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A link between England and Portugal goes back to the recapture of Lisbon in 1147, but it becomes particularly strong in the late 14th century - largely through the activities of John of Gaunt.
Gaunt's involvement stems from his second marriage, in 1371, to the heiress of the king of Castile. Her father has been murdered two years previously by a bastard half-brother who has usurped his throne. Gaunt, with a chance to win Castile for himself, begins to play a role in Iberian politics. His opposition to the present regime in Castile makes him a natural ally of the king of Portugal.
Chances of success are much improved by the Portuguese victory over Castile at Aljubarrota in 1385. The following year the new Portuguese king, John I, proposes an alliance with England. It is formalized in May 1386 as the Treaty of Windsor.
Binding in its terms, and never revoked, this treaty is the reason why Portugal is often described as England's oldest ally.
Drivelling in TPD is not a mental health issue. We're just community blogging, that's all.
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