Some weeks ago, I shared a post about Constanza Manuel, daughter of Don Juan Manuel de Villena who was not only a power-hungry Castilian noble, but also an erudite writer. Juan Manuel was the grandson of Fernando III, a member of the royal house of Ivrea, and was thereby an Infante of Castile.
“A legitimate member,” Infante Juan would tell us is he were around. “No illegitimacy up my family tree, not like in Alfonso’s.” He’d be referring to Alfonso XI, whose father, Fernando IV, was the son of Sancho IV and his wife, Maria de Molina. Except that in the eyes of the church, Sancho and Maria weren’t married. Why? Because Sancho was precontracted elsewhere, and besides, they were related within the prohibited degree and never got a dispensation. Fortunately, in 1307 the pope issued a retroactive dispensation, thereby declaring Fernando legitimate. Phew!
Don Juan should, however, be a bit careful when stating he was fully legitimate. If we’re going to be very, very picky, Fernando III was also considered illegitimate, the pope refusing to accept the marriage of his parents, Berenguela of Castile and Alfonso of Leon. But maybe Don Juan was of the opinion that as everyone close to the Castilian throne were descended from the great Fernando III, that illegitimacy was irrelevant.
Anyway: Juan Manuel was proud of his lineage. Very proud. He definitely felt entitled to have a say in how things were run, and was miffed when Alfonso XI made it very clear he planned to do the ruling on his own. Even more miffed when Alfonso went on to annul his marriage to Juan Manuel’s daughter, Constanza. In fact, Juan Manuel would be something of a thorn in Alfonso’s side for most of his reign, especially when his attempts to influence things through Alfonso’s beloved mistress, Leonor de Guzmán, fell flat. Leonor was a powerful woman—based on the king’s affection. She was also an intelligent woman, and knew better than to meddle in matters of politics (Which does not preclude offering her opinion/thoughts when the king asked for them)

Juan Manuel was married three times. Constanza Manuel was the fruit of his second marriage. In around 1330, Juan Manuel married Blanca de la Cerda y Lara. He was pushing fifty, she was in her teens. Blanca was the daughter of Fernando de la Cerda, a great-grandson of Fernando III. In 1332, she gave Juan Manuel a son, Fernando, and seven years later, a daughter. And so we come to today’s protagonist: Juana Manuel de Villena.
I imagine Juan Manuel would have preferred a son, a spare. Little Fernando was, at the age of seven, the military governor of Murcia, the foundations for a future career at court. Obviously, the boy did no governing—his father did, through the men he entrusted his son to.
Juana was probably well-educated, and according to the entry in the Spanish Royal Academy of History she was an energetic and socially adept young woman. Not that we know if that is true, of course. Very quickly, she became something of a marital prize—Juan Manuel would ensure his daughter was richly dowered.
And then Juan Manuel died, around when his son was sixteen, his daughter nine. Fernando Manuel was now to assume all his father’s responsibilities, which included securing a good marriage for little Juana. He was also recently wed and was to welcome a little girl to the world, so I’m thinking we can conclude Fernando was busy.
Enter Leonor de Guzmán, Alfonso XI’s mistress—although mistress feels rather belittling, given that Leonor had been the king’s loyal and loving companion since 1327-29 or so, more than two decades. Now, Leonor rarely meddled in politics, but she was something of a lioness when it came to protecting her children—she gave Alfonso ten in total, nine boys and one girl. In the late 1340s, two of her sons were already dead, but the surviving eldest son, Enrique of Trastámara, was in need of a wife. The king had been generous to his illegitimate brood (and their mother) loading them with lands and titles.. I believe Leonor always held out hope that one of her sons would one day become king, overcoming the stigma of their illegitimacy. A wife with Juana Manuel’s impeccable pedigree would provide Enrique with a relevant (and legitimate) claim to the throne—through his wife
So, Leonor reached out to Fernando—discreetly. She was fully aware of the fact that many of the powerful Castilian nobles would not necessarily approve her plans. Likewise, there was another potential husband for Juana: Alfonso’s legitimate son and heir, Pedro. (Who had recently lost a bride in transit, when Edward III’s daughter, Joan, died of the plague while travelling from England to Castile)
In 1350, Alfonso XI was besieging Gibraltar when he suddenly died of the plague. Leonor was shocked—and frightened, both for herself and her children. (Valid fear, given that over the coming decade at least three would die at the hands of their half-brother, some of them mere boys) Pedro was now king, and with the new king came the return of his mother, Queen Maria, who after years of humiliation had moved back to Portugal rather than remain in Castile where it was Leonor who ruled the royal court, not her.
It became imperative for Leonor to push through the marriage of Enrique to Juana, and in 1350, eleven-year-old Juana wed seventeen-year-old Enrique. Things went a bit wild and crazy, with Leonor accused of treason and taken prisoner before she was executed in 1351. Enrique and his new wife fled to Asturias, hoping that Pedro’s rage would blow over.
It didn’t. In fact, Pedro seems to have been an angry young man (he was sixteen when his father died) and hard to control. Maybe this was because his parents were first cousins on both sides. It soon became evident he had no intention of listening to his mother’s advice, and that relationship soured further when Maria more or less forced him to marry Blanche of Bourbon in 1353.
Unrest spread in Castile. Enrique, incensed by his mother’s death (although that was at the behest of the vengeful Maria, not Pedro) eventually rose in rebellion. He had the backing of France—Pedro’s deplorable treatment of Blanche (whom he ultimately had poisoned) had alienated the French—while Pedro received support from England.
Pedro has gone down in history as “the Cruel”—he had a tendency to rid himself of inconvenient people through violent means. One of his half-brothers was bludgeoned to death. His annoying cousin was also beaten to death and then thrown out of the window. At one point, he had the male members of his mother’s household assassinated before her. While he did do a lot of killing, Pedro has been the victim of a black legend, so I am thinking he had his brighter moments—like the enduring love for his mistress, Maria de Padilla, mother of the two little infantas who would one day wed John of Gaunt and his brother, Edmund of Langley. In fact, we must keep in mind that more or less everything we know about Pedro and his half-brother, Enrique, is based on the Chronicles by Pero López de Ayala – and this gent had every reason to present Enrique in the best of lights, seeing as he was Enrique’ chancellor.

Enrique’s initial efforts failed and he had to flee, leaving Juana Manuel under Pedro’s control. Not a good thing, given that Pedro was all about equal opportunity, and had female threats dealt with as ruthlessly as male opponents. Initially, it seems she was under the protection of Queen Maria, but after the incident with Maria’s male retainers she was on her own. Fortunately, another Pedro managed to help her escape in 1357, and together they made for Aragon and Enrique. The coming decade, Juana and Enrique stuck together, through thick and thin. Enrique suffered a defeat at the hands of Pedro in 1360 and had to flee to France. Juana Manuel rode with him.
Some years later, in 1363, they were back in Aragon, where Enrique signed an alliance with Pedro IV of Aragon—lands in return for his support—and the rather dastardly Carlos II of Navarra (a man one should never trust). By then, Enrique and Juana Manuel were also parents: their son was born already in 1358, a daughter a year or so later. Pedro, meanwhile, had no legitimate issue. Well, not according to Pedro, who insisted he’d been wed to Maria de Padilla before he wed Blanche, but while the Spanish bishops might be coerced into agreeing with this, the pope was not as lenient. In 1363, Pedro’s and Maria’s little boy Alfonso had already passed, while Enrique had a healthy young son, Juan.
The Castilian Civil War was not only a war between brothers. It was also a war between the high nobility and a king who, just like his father, Alfonso XI, believed in personal rule. Enrique may have been of the same opinion as Pedro—a king ruled best alone—but he needed the support of the nobles, making concessions that would, over time, weaken the crown. I imagine this was something he discussed with his wife—she, being the daughter of a man who felt his rights had been substantially truncated by Alfonso XI, may have been sympathetic to the nobles.
In 1366, Enrique was crowned in Burgos. Pedro was obliged to free the country, while Enrique did his best—together with Juana Manuel—to bring some sort of peace to the kingdom. Apparently, Juana Manuel was quite the doer when so required, captaining her own men to chase after Pedro’s supporters.
However, Pedro was not the type to give up. He made it to Bayonne and made an agreement with the Black Prince: English support for lands in Castile. The English were happy to involve themselves, especially as the French supported Enrique. Carlos II of Navarra was also more than happy to offer Pedro support—if he got lands in return. Carlos II, being an utter bastard, was also happily negotiating with Enrique for continued support. Told you he was a worm, who deserved his nasty, nasty death!)

In 1367, Pedro and his English allies trounced Enrique’s forces at The Battle of Nájera. But in the aftermath, Pedro was not all that eager to fulfill his promises and the English made their way through Castile towards Valladolid, sacking as they went. This did not help Pedro’s cause, neither did his penchant for killing the mothers and wives of men he considered traitors. Plus, now that he felt secure again, he had opponents summarily executed.
Enrique was yet again supported by the French. This time, Pedro IV of Aragon did not want to offer him help—this because he had in secret signed an agreement with the Black Prince to divide Castile between them—and told Enrique he would not allow him to cross through Aragonese territory. Enrique ignored him.
By late 1367, Enrique and his Juana were back in Castile, now in control of most of the Castilian meseta. But progress was slow, so the French decide to help things along by sending Bertrand du Guesclin over to help out. By early 1369, Enrique and his allies threatened Toledo and Pedro had to leave the relative safety of Sevilla to defend this pearl among cities. Mid March, he was surprised by Enrique’s army. Pedro was defeated and barricaded himself in the Castle of Montiel. Things were at an impasse, but according to López de Ayala, our Bertrand had explicit instructions from his king: sort this ASAP. So when Pedro reached out to Bertrand, offering him land in return for helping him escape, Bertrand agreed. Instead of helping Pedro to safety, he took him to Enrique. The two brothers flew at each other—with daggers. According to López de Ayala, Enrique succeeded in killing his brother without help, but according to Froissart, a certain Viscount of Rocaberti intervened. When, at one point, it seemed as if Pedro would kill Enrique, he tugged at Pedro’s foot so he overbalanced. Moments later, Pedro was dead, murdered by Enrique. Froissart doesn’t mention du Guesclin…

However the foul deed was done, I imagine Juana Manuel cheered mightily at the news that Pedro was finally dead. At last! Now they could concentrate on healing their kingdom, on raising their children and negotiating treaties with their neighbours. But Pedro’s ghost would likely haunt both her and her husband—especially as his two young daughters were wed to the mighty English princes, one of whom claimed he was the rightful king of Castile through his wife.
Juana Manuel seems to have had other trials. Her husband comes across as something of a womanizer, recognising 12 (!) illegitimate children in his final will. I can only imagine what Juana thought of this, especially given just how many problems Alfonso XI’s bastard brood (including her hubby) had caused their legitimate half-brother, Pedro. Did she at times spend her nights on her knees praying that history not repeat herself? Well, we do not know, but whatever the case, Enrique’s illegitimate sons never posed a threat to Juan.
Juana survived her husband by a couple of years and died in 1381, some years over forty. She is buried in the Cathedral of Toledo, as is her husband.

With Enrique and Juana Manuel, the Trastámara dynasty claimed the Castilian throne. This dynasty would survive for the coming two centuries, centuries in which the tendencies among the Iberian kingdoms to mainly marry close kin would result in successively weaker bloodlines. And things would not get better once Trastámara was replaced by Hapsburg, seeing as this new, vital bloodline very quickly embraced the old tradition of cousin marrying cousin—or uncle niece.

