The Older D. Juan

The scenario of Mary, Queen of Scots and D. Juan de Austria marrying is one that has always fascinated me. Although, IDK what would have to transpire to let D. Felipe II allow such a marriage to occur. And also, I doubt Mary Stuart would be overly eager to wed a royal bastard. D. Carlos, yes, D. Juan the Elder :confused:

Let's say that D. Felipe allows his half-brother to marry (perhaps after Elisabeth de Valois/Anna of Austria gives him a son, so that he doesn't feel so paranoid and order D. Juan's son killed). Besides the Scots Queen, who would make a good matriarch for a bastard cadet line of the Spanish Hapsburgs?
 
Would Juan count as a very important match for a Spaniard/Neapolitan noblewoman, or as a lower match for the daughter of a member of Europe's trade circle of kings?

Or, better yet, marry him to one of Cosimo I de Medici's daughters, then she's both. Through her mother, Eleonora de Toledo's family she's related to the duke of Alba, and through her father's line to the various Italian noble families.
 
Would Juan count as a very important match for a Spaniard/Neapolitan noblewoman, or as a lower match for the daughter of a member of Europe's trade circle of kings?

Or, better yet, marry him to one of Cosimo I de Medici's daughters, then she's both. Through her mother, Eleonora de Toledo's family she's related to the duke of Alba, and through her father's line to the various Italian noble families.

To be honest, the Toledos were a more distinguished family than the Medicis, whose ancestors were commoners. Given that Charles V's other illegitimate child married first a Medici, and then a Farnese (who were a family of considerably greater antiquity than the Medici), a Medici marriage for Don Juan seems totally plausible.
 
To be honest, the Toledos were a more distinguished family than the Medicis, whose ancestors were commoners. Given that Charles V's other illegitimate child married first a Medici, and then a Farnese (who were a family of considerably greater antiquity than the Medici), a Medici marriage for Don Juan seems totally plausible.

Maybe Isabella, the OTL Princess Orsini who got strangled by her husband with a dog leash (and then it was written off as an accident).

"Oh, look, the princess Isabella was taking the dog for a walk in her bedroom, tripped, and strangled herself with the leash.":p

. I'm pretty sure Juan would make a less crazy spouse.
 
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