Episode 257 was all about the six women who *could* have been the Queen of England as Henry’s wife, but escaped: Henry’s Six Almost Wives
Below the episode you’ll find a transcript for easy reading.
Hello, friend, and welcome to the Renaissance English History Podcast, a part of the Agora Podcast Network and the original Tudor History Podcast, telling stories of Tudor England since 2009. I am your host, Heather, and I’m a storyteller who makes history accessible because I believe it’s a pathway to understanding who we are, our place in the universe, and being more deeply in touch with our own humanity.
This is episode 257. And we are going to talk about the almost wives of Henry VIII. Everybody knows the six wives, right? Divorce, beheaded, died, divorce, beheaded, survived. Actually, I just put a really cool new t shirt up on my merch shop at TudorFair. com that has that divorce, beheaded, died, divorced, beheaded, survived thing.
Super cool. I ordered one for myself. Super excited to wear it. Anyway, I digress. But we remember the wives. But there were also at least six almost wives who you could say got lucky and escaped marriage to Henry. So, we are going to talk about them today. These almost wives also all tell us something new about Henry, his ambitions, his shifting priorities, and his evolving view of marriage as he grew older and more frustrated in his attempts to secure an heir.
So, we’re going to talk about six women who Henry seriously considered marrying but didn’t. We’re going to talk about Eleanor of Austria, the diplomatic powerhouse who could have replaced Katherine of Aragon. Maria of Guise, a towering presence in every sense of the word. Christina of Denmark, famous for a quip that stung Henry’s ego.
Anna of Lorraine, whose fate was tied up with the Dutch Revolt, Amelia of Cleves, sister of Henry’s fourth wife, and Katherine Willoughby, who might have been Henry’s last queen had fate and death not intervened. So let’s get right into it.
Eleanor of Austria
We’re going to start with Eleanor of Austria, and we’re going to talk about this in relation to Henry VII’s vision, and Eleanor’s suitability. So, Eleanor of Austria was born into the powerful Habsburg family. She was a highly sought-after bride in Europe. She was the daughter of Philip the Handsome and Juana of Castile, and the sister of Charles V, Holy Roman Emperor, and she was a key figure in all of these shifting alliances.
So just a side note, because she was the daughter of Juana of Castile, she was also then Katherine of Aragon‘s niece. Juana of Castile was Katherine of Aragon’s sister. So from an early age, Eleanor’s marriage prospects were considered important to secure political alliances for her family. Henry VII, always eager to secure powerful alliances for England, began considering Eleanor as a potential bride for his son, Henry, around 1506.
The timing was critical. In 1506, Eleanor’s father, Philip the Handsome, and mother, Juana, had been forced to seek shelter in England after their ship was caught in a storm while en route to Castile. We actually, I did a video on this on my YouTube channel a couple of weeks ago, this shipwreck that kind of changed history and especially how Katherine of Aragon felt about it.
Of course, she was in that weird limbo period in her life at that point after Arthur had died, where she was running out of money, she was a widow, things were hard for her, and here is her sister shipwrecked. On the way to Castile, and they spent some time together, but they were also kept apart because Henry VII didn’t really want Katherine telling Juana how kind of not well she was being treated, among some other things.
So you can check out that video of the shipwreck of Juana and her husband Philip the Handsome. Anyway, it was during this stay at the English court that negotiations for a possible marriage alliance were discussed, though nothing was finalized. Henry VII saw Eleanor as a valuable match because of her strong connections to the Holy Roman Empire and her substantial dowry.
He had grown disillusioned with the marriage arrangement between Henry and Katherine of Aragon, especially after the death of his older son, Arthur. Which, left Katherine as a widow in England. Henry’s frustration with Spain’s dowry payments and the shifting political landscape made the Habsburg connection much more appealing to Henry.
So marrying Henry, future Henry VIII, to Eleanor would bolster England’s standing in European politics and solidify a vital alliance against France. The potential marriage to Eleanor came at a time when Henry was actively looking for these new alliances. So Henry began pushing for Eleanor as the future Queen of England.
He even suggested a broader marriage alliance that would include his daughter Mary Tudor marrying Charles V, Eleanor’s brother. The idea was that this dual marriage would create a strong alliance between England and the Habsburgs. Strategically positioning England between the Holy Roman Empire and France.
The negotiations for the marriage progressed far enough that by 1507, serious discussions about Eleanor’s dowry and the terms of the alliance were actually taking place. However, these talks ultimately faltered. Henry’s health was deteriorating by this time and his ability to finalize negotiations was hindered both by his declining influence over his son and the complexities of dealing with the Habsburg family.
Despite his father’s diplomatic maneuvering, the future Henry VIII, Prince Henry, who had turned 18 in 1509, was not interested in Eleanor. He said he had been enchanted by Katherine of Aragon since her arrival in England years earlier, and the idea of marrying a woman he had never met, especially one not known for her beauty, did not appeal to him.
When Henry VII died in April 1509, all of his careful plans for Eleanor unraveled. The new king married Katherine of Aragon just two months later, on June 11th, officially ending any further negotiations with Eleanor’s family. Eleanor’s story continued on the stage of European politics, though. In 1518, she married King Manuel I of Portugal, only to be widowed soon after.
She then, interestingly, later married Henry’s great rival, Francis I of France, further cementing her role in Habsburg diplomacy. Although she never became the Queen of England, Eleanor remained a significant figure in the power dynamics of Europe throughout her life. So there is Eleanor of Austria, who slipped away very fortunately and avoided marriage with the young Henry VIII. But she would, of course, go on to be the Queen of Portugal and France, so all’s good.
Mary of Guise
Next we’re going to talk about Mary of Guise. She was known then as the widow of James V, the mother of Mary, Queen of Scots, and a staunch ally of Scotland. She was born in 1515. She was a noblewoman of considerable political and personal stature. She was the daughter of Claude, Duke of Guise, and a member of the very powerful Guise family of Lorraine, so she was a prime candidate for a dynastic marriage. By the mid 1530s, she had already made an impression on the European courts.
She married James V of Scotland after he personally wrote a letter to her pleading for her hand in marriage. She married him in 1538. But the marriage did not last long, she became a widow in 1542, and then she was also the mother of the infant Mary, Queen of Scots.
So Henry VIII’s interest in Mary of Guise came shortly after the death of his third wife, Jane Seymour. By this point in his reign, Henry was in search of a new wife, but the political climate of Europe was tense. He was particularly concerned with consolidating his influence in Scotland, and marrying Mary, a tall and commanding woman known for her intelligence and Catholic faith, offered the possibility of strengthening his hold over Scottish affairs.
Of course, France and Scotland had always been linked with that old alliance, so having a French wife, might help with that. So now at this point Mary was already being courted by James V of Scotland, so there was a rivalry too, which probably made her much more attractive to Henry. Then, if she had just been totally available, of course having someone else interested in her would have greatly raised her stock, I’m sure.
Henry’s proposal to marry Mary of Guise came during the period between 1537 and 1538. He was navigating this aftermath of Jane Seymour’s death and figuring out his next marital move. At this point, James V had also lost his first wife, Madeleine of France, and he was in search of a new queen. Henry saw this as an opportunity not only to secure a powerful match with Mary but also thwart James’ plans.
Politically, marrying Mary of Guise would have aligned Henry with one of the more powerful families in Europe, the House of Guise. And it also would have helped him thwart the old alliance between France and Scotland. So Henry dispatched ambassadors to begin negotiations, eager to solidify the connection.
Mary’s reputation as a devout Catholic and an intelligent, formidable woman was appealing, but Henry’s interest likely had more to do with the political advantage he saw in marrying her. Mary, though, had her own ambitions. Although Henry’s proposal seemed promising, she was already leaning towards a marriage with James V.
By 1538, it was clear that Henry’s bid to marry Mary of Guise had failed. She had married James V of Scotland in June of that year, so she was now the Queen of Scots, and the marriage solidified her role as a central figure in Scottish politics, especially after James’s death when she became regent for her daughter, Mary, Queen of Scots.
For Henry, this failed match signaled a missed opportunity to weaken the old alliance and left him with less influence in Scottish affairs. Mary’s rejection underscored the continuing division between Scotland, England, and France, ensuring that these rivalries would persist long after Henry’s reign.
Christina of Denmark
Next, we are going to talk about Christina of Denmark. She was the Duchess of Milan and the niece of Charles V. She was born in 1521, a key figure in the political landscape of Europe, particularly after becoming a widow at the age of 16. Her brief marriage to Francesco II Sforza, Duke of Milan, had ended with his death in 1535, leaving Christina in a vulnerable but strategically important position.
She was the niece of the Holy Roman Emperor Charles V, she was highly sought after for her dynastic connections, and Henry VIII. This is the period where again he was widowed after Jane Seymour’s death, and took notice of her as a potential fourth wife. By 1538, Henry was in active pursuit of a new bride to solidify his position and secure a spare to his heir that he had.
Mary and Christina would have brought him closer to Charles V, potentially mending the strained relationship between England and the Holy Roman Empire after Henry’s break with Rome. So Henry’s ambassadors were dispatched to negotiate a match, potentially with Christina. Her youth and beauty made her an appealing choice.
Hans Holbein was sent to Brussels to paint a portrait of Christina, capturing her charm and her elegance. For Henry, the match represented not just personal appeal but also significant political advantages. Of course, aligning with Charles V would bolster England’s standing against France and provide a very important Catholic ally in Europe.
There was all this tension after the formation of the Church of England, so this union would have helped in diplomatic efforts to ease the isolation that England was beginning to experience. Christina was still under the control of her uncle, Charles. And she had little to say in her marital prospects.
Despite this, she made it clear that she was not eager to marry Henry, a man with a growing reputation for difficult and deadly marriages. Christina’s sharp wit came to the forefront when she learned of Henry’s proposal. In one of the most memorable remarks of the period, she reportedly said, If I had two heads, one should be at the King of England’s disposal.
This quip reflected, of course, her reluctance to become the next in line to Henry’s throne. For by then, Henry had been married three times, his first wife, Katherine of Aragon, had been divorced, his second wife had been executed, and his third wife had died in childbirth. It was not a good track record.
It’s likely that Christina, though young, was acutely aware of the risks that came with being married to Henry VIII. Christina’s comment struck a chord and further cemented Henry’s already infamous reputation across the European courts. Ultimately, the proposed marriage between Henry and Christina never came to fruition.
Charles V was reluctant to tie his family to the increasingly unpredictable English king, the religious differences between England and the Holy Roman Empire were too great, and Charles, always thinking of the broader European political landscape, chose not to support the match. By 1539, the negotiations had officially ended and Henry’s pursuit of a bride shifted elsewhere.
Christina went on to marry Francis, the Duke of Lorraine, in 1541, further cementing her place in European politics but far away from the very, very dangerous throne of England. Next we are going to talk about Amelia of Cleves. Sometimes, her name is spelled Amalia, sometimes it’s Amelia. I’m going to say Amelia in this podcast, but just be aware that it’s also spelled Amalia.
Anyway, however you want to say it, she was born in 1517. She was the younger sister of Anne of Cleves. Both sisters were considered as potential brides for Henry in 1539. Now, at the time, Cromwell, Thomas Cromwell, Henry’s chief minister, sought to strengthen England’s alliances with Protestant powers in Europe.
to counterbalance the growing threats from Catholic France and the Holy Roman Empire. The Duchy of Cleves, strategically located in the Rhineland, was an attractive ally for England, and Cromwell saw marriage as a way to cement this alliance. During the initial marriage negotiations, both Anne and Amelia were considered, as it was practice for royal courts to assess the eligibility of multiple daughters from prominent families.
Hans Holbein was dispatched to paint portraits of the sisters, And it was actually Anne’s portrait that ultimately convinced Henry to choose her. However, Amelia was kept in consideration as a possible alternative should the match with Anne not go forward smoothly. Although Anne was the first choice, Amelia was a possible backup candidate.
And Cromwell likely saw her as that in case Anne didn’t meet Henry’s expectations. There was always the possibility that if Anne displeased the king upon meeting her, Amelia could be proposed as a replacement. Keep in mind, this would be the first marriage that Henry was going to have where he hadn’t met his wife before, which was really unusual for kings at the time.
Most of the time, you know, in these kind of dynastic marriages, international marriages, you wouldn’t meet beforehand. Katherine of Aragon didn’t meet Arthur beforehand. But, of course, Henry had known Katherine when he was young. Then he went right to Anne Boleyn, who he knew before, then he went right to Jane Seymour.
So he was pretty unusual in that, that on his fourth marriage, it wasn’t until his fourth marriage that he was marrying somebody that he had never met, and he actually was quite nervous about that. So Cromwell kind of kept Amelia in his back pocket in case things didn’t work out with Anne. The marriage negotiations with Cleaves were crucial for Cromwell’s diplomatic strategy, and having another option in the same family would ensure that the alliance could be secured.
However, when Henry finally met Anne in person, he was so disappointed that the idea of Emilia as a fallback became increasingly untenable. His deep dissatisfaction with Anne, whom, of course, he said he found unattractive, tainted his view of the entire Cleves family. Even though Amelia had been considered as a viable option before the marriage, Henry’s experience with Anne soured any chance of pursuing her younger sister.
The possibility of marrying Amelia never moved beyond these early considerations. Henry was not interested in any kind of further negotiations with the Cleves family, and once the marriage to Anne was annulled, he turned his attention to Catherine Howard right away. Amelia never married and lived out her life in relative obscurity compared to her sister.
The Cleves alliance, which had been Cromwell’s grand strategy for strengthening Protestant ties, collapsed with the failure of the marriage. And for Henry, the episode marked the end of his attempts to forge a politically motivated marriage without personal involvement. Now, after the Cleves debacle, there was Anna of Lorraine, another Habsburg match that was considered.
One of the names, after the short lived marriage to Anne of Cleves fell apart, one of the people that was considered was Anna of Lorraine, a member of a prominent European family with deep political connections. She was born in 1522. She was the daughter of Antoine the Duke of Lorraine and Rene of Bourbon Montpensier.
I’m sure I butchered that. Very sorry. Her family had strong ties to both the French and the Habsburg courts, making her an appealing candidate for another foreign alliance. An interesting historical connection further tied Anna’s family to Henry VIII. Her father Antoine, Duke of Lorraine, had once been promised to Mary Tudor, Henry’s younger sister, as a bride by Francis I of France.
Remember, Mary Tudor had gone over. To marry Louis XII in 1515. Louis XII died very soon after that and was succeeded by Francis I, who actually said that Mary should marry, Mary should marry, that’s a lot of Marys, um, said that Mary Tudor should marry Antoine the Duke of Lorraine. But Mary had defied expectations and married Charles Brandon, Duke of Suffolk, instead.
Despite this missed connection though, Anna of Lorraine was suggested to Henry as a potential bride. The failure of Henry’s marriage to Anne of Cleves had left him deeply wary of foreign matches, especially those brokered based on portraiture. Hans Holbein had painted Anne of Cleves in a flattering light, and Henry agreed to marry her based on that portrait, only to be disappointed when he met her in person.
Despite this, Holbein continued to paint other prospective brides, including Anna of Lorraine, who was regarded as politically viable. Now that is one reason why I don’t think the portrait of Anne of Cleves is actually that far off. Because, I mean, we all know Henry, right? Would Henry have really kept Hans Holbein employed, going around painting portraits, painting his own portrait, if the painting of Anne of Cleves was really that far off?
I don’t think he would have. Now this is totally getting sidetracked, but one thing that I have seen about Anne of Cleves is there’s another famous portrait of her that shows her from the side. And in that portrait from the side, she has a much more, shall we say, striking nose than the famous portrait that Holbein had painted.
And that portrait, of course, is just straight on, full face, just looking right at the, the viewer. So, a lot of historians think, and it makes sense. That maybe Holbein did that to make, maybe she had a big nose, right? Maybe that’s what it was. And he painted her. in that position, uh, in that pose to kind of downplay the schnoz.
Um, that’s just one thing I’ve heard. And when you look at that other portrait of her from the side, you can see that. But I don’t think that Hans Holbein was that far off because I don’t think Henry would have kept, kept, uh, using him for portraits if he really had thought it was that different. Anyway, I got sidetracked.
Anna of Lorraine. She was considered, but Henry was a little bit nervous about it, and he was also at that point beginning to focus on a different kind of bride, someone much younger and much closer to home, like, I don’t know, Catherine Howard. Henry’s growing distrust of foreign marriages Particularly, after the Anne of Cleves disaster led him to abandon the pursuit of Anna.
Now Anna went on to marry William Prince of Orange in 1542, and her marriage became significant during the Dutch Revolt. Her life took a different direction away from the English court and its turbulent monarch. For Henry, his repeated failures in foreign matches, coupled with his volatile personal preferences, shall we say, steered him away from the idea of another arranged political marriage with someone he had never met.
Speaking of brides close to home, Katherine Willoughby. A couple, maybe about 10 years ago, a book came out called, it was a biography of Katherine Willoughby and it was subtitled something like, Henry’s Potential Seventh Wife. And you know, there was all this news that broke that Henry was thinking about marrying Katherine Willoughby had he succeeded in executing Catherine Parr, I suppose.
We’ve talked a lot about Katherine Willoughby, but we’ll just talk a little bit more about her here and then talk about the potential marriage. So, she, of course, is one of the most intriguing women in Henry’s court. She was the daughter of William Willoughby, the 11th Baron Willoughby d’Aresby, and Maria de Salinas, who was Katherine of Aragon’s very dear and close friend.
Katherine’s early life was marked by her high status, her connections at court, but her position was further elevated when she married Charles Brandon, Duke of Suffolk, in 1533. So Brandon, of course, was Henry’s BFF. They had a bromance. And he was over 30 years older than Katherine, so there was that. But, despite her youth, Katherine Willoughby quickly became a favorite in Henry’s court.
She was known for her intelligence, her sharp wit, and her strong Protestant leanings. One of the most wonderful little snippets about her is that she had a dog named Gardner after, named after Stephen Gardner, and she used to like to call her Dog Gardner to heal. And, uh, got a kick out of that, so I like that sense of humor.
I approve. Anyway, by the time of Brandon’s death in 1545, Katherine was a widow. She was still quite young. She was wealthy and influential. Her staunch support of the Protestant cause and her presence in the royal court kept her in close proximity to Catherine Parr and to Henry as this final marriage to Catherine Parr unfolded.
So there’s a lot of speculation that Katherine Willoughby might have become Henry’s seventh wife had he outlived Catherine Parr. Of course, implied in that is the idea that the arrest for Catherine Parr would have gone through and she would have been executed for heresy. Katherine Willoughby was a young wealthy widow with strong Protestant ties.
She was seen by some as an ideal match for Henry in his later years. She had already been a close companion to Catherine Parr, and her deep involvement in court politics combined with her Protestant sympathies made her a potential contender for the role of Queen. Now the people who were pushing this were the reformers.
This was a period in Henry’s life where he was going back to Catholicism. You know, he waffled during, uh, the Reformation Month episodes that we did six, seven years ago. I talked a lot about how in that later period of Henry’s reforming the church, he went back and forth. The conservatives gained and then the reformers gained.
So this was a period where Henry’s pendulum was swinging much more towards the conservatives. And the Protestants, the Reformers, wanted to swing it back towards reform. Now Catherine also was very close friends with Henry’s children, especially Princess Elizabeth, with whom she shared her Protestant beliefs.
Now there was also the idea that Katherine Willoughby had already had children. Um, she had already had two sons by Charles Brandon that would survive to adulthood. And so Henry, who was still in his older age thinking about another heir. was still thinking about that, he would have been attracted to the idea that he, he could tell that Katherine Willoughby could have children.
But of course, Henry’s death in 1547 ended any chance of Katherine Willoughby becoming his queen. After his passing, Katherine remained deeply involved in the Protestant cause during the reign of Edward VI, where she used her influence to promote religious reform. Her support for Protestantism placed her in a very dangerous position when Mary I came to power, She fled to the continent where she remained in exile until Elizabeth ascended to the throne.
She also unfortunately lost both of her sons within hours of each other, uh, due to the sweating sickness. So that was quite tragic. And then she married later, for love, one of her servants, who was also a Protestant. So, yeah. Her story had a lot of ups and downs in it, but fortunately for her, she escaped marriage to Henry the Ape.
So there you go, six different women, six different stories of why they could have become queen, of what Henry’s priorities were, why they were even considered, and six different happy outcomes for those poor women. 20 25 minutes with me. Remember, you can always hop into the Tudor Learning Circle, which is a social media just for Tudor nerds, TudorLearningCircle.
com, and post your thoughts on these six women or anything else related to Tudor history. We’d love to see you in there. It’s totally free and especially right now as you go on to social media, there’s so much ugliness. We don’t do that in the Tudor Learning Circle. It’s just all Tudors all the time, the nicest, most Tudorific place on the internet.
You can also always drop me a line. You can text me 801 6-TEYSKO. That’s 801 683 9756 is my texting line. So go ahead and drop me a note if you like. Alright friend, thank you again so much for listening. I will be back next week. Have a phantasmal week. I will speak with you soon. Bye bye.
Heather Teysko is the creator, writer, and producer of The Renaissance English History Podcast, the original Tudor history podcast, started in 2009. She's been writing about history online for over 25 years, since her first site on Colonial American history became number one in history on Yahoo in 1998. In 2019 she created Tudorcon, which is now a yearly event, in addition to writing books, and running TudorFair.com - a whimsical Tudor Merch shop.
She has been passionate about Tudor England since she first read Alison Weir's The Six Wives of Henry VIII 30 years ago, and subsequently moved to London after college to spend her time immersed in Tudor history (how exciting when she got to interview Alison for the first time!). In addition to history, she is passionate about travel, and has lived in 3 countries and 4 states (not counting her perpetual state of confusion), and her family (who help her host her YouTube channel occasionally).
