John of Gaunt's Castillian Adventure Succeeds

John of Gaunt has always struck me as an interesting, educated and intensely ambitious man, so what if his ambitions for Castille were rewarded, and he managed to successfully place his wife Constanza on the Castillian throne? No doubt having an English-alligned Castille would prove a big problem for France in the Hundred Years' War. Though the lack of a male heir to the throne means there may be further problems down the road, unless John and Contanza's infant son survived into adulthood in this timeline
 
It's possible. All John would need to succeed would to get England and/or Portugal on his side.

For England, he could betroth his daughter Catherine of Lancaster to Richard of Bordeaux/Richard II. A papal dispensation would be needed, but considering Catherine married her uncle OTL it wouldn't be too difficult. For Portugal, I could see John pushing for Constanza's claim during the Treaty of Windsor.

IMHO, the most likely path to Constanza being Queen Regnant would be if John pushed a Jure uxoris claim. He and Constanza would be co-monarchs, and he is historically known to call himself the King of Castille. Should he and Constanza only have the one daughter, Catherine of Lancaster, then marrying her as in OTL to Henry III of Castile would be a strong possibility.

A more controversial marriage choice for Catherine could be Louis I of Orléans, who is closer in age to her, and might have a big impact on the Hundred Years War.

It'll be interesting to see what other people think.
 
Lancastrian Castile screws France, since Castile brings basically the whole Iberian peninsula with it. Charles the Bad of Navarre had his own ambitions and would surely throw his lot in with the English once more. Peter IV of Aragon already had English sympathies as a result of the duke of Anjou's ambition for the crown of Majorca, but Peter had never dared formalize an English alliance when he was surrounded by Trastámaran Castile and Valois France. Charles and Peter have axes to grind with France and they suddenly have nothing to fear from Castile in ATL.

As for an heir, one may come in ATL. John and Constance's marriage was loveless and it may be that they didn't have any relations after the mid 70s. There is speculation that she was pregnant again in the mid 80s, when in Castile, and if that's the case then they may have been trying for a son for exactly this reason.


It's possible. All John would need to succeed would to get England and/or Portugal on his side.
Gaunt had both English and Portuguese support in OTL 1386-8. Gaunt was given something like £26,000 from the exchequer and borrowed tens of thousands more from the crown on top of that -- a debt that Richard II forgave after Gaunt supported Richard throwing off the yolk of the Lords Appellant.


For England, he could betroth his daughter Catherine of Lancaster to Richard of Bordeaux/Richard II. A papal dispensation would be needed, but considering Catherine married her uncle OTL it wouldn't be too difficult. For Portugal, I could see John pushing for Constanza's claim during the Treaty of Windsor.
Catherine and Henry III were half-second cousins, not uncle and niece.

A marriage between Richard and Catherine makes no sense. Richard already had one claim to a foreign crown that he had neither the ability nor interest to pursue. Wedding Catherine only gives him a second, and the threat of an Anglo-Castilian personal union would only draw the Franco-Castilian alliance even tighter.


A more controversial marriage choice for Catherine could be Louis I of Orléans, who is closer in age to her, and might have a big impact on the Hundred Years War.
I've suggested this before and I think it's an interesting idea even if it is absolutely bonkers. Some of the pieces are there -- Gaunt offered to abandon his claim to the throne of Castile in exchange for Henry III dropping out of the Caroline War in the 1370s, but Henry refused. Both Charleses V and VI both tried to secure crowns for Louis, with Charles V trying to wed Louis to the heiress of Hungary and Charles VI supporting Louis's madcap Italian ambitions. But England never had anything to gain in supporting a French prince in Castile and France had a lot to lose by alienating the Trastámarans.
 
Gaunt had both English and Portuguese support in OTL 1386-8. Gaunt was given something like £26,000 from the exchequer and borrowed tens of thousands more from the crown on top of that -- a debt that Richard II forgave after Gaunt supported Richard throwing off the yolk of the Lords Appellant.

Catherine and Henry III were half-second cousins, not uncle and niece.
Ah, my bad. I got confused while going down the wiki rabbit hole.
 
An interesting thing would be if the York-Portugal alliance also worked out, so you have Edward of York married to the Portuguese heiress and Gaunt in Castile working together and supporting one another.
 
Top