Now and then I come across medieval women who wielded significant power. On the Iberian Peninsula there is Urraca and Berenguela, Maria de Molina, Isabel la Católica (better known as one half of the double act Isabel and Fernando)—and today’s protagonist, Leonor Teles de Meneses. In general, medieval chroniclers are a bit leery towards female powerhouses, and in the case of Leonor, what comes down to us drips of venom. Not, I am sad to say, that she doesn’t deserve substantial parts of the black legend that surrounds her.
So who was this lady? Well, we can start by saying she was Portuguese. Her father, Martim Afonso Telo de Meneses, was the loyal mayordomo (more or less steward) of Maria of Portugal, the unhappy wife of Alfonso XI. This poor man hit the dust in 1356, murdered on the orders of Queen Maria’s son, King Pedro of Castile. At the time, mother and son were at loggerheads, among other things because Maria had more or less forced Pedro to marry Blanche de Bourbon, a French princess, when he was madly in love with Maria de Padilla. (Some say he’d already married Maria secretly. Whether he had or not, she was the love of his life)
At the time of her father’s death, Leonor was around six. She’d probably spent most of her early childhood in Castile, but after her father’s death it is likely his family returned to Portugal. The Teles de Meneses family was a powerful noble family, and I imagine Leonor grew up adequately educated and pampered. And around the age of fifteen, she was wed to Joao Lourenco da Cunha. As happened quite often, bride and groom fell within the prohibited degree. But as there was a papal dispensation, the happy couple could safely set sail towards their happily ever after. Erm…
Leonor had at least two children with her husband. Maybe she was content, maybe she wasn’t, but that became totally irrelevant when King Fernando I fell head-over-heels in love with her. Fernando was the only surviving son of Constanza Manuel’s unhappy marriage with Pedro I, and had hitherto avoided the dynastic marriages proposed for him.
We are now around 1367-1370, and the Iberian political situation was an utter mess. In Castile, Pedro had been fighting a civil war off and on since the early 60s. The opposition, headed by Pedro’s half-brother Enrique, wanted to depose Pedro, citing his propensity for violence and assassinations of all those he disliked. We need to take this with a pinch of salt: yes, Pedro seems to have been quite relaxed about condemning people to death, but being a medieval king was very often about ridding yourself of potential threats to the throne.

Anyway: Portugal saw an opportunity to use the instability in Castile to expand their own lands, which is why Fernando, after Pedro’s murder in in 1369, claimed the Castilian throne, this based on Sancho IV being his great-grandfather. Did not go down well with Enrique who’d just bloodied his hands killing his brother to finally claim Castile for his own. Back and forth things went until the pope intervened in 1371 and managed to negotiate a treaty. As always with treaties, the kiss of peace was to be combined with a marriage, this time that of Fernando to the young Leonor of Castile, Enrique’s little daughter.
Fernando agreed to marry Leonor of Castile—but some months later he broke the betrothal, this as he had already secretly married Leonor Teles. Problematic that, seeing as Leonor was already married!
“Ah,” Fernando said, “there was no dispensation, hence her first marriage was never valid.” Thereby, Fernando reduced Leonor’s surviving son to a bastard, but she does not seem to have cared. Leonor had her eye on the prize, and the prize was Fernando and the Portuguese throne. More importantly, he lied, seeing as there was a papal dispensation—and he knew it. A man in the throes of passion, was our Fernando.
The Portuguese were less than pleased by their king’s marital antics, but maybe Fernando didn’t want what his father, Pedro I, had had: a political marriage to Constanza Manuel while his true love and affection was for Inés de Castro, with whom he had several children. Still: as a king Fernando was expected to wed so as to further his nation’s interests—and wedding Leonor definitely did not do that.
Leonor now had her backside firmly planted on the Portuguese throne and she had no intention of going anywhere. She also had every intention of involving herself in the actual ruling, which did not necessarily please the powerful nobles or the Cortes—the Portuguese equivalent to Parliament. One of her new husband’s half brothers, Dionisio, was even exiled from court because he refused to kiss her hand in greeting. To ensure loyalty among those in higher positions, Leonor actively promoted the “Petrists”, Castilian refugees who had fled their country after Enrique II had murdered Pedro I and claimed the throne. Putting foreigners in high places is never popular, so the Portuguese were less than impressed—and blamed the queen. Of course.
In 1373, Leonor presented her husband with a daughter, Beatriz. Already then there were mutterings indicating the little princess was illegitimate, this because Leonor’s first marriage had never been annulled. This caused Leonor quite some stress: after all, if Beatriz was illegitimate, then there were plenty of other royal bastards who could claim the throne should Fernando die, and where would that leave her, hey? This may be why Fernando in 1378 disinherited not only his de Castro half-siblings (children of Inés—whom Pedro I always insisted he had secretly wed the moment his first wife, Constanza Manuel died) but also his much younger half-brother, Joao of Aviz.
Now, having them disinherited was all well and good, but Leonor decided to take things a bit further. In 1376, Fernando’s oldest half-brother, Joao of Portugal (not to be confused with his half-brother Joao of Aviz. Why does a father give two of his children the same name???) secretly married Leonor’s elder sister Maria.
Maria was by all accounts drop-dead gorgeous. She was also close to two decades older than the eager groom, but our Joao was so, so much in love. When Leonor found out, she was enraged. Should Fernando die and Joao be acclaimed as the new king, her sister would become queen, and Leonor was not having that. Nope, not ever. So she somehow convinced her brother to drip poison in Joao’s ear, insinuating Maria was being unfaithful. In 1379, Joao stabbed his unfortunate wife to death, thereby causing a scandal so big he had no chance in hell of ever becoming king. Leonor, I imagine, smirked.
The Fernando-Leonor union may have started out in a blaze of passion but does not seem to have been all that happy. According to the chroniclers, Leonor was unfaithful to the king, taking one of those detested Petrists, Juan Fernández Andeiro, as her lover. One must, of course, take this with a pinch of salt: the chroniclers had little love for Leonor. In 1382, Leonor gave birth to a son who lived but for a few days. According to the rumours, this was because the king had realised he’d been cuckolded and had the child suffocated. Hmm.
A year later, Leonor gave birth to a daughter who also died in infancy. Once again, it was whispered the child was not the king’s, and so . . . At the time, Fernando was ill—had been for years, and in October of 1383 he died. Some say due to tuberculosis, other due to poison.

Whatever the case, Leonor chose not to attend his funeral, which did not sit well with people. Instead, Leonor threw herself into her new exciting role as regent for little Beatriz, now nominally the queen of Portugal.

This little girl had been bandied about as a marital prize from the time she was born. First, she was to wed a younger son of Enrique II of Castile, then, when Enrique died, she was to wed baby Enrique, son of the new king of Castile, Juan I. Sometime in the late 1370s, early 1380s, Fernando decided his interests were best protected by allying himself with the English, and hey presto, Beatriz was now betrothed to Edward of Norwich, son of the Duke of York. War broke out between Portugal and Castile, and at the treaty of Elvas, Beatriz was betrothed to yet another new groom, this time Juan I’s second son, the future Fernando I of Aragon. But when Juan I became a widower in 1382, things changed, and in May of 1383, the ten-year-old Beatriz wed the twenty-five-year-old Juan I. She was six years older than her oldest stepson.
None of this interested Leonor. What did interest her was gaining Juan’s support against the Portuguese nobles, so as to confirm her position as regent. She had other support—principally that of her long-time confidante (lover?) Juan Fernández Andeiro—but by now the Portuguese nobility had had it with her Castilian favourites. Supporters of Joao of Aviz decided to assassinate the Castilian count, and while the two first attempts failed, in December of 1383 Andeiro was killed—with the participation of Joao of Aviz himself. With that civil war in Portugal was a fact: on the one side, the dowager queen fighting for the rights of her daughter, on the other Joao of Aviz, fighting for a Portugal free of Castilian influence. No plus points for guessing who most Portuguese supported…

Leonor appealed to Juan for help to avenge Andeiro. He agreed—if she renounced the regency to him. So she did, but quickly realised he had no intention of avenging her favourite. No, what Juan wanted was to claim Portugal—through his little wife. The Portuguese weren’t having it. Soon enough, Leonor wasn’t having it either, incensed by what she perceived as Juan’s betrayal of her (not, apparently of little Beatriz, who seems to have been relatively incidental to her mother). She openly ordered her followers to support Joao of Aviz instead of her son-in-law, and even conspired to have Juan murdered. The plot failed and Juan and Joao found themselves in total agreement: Leonor had to be exiled from Portugal and imprisoned somewhere.


Which was how Leonor ended up at a convent in Tordesillas—not that she had any intention of becoming a nun. Meanwhile Juan and Joao were locked in a war over Portugal—a war Juan ultimately lost at the battle of Aljubarrota in 1385.
Joao of Aviz became Joao I of Portugal and, two years later, he welcomed Philippa of Lancaster as his wife and queen. Now that, dear peeps, was a very, very successful marriage—but we’ll have to come back to that some other time.
Juan died in 1390 and Leonor was released from her convent prison. She ended up in Valladolid, under the lordship of her daughter, Beatriz, who chose to make her home in Toro instead. I am guessing she had little fondness for her domineering mother. And here, the previously so powerful Leonor Teles de Meneses slips further and further into obscurity. We don’t know when exactly Leonor died, but it must have been before 1406 as she is not mentioned in the will of Henry III (who’d been covering her expenses since his father died)
Leonor is remembered today as Leonor the Treacherous—the Portuguese haven’t forgiven her for turning over the regency to Juan I in a desperate attempt to shore up her own position, or for her purported infidelity. She is remembered as cruel and self-serving—what she did to her sister is an especially black stain on her reputation. Who she really was, we will never know—beyond the fact that she was a woman who did not hesitate to go after what she wanted, no matter what it might cost others in her way. Not, I think, a particularly likeable quality, neither then nor now!

