The pace never relented for Isabella, who reached her early fifties in the years following the half millennium of 1500. As she continued to deal with wars overseas and domestic unrest, there were two remaining children to launch in life, her daughters María andCatherine, and she was in the process of recalling Juana, now the heiress to the thrones of Castile and Aragon, back to Spain so she could be sworn as the next queen. Juana had to be prepared to govern. All three relationships had their own particular problems, and as a mother, Isabella still had much to do.

But the queen was not well. Normally undaunted in her willpower, drive, and energy, she began to suffer periods of debilitating fatigue. She had chills and fevers. She deferred, delayed, or stopped doing the kinds of things that had made her so successful in the past.

When Juana came home in 1502, riding into Toledo with her husband to be recognized as the heir to the thrones of Castile and Aragon, Isabella was unable to ride out to greet her and instead waited at the palace for her daughter’s arrival. King Ferdinand and Archduke Philip rode ahead of Juana, taking precedence over her as they entered the city, something that should not have happened to the future queen of Spain. The misstep showed that Isabella, who had so carefully crafted her own succession to the throne, was slipping. She had always used her indomitable will to shape events and how they were perceived, but she no longer had the strength to control things as she once had.

The problems were both physical and psychological. Isabella had some unspecified internal ailment, possibly cancer or perhaps something else. She had also suffered three serious personal blows: the deaths of Juan and Isabel, her two favorite children and the ones she had raised to replace her, and the death of her tiny grandson Miguel de la Paz, who would have inherited Castile, Aragon, and Portugal. Isabella’s hopes and plans for the future had been dashed, and now she was having difficulty recovering. In the months following Miguel’s death in July 1500, she was so distraught that she could hardly communicate.

Many activities had to be postponed. The humanist scholar Lucio Marineo Siculo, a Sicilian living at the Castilian court, told a friend that the court had virtually ground to a halt. “So great grief has swept over our most Christian princes and the whole court that no one has been able as yet to approach or even address the queen,” he told a correspondent, Fadrique Manel. “For the king and queen are bowed down with great distress, as is no wonder since within so brief a time they have lost three renowned princes, all legitimate heirs.”1

The problems went beyond this most recent tragedy. In public Isabella maintained her stoic demeanor, but pain and ill health ravaged her appearance. The good looks of her youth had faded. She grew overweight. She covered her head with an unflattering cap, perhaps for religious reasons or because her hair was thinning or had turned gray. Portraits capture her increasingly careworn appearance.

In private, her positive outlook had dissipated as well. A young nobleman who had lived in the court described Queen Isabella to Peter Martyr as “sorrowful,” something that he struggled to understand. The queen was admired and feared by her subjects, but political clout and status had not made her happy, he told Martyr, who agreed with him.2

Soon it became apparent to people throughout Spain that something was seriously amiss with the queen and consequently with the nation as a whole. As her vigor eroded, a great many other things started to disintegrate as well.

Alonso de Hojeda, for example, who had served in the Granada war and then traveled with Columbus, arrived back on the island of Hispaniola with some news: he told the Castilian colonists that Queen Isabella was very ill and was believed to be dying. Everyone knew that Isabella had been hard hit by the deaths in her family, but it was almost impossible to imagine such a strong, indomitable person being struck down. Columbus considered the story a malicious rumor, and his son Ferdinand later recalled it as an attempt by Hojeda to undermine Columbus’s administration and oversight of the islands.3

But as the reports circulated around the islands, a subtle change in behavior soon became apparent. Isabella had made it clear that she was a protector of the Indians, and that people who hurt them would be chastised and punished. But with her health declining, the colonists gradually became emboldened to behave more aggressively toward the native Americans than they had at first.

Would-be colonist Bartolomé de Las Casas, then a young man seeking to make his fortunes in the Americas, arrived in Hispaniola in 1502 and saw this transition firsthand. He had been among the inner circle knowledgeable about the discoveries from the beginning. He came from a converso family from Segovia that had moved to Seville,4 and his father and three uncles had accompanied Columbus on his second voyage to the Americas. Las Casas had decided to go there himself and later recalled how warmly he had initially been welcomed by the native Americans. Spaniards had been in the islands for a decade by then, and they were still seen as benign forces by many Indians.

But as people internalized the news that Isabella was failing, Las Casas noticed that attitudes toward Indians became much harsher. The Spaniards demanded that the Indians serve and work for them. If the Indians objected or rebelled, the Spaniards responded at times with monstrous cruelty, turning their hunting dogs upon them to disembowel them, or slicing the limbs off men, women, and infants.

Making problems worse was the fact that the class of settler heading to the New World had deteriorated. The first group had been simple seamen. Hordes of promising young men had joined Columbus’s second voyage. But so many of these first explorers had died of syphilis or other diseases or had been killed that it was no longer easy to attract explorers and colonists. The crown attracted new entrants by offering amnesty from execution or long-term imprisonment to convicted criminals if they would emigrate to the Americas. Lower-quality people were crossing the Atlantic as emissaries of the Old World to the New. Columbus called the Spaniards living in Hispaniola then “little else but vagabonds.”5

Las Casas said these cruel practices had erupted because it had become easier to conceal information from the queen. Deeply disturbed by what he had seen, he was becoming a human rights advocate, traveling back and forth between the Americas and Europe trying to get the government in Castile to put a stop to abuses in the New World.

But in these years, trying to conserve her health, Isabella focused primarily on securing Castile. The succession issues were pressing, and the death of Princess Isabel had left the kingdom’s left flank, its border with Portugal, vulnerable once again.

With Isabel’s death, King Manuel of Portugal, now thirty-one, was a bachelor again. Queen Isabella had tried hard to convince him to accept María instead of Isabel because the older sister had not wanted to remarry, but Manuel had been adamant in insisting on Isabel and rejecting María. Now Queen Isabella had to once again offer him María, who was fifteen years old, and hope that this time he would accept. And he did, in fact, eventually marry her.

This was an immensely awkward situation for María, of course. But as the fourth child, as a twin who had lost her sibling in utero, and as the third sister in the family, she was accustomed to taking what was left over after everyone else got their first choice. There are fewer records of purchases of clothing and finery for María than for her older siblings. Cloth was expensive, and María likely got hand-me-downs tailored to fit her rather than the same number of new garments made to order for her brother and sisters.

So she might be able to accept a hand-me-down husband as well. It must have been excruciating for her, because Manuel turned down the offer several more times. Finally, he reluctantly consented, and in April 1500 the Portuguese and Spanish royal families signed an agreement for the marriage. Her parents made the match a profitable one for Manuel. He would receive a dowry of 200,000 gold doblas, payable in three installments, and María would be comfortably self-supporting thanks to an annual income of 4.5 million maravedis, based on rents from Seville.6 And María would be well attended, adding to the grandeur of the king’s entourage. In May it was decided that María would have a household of forty-seven, including six ladies-in-waiting, a chief of staff, a majordomo, scribes, accountants, footmen, and four pages. In addition, she would be accompanied by “two or three white slaves.”7 They were most likely to have been Russian or Greek slaves captured in war from Muslims but retained as slaves by the Spaniards.

There was one small problem. Manuel would be marrying the sister of his deceased wife, which would be skirting the prohibition in the book of Leviticus against marrying the brother or sister of a previous spouse. Manuel was, of course, a widower, and the ban was probably inapplicable to the situation, but just to be on the safe side, they decided to obtain a papal dispensation—an official religious forgiveness—granting specific approval for the union. Pope Alexander VI wasn’t as cooperative as he had been in the past. He was starting to feel that his contributions to Spain’s success were underappreciated, which had led to some testy scenes in the Vatican, and this time he required that Ferdinand make his nephew, Luis Borja, archbishop of Valencia in return. This had been Cesare’s former clerical post, but he had by now left the church. Rodrigo had come to feel that that seat, which had been his before he became pope, belonged to his family as a sort of hereditary right. The pope signed the dispensation on August 24.8

The wedding festivities for Manuel and María occurred in October 1500; the chronicler Hernando del Pulgar said that the king and the nobles of Portugal received the princess “with a great reception.”9 Queen Isabella’s Portuguese aunt and cousins showered María with attention and helped her make an easy adjustment to life in Portugal.

From the beginning, the reports on the union were favorable. “The Lady Queen dresses very well at all times, and she is plump and very gentle, thanks be to God, and the King shows her much love and is much attached to her, and all the gentlemen and ladies of the court do the same,” a courtier in Portugal wrote to Isabella and Ferdinand on November 24, 1500.10

Placid and easygoing, willing to let bygones be bygones, María re-ceived a warm welcome from her new husband. She was pregnant by the following summer and gave birth to a son, the future King João III, on June 6, 1502. She followed up the next year with a lovely daughter whom they named Isabel. And then she had another baby almost every year for a decade. Eight in all survived to adulthood, leaving the Portuguese succession nicely secured. “Great was the fruit that God gave them,” wrote the chronicler Fray Prudencio de Sandoval.11

With Queen María at his side, King Manuel’s life proceeded in an orderly and extraordinarily successful way. “From 1500 on, during his lifetime, the Portuguese obtained nothing but victories from Arabia to Malaysia, thoroughly controlling the Indian Ocean,” writes the Portuguese historian Antonio Henrique de Oliveira Marques.12 Isabella’s daughter was queen over the expanding Portuguese Empire at the time when her family at home in Castile was presiding over the vast and growing Spanish Empire. The explorerVasco da Gama had rounded the Cape of Good Hope and reached India by sea in 1498 and returned home to Portugal in a ship loaded with spices. Now the Portuguese had a pathway around the Ottoman bottleneck to Asia, and to its silks, spices, and other trade goods, by cruising around the coastline of Africa. The Portuguese also expanded their dominions in Brazil in South America, which was theirs through the division of the globe in the Treaty of Tordesillas of 1494.

It became apparent now how much that treaty had played into Isabella’s hands because now she was queen of Spain, and her daughter was queen of Portugal. Together they ruled over much of the world, and wealth poured into their countries, which gave them the resources to do many things. “Don Manuel was at the height of his royal grandeur. Honours, wealth, all things seemed to vie in laying their offerings at his feet,” writes the historian Edward McMurdo. They lived in “truly Oriental luxuriousness and decorations. From all parts of Europe came singers and players to amuse the King, and who performed in his bedchamber to lull him to sleep. Horse races, rides along the Tagus, sumptuous banquets, bull-fights, tilts and tournaments completed the palace life.”13

Queen María and King Manuel maintained the same focus on religious mission and Christian indoctrination in the New World as did Queen Isabella. The Portuguese sent many missionaries to Africa, South America, and Asia, swelling the number of Christian faithful. The great monastery of Belém, at the entrance to Lisbon, was, as the Cathedral in Seville had been, the starting place and final destination of every Portuguese trip to distant shores. Explorers attended mass there before setting out. Castile, of course, was similarly tying exploration to evangelization. For Queen Isabella and her daughter María, the alliance of Spain with Portugal was in all ways a success, and they attributed it to God’s favor resting on them.

María said this explicitly. Friar Hernando Nieto once asked her if she felt grateful to God for the gifts she had received in her life—for her happy marriage, for her children, and for the riches they enjoyed. Queen María fell to her knees and raised up her hands in prayer, saying, “I give you thanks, my great true God, for all the gifts and benefits you have given me.”14

But Queen Isabella’s work wasn’t finished yet. There was still one child left at home, Isabella’s youngest, Catalina, better known as Catherine of Aragon. During the years of deliberations over the marriage arrangements and the dowry, she had grown up being called the Princess of Wales. At last she was preparing to make the journey to England. Isabella hated to lose her and gave one excuse after another for delaying Catherine’s departure. A proxy marriage ceremony between Catherine and Arthur occurred on May 19, 1499, and in October, Prince Arthur wrote to Catherine asking her when she would arrive in person. In January 1500 the English royal family asked again. In April the Spaniards explained that Catherine’s departure had been delayed by an uprising of the Muslims, then was delayed again by stormy weather. In October the English asked once more when Catherine was arriving. In May 1501, Queen Isabella told them the girl’s departure had been delayed again because she was waiting to see her father before she left. On May 21 they said she was too ill to travel, and in July they said she was coming slowly because it was very hot in Spain.

The truth was that by 1501, when the travel plans were being finalized, Queen Isabella was widely recognized at home as being “in ill health,” and it made her reluctant to let her intelligent and thoughtful daughter out of her sight.15 The two women were very much alike in temperament and bearing, and both knew that once Catherine left Spain, she would probably never see her mother again.

When Catherine finally departed, in the summer of 1501, two years after the proxy wedding ceremony, her mother was too weak to accompany her to the coast to bid her farewell as she had done when Juana left for Flanders. They said goodbye in Granada. Catherine was fifteen years old when she set sail, on August 15, from Corunna, in the north. Her mother drafted anxious letters in her own hand to the ship’s pilots to ensure that Catherine would be protected as much as possible.

The trip was dangerous, as it had been for Juana and for Margaret. Ocean voyages were treacherous because shipbuilding techniques were still primitive, and people traveled aboard tiny vessels that were only marginally safe, even in calm waters. Catherine and her entourage spent six weeks making the voyage from Spain to England, crossing first the Bay of Biscay and then the English Channel. Early in the trip they were hit by a ferocious storm that bore down on them from the Atlantic Ocean. One of the ships in their fleet was lost, causing them to rush back to port to refit before they could set out once again. It was a terrifying ordeal, although Catherine remarkably retained her composure through it all.

Her ship dropped anchor at Plymouth on October 2, 1501. The princess was greeted by cheering crowds; King Henry VII had planned a spectacular arrival reception. He insisted on seeing the princess in person before the marriage ceremony was conducted. She raised the bridal veil covering her face for his inspection. He pronounced himself delighted and shared his exuberant reaction with her parents: “We have much admired her beauty, as well as her agreeable and dignified manners,” King Henry wrote to Ferdinand and Isabella on November 28, 1501. “… Great and cordial rejoicings have taken place.… The union between the two royal families, and the two kingdoms, is now so complete that it is impossible to make any distinction between the interests of England and Spain.”16

Catherine and Arthur were married at Old St. Paul’s Cathedral on November 14. There was a bit of confusion about whether the consummation of the marriage had occurred. The pale, slender young blond prince was said by some to have “swaggered boastfully out of his bride’s bedroom demanding beer,”17 while Doña Elvira Manuel, Catherine’s governess, said the young woman had been left “virgo intacta.”18 But Catherine and Arthur were still young, and the problem, if there was one at all, would surely rectify itself.

Now Isabella turned to her most difficult problem. Juana, the third-in-line, the daughter who had never been prepared to be queen, was now heiress to the thrones of Castile and Aragon, an inheritance that included Naples, Sicily, and as they were gradually becoming aware, immense lands across the Atlantic Ocean. She was bright and well-educated but had not been trained to rule, so it had been essential to recall her to Spain to begin preparing her for the huge tasks ahead. That meant she would need to travel back to Castile with her husband, the Archduke Philip.

But something had gone wrong with Juana. Perhaps Isabella had had a premonition of disaster when she stayed with her daughter so long in Laredo before she left for Flanders. It had not been a good sign when Archduke Philip had not been there to greet Juana when she arrived. In fact, the Flemish courtiers surrounding Philip, who were in the pay of the French king, had been trying from the beginning to drive a wedge between the young couple.

Philip’s standoffish behavior—leaving her cooling her heels while he slowly made his way to greet her—was a harbinger of worse things to come. It was a mismatch that had quickly become apparent. Juana was attractive, and Philip was quick to consummate the marriage. Soon Juana was pregnant. But the handsome and vain young archduke was accustomed to picking and choosing from among the comeliest women in Flanders and France, and in his eyes, Juana did not really measure up. Moreover, her seriousness and intense love for him left him bored and irritated. “He only cared for pleasure and amusement in his lively court at Brussels,” the biographer Christopher Hare wrote, and Juana’s “tears and complaints” of his neglect only made him impatient with her.19

Juana had been raised in a harmonious court infused with a sense of mission and purpose; she had been an admired and beloved child. But in Flanders she found it difficult to navigate the treacherous shoals of court politics, where people feigned friendship while they secretly maneuvered to undermine each other. The death of Philip’s mother when he was a small child had left the archduke open to manipulation by courtiers who learned how to control him through his interests, tastes, and libido.

Philip’s predilictions, consequently, were avant-garde verging on dissolute. He was, for example, a patron of Flemish painter Hieronymus Bosch, best known for his Garden of Earthly Delights. Bosch’s works, ostensibly on religious themes, depict fantastic and lewd humans and animals cavorting in dreamlike pastoral landscapes. The frequently pornographic and sado-masochistic imagery leaves the viewer uncertain whether the paintings are portraying a spiritual lesson or contemptuously mocking conventional morality.

The culture clash between the two kingdoms, Castile and Flanders, the latter dominated by the Burgundians, was immediately obvious, as it had been in the entourages of Princess Margaret and Prince Juan. Castile was sedate, solemn, austere, and religious; Burgundy was rollicking, sensual, and cynical. The companions whom Isabella had sent with her daughter were dismayed by what they considered the “moral corruption” at its court; the Burgundians thought the Spaniards were dowdy and puritanical.20 Flemish and French courtiers who wanted Philip to discard Juana soon found ways to discredit her and make her look foolish and, even worse, mentally incompetent.

Following the advice of his courtiers, Philip took control of Juana’s household by appointing new attendants for her from among the Flemish nobles and deciding how much they would be paid. This created tensions within the court. In some cases, the pay of the Flemings was decreased because the overall size of the royal household had grown, and more people needed to be paid than in the past. Some Spaniards who had traveled with Juana were not paid at all, moreover, and Juana was not given money to pay them herself. The Spaniards, meanwhile, were forced to conform to Burgundian customs and living standards and were treated as unwelcome outsiders.

The change of climate was a shock for the Spaniards as well. Juana’s Spanish entourage were chilled to the bone and demoralized by the cold and gloomy weather in northern Europe, and many of those who were able to do so went home, leaving her with a much smaller contingent of supporters. They were replaced by Flemish courtiers who took their orders from Philip, or more precisely, from the advisers who controlled Philip.

Conditions were particularly harsh for the crew of the fleet, who were forced to bide their time over the winter waiting for Margaret’s trip to Spain. Juana sought to rush Margaret’s departure but was not successful. Philip left the soldiers and sailors who had traveled in the fleet to fend for themselves in a harsh winter on the bitter northern European coast, where nothing had been done to prepare for their arrival or accommodation. Within the next few months, up to nine thousand of them died of cold and hunger.

This degree of intentional callousness stunned the Castilians. It had the effect of intimidating Juana’s remaining Castilian attendants and sent an important signal to the Flemings about how Spaniards could and should be treated.

Juana had no money to provide dowries for her ladies-in-waiting, which created a crisis for some of them. At least one Castilian attendant, from the high-ranking Bobadilla family, was consequently summoned back home for a Spanish marriage. The young woman remained loyal to Juana and decided to stay, along with eight other female attendants. But financial conditions were so difficult that the situation was inevitably untenable, and one by one they dropped away from Juana. Ultimately she was left almost entirely surrounded by Flemish courtiers, many of whom were actively working against her interests. Out of the thousands who had accompanied her in her bridal entourage, only the two or three slaves who had accompanied her to Flanders remained by her side. Presumably they had little choice in the matter.

This situation was a betrayal of Juana and a violation of her marriage contract. The accord of 1495, according to the historian Bethany Aram, had stipulated that both Juana and Margaret would receive annual allowances of 20,000 escudos to maintain themselves and their households.21 In Spain, that amount and more was liberally granted to Margaret, who received many other valuable gifts. But in Flanders, the money was disbursed to Juana through the Chambre des Comptes (House of Accounts) at Lille, which withheld it from her or allowed the money to be diverted to Flemish courtiers.

When Isabella learned about Juana’s dire financial situation in Flanders, she pushed her ambassadors there to make sure Juana received the money she was due. They tried to bribe top Flemish officials to make sure some money went to Juana, but other patrons were paying the same officials even more to advance their own ends, and the Spanish efforts were unsuccessful. Even gifts that were given to Juana were taken from her and distributed to others.

Philip seemed to intentionally exacerbate the situation. He refused to give his wife any money even for incidental expenses. In the eyes of her servants and Spanish envoys, she did not fight on their behalf, or did not fight effectively enough. She soon seemed resigned to the intolerable conditions.

A Spanish ambassador who visited the court in Flanders wrote that Juana “lived in such penury” and that her servants were “dying of hunger.”22 He said that Juana desperately needed financial support from her parents. In fact, the ambassador added, Philip was not allowing him to be fed either, for which reason he was pleading for cash to be sent to him from Castile.

Instead of giving Juana regular money, Philip lavished gifts on her, but at his discretion and his choice. He gave her valuable jewelry that had belonged to his family, and occasionally gave gifts and cash to her servants, which had the effect of making them more loyal to Philip than to her. In fact, they soon found they won more favor with Philip by circumventing Juana’s authority than by respecting it.

It was a classic abusive marriage, which leaves the subjugated partner confused and disoriented. Philip made Juana feel fearful, intimidated, and publicly humiliated; he withheld necessities and limited her access to money, friends, and family. “Philip… honed his sadistic treatment of Juana into a high art through a combination of sexuality, tenderness and intimidation,” writes the historian Nancy Rubin.23

Philip was himself dominated by one official in particular, François de Busleyden, the archbishop of Besançon, who had attained that same kind of control over the archduke that Álvaro de Luna had developed over Isabella’s father and that Juan Pacheco had developed over Isabella’s brother Enrique. Even the language used to describe the relationship was remarkably similar. Philip “would not know how to eat without [the archbishop] telling him to,” wrote Spanish ambassador Gutierre Gómez de Fuensalida, assigned to the Flemish court.24

Philip’s advisers controlled him by feeding his vices, as Álvaro de Luna had done with King Juan II of Castile, Isabella’s father. Juana was as little able to handle the situation as her grandmother Isabel had been when she found herself in a similar predicament, caught between her husband the king and his favorite.

On one occasion, the Spanish ambassador Fuensalida urged Juana to be more assertive in the relationship and to demand what she needed from the king when they were alone. Juana shook her head and sadly said that whatever she told Philip in private, he repeated to the archbishop. The latter, she told Fuensalida, was “absolute master of [Philip’s] soul.”25

There were soon signs that Philip had nefarious plans in mind for Juana. When her brother Prince Juan died in 1497, Juana went into mourning, but Philip quickly began calling himself Prince of Asturias, a title that now belonged to Juana’s older sister Isabel, who was married to the king of Portugal. Philip also began trying to find ways to get the French to support his claim to the Castilian crown, supplanting his sister-in-law Isabel, then the rightful heiress to the throne. Isabel’s death, and then the death of Isabel’s son Miguel, opened what appeared to Philip to be a direct route to control of all Spain. He seemed to view Juana’s existence as a nuisance. His entry into Toledo ahead of Juana in 1502 had not been accidental. He intended to displace her.

Philip’s attitude toward his children was chilling as well. He was controlling and abusive to Juana in connection with the births of their children, who began arriving perfectly on schedule. In late 1498 everyone was waiting with bated breath for the birth of a much-desired son, but on November 15 of that year, Juana instead gave birth to a daughter, Leonor. Juana was strong and healthy, and the delivery went smoothly.

Philip showed himself off after the delivery, dressing up in rich brocade and green silk to participate in jousts to celebrate the safe delivery of the child, earning the applause of the crowd. But he had privately told Juana that he considered the birth of a girl a disappointing failure, and that he would not provide any funds for the child’s support. According to the Spanish ambassador, the archduke had said: “Because this child is a girl, let the archduchess provide for the child’s keep, and then, when God grants us a son, I will provide it.”26

Juana nevertheless was soon pregnant again, and this time, in the city of Ghent, she delivered the desired male child. On February 24, 1500, she gave birth to a son, whom they named Charles. This was the child whom Queen Isabella in Castile had predicted, because of his birth on the feast day of Saint Matthias, would eventually become king of Spain.

A third baby, Isabella, was born in 1501 and was named for Juana’s mother. Sometime after little Isabella’s birth, Philip took the children away from Juana and arranged for them to be raised by others. This further traumatized her.

It is unclear how much Queen Isabella knew about what was happening, and what she could have done about it even if she did. She received only a partial picture from the ambassadors, and nobody seemed able to identify the strange dynamics that had enveloped Juana, although everyone agreed that something seemed badly amiss. The Spanish ambassadors prodded Juana to write to her mother but did not receive much of an answer as to why she did not do so more regularly. Under persistent questioning, she admitted that she missed her mother so deeply that it would hurt too much to try to write. She told a visiting cleric that she “could not think of her mother, and how far she was separated from her forever, without shedding tears.”27

For a variety of reasons, then, Queen Isabella wanted Juana to come home. She and King Ferdinand urged the young couple to come to Spain as quickly as possible, with their children, to secure their inheritance. Because of continuing tensions with France, the Spanish sovereigns told the young couple to travel by ship. By this point, Spain had been embroiled in a dispute with France for years over its invasion of Italy, and Ferdinand was still deeply aggrieved over continuing French possession of the border cities of Roussillon and Perpignan. If the French were to seize the heirs to the throne of Castile and Aragon, Spain would lose any leverage it had, and Juana could potentially be at physical risk.

But Philip insisted on traveling by land through France, nevertheless, where he agreed to give obeisance to King Louis XII in exchange for control of three towns on the frontier between their two countries. Juana refused to defer to the French, ostentatiously dressing in the Spanish style and performing a Spanish dance at a ball, angering their French hosts and embarrassing her husband, who seemed to have reached the point where he could hardly bear her presence.

That was the situation when the young couple arrived in Spain in 1502. To meet them at the border and escort them home to the court, Isabella sent her trusted friend Gutierre de Cárdenas, the man who had held the sword aloft when she had taken the throne in Segovia thirty years earlier. De Cárdenas had been a source of strength and a dependable ally to the queen from her teenage years, and she turned to him again for his counsel in handling the new family dynamics.

Isabella had not been able to stage-manage the initial entry of Juana and Philip into Toledo, but otherwise many other things went according to plan. They had come to the ancient Visigothic city because the Cortes was meeting there, and Isabella arranged for Juana to be sworn as heir apparent to her mother while Philip was given the lesser standing of prince consort. Then the couple went to Zaragoza, where the Cortes of Aragon swore the same oath to Juana, which was the first time they had ever named a woman successor to the realm. Philip was not happy when he realized that he had slipped down a notch in the succession. He did not want to be the king consort. Women had succeeded to the throne in Burgundy before, so he was not unfamiliar with the concept of women in positions of power, but he did not want it to happen to him. He was, in fact, furious.

The king and queen did their best to smooth the tensions. They attempted to get to know Philip better, to influence him, but he clearly cared more for entertainments than instruction. His boorish behavior, so different from his youthful charm, made these events uncomfortable for everyone. At a tournament in Burgos, he thought it was funny to throw leftover sweets into the crowd and watch poor people scramble for the scraps; he liked to masquerade in Turkish clothing and pretend to be a Moor. Isabella and Ferdinand nevertheless organized parties, banquets, and tournaments to keep Philip busy and amused. Pleasing Philip became even more important after the announcement that Juana was pregnant once more. Isabella and Ferdinand wanted Philip and Juana to stay in Castile for good.

But Philip was increasingly eager to leave. His close companion, Archbishop Busleyden, who had traveled to Spain with him, had suddenly died after a short illness, and Philip’s aversion to life in Castile became a sort of panic. He seemed to think the archbishop had been poisoned and that the same thing could happen to him. He was in a frenzy to get out of Castile as soon as possible. He announced he was leaving immediately.

Isabella and Ferdinand begged him to stay. It was Christmas. They were at war with France again, over Naples and also over Roussillon. Juana’s pregnancy was advanced, and it would be dangerous for her to embark on a long journey.

But Philip insisted, saying that he had promised his subjects he would return to Flanders within one year. It was a humiliating turn of events for Princess Juana to be abandoned by her husband at Christmastime. She still loved him, at least on some level, but his lack of interest in her made it impossible for her to exert any power in the relationship. She wept and sobbed, begging him to stay. He rebuffed her, which became common knowledge in the Castilian court. Peter Martyr was stunned by his intransigence: “Nor is Philip softened by these things, he is more adamant than adamant, he prepares his departure,” he wrote to a friend.28

Philip set out for Flanders at Christmas. When he crossed the border into France, however, he found plenty of new amusements—the French were masters at finding enjoyable pastimes—and he established himself there for some months, making it clear that his reasons for departing Castile had been merely subterfuge. Juana’s parents, who were at war with France over Naples, were appalled by his disloyalty and weakness of character. He was completely dominated by the French, and putting himself in their power created a risk both to himself and to Spanish interests. “So great is the influence of his counselors whom they think to have been corrupted by French bribes that he does not seem to be in his own power,” Peter Martyr wrote.29

Philip’s continuing presence in France exacerbated Juana’s sense of abandonment and left her obsessed with jealous suspicion about his sexual activities while they were separated. Her fears were not unfounded. “He was highly susceptible to his counselors, who made him drunk with a licentious life, taking him from banquet to banquet, from woman to woman, until he was owned body and soul by the French, who had made him their satellite,” wrote Gutierre Gómez de Fuensalida, the Spanish ambassador to Flanders.30

Mortified and hurt, Juana turned her anger on her mother, who had insisted that Juana remain in Spain. Ferdinand had returned to the battlefield to fight the French in Perpignan, and so Isabella was the parent who remained present as a target. She bore the brunt of Juana’s quiet fury. The princess “lives with clouded brow, meditating day and night and never utters a word without being urged and if she [does] it is a troublesome one,” Peter Martyr wrote.31

In March, still simmering with barely suppressed rage, Juana gave birth at Alcalá de Henares to her fourth child, who was her second son. He was named Ferdinand, after his grandfather. It was another easy delivery. Juana had scarcely recovered when she began insisting that she wanted to rejoin her husband, in a frenzy of jealousy to recapture his love and attention. She was willing to leave the baby behind with her parents to get started as quickly as possible. Isabella looked for every means to delay her, because going to Flanders would require her to journey overland in France, a kingdom with which they were now fully at war, or by sea, with all the risks the family by now realized that such voyages entailed.

Isabella persuaded Juana that they should go to their family home, the palace in Segovia, since it was on the route to Burgos and therefore on the way to Flanders. Once there she sent Juana on again, a bit farther along the road, to Medina del Campo, under the care of Juan de Fonseca. It was a sign of Isabella’s sense of the delicacy of the job that she recruited Juan de Fonseca, the official who was already busy overseeing expeditions to the New World, but whom she must have viewed as entirely trustworthy.

When Juana got to the castle at La Mota, in Medina del Campo, she received a letter from Philip asking her to rejoin him, and she became vociferously insistent that she depart immediately. She ordered her household staff to begin packing for the trip. This put Juan de Fonseca in a terrible spot, because if he blocked her, he would incur her wrath, and if he didn’t, he would be disobeying the queen. Fonseca ordered the doors to the fortress closed to prevent Juana from leaving. She raged at him, threatening him with death when she became queen. And indeed, Isabella’s declining health meant that Juana would soon have the means and power to punish those who had displeased her.

Fonseca sent out frantic messages to Isabella telling her what was happening, and then he set to work trying to persuade Juana to wait until her mother arrived to discuss the matter further. Juana, in a fury, tried to rush out of the citadel as though she would run to Flanders herself. Fonseca held his ground and would not allow the gates to be opened. Juana, screaming abuse and crying, refused to go back inside and spent the night outside on the fortress walls in the chilly winter air, her erratic and hysterical behavior drawing the attention of the entire town.

Queen Isabella’s health was poor, but she was a fiercely protective mother, and she immediately took to the road to take care of her daughter, the way she had rushed to rescue her eldest daughter Isabel when she had been at risk in Segovia as a child, trapped in the castle in an uprising during the war with the Portuguese. The confrontation between Isabella and Juana was painful for both women. Obsessive love in an abusive relationship is a sorry sight, but when it occurred within the royal family, it became an embarrassing public spectacle.

At last Juana calmed down and went on her way. Isabella, exhausted and drained, could go no further herself and settled into her home in Medina del Campo, a familiar place from her own childhood. The contretemps had left her weakened. Queen Isabella was “very distressed and fatigued by the Señora princesa,” one of her secretaries wrote.32

Isabella’s dreams for Castile, meanwhile, seemed to be crushed—Juana’s behavior had made it clear that she lacked the even temper and composure that were essential to establishing herself securely as queen. And she was anchored to a frivolous and venal man who was more interested in his own pleasure than in Spain’s interests.

There was more drama when Juana got home to Flanders. Philip had entered an intense love affair with a lady of the court. In a jealous rage, Juana threw herself at her rival and ordered the woman’s long blond hair shorn from her head. Philip was furious. “He spoke very cruelly to her, giving her much injury, and they say he put his hands on her,” wrote the chronicler Alonso de Santa Cruz. “And as the Princess Doña Juana was a delicate young woman, and raised that way, under the guidance of her mother, she felt very intensely the mistreatment that her husband gave her, and she fell ill on her bed.”33

To silence Juana, Philip ordered her sealed inside her bedchamber. She pounded on the floor and ceiling of her room and demanded to speak with her husband. He ignored her, and so she began starving herself. Reports from the ambassadors left Isabella even sadder, and she urged her envoys to find ways to foster “love and agreement” between the warring spouses.34

Isabella’s doctors worried that the emotional turmoil over Juana might precipitate a downward health spiral for the queen and, indeed, her condition steadily worsened from that time, with her fevers becoming almost continual. “The Queen brooded about it, greatly angered by the Prince Don Philip,” Santa Cruz wrote, “and it weighed upon her that she had arranged such a marriage.”35

But Isabella had another family problem to solve as well: another young family member had been struck down in the prime of life. Catherine’s husband, Arthur, Prince of Wales, fell dead from a plague on April 2, 1502. Catherine had contracted the ailment at the same time, but she had survived. Once more a royal court was plunged into deepest mourning. And again the question arose of what to do with a widowed princess.

Queen Isabella offered two suggestions to the English king: either send Catherine back home to Spain, or marry her to Arthur’s younger brother Henry. That latter option was under consideration in both courts, if only the financial arrangements could be handled smoothly. Of course, that immediately presented problems because of the financial wrangling that had occurred over the dowry when Catherine and Arthur had married, and a portion of that money had not yet been paid.

Grieving for his son and clutching his strongbox, King Henry VII demanded payment of the rest of the dowry. He made life difficult for the young princess by refusing to give her money for her living expenses and those of her attendants. It was bad enough that Catherine was a widow. Now she became a needy one as well, pressed to, in effect, beg for charity from home and from King Henry. Her only consolation was the kindness of her mother-in-law, Elizabeth of York.

And then that source of support was extinguished as well. Elizabeth of York died in childbirth, about ten months after Prince Arthur died. Henry VII shed some tears over the loss of his sweet and long-suffering wife, then began looking around for a new bride. He spied Catherine’s fresh young face and body. Perhaps he had been as eager to get a look at her when she arrived for his own interests as for his son’s. He wrote to Castile suggesting that Catherine marry him instead.

This idea appalled Queen Isabella, who denounced it in no uncertain terms. “It would be a very terrible thing—one never before seen, and the mere mention of which offends the ears,” she told her ambassador in England.36 The younger Henry was the only possible choice in England, she insisted. It was Prince Henry or home for Catherine.

But for Catherine to marry Henry, they would need yet another dispensation from Pope Alexander VI, this time for Henry to marry his brother Arthur’s widow. But was she really his widow? There was that awkward question of whether the marriage had actually been consummated. Some people said it had, some said it hadn’t.

King Ferdinand was drafted to make the request to the pope, who was by now a lifetime ally of his king, although their relationship had had some ups and downs. These long-distance deliberations over papal dispensations were time-consuming and complicated and sometimes expensive to procure, so Isabella began leaning on everyone she could to make sure that copies of the official document arrived in the Spanish and English courts as soon as possible.

In 1504 the long-awaited dispensation finally arrived. Isabella breathed a sigh of relief. She knew she was dying, and she was satisfied that she had secured a safe, and possibly even happy, future for Catherine as the wife and queen of the future King Henry VIII.

For with this dispensation in place, and the marriage blessed by the pope, what could possibly go wrong?

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