Henry VII and Catherine of Aragon

Say Arthur, Prince of Wales, son of Henry VII dies in January 1499, due to grief after her son's death pregnant queen Elisabeth miscarried and also died.
IOTL Arthur and Catherine of Aragon would marry by proxy in May of that year. Now Arthur is dead and his father widowed. Could you see Henry VII marrying Catherine in place of his son ITTL? Henry would be interested for sure-he is left with only one son so his line's future is uncertain, and Catherine due to her Lancastrian blood is perfect candidate for his bride. IOTL Henry really considered marriage with his widowed daughter-in-law, Isabella of Castile opposed that idea and tried to distract Henry's attention from her daughter. But it was OTL and few years later. Now Henry VII is only option if Catholic Monarchs want to forge anti-French alliance with England with marriage.
Could you see it happen?
 
So in 1499 Henry is 42 years old widower. Tudor position is still quite shaky. Marriage with princess with Lancastrian blood would strenght his position so marriage talks with Ferdinand and Isabella continues. Catholic Monarchs agree to marry Catherine to him. Future Henry VIII is only 7 years old at the time of brother's death, so they would need to wait several years to marry Catherine to him.
In 1501 Henry finally married his would-be daughtet-in-law, almost 30 years younger than him.
What does it mean?
Henry VIII would never marry Catherine IOTL, most likely candidate for his wife IMHO is now Eleanor Habsburg. So no "Great Matter". But I don't think Henry's problems with progeny were just bad luck-so many stillbirths, short living infants, sickly Henry FitzRoy and Edward VI. Henry propably had some genetic defect, so it is likely that he still would problem with male heir. But if he is married to Eleanor he has no excuse for annulment, she is not his brother's widow. And instead of being emperor's aunt she is emperor's sister. Good luck with divorce!
On the other hand-he could have half-brother or brothers by Catherine, so he will not be so worried about succession.
 
We'd have the OTL situation. Because this was suggested OTL. And Ferdinand and Isabella said "Hell, no." She was sent to England to be a Queen and the mother of a monarch, not wed the King and become the mother of the spare.
 
We'd have the OTL situation. Because this was suggested OTL. And Ferdinand and Isabella said "Hell, no." She was sent to England to be a Queen and the mother of a monarch, not wed the King and become the mother of the spare.
So let's make little modification-Arthur and Elisabeth die like IOTL, instead Henry (OTL Henry VIII, not his father) dies around 1500. Is Henry VII's marriage with widowed Catherine going to happen now?
EDIT:
Or even better-both Arthur and Henry died from disease (perhaps sweating sickness) in late 1498/early 1499 and then Elisabeth dies from grief, so there is no need for papal dispensation and questions about legitimacy of such union.
EDIT2:
I don't want to be so cruel to Henry VII-say that Henry VIII is born as girl, so only death of Arthur and Elisabeth in 1499 are necessary.
 
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Henry's kids ATL
-Arthur (1486-1499)
-Margaret (1489-)
-Elizabeth (1491-)
-Mary "the Older" (1492-1495)
-Mary "the Younger" (1496-)

In January 1499 Arthur dies from disease, due to grief after loss of her only son queen Elizabeth of York miscarried male child and died few days later.
 
January 1499, Arthur dies and his mother dies of grief, Henry VII is widowed and now on the marriage market. The betrothal is off and since Katherine didn't leave Spain until 1501, she's still with her mama. You've butterflied the reason for her coming with Arthur's death this early and I'm not sure they will offer one of the older daughters if Henry's still looking at Spain. Henry VII was born 28 January 1457; Katherine 16 December 1485 - that's an awfully big gamble for Ferdinand and Isabella to take; Henry is well into late middle ages by standards of the time, and odds are any child Katherine has with him will be too young to defend against conspiracy - remember how Henry VII came to the throne? He killed a sitting king. At this point, Henry VII would be better off finding a lusty English wench and siring a few brats on her. Time is against the Tudor dynasty at this point. Margaret is the heiress for the Tudor throne - she'll be popular. Because whoever weds her gets England and she doesn't got to Scotland until 1503, so I doubt her father will wed her to James now. He doesn't want England to be subsumed in Scotland and, by extension (Auld Alliance), France. Congratulations, Svetonius21, you've gotten rid of the Anne Boleyn question without ever bringing the family into the question!

Seriously, Katherine isn't coming to England if Arthur dies in 1499; doesn't matter what happens to his mama. The whole point of the betrothal was the uniting of the NEXT generation of both families/countries. And Arthur dying is a bad omen back in those days (they believed in those things, remember?), so F&I are liable to see this as a sign God ain't impressed with the usurper Tudors - after all, he only has daughters now. F&I's daughter Maria is already betrothed to her sister's widower Manuel, so she's out of the question. Henry will have to look elsewhere (or within England) for a bride. My bet would be England. [Simply because of the urgency of him needing a son pronto.]
 
So if CoA is out of reach, would Henry look for marriage with one of the daughters of Catharine Woodville and Henry Stafford? Especially because Staffords due to their Plantagenet blood are the ones who could potentially challenge his laws to the throne?
 
It would make more sense (given his age) than negotiating for one or three years for a princess. Remember, he's the first Tudor. He's not viewed with any degree of respect (beyond "I didn't want to fight him face to face when he was younger"), now he's an old usurper who has no son and whose daughter's husband will be the next king of England......ambitious English nobles will have no problem putting sisters and daughters in his way, hoping for just such an outcome (H7 pulling an E4).
 
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