Castile and England

Could someone rule England and Castile by the 14th century, if so how long could it last along with other changes from it?
 
Just England and Castille, or a larger empire?

Eleanor of England was married off with Gascony as her dowry. It ended up never happening. Louis VIII briefly claimed the English crown successfully by right of her daughter. In a TL where Eleanor's final brother John leaves no male heir, it's not impossible for one of her children to successfully claim Castille, Gascony, Anjou-Normandy and England. It'd be one hell of a pain to protect and govern, but hey.
 
What about having John of Gaunt successfully claimed Castile? That would give Castile an English King with a claim on England. The only question is how to get the Lancastrians the English throne. Perhaps Henry IV still overthrows Richard II?
 
What about having John of Gaunt successfully claimed Castile? That would give Castile an English King with a claim on England. The only question is how to get the Lancastrians the English throne.
Do it the other way round, with deaths amongst the English royal family (druing the War of the Roses?) making it possible for a Castilian monarch to claim England successfully on the basis of their own descent from John of Gaunt?

EDIT: Oops! Missed the cut-off date...
 
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Do it the other way round, with deaths amongst the English royal family (druing the War of the Roses?) making it possible for a Castilian monarch to claim England successfully on the basis of their own descent from John of Gaunt?

You'd need an inconceivable number of deaths for that to happen. You'd need to extinguish the Mortimers, Lancasters, Beauforts, York, Bourchier, Stafford and Holland families before you'd get an English embassy sailing off to Castile offering anybody a crown.
 
Four possibilities:

- The English throne is inherited by Eleanor of England or through her by one of her children.
- The English and Castilian thrones are inherited by her daughter Blanche or through her by one of her children; keep John Lackland alive longer and this enters the realm of possibility.
- The Castilian throne is inherited by Eleanor of Castile (wife of Edward I) or through her by Edward II.
- The Castilian throne is inherited by John of Gaunt (jure uxoris) and through a consanguineous marriage back into the Plantagenet lineage combined with what is left of the Angevin empire.
 
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