One Infanta for one Infanta: Catalina for Juana

What if in 1501 or 1502 Juana of Castilla died without having produced a male heir for Maximilian? (Charles V being a girl or stillborn, although I'd prefer the former)
Would Ferdinand look at the recently widowed Catalina and point out to Maximilian that there's still an unmarried infanta, and didn't both poor Juana and her mother show themselves most fertile?
Since Catalina is below Maria in the line of inheritance of the spanish crown, I'm not sure if she would be as attractive to the emperor, but even if she was, would Henry VII actually release Catalina, if the pressure came not only from her parents but also from the Emperor?
 
Juana married Philip of Burgundy, not Emperor Maximilian.

I'm not sure that Ferdinand would give one more daughter to the Hapsburgs given how their relationship went but added pressure from the Low Countries (as well as some money) might get Catherine freed from Henry VII's grasp.

One potential second wife for Philip is Elizabeth of Denmark b 1485 so that can be instead of Catherine.
 
Juana married Philip of Burgundy, not Emperor Maximilian.

I'm not sure that Ferdinand would give one more daughter to the Hapsburgs given how their relationship went but added pressure from the Low Countries (as well as some money) might get Catherine freed from Henry VII's grasp.

One potential second wife for Philip is Elizabeth of Denmark b 1485 so that can be instead of Catherine.

I know that Juana married Philip the Fair, but the one organizing the marriages was Maximilian. (and on a personal note, Philip seems to me to be a non-ruling entity)
The presence of other potential brides (like Elizabeth of Denmark, but weren't there a few eastern heiresses floating around?) is, together with Henry VII's attachment to Catalina's dowry, one of the sticking points.
My main interest is in having Catherine as HRE Empress-consort or as mother of the emperor - considering the early POD, she might be less attached to religion than OTL, but likely more so than Juana. Also, since any children by her will come after those of Maria, queen of Portugal, how would her relationship with Ferdinand go, after Isabella's death? (and there's also a potential POD: with so many of her children predeceasing her, will we see an Isabella kicking the bucked earlier or cling on in sheer spite?)
 
A Portugese ruler of Spain is a interesting idea, but that depends on if Juana's child is a girl, if she is then she and Joao III of Portugal should marry at once.

As for Isabel I, with Juana's early death, I can see her deteriorating earlier, so she might die in 1502 perhaps.
Maria I of Castile would be a interesting idea, but I'm not sure that she had the ruling personality.
On the whole the iberian kingdoms benefit more from Juana's death, but unless Maria has a strong and steady hand, short term problems will arise.
 
What if in 1501 or 1502 Juana of Castilla died without having produced a male heir for Maximilian? (Charles V being a girl or stillborn, although I'd prefer the former)
Would Ferdinand look at the recently widowed Catalina and point out to Maximilian that there's still an unmarried infanta, and didn't both poor Juana and her mother show themselves most fertile?
Since Catalina is below Maria in the line of inheritance of the spanish crown, I'm not sure if she would be as attractive to the emperor, but even if she was, would Henry VII actually release Catalina, if the pressure came not only from her parents but also from the Emperor?

Max is already married to a barren wife, his daughter's refusing to remarry, and now, his only male heir is suddenly widowed. I wouldn't be surprised if Max starts asking for an annulment from Bianca in order to remarry - especially if Philipp were to get sick and not have a male heir. That said, I'm with @BlueFlowwer in that Fernando isn't likely to want another match with the Habsburgs. He'd already realized that he'd harnesses his chariot (Aragon) to horses that couldn't be controlled (Philipp, the Tudors). In fact, if he pushes a Trastamara girl at all, it would probably be his niece, Giovanna, dowager Queen of Naples.


I wouldn't be surprised if Max likewise "forces" Margarethe to likewise remarry. She refused OTL, and her dad allowed her to, but Philipp had other ideas. He was willing to let her marry to the widowed Henry VII or even to Henry VIII with a nice fat dowry. Fernando had also tried to marry her off into Scotland (rather than sending one of his own daughters). Here, with the line in "jeopardy", they might just insist that she take one for the team and remarry. (Wladyslaw II of Hungary would be hilarious - for either Margarethe or Catalina).
 
Also with a dead Juana Philip does not go to spain and die as otl, so he might live longer, thus butterflying the need for a margaret regency.
 
I think Eleanor of Austria marries to John as originally planned in this TL and Isabella the Queen of Denmark is married off to the King of Navarre..and Ferdinand remarries to Magdalene of Navarre, his grand-niece(if she even lives).
 
Some things to consider in this scenario:
a) Philip, Duke of Burgundy will have full choice on his new bride, no way his father will arrange his new wedding (but Maximilian will surely make suggestions)
b) any daughters of Philip and Juana will be heiress of Spain before Maria and her children so a wedding between Leonor and João is guaranteed
c) Ferdinand will be without any doubt regent for his grandaughter in Castile and Philip will be unable to prevent it
d) Ferdinand next bride will still be Germaine if he wanted remarry but that is unlikely with Juana dead and Eleanor as heiress and likely engaged to John of Portugal.
 
Some things to consider in this scenario:
a) Philip, Duke of Burgundy will have full choice on his new bride, no way his father will arrange his new wedding (but Maximilian will surely make suggestions)
b) any daughters of Philip and Juana will be heiress of Spain before Maria and her children so a wedding between Leonor and João is guaranteed
c) Ferdinand will be without any doubt regent for his grandaughter in Castile and Philip will be unable to prevent it
d) Ferdinand next bride will still be Germaine if he wanted remarry but that is unlikely with Juana dead and Eleanor as heiress and likely engaged to John of Portugal.


If Magdalene of Navarre survives, she will be the one who will marry Fernando not Germaine.
 
If Magdalene of Navarre survives, she will be the one who will marry Fernando not Germaine.
I think Ferdinand will still marry Germaine as their wedding was part of an alliance with her maternal uncle, plus the main reason for Ferdinand’s second wedding was the need of an heir for Aragon and Magdalene is too young (she will be only 12 in 1806 while Germaine is 18).
In any case with the regency in Castil almost guaranteed after Juana’s death and little Eleanor as heiress (and engaged to her cousin Jõao) Ferdinand is unlikely to remarry as Philip of Castile will not be anymore a danger for him.
 
The Habsburg family tree will look like this around 1502 (well excluding the part about Leonor who is full spoiler)

Maximilian of Austria, Holy Roman Emperor (b. 1459) m a) Mary, Duchess of Burgundy (1457-1482) b) Bianca Maria Sforza (b. 1472)
1a) Philip, Duke of Burgundy (b 1478) m a) Juana of Castile and Aragon (1479-1501) b) ???
1a) Eleanor, Princess of Asturias and Girona (b. 15 November 1498)
Leonor, Queen of Spain (aka Castile, Aragon and Portugal) (b. 1498) m João of Portugal (b. 1502) King of Spain
2a) Isabella (b. 22 February 1500)
3a) Mary (b. 18 July 1501)
4a) Margaret (b. 18 July 1501)​
2a) Margaret (b 1480) m a) Juan of Castile and Aragon, prince of Asturias (1478-1497) b) Philibert of Savoy, Duke of Savoy (b. 1480)
1a) stillborn girl (1497)​
3a) Francis (1481)
In this scenario I can see easily Philip remarrying to Catalina (or Juana of Naples, but the first is more likely) as Ferdinand has little to lose in remarrying his last daughter to the father of the first four girls in line for Spain (and while the girls are unable to inhereit Austria and can lose Burgundy their position in the spsnish line of succession is looked) and Philip also has interest in keeping good relationship with Ferdinand and Isabella as he will never rule in Spain now..
Margaret of Burgundy here is still married to Philibert of Savoy (who OTL will die in 1504 but can live a little longer) and I think who at this point is pretty clear who her miscarriage has made her sterile (so her father will not force her to remarry and Philip will not have the autorithy for force her until their father’s death)
 
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