alternatehistory.com

Juan, Prince of Asturias, was the son and heir of Isabella of Castille and Ferdinand of Aragon. He died in 1497, leaving a pregnant wife, Margaret of Austria. But six months later she would give birth to a stillborn girl. After this, with the later deaths of Juan's eldest sister, princess Isabella, and her son, Miguel da Paz, the inheritance passed to Joanna of Castille and Philip the Handsome, and Spain became a Habsburg possession.

But WI Juan still dies, but his only daughter (let's call her Isabella, in honour to her grandmother) lives and is healthy? When Isabella I dies in 1504 the six-years-old Isabella II would become queen of Castile, and Philip the Handsome doesn't get Spain. But the young queen still needs to marry someone. Who could be the happy prince that Ferdinand of Aragon would choose (let's say around 1512, when she would be 14) to marry his granddaughter and get all the Castilian and Aragonese possessions?
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