What If Phillip II has no surviving male issue?

Ernest to Isabel, Albert to Catherine. Matthias could marry Philip's ATL daughter from fifth marriage.
Ernest and Isabel get Spain, Albert and Catherine-Netherlands. Maybe Albert would run for emperor ITTL after Matthias?
So Cath gets her OTL Brother-in-Law and Isabel with her maybe fertility Problems the never married Brother.

My Money is one Catherine for getting a few Children from her husband, maybe not 10 like OTL but about 5 or 6 pregnancies and maybe two living Boys and a couple living Girls should be in it for her.
I am not sure about Isabell.....
 
If Isabel marries earlier (which is more than likely) than IOTL her chances for surviving offspring increase.

Given how D. Felipe kept her on-side as a spare OTL, I'm not sure that that would happen. She's not marrying until Felipe's wife no. 5 can't have kids anymore (either cause she's dead or menopausal), which if the girl's a strapping (my autocorrect wanted to change it to strap-on :p) 16 in 1581, is likely not to be for another 15-20yrs (menopausal, not dead in childbed).

Also, as to a triple marriage, I'm not so sure. Even ICE's late periods didn't stop Felipe marrying his second daughter to the duke of Savoy, although he offered either to the duque of Bragança's heir, i.e. a non-Habsburg. So I'm not sure he'd waste all 3 on the Austrians TTL. And even if he does, he might spread it around:
Isabel to Ernst/Albrecht
Catalina to the duque de Bragança/duke of Savoy/second wife to Archduke Ferdinand II(if Felipe's swiping Ferdy's 2e wife)
Maria (girl-Felipe III) to OTL HRE Ferdinand II.
That way, no matter the outcome of these marriages, a Habsburg is left holding the Spanish baby and no fears of a reborn empire of Karl V's empire (which, come to think of it, he might marry ICE to Ferdinand II and Catalina to Ernst/Albrecht - but that might be too retroactive a look at things)
 
So who for Felipe's fifth wife? Christina of Lorraine?

Caterina de Medici wanted her favourite granddaughter to replace Margot as queen of Navarre, so probably not. Also, Felipe didn't like the French queen dowager much and had turned down a match with the bewitching Margot when the plainer Élisabeth died.

Anna Caterina Gonzaga or Eleonora de Medici or some other half-Habsburg princess seems likely. Although, if he wanted to, he might block the French petitions for an annulment of Henri IV's marriage and marry Madeleine de Bourbon - sure she's Protestant (but Felipe could be remarkably pragmatic - see his relationship with a certain Virgin Queen) but as long as her bro is childless, she's heiress to Navarre. It's a stretch, but it would be fun to see happen.
 
Caterina de Medici wanted her favourite granddaughter to replace Margot as queen of Navarre, so probably not. Also, Felipe didn't like the French queen dowager much and had turned down a match with the bewitching Margot when the plainer Élisabeth died.

Anna Caterina Gonzaga or Eleonora de Medici or some other half-Habsburg princess seems likely. Although, if he wanted to, he might block the French petitions for an annulment of Henri IV's marriage and marry Madeleine de Bourbon - sure she's Protestant (but Felipe could be remarkably pragmatic - see his relationship with a certain Virgin Queen) but as long as her bro is childless, she's heiress to Navarre. It's a stretch, but it would be fun to see happen.

Yeah that will be interesting to happen. Since it may mean that he gets to unite the whole of Spain, much earlier than possible. In this case, who gets France since Henry IV of France will certainly die childless if he remains married to Margaret of Valois.
 
Yeah that will be interesting to happen. Since it may mean that he gets to unite the whole of Spain, much earlier than possible. In this case, who gets France since Henry IV of France will certainly die childless if he remains married to Margaret of Valois.

The thing is, his Holiness can refuse to dissolve the Henri-Margot marriage on the grounds that Henri's a heretic. Once Henri takes the chalice that argument's gone. OTL Henri's marriage to Marie de Medici was due to her uncle, the grand duke's influence in Rome. And in the 1590s popes changed several times. Felipe can't block an annulment once he's dead either, and I can't see him repeatedly having to "buy" new votes to block the annulment every time the pope changes. Spain's already bankrupted 2ce in his reign, IDK if he'll go for a third out of spite against the king of France.
 
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