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The House of Trastamara rose into a great dynasty, stemming from Henry II, from whom the dynastic name came. His progeny soon became rulers not only of Castile, but eventually of Aragon, as Henry's grandson Ferdinand I ascended to the latter's throne by virtue of the Compromise of Caspe[1]. Both branches, however, would re-merge as a dynastic crisis in Castile led to the ascension of Isabella, John II's daughter and Henry IV's sister. Isabella then married Ferdinand II of Aragon in 1469, uniting the crowns of Castile and Aragon in a marital union.

The two, dubbed the Catholic Monarchs for their role in ending the Reconquista (and enacting controversial laws with regard to Muslims and Jews) would be known for consolidating power, and for discovering the New World[2] through their sponsorship of Columbus.

Castile and Aragon were secure, but the future of the Trastamara dynasty was uncertain until Isabella bore an heir. A daughter, also named Isabella, was born in 1470 and was heiress presumptive. In order to curry favor with Portugal (and bring an end to her intervention in the Castilian succession), she was betrothed to Afonso of Portugal.

However, a son was born to Isabella and Ferdinand in 1478, a healthy baby boy[3] named John (or Juan in Castilian). As he would end up being Isabella's only son, his mother would pay a lot of attention to him. John would be raised and educated as an heir to the throne would be, as his grandfather and namesake John II of Aragon warned his son (and Prince John's father) Ferdinand of letting a noble influence the young prince.

A betrothal for the young Prince was another priority of Isabella and Ferdinand's court - primarily as France had begun to reassert itself. Charles VIII's meddling in Italy, the start of the Italian Wars[4], had led to an alliance with the ruling house of the Holy Roman Empire, the House of Habsburg. The agreement was for a double marriage alliance, wherein John would marry Emperor Maximilian's daughter, the Archduchess Margaret of Austria, and John's sister Joanna would marry Maximilian's son and heir Philip. Although John and Margaret were in an arranged marriage, the two surprisingly got along well, and combined with the sensuous nature of the Trastamara, would lead to many a bedding.

The 1490s were an interesting time in European history, as storm clouds brewed over the political and religious landscape, and the Age of Exploration took hold...

[1] An OTL agreement, that basically allowed the various components of the Crown of Aragon to keep their practical autonomy. Needless to say, the Crown of Aragon was... convoluted.
[2] Of course the Norsemen got there first, but no one knew it yet.
[3] POD. John was pretty sickly in OTL, and he died of tuberculosis at the age of 19 (and it was rumored that it wascomplicated by being very active in the bedroom)
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