The Sadness of Henry, Prince of Wales


In David Starkey’s documentary called, “Henry VIII”, he briefly discusses Henry, Prince of Wales meeting King Philip I of Castile. Philip was also known as Philip the Fair (or Philip the Handsome) and was married to Katherine of Aragon’s older sister, Juana/Joanna of Castile. The couple came to England for a visit in 1506.

Katherine of Aragon
Katherine of Aragon

Juana of Castile
Juana of Castile

It appears the young Prince of Wales took a liking to the King of Castile. Henry hoped to one day model his kingship after Philip. It appears Henry’s father, Henry VII, had not allowed young Henry the recognition and voice he so desired. He rarely spoke in public, but when he did it was to answer his father or grandmother, Margaret Beaufort.

After the departure of Philip and Juana, Henry wrote his new friend a letter that shows how much he wanted to continue a friendship with the King of Castile. Soon he would be his brother-in-law after marrying Katherine.

Henry, Prince of Wales to Philip, King of Castile

[“Letters and Papers, Henry VII.,” Rolls Series]

Greenwich, April 9, 1506

Most high, most excellent, and mighty Prince,

I commend myself to you in the most affectionate and hearty manner that I can. Whereas the chamberlain of my most dear and well-beloved Consort, the Princess, my wife, is going to present to you for certain matters that he says he has to transact in that quarter, he has requested me to write to you in his favour. I pray you very heartily, most high, most excellent, and mighty Prince, that you will hold him recommended in his said affairs, and that you will apprise me from time to time, and let me know of your good health and prosperity, which I particularly, and with my heart, desire to be a long continuance as I would my own. And for my part, whenever I can find a fitting messenger, I am determined to do the like to you.

Moreover, on your intimating to me if there be anything here in which I can do you honour and pleasure, I will take pains to satisfy you in it with all my heart, by the good aid of our Lord, whom I pray to give you, most high, most excellent and mighty Prince, good life and long.

Your humble cousin,

Henry, Prince of Wales

Henry Vlll
Henry VIII – 1509

Philip I of Castile

On the 25th of September 1506, Henry’s friend, King Philip had suddenly died of typhoid fever. Henry is said to have been as devastated by the death of Philip as he had been for his own mother just a few years earlier.

In the letter he reflects on the sadness of losing his mother and now his dear friend, Philip – Henry states it had, “appeared to reopen a wound which time had begun to heal.

It is sometime after the death of Henry’s mentor that he took up King Philip’s favorite sport – jousting. The late king truly made an impression on the young Henry.

Henry, Prince of Wales to Erasmus

[“Epistles of Erasmus,” translated by F.M. Nichols, Vol. I]


I am much struck by your letter, most eloquent Erasmus, which is too elegant to appear composed on a sudden, and so lucid and simple that it cannot be supposed to be premeditated by so dextrous and intellect. For it somehow happens, that those writings which are elaborated by ingenious minds and produced with more than usual care, bring with them also a greater share of studied difficulty, for while we aim at a more refined eloquence, we lose, without being aware of it, that open and clear manner of expression. But your epistle, charming as it is in its grace, is no less transparent in its perspicuity, so that you seem to have carried every point. But why do I set myself to praise your eloquence, whose skill is well known through the whole world? There is nothing I can compose in your praise which is worthy of that consummate erudition. I therefore pass over your praises, about which I think it better to be silent than to speak insufficiently.

The news of the death of the King of Castile, my much lamented brother, I had received with regret long before I read of it in your letter. Would that it had come much later or had been less true! For never since the death of my most dear mother has a less welcome message come to me. And to speak the truth, I was not so ready to attend to your letter as its singular elegance demanded, because it appeared to reopen a wound which time had begun to heal. But those events that are determined by heaven, must be so received by mortals. Meantime pray proceed, and signify to us by letter any news you have, but let your news be of a pleasanter kind; and may God bring to a good event whatever may happen worth telling. Farewell.

Richmond, January 17, 1507

Young Henry, Prince of Wales first met Erasmus in 1499 when Thomas More introduced him to the royal family. The young Prince Henry asked Erasmus to write him a poem – and that he did. The poem was entitled, Prosopopoeia Britanniae.

Erasmus is introduced to Prince Henry and Princess Margaret by More.
Erasmus is introduced to Prince Henry and Princess Margaret, Princess Mary & Prince Edmund by More.


Erasmus c. 1523

Letters found in:

Mumby, Frank Arthur, The Youth of Henry VIII, A Narrative in Contemporary Letters – Frank Arthur Mumby


Social media no longer shows our posts to a majority of our followers - Don't want to miss out on new articles? Get notified! Subscribe to email updates from Tudors Dynasty.

Join 5,724 subscribers.

Henry VIII History

2 Comments Leave a comment

  1. I was struck by how facile Henry wrote and how grown up and educated he seemed as a young man. It seems a juxtaposition to the man he later became.

  2. I believe the wife went mad from grief. And Mary the frist went through depression after her father rejected her over ann boleyn. And almost lost it . with the death of Jane who finally gave herny a son.but died as well she was a close friend who treat mary with respect only to have her baby brother try to remove her from the throne. Her husband left her could not have kids and finally died alone with the name . BLOODY Mary not so ture makes you wonder were the tudor line curse

Leave a Reply

Your email address will not be published. Required fields are marked *