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This is something that's piqued my curiosity since I found out about it: Nicole de Lorraine, eldest daughter of Henri II, duke of Lorraine, was betrothed to both Louis XIII of France (until Henri IV died) and D. Carlos of Spain (middle brother of King Felipe IV). Ultimately, neither marriage took place and she was wed to her cousin, Charles IV, duke of Lorraine instead.

Archduke Albrecht (VII) of Austria and his wife, the Infanta Isabel Clara Eugenia, had two sons, Philipp (b.1605) and Albrecht (b.1607). Both boys died young, but had either lived, the elder would'vve succeeded their father as Holy Roman Emperor (in the most likely scenario, rather than Ferdinand II succeeding Emperor Matthias, we'd see Emperor Albrecht II (does the previous Albrecht of Habsburg who was king of Germany count?) and then Emperor Philipp II or Albrecht II/III)

WI both boys had survived - the elder to succeed to the purple, and the younger to establish a cadet line in the Spanish Netherlands. Said younger son marries Nicole and the Netherlandish line inherits the duchy of Lorraine (France will object, most likely), but could the Habsburgs hold this Brabant-Lorraine entity? Could it last? Or will it (be) split apart at earliest convenience?
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