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According to wikipedia, the elder son of Edmund of Langley, Duke of York, and his Castilian infanta wife, Edward of Norwich, was betrothed to Beatriz, Queen of Portugal. However, when England and Castile/Portugal kissed and made up, the betrothal was cancelled. Beatriz later married Juan I of Castile. However, neither Beatriz nor Edward OTL had issue (there's talk of Beatriz having a shortlived son, Miguel, but some believe this is a mere conflation of Beatriz' with the grandson of the Catholic monarchs a century later), but what if the marriage had gone through and the house of York ended up ruling Portugal instead of England?
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