THREE

FRIGHTENING YEARS

In February 1464, when Isabella was not quite thirteen years old, her brother Enrique accepted the English offer and agreed to give her in marriage to King Edward IV, in a gesture of political alignment between the two countries.1 This would at once make Isabella a queen.

It might have been a generous act on Enrique’s part, to help ensure an illustrious future for his half sister. Certainly Isabella and Enrique showed visible signs of affection from time to time. They both loved music, and sometimes he would sing while she would dance. They shared some of the same interests—riding, hunting, deep and thoughtful discussions—and they held the same religious convictions. However, it is just as likely that the marital alliance was Enrique’s attempt to remove Isabella from the direct line of succession in Castile and relocate her to a distant land, particularly at a time when rumors were brewing about Juana’s legitimacy.

Regardless of Enrique’s motives, however, the proposition of marriage to the English king would have been appealing to most young women. The twenty-two-year-old Edward of York had recently assumed the throne of England. Charming, blond, strong, and six feet four inches tall, he was intelligent, excellent at the courtly games of hunting and jousting, dressed elegantly in furs and rich jewelry, and was fond of chivalric romances. This combination of traits made him irresistible to women, upon whom the lusty young king was eager to lavish his own attentions.

Even discounting for the customary fawning by courtiers, Edward drew accolades that were seemingly genuine. “He was a goodly personage, and very princely to behold . . . of visage lovely, of body mighty, strong and clean made,” wrote Sir Thomas More. “Remarkable beyond all others,” said a German traveler, Gabriel Tetzel, in 1466. Even his critics acknowledged his physical beauty. “I don’t remember having seen a more handsome prince,” wrote the French courtier Philippe de Commynes.2

Marriage to Edward would of course have been an intriguing, even dazzling, prospect for Isabella, who loved hunting and stories of courtly love. It would give her a splendid husband, make her the envy of other women, and install her as queen of a kingdom with which she had long ancestral links. Isabella believed that Spain and England had a natural dynastic affinity. Her great-grandmother was Catherine of Lancaster, the daughter of the famous English nobleman John of Gaunt, son of King Edward III, whose marriage toConstance of Castile had made him a contender for the throne of Castile. Edward IV was also descended from John of Gaunt, making him a distant cousin of Isabella’s. If the alliance proceeded, an old family tie would be reconnected.

The marriage presented some strategic opportunities for England as well. Edward’s descent from King Pedro, through Pedro’s daughter, already made Edward a potential claimant to the Castilian throne, and this claim would be strengthened if he were to marry Isabella. English poets were already writing doggerel extolling Edward as not just king of England and deserving of France but also the future inheritor of Spain: “Re Angliae et Franciae, I say, It is thine own, why sayest thou nay? And so is Spain, that fair country.”3

Once the match was proposed, Isabella waited at home for the decision. Given the difficulties in communication at the time, messages from one court to another sometimes took months because courtiers needed to physically travel from one place to another. Finally she somehow learned, to her great disappointment, that another woman had been selected, in a most unusual way.

Unbeknown to the king’s councilors, who were negotiating Edward’s marriage prospects in both France and Spain, King Edward had already impulsively married a comely widow, Elizabeth Woodville. She was one of the few women who had successfully resisted his blandishments, and in a fever, he chose marriage to obtain lawfully what he could not obtain by courtship. They wed in a furtive ceremony on April 30, 1464, at the home of friends of her family, with only a handful of people in attendance.4 Edward must have regretted the elopement almost instantly because he sought to conceal the match for the next six months. Even his friends were not informed.

The circumstances were even more awkward for his officials who were abroad discussing terms of potential marriages with foreign princesses. The French king, Louis XI, wasn’t officially informed of the secret marriage until October 10, 1464, after six months of deliberations and negotiations over a possible marriage of Edward to Louis’s sister-in-law Bona. The Earl of Warwick, an important ally of Edward working on his behalf in France, was humiliated and chagrined to realize he had been left uninformed while “pressing actively” for the French alliance.5 An English chronicler described his reaction: “And when the Erle of Warwyke come home and herde hereof, thenne was he gretely displesyd.”6

The course of European history could have been shifted in many ways if Isabella had managed to marry, win over, and provide assistance in governing to the high-spirited but short-sighted and pleasure-loving king of England. Both countries might have evolved in better directions. Edward’s marriage turned out to be disastrously bad for him, as the woman he wed was “grasping and ambitious for her family’s interests, quick to take offense and reluctant to forgive.”7 She was also a member of the Lancaster clan, enemies to the Yorks, and to please his wife, Edward was forced to find posts at court for her two children from her first marriage, five brothers, and seven unmarried sisters. Like King Enrique, Edward ended up surrounding himself with people who did not have his best interests at heart. The king’s irritated emissary to France and former ally, the Earl of Warwick, turned against him. Edward’s dynastic aspirations collapsed even though he had ten children with Elizabeth, and after his death, his two oldest boys, aged ten and thirteen, were spirited away and rumored to have been killed in the Tower of London by persons unknown.

In faraway Castile, Isabella, still a young teenager, brooded over her rejection, much later telling ambassadors that she had been passed over for a mere “widow of England,” making it clear she had harbored resentment at her rejection for the next twenty years. Like Elizabeth Woodville, she was not a woman to suffer a slight lightly or forgive easily.8 In addition to Isabella’s good qualities, a certain hardness of character was developing in her. It made her able to survive the difficulties of her childhood and adolescence, but it also made her rigid and unforgiving.

While Enrique awaited word from England, at some point suspecting that the match with Edward would evaporate, he began to consider instead marrying Isabella to King Afonso V of Portugal, a war hero whose support would bolster Castile’s defenses. Such a match would be equally effective in getting Isabella out of the kingdom and out of the path of little Juana’s claims, and it would also improve relations with Portugal. And Portugal already had an heir apparent, Afonso’s son João. In this scenario, João’s children would rule Portugal; Juana’s children would rule Castile. Isabella’s children would be safely out of any line of succession.

In April 1463 Enrique took Isabella, just turning thirteen, and Queen Juana to El Puente de Arzobispo, in central-western Castile, closer to the Portuguese border, to meet King Afonso. The thirty-one-year-old Portuguese king—paunchy, middle-aged, and pompous—was “much taken” with his young cousin. Isabella, for her part, under pressure from the queen and her own mother, who was Portuguese, and undoubtedly playing for time while she awaited word on the English alliance, tactfully or innocently led the Portuguese king to believe he was her choice as well.9 This was an error on her part.

King Enrique’s popularity in Castile was plummeting, however, and the proposed Portuguese marriage was not well received. Two men in particular took it as an affront. Alfonso Carrillo, the rich and powerful archbishop of Toledo, had grown weary of Enrique’s vacillating leadership. He was also a partisan of the envious Aragonese cousins and had long hoped to steer public policy in Castile toward Aragon rather than toward Portugal. Juan Pacheco, meanwhile, was angry and out of sorts because he was being supplanted in the king’s affections by other men. Carrillo and Pacheco began to foment a rebellion against Enrique. As a first step, they wanted to get control of young Prince Alfonso and Princess Isabella and insisted they be given custody of the children, ostensibly to ensure their continued security. They warned that people of “damnable intent” had planned to kill Alfonso and marry off Isabella, to give “succession in these realms to [one] to whom by right it does not belong,” by which they meant the child Juana.10

They announced their split from the king in an open letter to the kingdom that was widely circulated. The document, called the Representation of Burgos, oozed contempt and derision and made a series of demands. Enrique was ordered to get rid of his Moorish bodyguard, whom they accused of sexually assaulting both men and women; to discard his new favorite, Beltrán de la Cueva; and to drop the charade about Juana’s legitimacy. “It is quite manifest that she is not the daughter of your highness,” the statement read.11

Enrique, always eager to mollify his critics, deferred to Pacheco and Carrillo and agreed to their demands, even to the extent of repudiating his daughter’s claim to the throne and giving it to his young half brother Alfonso: “Know ye, that to avoid any kind of scandal . . . I declare that the legitimate succession of this kingdom belongs to my brother the Infante don Alfonso and to no other person whatsoever.” Beltrán was sent away. At a ceremony in Cabezón, the nobility took oaths in support of Alfonso as the successor, and the mastership of Santiago was transferred to him. Young Alfonso was handed over to the custody of Juan Pacheco, the Marquess of Villena, who had played such a pivotal role in Enrique’s own youth.12

This was an unfortunate period in Alfonso’s life, for there were reports that he was badly treated, and perhaps sexually molested, while he was in Pacheco’s care. The chronicler Palencia said that Pacheco attempted a pedophilic seduction of the boy, in hopes of making him more malleable, something that was widely believed to have been done to Enrique in his youth. In fact, by this time, similar allegations had been raised regarding three generations of Trastámara men—their father Juan, Enrique, and now Alfonso.

This is a distinct possibility. There is a long tradition of sex being used to manipulate politicians and other powerful people. In this case, an unusual set of facts seems to suggest a possibility of adolescent sexual abuse. Sexual predators generally seek out their victims when they are young, often almost under the noses of their parents or guardians, woo them in a pattern known as “grooming,” and after having sexual relations with them, assert dominance over them in other ways. Certainly patterns characteristic of molestation were visible among the men in Isabella’s family. In all three cases, the parents were absent or preoccupied by serious problems, leaving a void in the child’s life. Sexual predators thrive in those conditions.

King Juan, Isabella’s father, had been just six years old when he fell under the spell of eighteen-year-old Álvaro de Luna, who was soon sleeping in the child’s bed. Juan’s father had died, and his mother was trying to administer the nation at a time of terrible civil strife; she was initially appreciative when Álvaro took such a kindly interest in the boy. “The king did not want to be without Don Álvaro de Luna either by night or by day,” wrote a chronicler of the time.13 At some point, however, the queen mother became concerned that the relationship had become so “intimate,” writes historian Teofilo Ruiz. She ordered “Don Álvaro removed from the court, only to bring him back at the pleading and insistence of her son.”14

Álvaro, for his part, had been the illegitimate son of a nobleman who took no interest in him. He had been separated from his mother and raised in the household of the Catholic pope who was his uncle, surrounded by priests whose religious vows kept them from marriage. Álvaro de Luna was handsome, charming, and amiable; he eventually married and had children. In his twenties, however, though many women were attracted to him, he was never associated publicly with any of them, which he encouraged people to believe was evidence of his unusual gallantry toward the ladies of the court. But it could also have meant that his sexual interests were primarily elsewhere. In Álvaro’s own household, for example, an unusual boy, Juan Pacheco, served as a teenage page, and Pacheco repeated the pattern established by Álvaro de Luna.

After King Juan grew up, married, and had a son, Enrique, Álvaro de Luna similarly introduced Juan Pacheco, six years older than Enrique, to the young prince and placed him in the prince’s household. Soon Juan Pacheco held Enrique in thrall as Álvaro had done with his father.

Both Álvaro de Luna and Juan Pacheco had exhibited a remarkable degree of personal power over Juan and Enrique—in both cases, it was so noteworthy that it was likened to witchcraft. This pattern is common among sexual predators and their victims. The sexual involvement is not a romance but an abuse. The molester often takes satisfaction from humiliating the object of his or her attentions, sometimes in a public place, with the goal of demonstrating dominance. The victim often feels some combination of anger and shame, because at times the interactions are sexually pleasurable. Adults who were molested as children frequently have difficulty maintaining relationships and are either easily sexually aroused or become incapable of having sex. Moreover, the victims frequently become very religious out of a sense of guilt, in seeking redemption for what they believe to be their own culpability for what occurred.

A chronicler of Juan who lived at the court said: “Juan II… lived his life under the influence of Don Álvaro de Luna, up until the time when, under pressure from nobles, the King, crying, ordered him decapitated.”15 Another added: Juan was “weak of character and suggestible to the point of shameful submission” to the tutelage of Don Álvaro de Luna.16 This relationship, of course, had been the insuperable obstacle for Isabella’s mother, who had struggled to get her husband to break from Álvaro’s spell, then watched as her husband descended into black melancholy at Álvaro’s death.

Similar things were said about Enrique and Juan Pacheco a generation later. A chronicler of Enrique, an eyewitness, reported that “abuses and delights became his habit” under the influence of Juan Pacheco. He became a “passive instrument of Don Juan Pacheco, intentionally placed at his side by Álvaro de Luna . . . Not a single thing was done unless he had ordered it.”17 One contemporary historian went so far as to call Pacheco a “monster of nature.”18 Another, Fernando del Pulgar, said Enrique was introduced at age fourteen to “unseemly pleasures” he was unable to resist because of his sexual inexperience.19

For both King Juan and King Enrique, the relationships between king and favorite had sparked criticism and ridicule, undermined their authority, and led to open hostilities in their kingdoms. To gain even a small advantage, Juan Pacheco had been willing to shed blood, and in some cases innocent bystanders were killed as a result of his machinations.

At this point, however, angry over the long chain of insults and humiliations by Juan Pacheco, King Enrique unexpectedly began to resist his control. That, sadly, was his undoing. Enrique called his new favorite, Don Beltrán, back to court and elevated him further, by making him not just a count but also the Duke of Alburquerque. This was a final straw to many people around Castile. A large faction of the nobles exploded in anger. Burgos, Seville, Córdoba, and even the ancient capital city of Toledo rose against Enrique. The king retreated, barricading himself in Segovia. His most implacable enemy turned out to be the chief Christian prelate, the warlike archbishop of Toledo, Alfonso Carrillo. Enrique wrote to the clergyman, asking for his support. Carrillo responded curtly to the messenger bearing the request: “Go tell your King that I am sick of him and his affairs, and that we shall now see who is the real king of Castile.”20

On June 5, 1465, in a fateful act of revolution, nobles gathered in the walled city of Ávila to enact an unusual ceremony. They essentially staged a coup against Enrique by dethroning him in effigy. A life-size mannequin representing the king was placed in a chair on a stage. One noble approached and knocked the crown off its head. Another removed the scepter. It was a ritual designed to be a public spectacle, just as the execution of Álvaro de Luna had been a real decapitation but also a symbolic event. The effigy puppet was kicked to the ground. As the final act, the twelve-year-old Prince Alfonso was brought into the plaza, carried on the shoulders of other officials, and the crown was placed on his head. The rebels now had control of a boy pretender to the throne. It became obvious why the courtiers around Enrique had insisted so strenuously on obtaining physical control of the king’s brother.

King Enrique was horrified, feeling stricken and defenseless against the assault, which seemed not just a parody of Castilian succession tradition but also something close to sacrilege. He was blindsided and desperate for allies because many of the kingdom’s leading noblemen had participated in the events at Ávila. This played precisely into the hands of Juan Pacheco, who promised Enrique he would return Alfonso to him and bring troops to the king’s defense and support, but only if Enrique would permit his brother,Pedro Girón, master of the Calatrava religious order, to marry Princess Isabella. This extraordinary proposition would have placed Pacheco’s family in the direct line of succession and possibly even permit them to rule Castile, if Alfonso were to die and if Juana’s legitimacy continued to be questioned.

The fact that this proposal became a matter of such high-level deliberations makes it clear that Isabella was being pulled out of the shadows. The symbolic dethroning of King Enrique meant she too had become a contender for supremacy in the nation. From this point on, Isabella’s existence became a topic of interest to court chroniclers, and her comings and goings were noted with some regularity. After the king had deferred once to the nobility on the question of Juana’s legitimacy, that child’s right to succession was forever diminished, and now Enrique’s own right to rule had been challenged.

King Enrique caved in once more. The weak-willed king, always pitifully eager to find a peaceful resolution to a problem, agreed to Juan Pacheco’s proposition, promising his fifteen-year-old sister to a religious leader who had pledged to remain chaste but was in fact notoriously debauched. Enrique dispatched an emissary to the pope, asking for a dispensation releasing Girón from his purported vow of celibacy.21

Now it was Isabella’s turn to be horrified. Just a year or two before, she had believed she was being affianced to one of the most admired young kings in Europe; now she was being thrust into the arms of a degenerate man who regularly betrayed his obligation of celibacy, who was far beneath her in lineage, and who was considerably older than she. There was even the embarrassing family memory of the vulgar sexual advance Pedro Girón had once made to Isabella’s mother.

Pedro Girón set out on horseback for Madrid, where Isabella was staying, eager to make her his bride. This is the first event in Isabella’s life that is fully described in court records. Chroniclers wrote that she turned to God for help and guidance, begging to be spared the marriage and spending almost two days on her knees in prayer.22 Despairing, she asked God to preserve her from the marriage by death if necessary—either hers or that of Pedro Girón.

The members of her household circle were similarly disgusted and appalled by this new development. According to some stories, Isabella’s loyal friend, Beatriz de Bobadilla, grabbed a knife and vowed to kill Pedro Girón. But fortuitously, at least in the view of Isabella’s supporters and chroniclers, Girón suddenly dropped dead. He had been making haste to marry Isabella when he fell ill from an acute infection of the tonsils that blocked his breathing, and he died on the road. Girón’s abrupt and unexpected death was a huge relief to Isabella and her friends. Later, after many other events occurred, some people even began to say it had been a miracle.

Princess Isabella was transferred to Enrique’s most secure base, the beautiful city of Segovia, whose solid walls, stout fortress, and perch on a rocky precipice created an air of impregnability. Girón’s death had freed her from her immediate fear, but it had also dealt a blow to the peace negotiations between Enrique and the nobles of Castile. Alfonso remained in the nobles’ custody and continued his claim to the throne, while animosities turned into hostility once again. Isabella sheltered in Segovia, accompanied by QueenJuana, Enrique’s wife, who by now was more her captor than her companion. Isabella’s existence had long been beside the point for the young queen, but now Isabella was an actual threat to her, her husband, and her daughter. It placed Isabella in a most precarious situation, and some courtiers feared the queen would have her killed to get rid of the problem.

The tensions in Segovia spread all over the kingdom. Everyone was forced to pick sides between Enrique and the young claimant Alfonso, and sporadic violence turned to civil war. “All the realm was arms and blood: no nobleman or city remained neutral,” wrote chronicler Diego de Colmenares.23

Chaos broke out everywhere, and criminals took advantage of the situation. A group of noblemen visiting Spain from Central Europe that year on pilgrimage had a safe-conduct from a Portuguese princess who had married the Holy Roman emperor but found it provided almost no protection. They reported being attacked by a polyglot gang of Christians, Jews, and Muslims in the far north, on the banks of the Cadagua River, and escaped only by bribing them; in Valmaseda, near Bilbao, they were threatened with murder and again had to pay in order to escape with their lives; and in Olmedo, armed robbers tried three times to force their way into the house where they were staying, pelting them with stones when they ventured outside, in hopes of provoking a response that would permit a more open assault. One member of their group disappeared and was believed to have been sold into slavery in Muslim lands; and in Molins de Rei, near Barcelona, they narrowly escaped execution at the hands of a local vigilante group that was hunting for a stranger who had committed a murder. The pilgrim group found life considerably more peaceful in Italy, where they went after they left the Iberian peninsula.

The troops of Alfonso and Enrique met in an inconclusive clash of arms near Olmedo, in August 1467. Prince Alfonso, now thirteen and styling himself King Alfonso, fought alongside Alfonso Carrillo, the archbishop of Toledo, who wore his priestly robes over a coat of armor. King Enrique humiliated himself by fleeing the battlefield, hiding out in a nearby village until the fighting was over, but Alfonso fought valiantly. In the following days, some of Enrique’s supporters defected, and most shockingly for Enrique, the city of Segovia, his hometown and the place on which he had lavished his largesse and support, willingly opened its gates to Alfonso and his troops. Even Segovia had repudiated Enrique.

As Alfonso came to the city, accompanied by the malevolent Juan Pacheco, who had helped foment the rebellion, the boy stopped to take revenge on his older half brother in a particularly unsettling way. Normally a good-natured child, Alfonso ordered the beasts in Enrique’s menagerie slaughtered. Only one animal was left alive—Enrique’s beloved mountain goat, because Juan Pacheco intervened to ask Alfonso to spare that one animal. Alfonso’s strange and disturbing brutality is so unusual that it provides another piece of evidence that Alfonso might indeed have endured some sort of humiliating mistreatment. Cruelty to animals is another common indicator of child sexual abuse; sociologists have found that there is a 90 percent correlation between domestic abuse and animal abuse.

Alfonso’s arrival put Isabella on the spot. The young princess, who had been sequestered in Segovia with the queen, her hostile sister-in-law, faced a stark choice. She could continue to ally herself with her older brother, King Enrique, which would be a precarious position with the city now about to fall; or she could take her chances with the young upstart, her brother Alfonso. She made her decision. She cast her lot with Alfonso and switched her allegiance to him. Her teenage brother made a triumphant entry into the city, and Isabella rushed to join him. In the next months, she frequently traveled by his side, an enthusiastic supporter of his claim to the throne. They rode together to their first destination: home, to their mother’s side, and to safe refuge once again, in Arévalo.

As Isabella and her entourage became part of Alfonso’s court, and as the prince engaged in an intense civil war against their half brother, another important figure in Isabella’s life made his first appearance. Most of the rebels surrounding the young people, of course, were adults, some of them very mature, even elderly. But this young man was only about fourteen years old, which made him a year older than Alfonso and a year younger than Isabella. His name was Gonzalo Fernández de Córdoba. When the rebellion against Enrique started, Gonzalo’s family had promptly joined the rebels. His older brother was slated to inherit the family’s prosperous estate in Andalusia, and Gonzalo was being groomed for a life as a soldier. In 1467 Gonzalo was sent to Castile, under the care of a tutor, to become a page to Alfonso, with the idea that he would establish ties to the court that could secure his future life. Soon he grew close to both Alfonso and Isabella, who were similarly trying to find their footing in the adult world.

Traveling from place to place, coping with the uncertainties of the campaign trail, Gonzalo and Isabella developed a deep friendship. The relationship appeared to be platonic—she was going to be a queen, at least through an eventual marriage, and he would always be the second son of a nobleman—but it was an era that romanticized courtly love, where a nobleman of sterling character would pledge undying affection for a noble gentlewoman. Early on, Gonzalo pledged himself to defend Isabella’s interests, and she soon began to do the same for him.

In many ways, they were mirror images of each other. Gonzalo was idealistic, articulate, and poised, even as a teenager. An avid reader with a gift for language, he was a keen student of military history and viewed military prowess as a manifestation of religious devotion. He chose as his personal motto these words: “For your honor, give your life. For your God, give both honor and life.”24

He spent hours each day perfecting his soldiering skills, preparing himself for battle, if and when it came. “I used to take a rapier and spend hours fencing in a room all alone where no one would see me,” he later recalled. “For not only did swordsmanship come as naturally to me as walking or running, but it seemed to me an activity perfectly suited to the natural movement of the body.”25

Gonzalo was attractive and stylish. He was greatly loved by his older brother, who gave him the money to live an elegant life at court. He dressed beautifully, once described as wearing a “carmoisine velvet cloak, lined with sables, which cost 2,000 ducats,” on a day that was “not a major festival either.”26 He had been short as a boy but grew up strong and tall, an excellent horseman, skilled at games of martial arts. He was particularly gifted at a popular medieval game called canes: “He would come… now entering at a gallop, now turning in flight, still riding at top speed, bending over and snatching canes from the ground as he flashed past.… Again he could be seen, wheeling suddenly and galloping, shield up, so that though the others threw a thousand canes at him nothing or no one could harm him.”27

Isabella came to look on Gonzalo with considerable favor, calling him the Prince of the Caballeros.28 Soon, as a result of his military victories, he became known to others as the Great Captain. Indeed, he was confident of a glorious future.

His brother, who held the family purse strings, pleaded with him to restrain his extravagance, lest he be “ruined before a year.” But Gonzalo brushed him aside. “Surely you do not wish to abandon the great aspirations God has given me with such vain threats of future poverty,” he wrote to his brother. “But I am as certain that you will never fail to provide for your much-loved brother as I am that God, whose unfailing Providence always seems to favor those who have no goal but honor, will not see me go short of the confidence to achieve that which my stars foretell.”29

It was a time of soaring great expectations in the court of King Alfonso, and an exuberant time for the young people who were preparing themselves to govern, imagining themselves as rulers of a better world. Isabella was confident that Alfonso was intended for glory. She organized a great party for his fourteenth birthday, performing in a masque at the celebration, predicting in verse his greatness: that he would go forward in dispensing justice, prove victorious, and be generous to his subjects; that God would find him praiseworthy; and “that his dominions would extend as far as the eye could reach.”30 She said his riches would equal those of King Midas, and his military triumphs would rival those of Alexander the Great. And she foretold eternal fame for him, that his actions would win him both “earthly and celestial glory.”31

Prince Alfonso returned Isabella’s love and affection and responded warmly to it. In Arévalo, while they were at their mother’s home, he made her a generous gift. He presented to her the jurisdictions and rents of Medina del Campo, one of the cities that had early pledged its support to him. This was a tribute to her and a highly satisfying grant because she had always loved going to the fair there and had enjoyed many happy childhood hours in its abundant and overflowing market stalls and shops.

That was the high point for Alfonso and his allies, for afterward the political tide began to run against the prince-turned-king. When Gonzalo Chacón, the long-time family friend who now served as Isabella’s chief of staff, went to Medina del Campo to take possession of the city on her behalf, he encountered resistance to the transfer. Medina del Campo’s residents were shifting sides and returning to their support of King Enrique.

Then bad tidings arrived from Toledo, which had been one of Alfonso’s strongest bases and where his ally, Carrillo, served as archbishop. An explosive set of events had erupted into warfare in the streets, in such a way that Alfonso’s good character would become a political handicap to him. The facts were murky and complicated, but they went to the heart of the religious dissensions that were pulling Castilians in different directions. Toledo had early declared its allegiance to Alfonso, but as the civil war wore on, the absence of an effective central government invited social disruptions.

The most thorough account of the key events comes from the Israeli historian Benzion Netanyahu, who traced their origin to the summer of 1467, when church officials in Toledo hired a Jewish tax collector to seek payment of some debts owed to the church. A pro-Alfonso judge who was a converso, a man of Jewish descent who had converted to Christianity, opposed the appointment of this individual, saying he had not authorized it. Church officials responded by excommunicating the judge. Enraged and indignant, he gathered a band of heavily armed conversos and attacked a church during worship services, killing two of the officials who were involved in the dispute. Some longtime Christians began preparing for war against the conversos, fearing a broader assault by people who were only posing as Christians.

The conversos, for their part, began to fear another anti-Semitic massacre like the one that had happened in 1391; they mobilized four thousand recruits, using the cathedral as a base, placing artillery at its gates and firing upon passersby and people they suspected might be preparing an attack. They maintained this position for almost a day, causing many injuries. But then Christian mobs organized a response, and they greatly outnumbered the converso group. Pitched battles broke out between roving bands of longtime Christians and conversos. Entire blocks of streets were put to the torch. More than 150 conversos were killed in the ensuing battles, and many more had their homes and possessions stolen. Others were protected from injury by their neighbors who were longtime Christians and believed they were being unfairly attacked.

Tensions were so high that many people believed peace between the religions was no longer possible in Toledo. In the aftermath of the riots, a great many conversos left Toledo and moved elsewhere. Greedy Christian officials took advantage of the situation and passed regulations that stripped all conversos of government positions and allowed their assailants to keep stolen goods.

Christian officials in Toledo wrote to Alfonso and asked him to confirm the new rules and pardon them for any wrongdoing done to the conversos. They reasoned that Alfonso was so weak and young that he would simply agree. Instead, however, he told them that the actions in Toledo had been “dishonorable and shameful” and that he would rather risk losing Toledo from his camp than condone what they had done. King Enrique struggled with the issue as well but ultimately agreed to the demands set by the Christians and authorized them to keep the goods taken from the converso families. Consequently, Toledo moved back to Enrique’s side in the civil war. This was a major blow to Alfonso, because of the strategic and historic importance of the city.

Alfonso and Isabella had been enjoying a day at the fair at Medina del Campo when they learned what had happened in Toledo and how city officials had repudiated him. Alfonso decided to hurry to Toledo to lay siege to the city and reclaim it. Isabella rode with him southward toward the great walled city of Ávila, a way station on their path to Toledo.

Then in Cardenosa, a small village almost within sight of Ávila, Alfonso fell ill. A chronicler recounted the events:

With the king, Don Alfonso[,]… was Her Most Serene Highness, the Princess, Doña Isabella, his sister. And as they sat at dinner, among the other viands was brought a trout pastry, which he partook of willingly, though he ate only a little of it. And afterward he fell in a heavy sleep, most unusual for him, and went off to bed without speaking to anyone, and slept until the hour of terce [nine a.m.], a thing he never did.

And those of his bedchamber came and felt him with their hands and there was no heat in him. As he did not waken they began to call loudly and yet he did not respond. And their shouts made such a din that the archbishop of Toledo and the Master of Santiago [Juan Pacheco, the Marquess of Villena] and My Lady the Princess came, but he answered them not. And they felt all his members but found no swellings.

The physician, coming in haste, ordered him to be bled, but no blood came; his tongue was swollen, and the mouth seemed black, yet no sign of plague appeared. So, despairing of the life of the King, those who so greatly loved him, their wits forsaking them, began shouting out, begging Our Lord for his life. Some made vows to enter religion, some to go on distant pilgrimages. Others made different promises. And, no remedy availing, the innocent King gave his soul to Him who created it on July 5, 1468.… His death was believed to have been brought about by poisonous herbs because, though young in years, he seemed to his followers more likely to become a more vigorous governor than his brother.32

It was unclear whether Alfonso had plague—in which case no one knew where it might strike next—or even worse, that he had been poisoned. Suddenly Isabella was alone and exposed, after having defied Enrique in the most dramatic way. Her grandmother by now was dead; her mother could provide no assistance. And Isabella was now dangerously high in the line of succession in a kingdom where the heirs to the throne frequently suffered untimely deaths. Certainly many were hoping she would soon be gone as well.

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