Henry VII of England and Isabella I of Castile: Unlikely Allies, Unwilling Contraries

Henry 7 and Isabella 1

A century before the Holy League was formed to combat a powerful woman who was Queen in her own right, and strip her of that right, there was another woman, a powerful ancestor of her late sister, the first Queen Regnant of England, and of her dreaded rival, Philip II of Spain. Her name was Isabella and this woman was the first to head this Holy League, as well as the first to set a precedent of this scale. Isabella’s path to the throne has been widely explored many times in countless biographies, and indeed she deserves many more for her rise as her English counterpart, is fascinating. But this thread is not about her ascension but instead of her leadership and bringing Christian countries together at a time when they couldn’t be farther apart.

Isabella was born in 1451, she came to the throne in the early 1470s, taking the crown instead of waiting for the Cortes to appoint a legal successor to her late half-brother, Enrique IV. Isabella *took* the Crown and she owed her ascension to no one else but herself. And she brought many nobles to heel and appointed many conversos and people of humble beginnings to important posts that of course caused a lot of dissension among the “Grandees” –the noblest families of Spain. But Isabella was there to stay, and her decisions would not be questioned –even by her husband. However, as we all know, there was a darker aspect to Isabella. This was an age of massive religious intolerance. Though there was the practice of “convivencia” or healthy living in Spain between Moors, Jews, Conversos (converted Jews) and Christians, this tended to fluctuate. Finally when the Turks made their intentions clear to encroach on the Italian peninsula and started taking on Eastern Europe, the Christian kingdoms became more hostiles. There were reasons for these hostilities. The Turks tended to capture Christians and sell to slavery and the women would fare worse. One of the few captives who managed to escape was a student at the time his country (Romania) fell to the Turks. His name is Georgius de Hungaria, his memoir bemoans how he saw “public selling ground, the poor captives are brought, bound with ropes and chains, as if sheep for slaughter. There, they are examined and stripped naked … There a son is sold with his mother watching and grieving. There, a mother is bought in the presence and to the dismay of her son. In that place, a wife is made sport of, like a prostitute, as her husband grows ashamed, and she is given to another man…”

Georgius’ memoir became a best-seller and was reprinted between 1480 and 1500. During these twenty years, Isabella was waging war on the Nazari Empire on the borders of Castile. This dynasty was the ruling dynasty of the last Taifa Kingdom on the Iberian Peninsula. Since the Reconquista started shortly after the Muslim invasion in 711, the Iberian Peninsula had been comprised of many of these kingdoms. Slavery was not exclusive to Muslim kingdoms, in fact, Christians practiced it too and as Downey notes in her biography of Isabella of Castile, at least two or three of the women in her daughters’ retinue were Moorish or African slaves. But  Christianity had become more militant and prone to paranoia since these developments. Isabella turned her faith in Spain into a fiercer weapon, with an arduous belief that they needed to expel the “infidels” from their Christian lands. At the same time, the Turks advance into the Italian Peninsula was a very real threat to Isabella. Even after Boabdil’s surrender on the second of January in 1492, she continued to press many monarchs to unite against further attacks. Many did not listen to her. They did not have to because if anyone was to suffer any attack, it would be Spain or Italy, and even then with so great a cost into this enterprise, the Turks were likely to withdraw once these were exhausted. But with a new Sultan, Bayezid II, who was more conservative than his predecessors, this was not so. Also, the enmity between the Vatican and France and the latter’s invasion to the papacy in 1496, made it possible for Bayezid to believe that Western Europe was vulnerable. Finally, when Isabella convinced many of the Italian city-states and Republic of Venice to turn against France, she turned to Henry VII and James IV.

James IV of Scotland said it bluntly, that it was not his business. Henry VII, more diplomatic, said that he would love to do something but he had no resources. Isabella however was not about to be dissuaded and she blackmailed him for the lack of a better word, with her daughter Katherine. One simple decision and she could call the whole engagement between his son and her daughter off.

Charles VIII wanted to take the Holy See as its prisoner and force the Pope into giving him Naples, the family there, the cousins of Ferdinand II of Aragon, Isabella's husband, were not loved and so this became easy for him, but as his campaign progressed and he found the city plagued with the new disease known as syphilis, things turned worse for him and this allowed for Isabella to convince others to turn against him and form a Holy League.
Charles VIII wanted to take the Holy See as its prisoner and force the Pope into giving him Naples, the family there, the cousins of Ferdinand II of Aragon, Isabella’s husband, were not loved and so this became easy for him, but as his campaign progressed and he found the city plagued with the new disease known as syphilis, things turned worse for him and this allowed for Isabella to convince others to turn against him and form a Holy League.


Henry VII finally relented and in March 1496, he agreed to form part of her new League, a Holy League that repelled France. That same month, saw the finalization of the marriage treaty between their offspring, with the seal of approval from the Pope, Alexander VI.

France was one minor objective of this league. Charles VIII had been obsessing over the throne of Naples, and although the Catholic Kings were not happy with having Ferdinand’s nephew on the throne, it was better than the French alternative. In December they were granted the title of “Catholic Kings” with the Pope praising them for their defense of the Holy See:

“You serve as a public notice and example to Christian princes, because your strength and arms have not been for the ruin and killing of other Christians out of ambition for territory and dominion but instead for the benefit of Christians and in defense of the Church and faith … Your reverence and devotion to the Holy See, so many times demonstrated, is once again patently clear in the recent war in Naples. To whom, then, is the title Catholic Monarchs better suited than to Your Majesties, who continually strive to defend and enlarge the Catholic faith and the Catholic Church.” (Pope Alexander VI, December 1496)


Less than four years later, a year after the Turks began to advance into Venice, Isabella once again contacted Henry VII, and reminded him of his promise. This time however, the King of England was not about to be cowed by his future daughter-in-law’s mother. Ambassador de Puebla, the Spanish Ambassador to England wrote to the Queen that the King of England “greatly praised” her intention and Ferdinand’s “of sending a fleet against the Turks but added that, although he was on very intimate terms with Venice, the Venetians had said nothing to him about their great need” and therefore, he felt his help was not required.

Both of these monarchs were very headstrong. They were going to have their will no matter what, but as often happens when strong personalities clash, one has to give in or both parties do and that is what happened. Isabella reflected that she could not blackmail Henry anymore, he had his own problems, and this was entirely her enterprise now. Besides, she could not afford to lose England as an ally over this. If she did, then England would seek France as an ally. So Isabella dropped the matter and each resolved to solve their own issues, domestic and foreign.

Meanwhile, Isabella and Henry VII’s Consort, Queen Elizabeth of York, remained in tight correspondence with each other. So much so that Elizabeth also wrote to her future daughter-in-law, Isabella’s youngest daughter and future Princess of Wales, Katherine of Aragon. In 1497 when Marguerite of Burgundy had married Prince Juan of Asturias, Elizabeth of York wrote to Isabella advising her to tell Katherine to practice her French with the Princess of Asturias as it would help her communicate with her son better when she came to England. The two women often asked each other about their offspring’s health and in spite of her higher rank, Isabella was always very cordial and polite to the Queen of England, and Katherine of Aragon herself, was very warm to her as well.

In addition to writing to Henry VII, Isabella was in constant communication with his Queen. It was not uncommon for Queens to communicate with each other, however higher position was, Isabella was always humble with Elizabeth and both women discussed their daughter and son's upbringing. Elizabeth of York noted that water in her country was not drinkable so the Queen Regnant would do well on telling her daughter to start drinking wine and she also added that since her daughter in law Margaret was with them, that she could practice with Katherine some French.
In addition to writing to Henry VII, Isabella was in constant communication with his Queen. It was not uncommon for Queens to communicate with each other, however higher position was, Isabella was always humble with Elizabeth and both women discussed their daughter and son’s upbringing. Elizabeth of York noted that water in her country was not drinkable so the Queen Regnant would do well on telling her daughter to start drinking wine and she also added that since her daughter in law Margaret was with them, that she could practice with Katherine some French.

“The Queen and the mother of the King wish that the Princess of Wales [Katherine] should always speak French with the Princess Margaret who is now in Spain, in order to learn the language, and to be able to converse when she comes to England. This is necessary, because these ladies do not understand Latin, and much less, Spanish.” (De Puebla)


It is hard to say how much influence did Isabella had in the Western European stage, the answer is likely to be a lot, but so many events happened that made this possible and she was not always successful. She recognized at some points her weaknesses, as well as her allies who also recognized their own weaknesses. In spite of these, Isabella recognized the importance of compromise and after her second youngest daughter married the King Manuel I of Portugal, she agreed with Henry VII with the betrothal of his eldest daughter Margaret with the King of Scotland. If both countries were at peace, it meant that her daughter as future Queen of England, would stir both countries into Spain’s influence and keep Scotland away from French interests. Henry VII also knew this very well. Henry VII saw things in the long run, and war was always too costly, peace was better and during his reign there was a mutual cooperation between England and Scotland where both countries set up law courts that prosecuted border criminals by a jury of Scottish and English peers –something unheard of years before.

Sources:

  • Tudors vs Stewarts: The Fatal Inheritance of Mary, Queen of Scots by Linda Porter
  • Isabella: Warrior Queen by Kirstin Downey.
  • Katherine of Aragon by Patrick Williams
  • Six Wives and the Many Mistresses by Amy Licence
  • Elizabeth of York: A Tudor Queen and her World by Alison Weir
  • Henry VII by SB Chrimes
  • A World Lit by Fire by William Manchester
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