WI: Maximilian I, Holy Roman Emperor and Philipp, Duke of Burgundy Switch Wives

Apologies if the title is a bit vague. But say that in 1490, it is Philipp of Austria, Duke of Burgundy, who weds Anne, Duchess of Brittany. While in 1492 (the date of his OTL annulment from Anne) or 1494 (the date of his OTL wedding to Bianca, Max marries Juana of Castile?

Obviously, in this scenario Charles VIII is married to Margarethe of Austria. I imagine that with Philipp not being bogged down in Hungary (like his dad) he might actually be able to do something about preventing Anne's forced marriage, or perhaps enforce the marriage between Charles VIII-Margarethe.

As to why Fernando and Isabel offer Juana to the emperor, Spain-Naples and the Empire have converging interests in Italy, as well as a mutual interest in controlling France (should Charles not wed Margarethe).

Thoughts?
 
Apologies if the title is a bit vague. But say that in 1490, it is Philipp of Austria, Duke of Burgundy, who weds Anne, Duchess of Brittany. While in 1492 (the date of his OTL annulment from Anne) or 1494 (the date of his OTL wedding to Bianca, Max marries Juana of Castile?

Obviously, in this scenario Charles VIII is married to Margarethe of Austria. I imagine that with Philipp not being bogged down in Hungary (like his dad) he might actually be able to do something about preventing Anne's forced marriage, or perhaps enforce the marriage between Charles VIII-Margarethe.

As to why Fernando and Isabel offer Juana to the emperor, Spain-Naples and the Empire have converging interests in Italy, as well as a mutual interest in controlling France (should Charles not wed Margarethe).

Thoughts?
Philip of Burgundy was too young for marrying in 1488 or 1490 and Anne needed an older husband not a boy younger than her. Maybe if Francis II of Burgundy lived until 1492 (Philip would be able to marry at the end of that July) a wedding between Philip and Anne would be possible. Plus with such POD Charles VIII would be already married to Margaret of Austria (12 years old in that January) and her dowry and unable to marry Anne for Brittany.

Only with Philip married to Anne and Margaret married to Charles both Juan and Juana are without husband as Maximilian at the OTL time of Juana and Philip’s wedding will be already married to Bianca Maria (or maybe a Jaggiellon princess)
 
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Philip of Burgundy was too young for marrying in 1488 or 1490 and Anne needed an older husband not a boy younger than her. Maybe if Francis II of Burgundy lived until 1492 (Philip would be able to marry at the end of that July) a wedding between Philip and Anne would be possible. Plus with such POD Charles VIII would be already married to Margaret of Austria (12 years old in that January) and her dowry and unable to marry Anne for Brittany.

Only with Philip married to Anne and Margaret married to Charles both Juan and Juana are without husband as Maximilian at the OTL time of Juana and Philip’s wedding will be already married to Bianca Maria (or maybe a Jaggiellon princess)

Well, if the POD lets Fransez II live longer, it might delay Maxi's second/third marriage.
 
Francis II living longer means, that Max could concentrate on Hungary so Habsburg spring campaign in 1491 could be more successful, although it is still not guaranteed, that Max would get the throne-IMHO his case was practically lost after sack of Székesféhervár in November 1490.
 
Well, if the POD lets Fransez II live longer, it might delay Maxi's second/third marriage.
Still from Max prospective a Jaggiellon princess would be a better political match and once she was proposed Bianca Maria was the best match possible as she had a enormous dowry and her uncle was a powerful ruler and a good ally of Maximilian before his fall.

Instead Kellan if we have Max remarrying to Bianca as OTL, Philip married to Anne and Margaret to Charles what do you think will happen to Naples?

And I wonder without Margaret who can be Juan’s bride? And as husband for Maria? Juana will marry Manuel here instead of Isabel and Maria
 
Still from Max prospective a Jaggiellon princess would be a better political match and once she was proposed Bianca Maria was the best match possible as she had a enormous dowry and her uncle was a powerful ruler and a good ally of Maximilian before his fall.

Instead Kellan if we have Max remarrying to Bianca as OTL, Philip married to Anne and Margaret to Charles what do you think will happen to Naples?

And I wonder without Margaret who can be Juan’s bride? And as husband for Maria? Juana will marry Manuel here instead of Isabel and Maria

For Juan there aren't many royal options who would have an interest for Spain. His cousin in Naples (Giovanna of Naples) might be considered, but I doubt it'll be considered seriously. Henry VII might seek to dust off Juan's betrothal to Anne/Katherine of York as part of a double match (he apparently did consider resurrecting some of Edward IV's plans for his daughters at some point), but I'm not sure if the Spanish would take her.

@BlueFlowwer might have some ideas about Italian ladies for Juan. I'd personally find it hilarious - if unlikely - if Ludovico offers Bianca and her outrageous dowry to the Spanish instead of the emperor (IIRC he offered her to the French too) - sort of as a way to "mend fences" with the Trastamara if he were to have his nephew-Isabella of Naples' marriage annulled.

As to the Neapolitan future - it's difficult to say. Fernando II was itching for an Italian adventure until after the Siege of Granada (Isabel had basically promised him that if Aragon backs Castile in conquering Granada, Castile will back Aragon in Italy AIUI). Then, Ludovico's invitation to Charles gave Nando a reason to get involved
 
For Juan there aren't many royal options who would have an interest for Spain. His cousin in Naples (Giovanna of Naples) might be considered, but I doubt it'll be considered seriously. Henry VII might seek to dust off Juan's betrothal to Anne/Katherine of York as part of a double match (he apparently did consider resurrecting some of Edward IV's plans for his daughters at some point), but I'm not sure if the Spanish would take her.

@BlueFlowwer might have some ideas about Italian ladies for Juan. I'd personally find it hilarious - if unlikely - if Ludovico offers Bianca and her outrageous dowry to the Spanish instead of the emperor (IIRC he offered her to the French too) - sort of as a way to "mend fences" with the Trastamara if he were to have his nephew-Isabella of Naples' marriage annulled.

As to the Neapolitan future - it's difficult to say. Fernando II was itching for an Italian adventure until after the Siege of Granada (Isabel had basically promised him that if Aragon backs Castile in conquering Granada, Castile will back Aragon in Italy AIUI). Then, Ludovico's invitation to Charles gave Nando a reason to get involved
Bianca Maria will have a much smaller dowry (less than a third of the one she brought to Maximilian) if she married anyone else as in OTL her dowry was part of Ludovico’s plan for receiving the Duchy of Milan from the Emperor as feud for himself (and so having the legitimacy needed for stripping the title formally from his nephew)...
If Gian Galeazzo do not consummate his wedding (and I think who pushing his nephew to make his duty was something who Ludovico really regretted later) then Isabella will be sent back to Naples with her dowry as requested by her father as Ludovico had little to do with such annulment.
Bianca Maria is born in 1472 so she is six years older than Juan (born in 1478) so most likely too old for him and that make a wedding between them improbable.
Isabella of Aragon-Naples also is out of question being born in 1470.
Naples can offer two princesses of the right age: Juana https://en.m.wikipedia.org/wiki/Joanna_of_Naples_(1478-1518) who was niece of Ferdinand II of Aragon or https://en.m.wikipedia.org/wiki/Charlotte_of_Naples (who can be also a French proxy).

If Gian Galeazzo and Isabella’s wedding is annulled then Ludovico will not have any need to marry Bianca Maria to Maximilian with that kind of dowry so we can have a wedding between Maximilian and Juana.

The POD might butterfly the death of Infante Afonso of Portugal.
For me the deaths of both Francis Phoebus of Navarre and Alfonso of Portugal are pretty much inevitable
(the first can live only if he do not ever think to marry la Beltraneja and Catherine is already engaged/married or still out of Ferdinand’s reach; the survival of the latter require either marrying Juana or Maria instead of Isabella or Juan having a very good health and likely at least one younger brother)...

[Yes, both deaths were too convenient for Ferdinand for him so I believe his involvement more likely than not]
 
Working on a plausible scenario for a Philip/Anne and Maximilian/Juana’s wedding:

  1. Main POD is in 1488 with Francis II of Brittany living until 1492 instead of dying
  2. the wedding of Isabella of Aragon-Naples to Gian Galeazzo Sforza, Duke of Milan annulled in 1490 as non consummated (and annulling this wedding we are most likely butterflying the Italian Wars, removing the hostility between Ludovico and Alfonso)
  3. Charles VIII of France married Margaret of Austria-Burgundy in early 1492 (Francis is still alive, will not support the wedding of Anne to Charles and while he is alive he can always remarry and have a son)
  4. Anne of Brittany marry Philip of Burgundy in August 1492 after her father’s death
  5. Maximilian will be engaged to the 15 years old Juana of Aragon and Castile in 1495 marrying her in the next year.
  6. Juan, prince of Asturias will marry either a surviving Isabeau of Brittany (OTL she died in the same year of her father) or Charlotte of Naples (maybe as French proxy princess).
  7. Manuel will marry first Isabella then Maria of Aragon (Isabella surviving to childbirth is pretty unlikely as she most likely do not wanted live

About Juan and Miguel eventual survival (and so the fate of Spain) or husbands for Bianca Maria and Isabella of Naples I really have no idea.
Maybe we can have earlier death of both Charles II of Savoy and his sister Yolande Louise (maybe him dying in 1493/4 and she some months later) so Bianca will marry Philibert II in 1495/6
 
What about Bianca to Janos Corvinus (say Beatrice of Aragon is somehow unable to prevent the match)?
Pretty unlikely to go ahead, before the POD and will complicated more things in Hungary. At this point why do not have Bianca marrying James IV of Scotland around 1492 as was proposed and kill off her childless (or with only one or two daughters) in 1500/2 freeing James for his OTL match with Margaret Tudor?

I believe who the only match for Janos who would have some chances to go ahead would be one with Isabella of Aragon-Naples when she was sent back at home from Milan (but that would require a longer living Matthias Corvinus) and would still mess too much things in Hungary...

EDIT:
If not James, mess for mess and using an earlier POD prevent the 1482 death of Bianca Maria’s first husband (and maternal first cousin) Philibert I of Savoy...
Her namesake (and paternal first cousin) Bianca of Montferrat can marry Charles of Savoy as OTL (only her husband will be the brother of the Duke instead of being the Duke himself)
 
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At this point why do not have Bianca marrying James IV of Scotland around 1492 as was proposed and kill off her childless (or with only one or two daughters) in 1500/2 freeing James for his OTL match with Margaret Tudor?

That sounds like an awesome idea (well, besides the fact the part where she dies). Let's go with that one.
 
That sounds like an awesome idea (well, besides the fact the part where she dies). Let's go with that one.
Well she still died young and childless in OTL... Or you can go with either Savoy option:

Maybe we can have earlier death of both Charles II of Savoy and his sister Yolande Louise (maybe him dying in 1493/4 and she some months later) so Bianca will marry Philibert II in 1495/6

If not James, mess for mess and using an earlier POD prevent the 1482 death of Bianca Maria’s first husband (and maternal first cousin) Philibert I of Savoy...
Her namesake (and paternal first cousin) Bianca of Montferrat can marry Charles of Savoy as OTL (only her husband will be the brother of the Duke instead of being the Duke himself)
 
Well she still died young and childless in OTL... Or you can go with either Savoy option:

I like a Queen Bianca in Scotland. Maybe one or two short-lived children. Or perhaps she and James even manage a surviving son and Henry VII decides that it may be better to engage his younger daughter (Elizabeth or Mary) to James-Bianca's son, and free up Marge to wed elsewhere.

That said, how would a united Burgundy-Brittany fare? I imagine France would not be comfortable with such a state on its borders, correct? Would Philipp and Anne split the inheritances between two sons (assuming that Anne has a better obstetric record here than OTL)? Or would everything be left to one kid?
 
I like a Queen Bianca in Scotland. Maybe one or two short-lived children. Or perhaps she and James even manage a surviving son and Henry VII decides that it may be better to engage his younger daughter (Elizabeth or Mary) to James-Bianca's son, and free up Marge to wed elsewhere.

That said, how would a united Burgundy-Brittany fare? I imagine France would not be comfortable with such a state on its borders, correct? Would Philipp and Anne split the inheritances between two sons (assuming that Anne has a better obstetric record here than OTL)? Or would everything be left to one kid?
Maybe we can have James and Bianca marrying a little earlier (1490) and a son born in 1491 would be a good match for Margaret (marrying her in Scotland would still be the best option for everyone).

If Anne and Philip had two sons most likely the elder would get Burgundy and the younger Brittany. If Anne and Philip had only a daughter she would most likely marry either Margaret and Charles’ son or Orléans ATL son (or Francis of Angoulême if Louis of Orléans die childless as is likely here). If you want go for the maximum screw for France then have Charles and Margaret die childless while Anne and Philip’s only daughter (most likely another Margaret) marrying https://en.m.wikipedia.org/wiki/Antoine,_Duke_of_Lorraine... An united Lorraine, Burgundy and Brittany would be Francis I ATL nightmare...

Austrian’s succession would be pretty guaranteed by Max and Juana’s children. If Yolande Louise of Savoy survive and had children by Philibert II Savoy is fine. For Juan and Spain what we will do? He will marry Charlotte of Naples, Isabella of Brittany or die unmarried? Spain will be inherited by a child of Juan, Miguel of Portugal or a son by Max and Juana?
Miguel inheriting Spain and marrying ATL Eleanor of Austria or Madeleine of Navarre would be interesting (specially if the latter ended as heiress of Navarre). Max and Juana’s daughters can end as Queens in Poland and Bohemia/Hungary and Duchess of Milan (as daughter-in-law of Ludovico and Beatrice)
 
For Juan and Spain what we will do? He will marry Charlotte of Naples, Isabella of Brittany or die unmarried? Spain will be inherited by a child of Juan, Miguel of Portugal or a son by Max and Juana?

I wonder if Juan will be able to manage kids? OTL, his health was rather precarious FWIG, so I wonder if even if he does marry, he will manage children? OTL Charlotte married in 1499 and had her first kid the following year. But even if she weds Juan earlier here (say 1495), that's not to say that she's necessarily going to be able to get pregnant before he dies. OTOH, she could just as easily pop out more than one (1496, 1497 and a posthumous one in 1498), I suppose.
 
I wonder if Juan will be able to manage kids? OTL, his health was rather precarious FWIG, so I wonder if even if he does marry, he will manage children? OTL Charlotte married in 1499 and had her first kid the following year. But even if she weds Juan earlier here (say 1495), that's not to say that she's necessarily going to be able to get pregnant before he dies. OTOH, she could just as easily pop out more than one (1496, 1497 and a posthumous one in 1498), I suppose.
Is pretty unlikely who Juan will marry before 1496 so I think who they can not have more than two kids if they marry as soon is possible..
 
Trying to work on some trees
Maximilian I, Holy Roman Emperor (1459-1522) marry a) Mary of Burgundy (1457-1482) in 1477 b) Juana of Castile and Aragon (1479-1540) in 1496

1a) Philip of Burgundy (1478-1508), Duke of Burgundy and Brittany
2a) Margaret of Burgundy (1480-1510), Queen of France
3a) Francis of Austria (1481)
4b) Eleanor of Austria (1497-?), Queen of Poland and Hungary
5b) Maximilian of Austria (1499-?), Holy Roman Emperor, Archduke of Austria, King of Bohemia
6b) Isabella of Austria (1501-?), Duchess of Milan
7b) Frederick of Austria (1503-1504)
8b) Mary of Austria (1505-1505)
9b) John of Austria (1507-1510)
10b) Joanna of Austria (1510-1512)


Ferdinand II of Aragon (1452-1518), King of Aragon and Sicily marry Isabella I of Castile (1451-1510) in 1469

1) Isabella of Castile and Aragon (1470-1498), Queen of Portugal, Princess of Asturias and Girona
2) miscarried son (1472)
3) Juan of Castile and Aragon (1478-1497), Prince of Asturias and Girona
4) Juana of Aragon (1479-1540), Holy Roman Empress
5) Maria of Aragon (1482-1522), Queen of Portugal
6) stillborn daughter, twin of Maria (1482)
7) Catalina of Aragon (1485-1520), Queen of England
 
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Maximilian I, Holy Roman Emperor (1459-1522) marry a) Mary of Burgundy (1457-1482) in 1477 b) Juana of Castile and Aragon (1479-1540) in 1496

1a) Philip of Burgundy (1478-1508), Duke of Burgundy and Brittany
2a) Margaret of Burgundy (1480-1510), Queen of France
3a) Francis of Austria (1481)
4b) Eleanor of Austria (1497-?), Queen of Poland and Hungary
5b) Maximilian of Austria (1499-?), Holy Roman Emperor, Archduke of Austria, King of Bohemia
6b) Isabella of Austria (1501-?), Duchess of Milan
7b) Frederick of Austria (1503-1504)
8b) Mary of Austria (1505-1505)
9b) John of Austria (1507-1510)
10b) Joanna of Austria (1510-1512)

Would Isabella not be considered for the king of Denmark here? It seems like a more prestigious match than merely duchess of Milan, no?
 
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