Henry VII: Search For a New Queen

Death of a Queen Consort

After the death of his wife and queen consort (Elizabeth of York), Henry VII grieved for a long period of time. Unlike numerous monarchs before him Henry appears to have loved his wife deeply. The two had grown very fond of each other over their marriage, and had experienced extreme loss together with the death of multiple children. But their relationship, as emotional as it may have been was blessed with four healthy children who survived to adulthood – two of which were sons and heirs to the throne. Henry and Elizabeth’s union may have been arranged, but their love was not.

Elizabeth of York
Elizabeth of York
Henry VII

Elizabeth of York died on her 37th birthday, in the royal apartments in the Tower of London, she had recently given birth to a daughter and died from puerperal fever – a very common cause of death for women at the time.

The day before Elizabeth died their infant daughter, Katherine, died as well. Not only was Henry grieving for his beloved wife, but also for the child they so desperately wanted.

When the heir to the throne, their eldest son Arthur died, Elizabeth told Henry that they were both still young enough to have more sons. Unfortunately the birth of their daughter Katherine would be her final act as queen. The baby was not the son (and spare heir) they had hoped for, but they were both very happy to welcome another child into their family.

In Alison Weir’s book, Katherine of Aragon – The True Queen,  she claims their daughter was named after Katherine of Aragon. This seems highly plausible to me since it appears that Katherine and Elizabeth had grown very close to one another during their time together. In those early years she was treated like a daughter by both the king and queen.

After the death Arthur Tudor, Prince of Wales Katherine of Aragon was titled dowager princess of Wales, however, by birth she was Princess (Infanta) of Spain — a country ruled by her parents, Ferdinand of Aragon and Isabella of Castile. Spain was a very powerful country to be aligned with, and a powerful ally against France, a mutual enemy of both England and Spain.

Katherine of Aragon, dowager princess of Wales

When Arthur Tudor, Prince of Wales died so did the marriage treaty between Spain and England. With the death of Arthur should have come the end of the alliance between England and Spain, but it did not. The idea of a marriage between Henry, Prince of Wales (future Henry VIII) and Katherine was under negotiations, and a papal dispensation was sought since Katherine had been married to Henry’s brother. In the meantime Henry VII came up with the idea of taking the dowager princess of Wales as his own bride. This would surely maintain the alliance between the two countries and offer him another opportunity for more sons. Would the Spanish monarchs agree to a marriage between this young daughter and the aged King of England?

Here is a letter written by Katherine’s mother Queen Isabella when she heard of Henry VII’s  intentions:

Regarding: Death of the Queen of England.  Marriage of Henry VII to the Princess of Wales. Opinion entertained of it by Queen Isabella.

…The Doctor (Roderigo De Puebla) has also written to us concerning the marriage of the King of England with the Princess of Wales, our daughter, saying that it is spoken of in England. But as this would be a very evil thing,—one never before seen, and the mere mention of which offends the ears,—we would not for anything in the world that it should take place. Therefore, if anything be said to you about it, speak of it as a thing not to be endured. You must likewise say very decidedly that on no account would we allow it, or even hear it mentioned, in order that by these means the King of England may lose all hope of bringing it to pass, if he have any. For, the conclusion of the betrothal of the Princess, our daughter, with the Prince of Wales, his son, would be rendered impossible if he were to nourish any such idea.

If you should find that the King of England wishes to marry, we will tell you, at the end of this letter, the match which we think would be suitable for him, and all that occurs to us relative to it.

The Spanish monarch, Isabella was not keen to the idea of Henry VII taking her daughter as a queen – as a matter of fact, she seemed almost disgusted by the thought. We must also keep in mind that this may all have been a rumor since the ambassador mentions that it was spoken of in England and does not say the King of England told him. With all that being said Isabella wanted no part of it, rumor or not. Instead, Isabella suggested her niece, Joanna of Aragon (dowager queen of Naples). Joanna of Aragon (15 April 1479 – 27 August 1518) had been married her half-nephew, Ferdinand (Frederick) II of Naples.  Joanna was the daughter of Ferdinand’s grandfather Ferdinand I and his second wife, Joanna of Aragon. Joanna’s husband (and nephew) died in 1496 not long after their wedding. Joanna was 17/18 years old at the time. With the absence of a direct heir from Ferdinand (Frederick) II of Aragon and Joanna, the crown was inherited by his uncle Frederick, legitimate brother and Joanna’s half-brother.

(Side note: I must be honest, this paragraph confused me immensely. I checked and re-checked names to ensure I had the correct people and titles but the more I researched the more confused I became. There is more than one Joanna of Aragon and Ferdinand/Frederick is a little confusing as well. If you see an error in the paragraph please let me know.)

April 1503 – dowager queen of Naples

A Letter from Queen Isabella Of Spain to Ferdinand, Duke De Estrada:

(Where you see … is part of the letter that is illegible)

Regarding: Marriage of the King of England to the dowager queen of Naples.

Returning now to the affair of the betrothal of the King of England, it seems to us that it would suit him very well to … (fn. 1) the Queen of Naples, our niece, because in addition to … her much … which is suited for the consolation and comfort of the King of England. By this marriage the alliance and friendship subsisting between the two parties would, at any rate, be strengthened. On this account, if you find that the King of England wishes to marry, act in the way and manner which may seem best to you, being careful of the honour of both parties. If the King of England think well of this proposal, confer with him in detail on the conditions, and inform us of them, that we may make such provision as may be requisite, and let what passes in the matter be kept secret. But do not on this account defer the departure of the Princess of Wales, unless it be for the cause, and in the manner, above said.

At the time Isabella wrote the above letter she was working on bringing her daughter Katherine back to Spain. The negotiations for marriage with Henry, Prince of Wales (future Henry VIII) had turned sour and looked as though the marriage would never happen.

Isabella of Castile c. 1485
Katherine of Aragon by Michel Sittow
Katherine of Aragon c. 1502










On 26 November 1504, Isabella of Castile died. The below letters from De Peubla, the Spanish Ambassador, were dated the 5th of December 1504. It appears that he was not aware of his queen’s death when he wrote this letter. It is broken into passages. These passages all appear to be part of the same letter and are broken down by subject.

5 December 1504 

Passage #1

Ambassador Roderigo De Puebla to Ferdinand and Isabella (Spanish Monarchs):

Regarding: dowager queen of Naples.

As to the match between the Queen of Naples and the King of England, your Highnesses may rest assured that a business of so much importance has not been allowed to lie dormant. On the contrary, I have spoken many times to the King about it, sometimes in private, and sometimes in presence of the members of the Privy Council. The marriage is much approved by the King and the Privy Council, and is thought a better one than any other which has been or can be offered him, search all the world over. While making this declaration, they lauded your Highnesses, on many accounts, and for many considerations, above the Cherubim.

It is true that the King has had letters from France, which he showed me, and in which he is assured that your Highnesses are going to give this lady, your niece, to the son of Don Fadrique, (fn. 1) should it be agreeable to the King of France. He is also told that the King of France did not wish for the match, and that the ambassadors of your Highnesses, who are in France, had departed, taking this answer with them from the King of France, and without being able to come to any conclusion respecting the peace.

The dowager queen of Naples was rumored to be considered in marriage to the son of Don Fadrique (Frederick of Aragon) to strengthen the throne of Naples. The rumor was that Ferdinand and Isabella had suggested the match. This would be the Frederick we referred to above that inherited the throne when his predecessor did not have an heir.

Passage #2

Henry VII desires further particulars respecting her:

I replied to all this, that I did not believe it, as your Highnesses yourselves had written to make the offer (of the marriage with the Queen Dowager of Naples) to his Highness. He answered, with all respect to your Highnesses, that such a thing might have taken place before your Highnesses made him the offer. Finally, the conclusion arrived at by the King and his Council is, that it seems a thing which ought not to be, and an improper thing, for the King to conclude such a marriage without being first certified by his ambassadors and envoys as to the person and appearance of the said Queen. For your Highnesses must know that if she were ugly, and not beautiful, the King of England would not have her for all the treasures in the world, nor would he dare to take her, the English thinking so much as they do about personal appearance. Moreover, I was told that neither the King nor his Council had seen any letters or instruction from your Highnesses, in writing, to which they might have given entire credence, but had had to rely solely upon my relation, saying that your Highnesses had always written to me in cipher. Nor had they even seen the picture which I had begged your Highnesses to send. Therefore, on account of all these things, the King greatly desired, as did also the Privy Council, that, provided it were agreeable to your Highnesses, he would send ambassadors to Valencia, or to your Highneses, about the matter, when and how and where your Highnesses might direct, and in case the request should appear to you to be a proper one.

I find the above correspondence quite interesting. Like his son later, Henry VII insisted the Spanish ambassador provide a portrait of the queen dowager of Naples before anything is made final – as appearances meant much to him. Since there were no portraits available of her the ambassadors were sent to Naples to report on the appearance of the queen dowager themselves. The reports were satisfactory, however, negotiations eventually fell through due to political and financial reasons.

Prior to March 1505 – Margaret of Savoy

According to S.B. Chrimes book, Henry VII, sometime prior to March 1505, Maximilian (Holy Roman Emperor) had offered his daughter, Margaret of Savoy as a suitable spouse for Henry VII. He appears to have looked further into the matter. Henry was as much of a prize to other countries as they were to him. More on this shortly.

Margaret of Savoy c. 1500
Margaret of Savoy c. 1500
Marguerite d’Angoulême

July 1505 - Marguerite of Angoulême

Getting into the game, King Louis XII proposed his niece, Marguerite of Angoulême, to wed the King of England. Marguerite was the daughter of Charles, count of Angoulême. Louis XII proposed the marriage along with some conditions, of course. He also offered a comparable dowry to the one that had been offered by Ferdinand and Isabella for the dowager queen of Naples.  Whether it be the possible alliance with his enemy, or another reason, Henry VII only briefly entertained this option. It appears at this time that the King of England was more interested in the match with Margaret of Savoy.

The possibility of marriage to Margaret of Savoy was a very attractive match for Henry. If it had come to fruition it would have changed the balance of power between Henry and Maximilian. The possibility of this match dragged out until 1508. It was then that Margaret of Savoy declined the offer and chose to remain a widow. Not a bad idea for her as she was now regent of the Netherlands for her nephew, Archduke Charles.

**On To the Next**

After the death of Isabella of Castile, her daughter Juana inherited the throne of Castile. When Juana’s husband, Philip (the Handsome) passed away unexpectedly on 25 September 1506, it left Juana as a prize to be claimed – especially by a money and status-hungry English monarch.

Juana of Castile
Juana of Castile
Philip the Handsome











After the death of her husband, Juana is said to have gone mad. It was reported that she traveled with her husband’s body because she could not bear to be apart from him. Many have stated that Juana was very jealous of the attention that her husband received from other women, and that she did not approve of his actions toward them either. When he passed away it was her opportunity to have him by her side at all times.

Henry VII didn’t seem to mind the “madness” that ensued in Juana’s life after the death of her husband, as long as she was able to bear children for him. Or was it that he understood the grief that a spouse goes through after losing someone they loved so greatly?

Juana the Mad Holding Vigil over the Coffin of Her Late Husband, Philip the Handsome
Juana the Mad Holding Vigil over the Coffin of Her Late Husband, Philip the Handsome

March 1507 – Queen Juana of Castile

The possible match between the dowager queen of Castile and Henry VII seems to have been one of most interest to both parties. There were far more correspondences found between these two countries than with the others that were mentioned above.

A Letter from Katherine of Aragon, Princess of Wales to her father, Ferdinand of Aragon:

Regarding: Proposal of Henry to marry Queen Juana.

Has read her letter, by which she has communicated to him the wish of the King of England to marry her sister, Queen Juana. She must tell the King that it is not yet known whether Queen Juana be inclined to marry again ; but if the said Queen should marry again, it shall be with no other person than with the King of England, especially as he has proposed such acceptable conditions. Expects that the King of England will send him an ambassador with whom he can treat about this marriage of Queen Juana, as soon as it is known in England that he has returned to Castile. But the affair must be kept most secret; for if Queen Juana should hear anything about it, she would most probably do something quite to the contrary. No one knows her better than himself. For this reason nothing must be done before his return to Spain.

Katherine of Aragon is attempting to give advice to her father on the actions on England and how things should be handled. She appears to understand her sister very well and agrees that Henry would be a great husband for Juana as well as a continued ally for Spain. At the time Katherine was also looking forward to having her sister with her in England as company.

Ambassador De Puebla later wrote a letter to Ferdinand of Aragon to confess that the English king did not seem very concerned with the sanity of Juana. That Henry VII would make a great husband for her and that he believes after marrying the English king she would recover from her illness. However, if she would not recover from said illness it would be better for her to be in England than Spain.

Part of the negotiations included Henry living for a short period of time in Spain with Juana after they were married. I nearly laughed out loud when I read that part because there is no way (in my mind) that Henry would have left England for fear of invasion from an enemy or fear of someone usurping his throne.

19 May 1507 – Queen Juana of Castile

Letter from King Ferdinand to Ambassador De Puebla:

Regarding: Opinion of Ferdinand respecting the proposed marriage between Henry and Queen Juana.

Does not yet know whether the Queen of Castile can be persuaded to marry at all ; but if she marries, her husband shall be the King of England, and no other person. The conditions which the King of England offers are as favourable as possible. Besides, the said King is a Prince of great virtue and experience. It would be a consolation to him at his hour of death to know that his daughter, his grandchildren, and his kingdoms would remain under the protection and guidance of such a man as King Henry. The only reason why his reply to the King of England is not a definite answer, is, because it is necessary first to speak with the Queen of Castile.

Ferdinand by Meister der Magdalenen Legende
Ferdinand by Meister der Magdalenen Legende

June 1507 – Queen Juana of Castile

Letter from King Ferdinand to Ambassador De Puebla:

Regarding: Queen of Castile

Thinks the King of England is right not to send an embassy to the Queen of Castile before his return. Could the business have been arranged during his absence, it would already have been done. But if any other person were first to speak to the Queen of Castile about her marriage, the whole affair would be thrown into confusion. Will do his utmost to persuade the Queen of Castile to marry the King of England. He may rest sure that, if the Queen marries, her husband will be no other Prince than King Henry. Loves Henry like a brother ; and, besides, the conditions which he offers are very advantageous to himself, to the Queen, to his grand-children, and to Spain.

I read through the Letters, Despatches and State Papers Relating to The Negotiations between England and Spain and in there it sheds new light on the “madness” of Juana. It implies that Juana’s madness was created by Ferdinand of Aragon so he could retain the power of Castile himself. What do you believe?

From the letters written to the ambassador from his king is truly appears as if Ferdinand of Aragon wishes his daughter to marry only King Henry of England. I’m sure he saw the benefit of having two daughters in England, just as Henry saw the benefit of being aligned with Spain.

8 June 1507 – Queen Juana of Castile

Letter appears to be written by De Puebla to Henry VII after he received the letter from Ferdinand of Aragon:

Regarding: Sentiments entertained by Ferdinand toward Henry

King Henry may rest sure that he (Ferdinand) will do all in his power to secure this marriage. If the Queen of Castile is to marry, she shall marry no other person than the King of England, who is so distinguished by his virtues. No other Prince would offer the same advantages. Would live and die in peace if he knew that his daughter, his grand-children, and his kingdoms were under the protection of Henry VII. King Philip has been his enemy, but King Henry would be his loving son. Has a firm desire to show his fondness for the King of England, not only in words, but also by deeds.

By September, Henry VII is growing very anxious on the matter and would like an answer regarding the marriage proposal. It has been six months already and he still does not have an answer. Katherine of Aragon seems to be the moderator between her father and Henry VII, trying to keep things calm between them.

September 1507 – Queen Juana of Castile

Letter from Katherine to her father Ferdinand of Aragon:

Regarding: Impatience of Henry respecting his marriage with Queen Juana

The King of England is very impatient to have an answer respecting his intended marriage. It is most inconvenient to him to wait, because he has other marriages in view. The King of England says he fears that the affair will be much protracted, and the answer of the Queen of Castile unfavourable. Tells him that he must be patient; the King her father has scarcely arrived in Spain, and such a delicate business as this cannot be hurried.

Henry VII
Henry VII

October 1507

Katherine decides to write her sister in Spain. It’s such a great insight into Katherine’s mind.

Letter from Katherine, Princess of Wales to Queen Juana of Castile:

Regarding: Sorrow felt by the Princess Katharine on the departure of Queen Juana

Most noble and most mighty Princess, Queen and Lady, after having kissed the royal hands of your Highness and humbly commended myself to you, I have to express the very great pleasure it gave me to see you in this kingdom, and the distress which filled my heart, a few hours afterwards, on account of your sudden and hasty departure.

Regarding: Feeling of Henry VII towards Queen Juana:

My Lord the King was also much disappointed in consequence of it, and if he had acted as he secretly wished, he would, by every possible means, have prevented your journey. But, as he is a very passionate King, it was thought advisable by his Council that they should tell him he ought not to interfere between husband and wife. (fn. 10) On which account, and for the sake of other mysterious causes with which I was very well acquainted, he concealed the feelings occasioned by the departure of your Highness, although it is very certain that it weighed much upon his heart.
The great affection he has felt, and still feels, towards your Royal Highness from that time until now, is well known. I could not in truth express, even though I were to use much paper, the pleasure which my lord the King and I felt on hearing that the King, our lord and father, had returned to Castile, and was abiding there with your Highness, and that he was obeyed throughout all the kingdom, peace and concord prevailing everywhere.

Proposal made by the Princess Katharine to Queen Juana:

It is true that I have experienced, and am still experiencing, some sorrow and depression of mind on account of having heard, a few days ago, that the French have taken a large and beautiful city called Tilmote, belonging to my nephew, and that all his subjects and the whole land are in great fear of the French. Wherefore, as a remedy for everything, and not less for the destruction and chastisement of the Duke of Gueldres his rebel, I have ventured to write these lines to your Highness, entreating you to hearken to my wishes respecting this matter. I have, moreover, written to my lord the King, our father, about this business, which is of great advantage and importance to your Highness, to the increase of your state, the tranquility and welfare of your subjects, and those of the said Prince, my nephew, and which also affects my lord, the King of England. He is a Prince who is feared and esteemed at the present day by all Christendom, as being very wise, and possessed of immense treasures, and having at his command powerful bodies of excellent troops. Above all, he is endowed with the greatest virtues, according to all that your Highness will have heard respecting him.

Regarding: Contemplated results of a marriage between Henry VII and Queen Juana:

If what my lord the King, our father, shall say to you should please, as I think it will please, your Highness, I do not doubt but that your Highness will become the most noble and the most powerful Queen in the world. Moreover, nothing will more conduce to your pleasure and satisfaction, and the security of the kingdom of your Highness. In addition to all this, it will double the affection subsisting between my lord the King, our father, and my lord, the King of England. It will also lead to the whole of Africa being conquered within a very short time, and in the hands of the Christian subjects of your Highness, and of my lord the King, our father.
I entreat your Highness to pardon me for having written to you, and for having meddled in so great and high a matter. God knows what my wishes are, as I have already said ; and I have not found it possible to resist the desire I felt to write to you. For it appears to me that if this be not done, it will be committing a great sin against God, against the King, our lord and father, and against your Highness, whose life and royal estate may our Lord guard and increase.—Richmond, 25th October.
The Princess Of Wales.

After all the negotiations to choose the right partner, the right country to ally himself with, Henry VII died before concluding ANY of his negotiations.


Supplement to Calendar of Letters, Despatches, and State Papers, Relating to the Negotiations Between England and Spain: Henry VII 1485-1509 https://play.google.com/books/reader?id=P_wUAAAAQAAJ&printsec=frontcover&output=reader&hl=en&pg=GBS.PR1

Chrimes, S.B., Henry VII

Spanish letters referenced only as I do not have access to the English version. This provides the unique insight from Spain during the negotiations.

‘Spain: April 1503’, in Calendar of State Papers, Spain, Volume 1, 1485-1509, ed. G A Bergenroth (London, 1862), pp. 294-305. British History Online http://www.british-history.ac.uk/cal-state-papers/spain/vol1/pp294-305 [accessed 9 May 2016].

‘Spain: December 1504’, in Calendar of State Papers, Spain, Volume 1, 1485-1509, ed. G A Bergenroth (London, 1862), pp. 342-348. British History Onlinehttp://www.british-history.ac.uk/cal-state-papers/spain/vol1/pp342-348 [accessed 30 April 2016].

‘Spain: July 1505’, in Calendar of State Papers, Spain, Volume 1, 1485-1509, ed. G A Bergenroth (London, 1862), pp. 362-366. British History Online http://www.british-history.ac.uk/cal-state-papers/spain/vol1/pp362-366 [accessed 13 April 2016].

‘Spain: March 1507’, in Calendar of State Papers, Spain, Volume 1, 1485-1509, ed. G A Bergenroth (London, 1862), pp. 403-406. British History Onlinehttp://www.british-history.ac.uk/cal-state-papers/spain/vol1/pp403-406 [accessed 27 May 2016].

‘Spain: May 1507’, in Calendar of State Papers, Spain, Volume 1, 1485-1509, ed. G A Bergenroth (London, 1862), pp. 414-417. British History Online http://www.british-history.ac.uk/cal-state-papers/spain/vol1/pp414-417 [accessed 31 May 2016].

‘Spain: June 1507’, in Calendar of State Papers, Spain, Volume 1, 1485-1509, ed. G A Bergenroth (London, 1862), pp. 417-418. British History Onlinehttp://www.british-history.ac.uk/cal-state-papers/spain/vol1/pp417-418 [accessed 17 May 2016].

‘Spain: September 1507’, in Calendar of State Papers, Spain, Volume 1, 1485-1509, ed. G A Bergenroth (London, 1862), pp. 425-433. British History Onlinehttp://www.british-history.ac.uk/cal-state-papers/spain/vol1/pp425-433 [accessed 29 May 2016].

‘Spain: October 1507’, in Calendar of State Papers, Spain, Volume 1, 1485-1509, ed. G A Bergenroth (London, 1862), pp. 433-441. British History Onlinehttp://www.british-history.ac.uk/cal-state-papers/spain/vol1/pp433-441 [accessed 17 May 2016].

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History Katherine of Aragon

1 Comment Leave a comment

  1. “Or was it that he understood the grief that a spouse goes through after losing someone they loved so greatly?”
    A beautiful line and valid point

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