WI: Archduke Ferdinand II of Austria Marries a Different Second Wife?

Probably my favourite among the 16th century's Austrian Habsburgs - thanks in no small part to @SpaceOddity's TL, Now Blooms the Tudor Rose - the guy flipped the bird at his family and married a woman he loved rather than contracting a dynastic match as was expected of him (and Elizabeth, the Virgin Queen, was one of the possible spouses mentioned for him). But then, his darling Philippine died and he bowed to pressure from his family and married again. Only to still die with no sons - except the two that he'd had by his morganatic first marriage.

My question is this: suppose we leave Ferdinand II's second wife in the convent? She wanted to be a nun, OTL, and the daughters she had with Ferdy either went into a convent themselves, or died childless. Now, interestingly enough, Ferdinand's son, the Margrave of Burgau, married Sibylle of Cleves in 1600, when she was in her mid-40s. So, what if Ferdinand II were to marry Sibylle as his second wife? Ferdinand and Anna Caterina Gonzaga married in 1582, when Sibylle was already spinster-age (25yo). Now, I know Sibylle's Ferdinand's niece (but so was Anna Caterina), but could it have any difference on the outcome? A surviving, non-morganatic son for him, perhaps?

Alternately, I'm open to other suggestions for a Mrs. Ferdinand.
 
Charles of Burgau, his son, was betrothed to his cousin Anne de Medici in 1579, though nothing came of it, and Anne died in 1584.
However, if it's Ferdinand who proposes to Anne/her elder sister Eleonore... yes, that's another uncle-niece thing, but that's Habsburgs we're talking about.

More outlandish variant, though possible in the time window suggested: https://en.wikipedia.org/wiki/Anna_Vasa_of_Sweden
Still a Catholic by 1580, can be offered. With massive implications for PLC/Austrian future. Bonus: not a niece.
 
Anna Vasa had Protestant leanings already, so she need to be married to Ferdinand as soon as possible to prevent her from converting.
 
Anna Vasa had Protestant leanings already, so she need to be married to Ferdinand as soon as possible to prevent her from converting.
The window is 1580-1582, anyways she's the only non-incestual degree of relation Princess I was able to think of in this case.
 
John Vasa raised his son as Catholic with intention to enable him to run for Polish throne (although seeing how unpopular his decision was among Swedish nobility, he later unsuccessfully tried to force Sigismund to convert to Lutheranism-Sigismund, despite being beaten by father, refused). So if there is Ferdinand-Anna match, there must be change in Sweden. Vasa do not want Polish crown for son anymore, instead makes secret deal with Habsburgs-Anna's hand for renouncing PLC claims to Estonia once Ferdinand won election?
 
So if there is Ferdinand-Anna match, there must be change in Sweden. Vasa do not want Polish crown for son anymore, instead makes secret deal with Habsburgs-Anna's hand for renouncing PLC claims to Estonia once Ferdinand won election?
Well within the realm of possibility.
TTL Sigismund may also be married to his original suggestion of wife, AKA the OTL second wife of Charles IX.

It would be interesting if Ferdinand + Anna are elected as the PLC rulers, but Anna still has pro-Lutheran leanings (not to the degree of conversion, but being a sympathizer). In religious environment of the PLC the results may be... interesting.
 
Support of another Anna would be crucial-I mean Anna Jagiellonka. Candidates backed by her were the winnig ones.
Her initial plan, formulated while her husband was still alive, was to wed Anna Vasa and one of the nephews of Stephen Báthory and promote the couple to the throne.[33] However, this plan did not gain support among the nobility. She then planned to sponsor Sigismund Vasa to the throne. Initially, King John III did not want to let his sole heir out of his sight, but Anna managed to convince him.[32] As a back up plan, she pursued marriage between Anna Vasa and Maximilian III, Archduke of Austria, the other likely candidate to the throne.[33]
In OTL she was pretty ready to support Anne's husband for throne anyway. If Anna is an Archduchess by marriage, then the support of her aunt may go to Ferdinand + Anna.
 
Still, I think this match is unlikely. Ferdinand was older than Stephen Bathory and would not be expected to outlive him. Vasas should be aware about this, Habsburgs would also try their luck with younger candidate-likely Archduke Maximilian like IOTL.
 

Vitruvius

Donor
What about another niece, Maximilian's youngest daughter, Margaret? I realize her mother was pushing her for another avuncular marriage to Philip II (which ultimately didn't happen) but it would have the potential of tying up the Habsburg succession nicely if Rudolf and his brothers still fail to produce children and if Margaret and Ferdinand can manage a healthy son.
 
What about another niece, Maximilian's youngest daughter, Margaret? I realize her mother was pushing her for another avuncular marriage to Philip II (which ultimately didn't happen) but it would have the potential of tying up the Habsburg succession nicely if Rudolf and his brothers still fail to produce children and if Margaret and Ferdinand can manage a healthy son.
Interesting idea.
 
Charles of Burgau, his son, was betrothed to his cousin Anne de Medici in 1579, though nothing came of it, and Anne died in 1584.
However, if it's Ferdinand who proposes to Anne/her elder sister Eleonore... yes, that's another uncle-niece thing, but that's Habsburgs we're talking about.

More outlandish variant, though possible in the time window suggested: https://en.wikipedia.org/wiki/Anna_Vasa_of_Sweden
Still a Catholic by 1580, can be offered. With massive implications for PLC/Austrian future. Bonus: not a niece.

A Medici match could make things interesting. Particularly if Grand Duke Francesco still marries Bianca Cappello and tries to get their kid to succeed him. What about a double match? Karl of Burgau to Anna (who survives) and Rudolf II to her sister Maria (as was proposed OTL). Doesn't mean that both parts of the marriage go through, but it could make for fun times.

Now that you mention it, I find the idea of a Habsburg Poland very intriguing. I think it has massive implications for the Swedish future as well, since they'd be without OTL's Gustaf Adolf if Siggie marries Kristina of Holstein. How do you think it would happen if we have Ferdinand II being the Habsburg candidate instead of Maximilian III? And how do think it would go if the Imperial line still goes extinct as OTL? The next line would be kings in Poland, but Karl of Steyr or his son might try to jump the queue
 
I think it has massive implications for the Swedish future as well, since they'd be without OTL's Gustaf Adolf if Siggie marries Kristina of Holstein.
OTOH, if you combine half genetic material that produced Wladyslaw IV and half genetic material that produced Gustav Adolf... you get either a mediocre ruler or an extreme badass.
 
Ferdinand II as Habsburg candidate in 1587 would be seen as waste by both Habsburgs and Polish nobles due to his age.
From Polish POV: why should we elect a man, who is almost 60? He'll die soon and we'll need to repeat election (IOTL one of Siggie's advantage was his age, being just 21 he was expected to rule for decades, bringing some stability after 3 elections within 13 years).
From Habsburg POV: Why should we waste our money to support candidate, who is almost 60? He'll die next year and we'll need to spend our resources again to secure election of our candidate. Better select someone younger.
 
OTOH, if you combine half genetic material that produced Wladyslaw IV and half genetic material that produced Gustav Adolf... you get either a mediocre ruler or an extreme badass.

Could certainly make for an interesting time. So Siggie marries Kristina then?

Ferdinand II as Habsburg candidate in 1587 would be seen as waste by both Habsburgs and Polish nobles due to his age.
From Polish POV: why should we elect a man, who is almost 60? He'll die soon and we'll need to repeat election (IOTL one of Siggie's advantage was his age, being just 21 he was expected to rule for decades, bringing some stability after 3 elections within 13 years).
From Habsburg POV: Why should we waste our money to support candidate, who is almost 60? He'll die next year and we'll need to spend our resources again to secure election of our candidate. Better select someone younger.

Good point. With Ferdinand married to Anna, would the Habsburgs back Siggie's play for the throne? Or would they still field Maximilian III? Do you think Ferdinand-Anna would produce (male) issue?
 
Good point. With Ferdinand married to Anna, would the Habsburgs back Siggie's play for the throne? Or would they still field Maximilian III? Do you think Ferdinand-Anna would produce (male) issue?
In first place, I think, John Vasa would not like to marry his daughter to man, who is 40 years older than her, if he he wants her to became Queen of Poland one day. He will be as much aware about his age disadvantage as I am.
 
In first place, I think, John Vasa would not like to marry his daughter to man, who is 40 years older than her, if he he wants her to became Queen of Poland one day. He will be as much aware about his age disadvantage as I am.

Except, his hope is for Siggie to become king of Poland, Anne's treaty bait just like any other princess of her generation. It's not like Ferdinand was senile or infertile - he had kids, just none who were recognized by the Habsburgs as legitimate. And so long as Rudolf II stood in the way of his brothers marrying, there would've seemed a good chance that she would be the mother to an emperor or at the very least, mother to the wife of an emperor/king of Spain.
 
OK. So in such case there is chance, that more than one Habsburg would run for Polish crown in 1587-Ferdinand and Maximilian (nothing new, but that would decrease Habsburg chances).
 
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