WI John of Gaunt pushed his candidacy for the Castillian throne harder?

King Juan I had to contend with the hostility of John of Gaunt 1st Duke of Lancaster, who claimed the crown by right of his wife Constance, the eldest daughter of Pedro of Castille. The king of Castille finally bought off the claim of his English competitor by arranging a marriage between his son Henry and Catherine, daughter of Constance and John of Gaunt in 1387.
WI John of Gaunt wasnt pacified by the marriage of his daughter to the heir of Juan I and pressed his claim harder? By starting a war perhaps? Is this possible?
 
King Juan I had to contend with the hostility of John of Gaunt 1st Duke of Lancaster, who claimed the crown by right of his wife Constance, the eldest daughter of Pedro of Castille. The king of Castille finally bought off the claim of his English competitor by arranging a marriage between his son Henry and Catherine, daughter of Constance and John of Gaunt in 1387.

WI John of Gaunt wasnt pacified by the marriage of his daughter to the heir of Juan I and pressed his claim harder? By starting a war perhaps? Is this possible?

John of Gaunt gave the claim to Castile because a year after he left a group of English lords (called the Lords Appellant) seized power from the royal court. John returned to England and allied with the King, spending the rest of his life rebuilding royal power, leading to the destruction of the Lords Appellant in 1397.

Something needs to be done to maintain royal power in England, so that John of Gaunt can pursue his claims in Castile without distraction by politics in England. Basically, I think he needs England to remain stable so that his possessions in England can continue to finance is claim on the Castilian throne. Chaos in England means an end to those funds. If this is accomplished, then John of Gaunt can engage in a nice long, costly war with the King of Castile.

If John of Gaunt is engaged in this enterprise, then I think that his son, Henry Bolingbroke (Henry IV of England OTL) would probably come down to Spain to fight with him. In OTL Henry went to war in Lithuania in support of the Teutonic Knights, and went to Jerusalem on a pilgrimage. So in this TL his foreign trips are made to support his father.

The really big effect that this will have is if John of Gaunt wins the Castilian throne. Henry would be his logical heir, which would really throw the politics of England into a whole different set of circumstances. Without Henry will someone else act to overthrow Richard II, and thus begin that most popular and confusing of English wars, the War of the Roses? Who will lead the Lancasters if their leadership is the Royal family of Castile? How will everyone's favorite legitimized bastards the Beauforts come out of this royal rumble?
 
I think it would be a disaster. Nobody supports Gaunt in Castile and the combined Franco-Castilian fleet has already proved to be stronger than the English in this period (see here). Perhaps if he gets the support of the Portuguese and attacks by land... then there could be some victories thanks to the Welsh longbows, but ultimately I think that the vastness of Castile and the overextension of supply lines would own him and force his troops to retreat.
 
John of Gaunt gave the claim to Castile because a year after he left a group of English lords (called the Lords Appellant) seized power from the royal court. John returned to England and allied with the King, spending the rest of his life rebuilding royal power, leading to the destruction of the Lords Appellant in 1397.

Something needs to be done to maintain royal power in England, so that John of Gaunt can pursue his claims in Castile without distraction by politics in England. Basically, I think he needs England to remain stable so that his possessions in England can continue to finance is claim on the Castilian throne. Chaos in England means an end to those funds. If this is accomplished, then John of Gaunt can engage in a nice long, costly war with the King of Castile.

If John of Gaunt is engaged in this enterprise, then I think that his son, Henry Bolingbroke (Henry IV of England OTL) would probably come down to Spain to fight with him. In OTL Henry went to war in Lithuania in support of the Teutonic Knights, and went to Jerusalem on a pilgrimage. So in this TL his foreign trips are made to support his father.

The really big effect that this will have is if John of Gaunt wins the Castilian throne. Henry would be his logical heir, which would really throw the politics of England into a whole different set of circumstances. Without Henry will someone else act to overthrow Richard II, and thus begin that most popular and confusing of English wars, the War of the Roses? Who will lead the Lancasters if their leadership is the Royal family of Castile? How will everyone's favorite legitimized bastards the Beauforts come out of this royal rumble?

The problem is that Henry IV could not be the heir of Castille. John of Gaunt's claim came from his second wife, Constance of Castille, while Henry was born from John's first wife, Blanche of Lancaster. He would not have rights to the throne of Castille.
The only surviving child from John and Constance was Katherine, who IOTL married the son of Juan I, Henry III of Castille. She would be the legal heir of the throne, not Henry Bolingbroke.
 
Oops forgot that... Have Catherine made Queen of Castille and marry her off to England's royal family... (with Papal dispensation of course because of consaguinity...)
 
Oops forgot that... Have Catherine made Queen of Castille and marry her off to England's royal family... (with Papal dispensation of course because of consaguinity...)

Perhaps a good candidate could be Peter of Navarre, brother of Charles III of Navarre. Charles was married to a sister of Juan I of Castille, and maybe such agreement could be done. But I'm not sure how likely is it. If Juan and his sons are dead maybe Charles could even claim the Castillian throne on behalf of his wife. So John would have to fight the Navarrese king.
 
John of Gaunt.

I don't remember that much about this. I don't think that the Castilian nobles cared much for John of Gaunt. Had he become king, he would have utilized Gascon armies, since Gascony was the closest English territory to Castile. This would have lead to increased taxes and an erosion of English popularity there, I'm sure.
 
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