An Imperial Match: Anne Boleyn marries Charles V

Absolutely false. Eleanor and John proposed wedding was called off by Portugal when Charles V refuted to marry Isabella of Portugal. As Eleanor was a potential heiress of Spain and Burgundy (Charles was engaged to a girl of few years and Ferdinand was still very young and so was not impossible seeing both of them die childless) she was offered by Charles to the widowed Manuel as mean for repairing relationship between Spain and Portugal without marrying Isabella
With João and Eleanor already married ITTL then, Charles will be good with Portugal? I mean he has still scorned Isabella (and not even for a princess, for some English knight's daughter) but at least Eleanor is married there.
 
With João and Eleanor already married ITTL then, Charles will be good with Portugal? I mean he has still scorned Isabella (and not even for a princess, for some English knight's daughter) but at least Eleanor is married there.
Charles‘ wedding can not be a slight to a princess to which he was NOT engaged and who, while proposed to him, was never taken in consideration by him. Likely ATL Manuel was less insistent in proposing Isabella to Charles or had not tied the two matches (so either both or none) or simply Eleanor and John’s match was already established before Charles had taken possession of his inheritance in Spain. Maybe they were engaged and married in 1516 (so as soon John reached the legal age for marrying) or early 1517?
 
Charles‘ wedding can not be a slight to a princess to which he was NOT engaged and who, while proposed to him, was never taken in consideration by him. Likely ATL Manuel was less insistent in proposing Isabella to Charles or had not tied the two matches (so either both or none) or simply Eleanor and John’s match was already established before Charles had taken possession of his inheritance in Spain. Maybe they were engaged and married in 1516 (so as soon John reached the legal age for marrying) or early 1517?
In my head, the reason why Leonor and João got married and Isabella and Charles did not is that as the heir, John's wedding was more of a priority to Manuel than his sister's and so, he got that locked down before dying. Eleanor brought with her a hefty dowry, as the sister of the King of Spain and Lord of the Low Countries, while Isabella, as his eldest daughter, would need a big dowry herself (I mean look at that large amount of money she brought Charles OTL). To me, it doesn't make sense to receive money and then send more money to the same person who gave the money to you.

So yeah. Eleanor and John are married.
 
In my head, the reason why Leonor and João got married and Isabella and Charles did not is that as the heir, John's wedding was more of a priority to Manuel than his sister's and so, he got that locked down before dying. Eleanor brought with her a hefty dowry, as the sister of the King of Spain and Lord of the Low Countries, while Isabella, as his eldest daughter, would need a big dowry herself (I mean look at that large amount of money she brought Charles OTL). To me, it doesn't make sense to receive money and then send more money to the same person who gave the money to you.

So yeah. Eleanor and John are married.
Do not work like that and marrying well his eldest daughter was a priority for Manuel. He had many sons, while available Kings for Isabella were very few. And paying Isabella’s dowry would NEVER be a trouble for Portugal. Also Maria’s last wish/request to Manuel was to marry well Isabella and Manuel was interested to respect and Charles V the natural candidate for Isabella‘s hands, specially as the Cortes of Castile and Aragon were highly in favor of that match. Maybe Manuel died in 1518 and John, now King, recovered his own match, without pushing his sister as bride for Charles?
 
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10th of July, 1522.
Winchester, England. 10th of July, 1522.

There was a sense of calmness in the rooms of Her Majesty, the Queen. Catherine of Aragon patiently sewed a new shirt for her loving husband as María de Salinas played the lute and another maid, Lucy Talbot, the virginals. Some of her ladies-in-waiting were sewing clothes of their own, while others read books and relaxed in the peaceful environment of Her Majesty’s court.

But this peace was broken when the door opened and the King strummed in, his face flushed with anger. “That whore!” he screamed as the doors slammed shut and all ladies gasped at both his intrusion and his language.

“Henry,” Catherine said, used to calming his fiery temper, as she stood up, her sewing set aside, “What is wrong?”

The King looked at her with wide eyes and she saw how he was shaking, how furious he was. Despite their many years together, Catherine had seen him like this only once before, when his sister married the Duke of Suffolk without his permission in France. Could something like it have happened again? Who would dare to go against such a marvellous King and marry without his permission? Who could have possibly offended him so?

“Leave us,” the King tells his wife’s companions and they turn to the Queen, eyes as wide as saucers. She nods and quickly, they scurry away, not wanting to remain in the room lest the King’s anger be directed at them.

When they were alone, Catherine stepped forward, and touched his sleeve, “What has happened? Tell me. You know you can tell me anything.”

“I have found your missing lady,” said Henry, almost shouting, “Mistress Boleyn is on a ship headed to Castile, or should I say Mistress Habsburg?”

“What?” Catherine swallowed down the urge to press a hand to his forehead to see if he had a fever because he was not making any sense, “What do you mean?”

“Anne Boleyn has secretly married the Emperor, Cathy!” he announced, splaying his arms wide to make his point known, “Anne Boleyn!”

“What?” Catherine asked again because this was not possible. Anne Boleyn was a righteous lady, pious and clever, she would never do something like this. And Charles… Charles was betrothed. He could not marry. He was promised to their daughter, the Princess. Why would he jilt the heir of England to marry a knight’s daughter? This could not be.

“Yes, her father has just informed me!” he said, “He begs for my forgiveness, says he and his family had no knowledge of her mischievousness. I should hang the lot of them.”

“Are you certain?” asked Catherine, a hand on her stomach. She did not feel well.

“Yes, I’m certain!” the King bellows, “I have found the priest who performed the marriage, who says the imperial ambassador was a witness. The ambassador!”

“Oh, no,” Catherine said, pressing her other hand to her mouth, “Oh no, what have they done?”

Oh, Charles. How could he have been so foolish? She was no wife for a prince such as himself, for she was not the daughter of a duke or earl. Catherine could not see the Cortes of her parents approving of such a match or any of the imperial diets and Anne Boleyn… Had she not told her to ignore Charles’ attempts? Perhaps this was her fault. If she had told Mistress Boleyn… Queen Anne that she could consummate an affair with Charles, this marriage would have never happened.

“It seems to me that all Boleyn girls are whores,” said Henry, oblivious to her thoughts, “And I will no longer assist such a tricky man as your nephew. No, I think I shall not go to war against France.”

“Oh, Charles,” sobbed Catherine, “Oh, how could you, Charles?” She remembered the letters they had exchanged. Catherine had tried to be like a mother to him, as he did not know her sister, and he often told her of his love and admiration for her. If you had any love for me, you would not have done this.

“And Mary will marry the Dauphin, as was planned before I was fooled into allying myself with the Emperor,” continued Henry, “I will inform the French ambassador. Of the two marriages. As will all other ambassadors know. I want Europe to know this before the month is out!”

This was too much for her. Catherine turned, wanting to sit down, and felt her legs give out from underneath her. Black spots swam her vision and, without warning, she fainted.
 
Uh oh. Looks like this ain’t gonna go well for Catherine. She is set to be the biggest loser of this arrangement. Great update!
 
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Well, honestly, I have major fingers crossed she does give Henry a son. I'd love to see that happen in a TL.

But either way, hoo boy will things go different.
 
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