the most prominent of them.

All talk of pardons was now forgotten. Robert was hanged from chains – left to dangle from Clifford’s Tower at York Castle until he died. More than 200 other rebels were also apprehended and executed. Tragically, many suffered gruesome fates. One – Sir Nicholas Tempest – was hung, drawn and quartered, while his wife Margaret Stafford was burnt at the stake.

The harsh suppression of the Pilgrimage of Grace exposed Henry’s propensity for brutality. Although arguably, the prior fate of his second wife Anne Boleyn had been pretty good evidence of his ruthlessness. The queen had failed in her principal duty: to produce a male heir. So, in cahoots with his principal advisor Thomas Cromwell, Henry fabricated an extravagantly Baroque conspiracy.

Anne, it was alleged, had conducted affairs with no fewer than five different men. And one of those had been her own brother: George Boleyn, Viscount Rochford. Anne was committed to the Tower of London – tried and charged with a number of counts including adultery and incest. At her trial she vigorously denied the allegations, but the court found her guilty and Anne was subsequently beheaded by a French swordsman.

The five men who had allegedly had affairs with Anne – including her brother – soon fell victim to Henry’s revenge. But this is despite the fact that they were almost certainly innocent. Granted, one – a court musician called Mark Smeaton – admitted his guilt under torture. Though his fellow accused were not tortured as they were noblemen and all rejected the charge of adultery.

Yet their denial did them no good. Smeaton and the four other alleged lovers were publicly beheaded on London’s Tower Hill two days before Anne met her fate. She at least was spared the ordeal of a public death. So, to get out of the second marriage he no longer wanted, Henry ordered the beheading of six people who were almost certainly innocent of the crimes they were accused of.

Now freed of Anne Boleyn, Henry quickly married again – just 11 days after he’d had his second wife beheaded. His third wife was Jane Seymour, who had been a lady-in-waiting to both of his previous spouses. Jane gave birth to a son in 1537 called Edward, but she died less than two weeks later. It was a natural death brought on by childbirth complications, and Henry is said to have been genuinely grief-stricken. At least this was one wife whom he didn’t kill or imprison.

After a gap of almost three years, Henry moved on to his fourth wife: Anne of Cleves. She was French and apparently Henry was distinctly underwhelmed when she arrived in England for the wedding. It’s said that after meeting Anne, he called her the “Mare of Flanders.” Yep, this gratuitous insult doesn’t sound like a great start to a marriage.

Despite Henry’s blunt assessment of his new bride, the marriage went ahead in January 1540. But it wasn’t to last long. After six months Henry had obviously tired of Anne and divorced her. Perhaps surprisingly, Henry treated her generously – giving her a castle and the title of the “King’s Sister.” Though once again, it was time to find another wife.

Enter wife number five: Catherine Howard. In a familiar set-up, she had been one of Anne of Cleves’ attendants at court when Henry spotted her. Seldom a man to hang around, Henry married the woman less than three weeks after divorcing Anne in July 1540. The marriage seems to have gone well at first. But then Henry found out that Catherine had been far from a virgin when he married her.

Enraged, the king decided there was only one thing to be done: another beheading. Fourteen months after he’d married her, Catherine Howard’s head was lopped off at the Tower of London. It was now time for wife number six. She was the third Catherine he married – this time Catherine Parr. In fact, she lasted the rest of Henry’s life and even outlived him.

So we’ve seen that Henry was ruthless in suppressing religious dissent. He was quite capable of getting rid of troublesome wives by using what can only be described as judicial murder. But there were others who attracted the wrath of the merciless king. Yes, men who had been his closest advisors and confidantes could easily lose his favor. And the outcome was all too predictable if they did.

One such was Sir Thomas More, who for many years was a trusted aide to Henry. Yet the former got on the wrong side of his monarch by opposing the break with the Church of Rome and the divorce from Catherine of Aragon. Unwisely, he even went as far as to snub Henry by failing to attend the crowning of Catherine’s successor Anne Boleyn. The upshot was that Sir Thomas was convicted of treason and beheaded in 1535.

Thomas Cromwell went on to prove how difficult it was to be a close associate of Henry’s and yet hold on to your head. A lawyer, he served as the king’s principal minister and played a key part in helping Henry to get rid of Catherine of Aragon so that he could marry Anne Boleyn. But ultimately, that loyal service was not enough to save his neck.

We’ve heard how Henry was greatly displeased by his fourth wife Anne of Cleves, who he divorced after just six month of marriage. The king decided that the whole regrettable affair was actually Thomas’ fault. As sure as night follows day, Henry charged him with treason. His unfortunate minister was executed and his head was publicly displayed on a spike on London Bridge.

Another sure fire way to get yourself killed during Henry’s reign was to be branded as a heretic. This could involve allegations of witchcraft of any kind, and the penalties were severe. Heretics were either burned at the stake or hung, drawn and quartered. And one who suffered such a fate was Elizabeth Barton.

Elizabeth – who was known by various colorful nicknames including the “Mad Maid of Kent” – became a public figure because of her apparent talent for prophecy. For his part, Henry is said to have been impressed by her ability to peer into the future. But the king’s admiration only lasted as long as her soothsaying pleased him.

Henry’s attitude towards Elizabeth changed abruptly and fatally once she turned her attention to his divorce of Catherine of Aragon. In an extremely ill-judged move, Elizabeth prophesied that the king would die within months if he married Anne Boleyn. The 28-year-old was found guilty of conspiring to kill the king and was publicly hanged at Tyburn in 1534. Today, you can find the site of the Tyburn gallows near the west end of London’s main shopping drag: Oxford Street.

Another who was regarded as a troublesome woman was Anne Askew – who preached Protestant doctrine. Apparently an early rebel against male dominance, she was spirited enough to demand a divorce. That was enough to put her in the heretic category and Anne was arrested. She was later tortured in the Tower of London by being stretched on the rack.

The aim of the torture was to force Anne to reveal the identities of fellow Protestant dissidents. But despite two excruciating sessions on the rack, she resisted and gave no names. In 1546 Anne was burnt at the stake along with three male heretics. Somehow, friends had manage to smuggle bags of explosives to the condemned which they concealed in their clothes. And the explosion when the fires were lit beneath the four unfortunates brought a speedy end.

As we’ve seen, there was a variety of ways to find yourself at the wrong end of a rope, an axe or a pile of kindling during Henry VIII’s reign. If you were lucky, you were executed with a quick slash of an axe. But many were subjected to prolonged deaths involving being hung, drawn and quartered or suspended from castle walls in chains.

But just how many were executed during the 36 blood-soaked years that Henry occupied the English throne? It’s not an easy question to answer since accurate and complete records – if they ever existed – have not survived the passage of time. Though various historians have taken a stab at estimating the likely number of violent deaths that can be attributed to Henry.

One estimate puts the number executed at 57,000, though another claims the death toll was as high as 72,000. Approaching 500 years after the events, it’s always going to be difficult to come up with an entirely dependable number. But we can be sure that there were certainly tens of thousands who died brutal deaths at the whim of Henry.

The killing didn’t quite come to an end when Henry died in 1547 to be succeeded by his daughter Mary I, but it did abate. The new queen ended up with the nickname “Bloody Mary” because of the religious dissenters she executed – many of them burnt at the stake. She killed rather more than 300 during the five years she reigned. Scarcely commendable, but at least it was an improvement on her father’s record.