1: 1500 - 1501
"The marriage of Maria of Aragon to James IV of Scotland would take place on the 18th of June 1500, a little more than a week before Maria's birthday and just a month prior the death of Miguel de Paz, the heir apparent to Portugal, Castile and Aragon. Miguel's death left his father, King Manuel I of Portugal, a childless widow that was in need of heirs, and these heirs were expected to be from the womb of the eldest unmarried daughter of the Catholic monarchs, to which there existed only one, Catherine of Aragon."

--Carlos de Granada y Fernandez "El Catalico: Fernando II de Aragon"


"The Catholic Monarchs ruled that the arrangements for their daughter Catalina's marriage to the English Prince were too far along to abandon them, considering the fact that their daughter was planned to begin her voyage to England in a year's time. However, the Catholic Monarchs presented Manuel of Portugal with a compromise candidate. Margaret of Austria and Burgundy was the only daughter of Emperor Maximilian and Mary of Burgundy, she had Portuguese blood on both sides of her family and was also the paternal aunt to Charles, the eldest grandson of Isabella and Ferdinand who many believed would one day be King of Spain too.

Margaret was also the widower of Isabella and Ferdinand's late son, Juan, who died in 1497 after being married only a few months. King Manuel accepted the compromise, as not only would she come with a handsome dowry, but it would also mean the next King of Portugal would not only be cousin to the King of Spain, but to the Duke of Burgundy and likely the Holy Roman Emperor too. His Austrian bride would also come with a good alliance for Portugal as well as better trade with Burgundy.

Both the Catholic Monarchs and Manuel would write to Emperor Maximilian and his son, Philip of Burgundy, persuading them to accept this marriage which they thankfully also saw the benefit of, and on the 28th of July 1501, Margaret of Austria would become Queen of Portugal."

--Joana Malheiro "Portugal: A Puzzling Past"


"Catalina de Aragon would depart from La Coruna in August, but violent storms in the Bay of Biscay would force her retinue of ships to return to Castilian shores, where she would remain for another month before voyaging from Laredo on the 27th of September 1501 and arriving in Plymouth and her new life on the 2nd of October 1501. On the 10th of November Catalina, now known as Catherine, would receive a letter from her sister the Scottish Queen, congratulating her on her upcoming marriage and to inform her of the birth of her son, James, who was born on the 6th of November. Catherine would marry Arthur Tudor on the 14th of November.

--Lewis Bell "The Pomegranate Queens: Maria and Catherine"
 
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Isabella still dies in 1504, Ferdinand still remarries in 1505, but not to Germaine
A split between Castile and Aragon butterflies entirely the current Spain. That will be interesting...and of course I feel bad for the poor girl who now has to be placed against Ferdinand's first wife, because her predecessor is literally Isabella "Most Catholic Majesty" of Castile
 
If Margaret have a son with Ferdinand here (the title suggests it), then it would be extremely weird if Charles V marries Mary Tudor and inherits Castile.
 
A split between Castile and Aragon butterflies entirely the current Spain. That will be interesting...and of course I feel bad for the poor girl who now has to be placed against Ferdinand's first wife, because her predecessor is literally Isabella "Most Catholic Majesty" of Castile
Well, I doubt who Isabella was highly popular in Aragon so…
 
This scenario do not work. Maria will NOT be married in Scotland after Isabella’s death (and she wanted die so no way she will survive childbirth) and Ferdinand and Isabella will marry Catherine to Manuel over Arthur Tudor
 
This scenario do not work. Maria will NOT be married in Scotland after Isabella’s death (and she wanted die so no way she will survive childbirth) and Ferdinand and Isabella will marry Catherine to Manuel over Arthur Tudor
In theory, could the scenario work if Isabella of Aragon survives until 1500?
I ask because I thought that the catholic monarchs considered the double marriage of England & Scotland (IIRC Maria didn't have a set alliance as her older siblings) so in a situation where she's not needed top shore up the portuguese link she seems the logical way to pry Scotland away from France.
 
2: 1502 - 1504
"His parents marriage was a rather short one, for on the 2nd of April 1502, his father Arthur Tudor would expire at Ludlow Castle of the sweating sickness, leaving Catherine of Aragon an unknowingly pregnant widow. Arthur's burial was on the 25th of April and it was little more than a week later that the young Spanish widow reported to the King's mother Margaret Beaufort that she had missed her monthly courses and that she had a furious desire to eat nothing but apples."

--George Hardwick "The Book of Tudors: Henry VIII of England"


"Margaret of Austria would give birth to a daughter on the 11th of April 1502, named Margaret after herself. The birth of Margaret of Portugal would be somewhat of a disappointment for her father, who despite loving her nonetheless, still needed and heir for Portugal, a male heir at that. However, he and Margaret weren't too old yet, and there was still time for a dozen male heirs in the future, a fact which gave the King some piece of mind."

--Joana Malheiro "Portugal: A Puzzling Past"


"As 1502 drew to a close, it would be discovered that all three of the Catholic Monarch's remaining children were with-child, with Catherine being the first of the three to give birth on the 24th of October 1502 to a baby boy, named Henry for his grandfather. Catherine's son was the heir to the Kingdom of England and was styled with the titles Duke of Cornwall and Earl of Chester, the customary titles for the heir to the English crown. The next to be rid of the child in their womb would be Joanna, who too would birth a boy named Ferdinand on the 10th of March 1503, meaning the boy carried not only the same name as his grandfather but the same birthday too. The third and final birth would be Princess Isabella of Scotland on the 22nd of April 1503, to Maria of Aragon and James IV of Scotland."

--Carlos de Granada y Fernandez "El Catolico: Fernando II de Aragon"


"I couldn't be happier - First I get a grandson and heir to replace my boy Arthur, and then I receive word that the King of Scots shares my desire for our countries to have peace, a peace he wishes to make possible with the marriage of his newborn daughter Isabella to my newborn grandson Henry. Although I personally believe Henry could do much better in terms of standing, this match would ensure peace between England and Scotland."

--An extract from Henry VII's diary, dated 2nd of May 1503


"The year 1504 would see Portugal welcoming yet another Infanta, named Beatrice for the King's mother, but in Spain, it was a different situation. On the 26th of November 1504, Queen Isabella of Castile - more commonly known as Isabella the Catholic - passed away in Medina del Campo after previously withdrawing from governmental affairs on the 14th of September. The cause of her death was because of the bad health she experienced towards the end of her life, though more poetic souls liked to say she died of grief for her son John, who had been dead for seven years. Her death cast a dark shadow over Europe, as this meant that the Kingdoms of Castile and Aragon were once again separated, as Aragon would continue to be ruled by her widow Ferdinand while Castile would fall into the hands of her daughter Joanna and her husband Philip, who Ferdinand of Aragon despised."

--Alvaro Antonio "The life of the Catholic Queen: Isabella I"
 
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iberian family trees - c.1504
Ferdinand II, King of Aragon (11th of March 1452 - ) married Isabella I, Queen of Castile (22nd of April 1451 - 26th of November 1504)
  1. Isabella, Queen Consort of Portugal (2nd of October 1470 - 23rd of August 1498) married firstly Afonso, Prince of Portugal (18th of May 1475 - 13th of July 1491), secondly Manuel I, King of Portugal (31st of May 1469 - )
    1. Miguel de Paz, Prince of Portugal (23rd of August 1498 - 19th of July 1500)
  2. Miscarried son (31st of May 1475)
  3. John, Prince of Asturias (30th of June 1478 - 4th of October 1497) married Margaret of Austria and Burgundy (10th of January 1480 - )
    1. Miscarried daughter (April 1498)
  4. Joanna I, Queen of Castile (6th of November 1479 - ) married Philip of Austria, Duke of Burgundy (22nd of July 1478 - )
    1. Eleanor of Austria-Burgundy-Castile (15th of November 1498 - )
    2. Charles of Austria-Burgundy-Castile (24th of February 1500 - )
    3. Isabella of Austria-Burgundy-Castile (18th of July 1501 - )
    4. Ferdinand of Austria-Burgundy-Castile (10th of March 1503 - )
  5. Maria, Queen Consort of Scotland (29th of June 1482 - ) married James IV, King of Scotland (17th of March 1473 - )
    1. James Stewart, Duke of Rothesay (6th of November 1501 - )
    2. Isabella Stewart of Scotland (22nd of April 1503 - )
  6. Stillborn daughter (29th of June 1482)
  7. Catherine, Dowager Princess of Wales (16th of December 1485 - ) married Arthur Tudor, Prince of Wales (20th of September 1486 - 2nd of April 1502)
    1. Henry Tudor, Duke of Cornwall (24th of October 1502 - )
......

Manuel I, King of Portugal (31st of May 1469 - ) married firstly Isabella, Infanta of Aragon and Castile (2nd of October 1470 - 23rd of August 1498), secondly Margaret, Archduchess of Austria and Burgundy (10th of January 1480 - )

  1. a) Miguel de Paz, Prince of Portugal (23rd of August 1498 - 19th of July 1500)
  2. b) Margaret of Portugal (11th of April 1502 - )
  3. b) Beatrice of Portugal (1st of October 1504 - )
 
Duke of Cornwall and Earl of Chester, the customary titles for the heir to the English crown.
Shouldn't baby Henry be the new Prince of Wales too?


Otherwise than that, a very very nice idea for a TL.

I really want to see if Maggie Habsburg bears her second husband a few sons too or "only" more daughters.
And Ferdinand's marriage with Maggie Tudor is certainly very interesting and new as an idea too.
 
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