In 1502, Arthur Tudor, the heir apparent to the English throne and the son of King Henry the VII, died in Ludlow Castle. King Henry the VII and Queen Elizabeth of York are beset with grief, and are inconsolable. The King sobs openly on his throne before his courtiers. Arthur has left behind his widow, the beautiful and noble Catherine of Aragon.

In 1503, Elizabeth of York dies, and the King is once more inconsolable. As he gradually emerges from his grief, he comes upon an idea. His son's widow, Catherine, is now without a husband. Could he possibly marry her? His advisors are completely against the idea, saying that there would issues of legitimacy with any of their children, and to top that she is his daughter in law, within the forbidden grounds of relations. Henry retorts that he will have his way, and orders his advisors to draw up a request from the Pope for a papal dispensation to marry Catherine.

Surprisingly, the Pope agrees to the marriage. Henry and Catherine are wed in early 1504, soon after consummating her marriage. Queen Catherine prays for an heir daily, but she and Henry are not blessed with children. Despite this, Catherine is a constant source of comfort for Henry, and cares for him as best she can. She also forms a close motherly bond with her stepson and heir to the throne, Henry. In 1509, Henry the VII dies, and Henry the VIII rises to the throne, crowned in the presence of his stepmother, Catherine.

If Catherine had married Henry the VII rather than Henry the VIII, how would history have been changed? Would Henry the VIII have still remarried several times in order to bear a son? Catherine most likely would have gone into a convent after her second husband's death, but what influence would she still have over England as the Queen Dowager?
 
This was discussed in OTL and the Catholic Monarchs refused. They knew their daughter would not be Queen for long and her children would not inherit the throne with Henry VIII waiting in the wings. Even if the Pope was agreeable to it, I do not think he would go over Ferdinand and Isabella's heads to allow Henry VII to marry THEIR daughter.
 
This was discussed in OTL and the Catholic Monarchs refused. They knew their daughter would not be Queen for long and her children would not inherit the throne with Henry VIII waiting in the wings. Even if the Pope was agreeable to it, I do not think he would go over Ferdinand and Isabella's heads to allow Henry VII to marry THEIR daughter.
If Isabella had died earlier is likely who Ferdinand will accept the lesser match for Catherine...

Maybe Henry VIII can marry Eleanor of Austria?
Henry VIII will marry Eleanor here without doubt...

Kate of Aragon can marry Henry Brandon pulling what her Namesake Kate of Valois did.
You are talking about Charles Brandon maybe?
 
This was discussed in OTL and the Catholic Monarchs refused. They knew their daughter would not be Queen for long and her children would not inherit the throne with Henry VIII waiting in the wings. Even if the Pope was agreeable to it, I do not think he would go over Ferdinand and Isabella's heads to allow Henry VII to marry THEIR daughter.

If by some miracle the Pope did go over Isabella's head, which given she was ill and dead by 1504 wouldn't be impossible, her devotion to the Catholic faith would mean she'd have no choice but to accept her youngest daughter's new marriage. And it might actually be a better match for Katherine. Henry VII doesn't seem to have been cruel to Elizabeth of York, so he'd probably be a decent husband by the standards of the time. But I don't see Henry VIII marrying Katherine's niece ITTL. Dispensation may be too difficult to swing with her aunt both his sister-in-law and his stepmother. Perhaps a Danish or French Princess here?
 
If by some miracle the Pope did go over Isabella's head, which given she was ill and dead by 1504 wouldn't be impossible, her devotion to the Catholic faith would mean she'd have no choice but to accept her youngest daughter's new marriage. And it might actually be a better match for Katherine. Henry VII doesn't seem to have been cruel to Elizabeth of York, so he'd probably be a decent husband by the standards of the time. But I don't see Henry VIII marrying Katherine's niece ITTL. Dispensation may be too difficult to swing with her aunt both his sister-in-law and his stepmother. Perhaps a Danish or French Princess here?
Papal dispensation at the time were continuously given and I do not see insurmountable obstacles for this wedding considering who Henry VIII and Eleanor were not directly related and Henry VII had married Katherine and not Juana. Only a wedding between their parents will make a (later) match between Henry and Eleanor canonically impossible.
 
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