I've always had a soft spot for Pedro the Cruel (aka Pedro the Just) of Castile. His victory over Henry of Trastamara would have monumental consequences both for Iberian Kingdoms and for Europe in general (I will list some of them further down).
While there are a few threads on the forum discussing the possibility of his victory over Henry they are all rather short and usually either discuss earlier PoDs (e. g. Joan of England surviving and marrying Pedro) or more decisive battle of Najera (with Henry being killed or captured in battle). The former is definitely plausible, but would alter 1350s and 1360s quite a bit, while the later doesn’t strike me as all that consequential (after all in 1367 Henry has a son as well as two brothers who could potentially lead the Trastamara party to victory even without Henry).


IMHO the main reason for Pedro losing the Castilian Civil War were not particular mistakes on his part or successful moves on Henry’s, but rather the military dominance of du Guesclin’s routier army over Castilian one. So, if we want Pedro to retain his throne, we need to either occupy or counterbalance routiers until the Caroline Phase of the Hundred Years’ War starts. The latter was successfully done IOTL with the help of Edward the Black Prince in 1367, but the relations between Pedro and Edward quickly deteriorated mainly because Edward didn’t receive his pay as per treaty of Libourne and thus Pedro was left to his own devices in 1368-1369 and was defeated and killed. Presumably Pedro didn’t pay Edward simply because he was unable to raise such an enormous sum.

The PoD I present is Pedro marrying Philippa of Clarence as part of negotiations with English. Philippa is the eldest granddaughter of Edward III and has just reached marriageable age in 1367. IOTL, she married Edmund Mortimer but of course king of Castile is a way more prestigious match (there are conflicting records about when exactly Philippa was betrothed to Edmund IOTL, but for the purpose of this PoD let us pick the latest option 1368).
Pedro on the other hand is in his thirties, has not legitimate issue and both his wife and his beloved mistress are dead since 1361.
The purpose of the marriage is twofold: firstly, to bring Castile closer to England and secondly to be a neat way to subsidize Edward’s expedition. I am not sure how large Philippa’s dowry was IOTL, but presumably if she has a royal marriage, it definitely should be quite large. So Edward’s army can at least partly be subsidized with his niece’s dowry.

I am not sure if such an arrangement is plausible, but if it does happen consequences are massive. Presumably if the relationship between the Black Prince and Pedro is unstrained (or at least is significantly better than IOTL), the second invasion of Henry and de Guesclin would seem futile and probably doesn’t happen. In 1369 the Caroline Phase begins (even if IOTL Charles V summoned Edward because he already realized that Castille would fall to Henry, which is debatable, ITTL Charles presumably understands that Edward would help Pedro no matter what and thus he might as well go on with his plan). Thus, Henry would have very little military support and will stand no chance against Pedro and his allies.

Possible consequences of the PoD:

1. Castille itself has a radically different social structure.
a. IOTL Henry and his heirs had to give out large parts of royal domain for their supporters from lesser nobility that formed new aristocratic elites (since pedristas were active until mid-1380s Trastamaras needed their continous support for an extended period of time and thus royal domain suffered greatly). Quoting from Teofilo F. Ruiz-Spain's Centuries of Crisis 1300 - 1474:

The new dynasty came to power having given lavish grants and titles to supporting nobles, and territorial concessions to their royal allies in France and the Crown of Aragon. Henry II’s initial hold on the crown was a tentative one. New men came to the fore demanding a share of the victory, and the king also granted them substantial privileges and lands. Historians have long argued that the first decades of Trastámara rule witnessed the disappearance of the old nobility, a nobility dating to the late eleventh and twelfth centuries, and its replacement by a new nobility. In reality, the transformation was signaled by the rise to prominence of lesser branches of the great old noble houses, with a few new lesser nobles rising to very high status. This promotion in rank was tied to the granting of large estates and to extensive royal privileges. Such erosion of the royal domain and authority had, in turn, disastrous consequences for Castile over the next hundred years. Not unlike France or England in the late fourteenth and fifteenth centuries, the rise of the nobility led to waves of violence and instability. Securely grounded in their new economic power and high standing, the Castilian nobility challenged royal authority and even coveted, as was the case in the reigns of John II and Henry IV, the control of the Crown.

Pedro unlike Henry is a legitimate king and thus doesn’t need such drastic measures to obtain necessary support.

b. In the first half of XIV century one of the main pillars of royal power was municipal nobility (or more precisely non-noble municipal knights). At first kings bought their support against magnates by granting municipal knights’ extensive privileges, but since the latter felt constant pressure by disenfranchised bourgeoisie, they continuously welcomed royal entrenchment in cities and thus by 1340s urban centers were under firm royal control. Once again, quote from Teofilo F. Ruiz-Spain's Centuries of Crisis 1300 - 1474:

In less than 50 years the non-noble knights monopolized municipal offices in most Castilian cities, bought most of the land around the cities, and gained control, as they did in Burgos and Avila, of the most important ecclesiastical benefices. In return the king hoped for, and often received, their military support against the magnates and access to the cities’ fiscal resources. Moreover, as the non-noble knights gained control of their respective cities, they came into conflict with those below them. Pressured from below by the disfranchised petite bourgeoisie, the non-noble knights welcomed royal interference in the affairs of the cities and, by the 1340s, the takeover of municipal administration by royal officials (the regimiento) became a political reality. For a brief period, royal control of the urban centers became one of the most significant gains of the Castilian monarchy, but then the disorders of the late fourteenth century weakened royal control anew.

IOTL many cities supported Pedro against Henry and thus were severely punished by victorious Trastamaras which greatly weakened both cities themselves and royal control over them.



Thus, if Pedro retains his throne Castile is a lot more centralized with a strong royal power based on resources from a reasonably large royal domain as well as prosperous cities under firm royal control which is a stark contrast to magnate-dominated early Trastamara Spain.



2. Pedro IOTL had a firm alliance with Portugal. His uncle Pedro of Portugal helped him in his wars against both Peter of Aragon and Henry of Trastamara. When Pedro of Castile was slain, it was Portugal that was the main base for anti-Trastamara action in Iberia. Ferdinand of Portugal, Pedro of Castile’s cousin waged several wars against Trastamaras (first claiming the crown of Castile in his own right, later supporting John of Gaunt’s claim).
Pedro of course is a very strong clamant to Portuguese throne in his own right, but he can further cement his claim by marrying Beatrice of Portugal to his son (who presumably should be born in early to mid 1370s roughly similarly to OTL Roger Mortimer birth date and thus ideally match Beatrice).
Moreover, before Trastamara coup Portugal and Castile had the same allies and aligned economic interests (both benefited greatly from maritime trade between Northern Europe and Mediterranean, both had Genoa as a most important trade partner and England as a main ally outside of Iberia). IOTL when Portuguese interregnum happened the nobility was split with a significant portion of it supporting Trastamara claim. It were municipal elites of 4 main Portuguese cities (Lisbon, Porto, Coimba and Evora) that bankrolled anti-Trastamara faction. The main reason for these was economic (i. e. retention of profitable maritime trade with Genoa, England etc.) as well as desire to cancel Ferdinand’s pro-noble reforms (which were conducted in order to fund extremely expensive campaigns against Castille).
If IOTL Pedro continues to rule Castille, Portuguese municipal elites have no reason to dislike the union with neighboring kingdom (because Ferdinan’s reforms would be unnecessary and Castile and Portugal economic and political interest would continue to be closely aligned) and thus we can encounter Castilian-Portugese union in 1380s.

3. Pedro had an advantage in the War of Two Peters against Peter of Aragon. Presumably if Henry of Trastamara is no longer a threat, he can continue pressing Aragon for economic, political (most important one being the termination of Trastamara support) and perhaps even territorial concessions (getting back Alicante, Elche and Orihuela as part of kingdom of Murcia)

4. If Pedro marries Philippa, presumably John Gaunt and Edmund Langley would have alternative brides. IOTL the marriages happened to establish a claim over kingdom of Castile. ITTL Pedro would have legitimate heirs related to English royal family without such a match and thus daughters of Peter with at best debatable legitimacy are not ideal brides for English prices. Does anybody have suggestions who John and Edmund would marry in such a scenario?

5. Perhaps the most consequential consequence of the PoD is alternative Caroline Phase of HYW. The battle of La Rochelle that crippled English fleet IOTL was won by Castilian navy. If Castile continues to be an English ally, Castilian navy either doesn’t participate or participates on English side. Thus, English are able to get significant reinforcements to Poitou and Saintonge as well as £12,000 that were supposed to be used to pay for service of local troops (IOTL this booty fell to the hands of Castilians). This potentially a least allows English to retain control over Poitou, Saintonge and Angoumois and perhaps even reverse some French gains made in previous years.
Moreover with English fleet still dominating the waters around France, the main reason for the disastrous Great Chevauchee of 1373 is gone. ITTL, it makes a lot more sense to bring reinforcements by see, as was done in previous years.
Thus, the Caroline Phase of HYW can be radically altered in 1372-1373, perhaps to the extent of it being a draw rather than decisive French victory.



All these consequences seem rather juicy, but I am not sure if the marriage of Pedro and Philippa is all that plausible. What do you guys think? (of course if you have comments on consequences of PoD rather than the PoD itself, I would be happy to hear those too).
 
interesting premise, although given by 1367 Pedro has a reputation for bigamy and I think he's already murdered the little boy which started the latest round of war...would Edward III really go for it?
 
interesting premise, although given by 1367 Pedro has a reputation for bigamy and I think he's already murdered the little boy which started the latest round of war...would Edward III really go for it?
Little boy being his half-brother Pedro? I don't think he was considered a little boy at the time, he was almost 15. At the very least it didn't really strain Pedro the Cruel's relationship with his allies (after all the Black Prince's involvement in the Castilian Civil War was 8 years after the event).


Bigamy is of course a more serious issue, but in late 1360s almost a decade passed since both Pedro's wife and his mistress are dead. Pedro can claim that he has matured (maybe even truthfully) and its not like English royal family were averse to marrying the illegitimate issue of a bigamist IOTL. So IMHO if political circumstances require such a match, it can be done. If they really require it is of course an entirely different question.
 
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I think Charles V of France can marry Philippa of Clarence if his first wife dies prior to the birth of Charles the Mad.
 
Maud of Lancaster was a greater heiress and married the count of Hainaut around this time.
The count of Hainaut is neither the King of France or the King of Castile and that kind of continental matches was quite different as England had still lands and interests on the continent at that time
 
The count of Hainaut is neither the King of France or the King of Castile and that kind of continental matches was quite different as England had still lands and interests on the continent at that time
Lumping the king of Castile together with the king of France is a false equivalency. The kings of England and France had been rivals for centuries while the kings of England had been trying to cultivate closer ties with the kings of Castile for generations by this time. Henry III, Edward I and Edward III all put major diplomatic efforts into strengthening relations between the two crowns. They did so precisely for your last point -- Castile was positioned very close to English Gascony.
 
Philippa of Clarence will not marry abroad unless she has a full brother as she was a great heiress.
Maud of Lancaster was a greater heiress and married the count of Hainaut around this time.
To be fair, when the negotiations presumably happen (1366 or 1367 the latest) Philippa's father Lionel is alive, healthy and about to be married for the second time. I don’t think the perspective of Philippa inheriting his estates looks all that close at this point.

Moreover, I don’t think that the perspective of Pedro potentially inheriting domains in England and Ireland should scare Edward all that much. If anything, they could potentially serve as a hook to ensure the favorable Castilian policy towards England or otherwise they can be easily confiscated (it’s not like Castile can really try retain those estates against the wishes of Plantagenets).

If after Lionel dies Edward really wants to revert these estates back to the crown (although as mentioned before there are arguments for Edward not to do it), I think there is a really neat way to do it.
Presumably Philippa’s dowry however large can it be (BTW how large can it be? Up to £10,000 perhaps?) would not be enough to pay for Black Prince’s army (even if ITTL Edward, helping the future husband of his niece, can be a bit more moderate in his pricing). While Pedro can raise some money on his own (he was ready to pay de Guesclin 200000 gold coins – presumably florins - in 1369, so he had some money, although of course it wouldn’t be enough to settle his OTL bill with Edward), he would probably still need to pledge some his territories in lieu of the rest of the payment. So, after Philippa inherits her father’s estates, the mortgage can be rearranged with English and Irish estates now serving as a collateral instead of Castilian territories. Or even perhaps these estates can be given to the Black Prince staight away in lieu of the rest of the debt.


@material_boy, what do you think about the proposed PoD and some of its consequences? I have been toying with the victorious Pedro for several years now, but the perspective of modeling the alternative HYW always seemed to daunting. It was your amazing TL that inspired me to approach it. So your opinion would be especially appreciated (although of course I would be happy to hear feedback from everyone).
 
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Lumping the king of Castile together with the king of France is a false equivalency. The kings of England and France had been rivals for centuries while the kings of England had been trying to cultivate closer ties with the kings of Castile for generations by this time. Henry III, Edward I and Edward III all put major diplomatic efforts into strengthening relations between the two crowns. They did so precisely for your last point -- Castile was positioned very close to English Gascony.
One is an ally, the other is the main enemy but I doubt who Edward III would feel comfortable with gifting Philippa’s considerable inheritance to the King of Castile.

To be fair, when the negotiations presumably happen (1366 or 1367 the latest) Philippa's father Lionel is alive, healthy and about to be married for the second time. I don’t think the perspective of Philippa inheriting his estates looks all that close at this point.

Moreover, I don’t think that the perspective of Pedro potentially inheriting domains in England and Ireland should scare Edward all that much. If anything, they could potentially serve as a hook to ensure the favorable Castilian policy towards England or otherwise they can be easily confiscated (it’s not like Castile can really try retain those estates against the wishes of Plantagenets).

If after Lionel dies Edward really wants to revert these estates back to the crown (although as mentioned before there are arguments for Edward not to do it), I think there is a really neat way to do it.
Presumably Philippa’s dowry however large can it be (BTW how large can it be? Up to £10,000 perhaps?) would not be enough to pay for Black Prince’s army (even if ITTL Edward, helping the future husband of his niece, can be a bit more moderate in his pricing). While Pedro can raise some money on his own (he was ready to pay de Guesclin 200000 gold coins – presumably florins - in 1369, so he had some money, although of course it wouldn’t be enough to settle his OTL bill with Edward), he would probably still need to pledge some his territories in lieu of the rest of the payment. So, after Philippa inherits her father’s estates, the mortgage can be rearranged with English and Irish estates now serving as a collateral instead of Castilian territories. Or even perhaps these estates can be given to the Black Prince staight away in lieu of the rest of the debt.
Only that estates had nothing to do with Lionel as they were Philippa’s inheritance from her mother( and were good enough for getting her a match with the second son of the King) meaning who they were not a potential inheritance but already belonged to Philippa who was the Countess of Ulster since her mother’s death.
 
Only that estates had nothing to do with Lionel as they were Philippa’s inheritance from her mother( and were good enough for getting her a match with the second son of the King) meaning who they were not a potential inheritance but already belonged to Philippa who was the Countess of Ulster since her mother’s death.
OK, I stand corrected (I knew that she was a countess of Ulster in her own right by the end of 1360s, but I believed she also got substantial inheritance after her father died).

I think, though, that my main point still stands. Having kings of Castile own a reasonably large domain in Ireland is not necessarily a bad thing for Edward III as it will add additional way to ensure Castile's friendship and apply a subtle pressure on its kings (as Castile really has no meaningful way to defend its Ireland domains should kings of England decide to confiscate it). The only way it can be dangerous is if these Ireland holdings were substantial enough to create a separate center of power in Ireland that could potentially challenge the English dominance. But I don't think this is the case.

Moreover, if Edward really has a problem with it, these domains can be mortgaged in order to guarantee payment for Black Prince’s army at the initial negotiations in 1366-1367 (i. e. without the need to renegotiate after Lionel’s death as I have initially suggested). Philippa while perhaps not particularly thrilled with parting with her mother’s inheritance can be compensated with a large enough dower within the borders of Castile.
 
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One is an ally, the other is the main enemy but I doubt who Edward III would feel comfortable with gifting Philippa’s considerable inheritance to the King of Castile.
It was pretty common in Castile to give some land to second and third sons (or even daughters), so expect Ulster to be given to a second son, if there is one.

Moreover, if Edward really has a problem with it, these domains can be mortgaged in order to guarantee payment for Black Prince’s army at the initial negotiations in 1366-1367 (i. e. without the need to renegotiate after Lionel’s death as I have initially suggested). Philippa while perhaps not particularly thrilled with parting with her mother’s inheritance can be compensated with a large enough dower within the borders of Castile.
Well, the figure of "Infantado/Infantazgo" existed in Castile, which was like a middle ground between an Ecclesiastical Fief and a Royal Fief, so that could be given to Philippa in compensation for Ulster.
 
It was pretty common in Castile to give some land to second and third sons (or even daughters), so expect Ulster to be given to a second son, if there is one.
Didn't Eleanor of Castile's brother effectively become a French lord by inheritance? Aumale, I think it was. That's what came to my mind.
 
Didn't Eleanor of Castile's brother effectively become a French lord by inheritance? Aumale, I think it was. That's what came to my mind.
Yes, her brother became the Count of Aumale, while Eleanor eventually received the County of Ponthieu and returning a foothold in northern France back to the Plantagenets. These were inherited through the family of their mother and second wife of Fernando III of Castile and León, Joan of Dammartin.
 
John of Gaunt's marriage is an easy one to solve. Just have butterflies keep Blanche of Lancaster alive longer.

Not sure about Edmund, though!
 
@material_boy, what do you think about the proposed PoD and some of its consequences? I have been toying with the victorious Pedro for several years now, but the perspective of modeling the alternative HYW always seemed to daunting. It was your amazing TL that inspired me to approach it. So your opinion would be especially appreciated (although of course I would be happy to hear feedback from everyone).
Oh that's very flattering. Thank you :coldsweat:

I think the TL you're proposing is plausible and interesting re: the development of ATL Castile and Caroline War. I'm not sure the marriage with Philippa of Clarence is the way to achieve it, though. I don't share others' concerns about her inheritance, but it doesn't necessarily fit into Edward III's plans to create spheres of influence for his sons. Philippa, if she's not marrying Mortimer (who had some smaller land claims in Ireland before inheriting the Burke estates through Philippa) would seem to make more sense for a Fitzgerald or Butler or a knight of the Garter who Edward wanted to establish as a peer without alienating anything from the crown.

You could argue that I am overestimating the importance of these spheres of influence. (This is around the time that Lionel gets a Visconti bride -- an arrangement negotiated to put pressure on the papacy to approve the Langley-Flanders marriage, which demonstrates that Edward III still had an overarching and interconnected dynastic plan.) But this is a period in which the Black Prince set out his own foreign policy. He does not simply rubber-stamp his father's agreements. It is TBP's decision to end the Castilian alliance when Pedro executed the prisoners from Nájera. Just a few years later, TBP vetoed his father's alliance with Charles the Bad. All of which is to ask, how would it matter to the Black Prince that his niece is queen of Castile? Or would TBP end the alliance anyway if Pedro acts the way he did in OTL?

Then there is also the issue of Pedro's not-great treatment of his wives. We don't know much about Lionel (relative to his four more famous brothers), but we see Edward III and Gaunt have very close relationships with their daughters. Edward made his favorite daughter one of the greatest landholders in England and Gaunt was so fond of his eldest daughter (apparently because she reminded him of his late first wife) that he didn't marry her off until her mid 20s. If Lionel has this sort of affection for Philippa then he may not be willing to entrust his daughter to a king like Pedro. (Though, honestly, I think this is a less important point. Not only only is it entirely speculative of Lionel's personal affections, but Lionel does demonstrate a commitment to his father's plans in going through with the Visconti match for the main purpose of furthering his brother's marriage prospects in Flanders. Still, I don't thin Pedro's treatment of his wives can be entirely discounted.)


Only that estates had nothing to do with Lionel as they were Philippa’s inheritance from her mother( and were good enough for getting her a match with the second son of the King) meaning who they were not a potential inheritance but already belonged to Philippa who was the Countess of Ulster since her mother’s death.
I very strongly suspect that the marriage contract handed the Ulster estate over to Lionel in its entirety and entailed it to his heirs, regardless of remarriage. Heiresses in weak negotiating positions often lost everything to their husbands and, considering both that a) Elizabeth de Burgh only became an heiress because her father was assassinated by his cousin -- i.e., the man who would inherit if Elizabeth did not -- and b) that Elizabeth's guardian was her mother, Maud of Lancaster, who was a member of the English royal family herself, it just seems very likely that the marriage contract gave Lionel everything. Maud was predisposed to favor the royal family as a relative herself and would be very strongly predisposed to screw over the Burghs who murdered her husband by disinheriting them in favor of Lionel.
 
I am terribly sorry for a much belated resonse: I have cought a covid and a pneumonia, which lasted for more than a month in total and after that I had to catch up with everything I missed during my illness.
I think the TL you're proposing is plausible and interesting re: the development of ATL Castile and Caroline War. I'm not sure the marriage with Philippa of Clarence is the way to achieve it, though. I don't share others' concerns about her inheritance, but it doesn't necessarily fit into Edward III's plans to create spheres of influence for his sons. Philippa, if she's not marrying Mortimer (who had some smaller land claims in Ireland before inheriting the Burke estates through Philippa) would seem to make more sense for a Fitzgerald or Butler or a knight of the Garter who Edward wanted to establish as a peer without alienating anything from the crown.

You could argue that I am overestimating the importance of these spheres of influence. (This is around the time that Lionel gets a Visconti bride -- an arrangement negotiated to put pressure on the papacy to approve the Langley-Flanders marriage, which demonstrates that Edward III still had an overarching and interconnected dynastic plan.) But this is a period in which the Black Prince set out his own foreign policy. He does not simply rubber-stamp his father's agreements. It is TBP's decision to end the Castilian alliance when Pedro executed the prisoners from Nájera. Just a few years later, TBP vetoed his father's alliance with Charles the Bad. All of which is to ask, how would it matter to the Black Prince that his niece is queen of Castile? Or would TBP end the alliance anyway if Pedro acts the way he did in OTL?

Then there is also the issue of Pedro's not-great treatment of his wives. We don't know much about Lionel (relative to his four more famous brothers), but we see Edward III and Gaunt have very close relationships with their daughters. Edward made his favorite daughter one of the greatest landholders in England and Gaunt was so fond of his eldest daughter (apparently because she reminded him of his late first wife) that he didn't marry her off until her mid 20s. If Lionel has this sort of affection for Philippa then he may not be willing to entrust his daughter to a king like Pedro. (Though, honestly, I think this is a less important point. Not only only is it entirely speculative of Lionel's personal affections, but Lionel does demonstrate a commitment to his father's plans in going through with the Visconti match for the main purpose of furthering his brother's marriage prospects in Flanders. Still, I don't thin Pedro's treatment of his wives can be entirely discounted.)

You point about spheres of influence is extremely important.

However, either I didn't get the rest of your argument correctly or the fact that TBP has an enormous influence over England's foreign policy seems to make the marriage more plausible, not less so. It is TBP who signs the treaty of Libourne, not Edward III. So presumably he can offer Pedro a hand of his niece as a part negotiation process and the fact that his father would prefer to construct speres of influence for TBP's brothers impacts his decision in a limited way. Of course, Edward III and Lionel can probably veto the marriage, but it is a prestigious match (a lot more than the one Philippa had IOTL) and not allowing her to marry Pedro after TBP offered or even alluded to it would unnecessarily offend an important ally.

The alienation between BTP and Pedro came only after the battle of Najera and thus after the PoD (presumably the marriage negotiation happens in 1366 or 1367 if they happen at all).
I do think the main reason for the fallout was the fact that Pedro didn’t pay for TBP’s services (either because he couldn’t do it or chose not to) and this is partly offset by the possible marriage (TBP can provide Pedro “discount for a future relative”, plus Pedro has more cash or collateral thanks to Philippa’s dowry). However, if the execution of prisoners played a more important role than I believe, I think it can be butterflied away (Pedro has more incentive to listen to TBP’s requests plus some of the prisoners can avoid being captured ITTL).

Of course, the weak point here is Black Prince offering the hand of his niece on his own. If you think it is implausible, I guess I would have to look for another PoD.

However, either I didn't get the rest of your argument correctly or the fact that TBP has an enourmous influence over England's foreign policy seems to make the marriage more plausible, not less so. It is TBP who signes the treaty of Libourne, not Edward III. So presumably he can offer Pedro a hand of his niece as a part negotiation process and the fact that his father would prefer to construct speres of influence for TBP's brothers means a lot less to him. Of course Edward III and Lionel can probably veto the marriage, but it is a prestigious match (a lot more than the one Philippa had IOTL) and not allowing her to marry Pedro after TBP offered or even alluded to it
 
However, either I didn't get the rest of your argument correctly or the fact that TBP has an enormous influence over England's foreign policy seems to make the marriage more plausible, not less so. It is TBP who signs the treaty of Libourne, not Edward III. So presumably he can offer Pedro a hand of his niece as a part negotiation process and the fact that his father would prefer to construct speres of influence for TBP's brothers impacts his decision in a limited way. Of course, Edward III and Lionel can probably veto the marriage, but it is a prestigious match (a lot more than the one Philippa had IOTL) and not allowing her to marry Pedro after TBP offered or even alluded to it would unnecessarily offend an important ally.

The alienation between BTP and Pedro came only after the battle of Najera and thus after the PoD (presumably the marriage negotiation happens in 1366 or 1367 if they happen at all).
You probably didn't get it because I didn't explain it terribly well. Even if we get past the issue of whether it makes sense for Edward and Lionel to support this marriage, it's not like Philippa would go to Castile straight away. Libourne would probably only include the promise of a marriage, and its details (her dowry, dower estates in Castile, the timing of her move, guarantees of her safety considering Castile's unstable situation at the time, etc.) would all probably be ironed out later. That means Nájera may go as planned and the Black Prince may still fall out with Peter, leading to the end of the alliance and the breaking of this betrothal before there's ever actually a marriage.
 
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