The so-called Golden Age of Spain had many tarnished secrets, and King Philip II was behind the darkest of them. Cold, cruel, and inflexible in his ways, Philip viewed himself as the pious hero of Roman Catholicism—but behind closed doors, his actions were nothing short of depraved.
Most kings are born with privilege, but few had the power that Philip held in his baby fists. His father was the imperious and intimidating Charles V, Holy Roman Emperor—and at the time of his birth in 1527, the royal family wasn’t messing around with their heir. Spain had only just started exploiting the colonial resources of the New World a couple generations before, and they intended to keep it going.
As Philip grew up, his parents molded him into a terrifying and tiny absolute monarch, giving him lessons in conflict, statecraft, and being a strict Catholic…but the other lessons they taught him were bone-chilling.
Philip’s father had enormous expectations for his son, and none of them included “emotional maturity” or “a well-adjusted childhood.” In fact, thinking he was helping his son become a better future monarch, Charles V even made a creepy motto for the boy to live by as he went through his studies: "piety, patience, modesty, and distrust."
Soon enough, the weight of his responsibilities began to contort Philip in alarming ways.
The young prince soaked in these early lessons like a sponge and emerged from his pre-teen years as a serious, studious young man. But he also had a dark side. Even those who knew Philip best were alarmed by how cold and calculating the young man could be. One minister described him by saying, "he had a smile that was cut by a sword.”
In other words, the psychopath vibes were strong in Philip. And he already had some dirty little secrets.
Philip might have been a cold fish in the throne room, but he was still steamy in the bedroom. When he was still a teenager, he seduced his mother’s own lady-in-waiting, Isabel Osorio. Given that Philip was five years older than Osorio, he was probably romancing a prepubescent girl—at best. But neither of them seemed to mind; they would likely go on to have two illegitimate children together.
Philip’s life was becoming very adult in other ways, too.
When Philip was 16 years old, his father dropped a weighty gift in his lap. Seeing just how intensely his son was taking his monarch studies, Charles gave his son regency over all the kingdoms of Spain as a kind of starter pack for absolute rule, then left him to his own devices as he continued looking after the rest of the Holy Roman Empire.
Only, he didn’t leave Philip completely alone, because another development was coming through the pipes.
Philip and his family belonged to the House of Habsburg, an Austro-Spanish dynasty infamous for its commitment to inbreeding its members to keep the, er, “sanctity” of their royal blood. So when it came time for Philip to marry a nice, respectable girl, his parents looked no further than his own cousin, Maria Manuela, Princess of Portugal.
Sure, for the 16th century marrying a cousin is pretty common, but the Habsburgs did this all. the. time. Yes, you can say “ew” now. And by the end of their marriage, it would get a whole lot darker.
According to rumor, Philip’s marriage to Maria Manuela was doomed from the start. One persistent whisper claims that when he gave his hand in marriage to the Portuguese princess on November 12, 1543, Philip was already married, in secret, to his mistress Isabel Osorio. He had even possibly given Isabel a clandestine document proclaiming her as his wife.
If that was the case, he was starting off marriage number two as a bigamist. Not that it stopped him from jumping right in.
Philip and Maria set about doing their duty to make an heir as quickly as possible—something Philip obviously already had extensive experience doing. By 1545, Maria was heavily pregnant, and the entire kingdom waited with bated breath for the announcement of the child’s birth. Unfortunately for Maria, it was about to turn into an utter nightmare.
On July 8, 1545, Maria gave birth to a baby boy—the only kind of baby anyone wanted in those days—whom she named Carlos, fulfilling her (quite limited) duty as Philip’s wife. And then, quite promptly, tragedy came for her. Just four days after the birth, as she was recovering, Maria suffered a brutal hemorrhage. She did not survive.
Less than two years into his marriage, Philip was a widower. On the bright side, he now had a son…except, that wasn’t quite the bright side you’d think.
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As Philip’s only son and heir Carlos grew into a little boy and then a young man, it became clear that something was very, very wrong. The boy was constantly sick, and there didn’t seem to be many lights on upstairs, if you know what I mean. After all, Carlos was the product of extreme, generational inbreeding—for God’s sake, the boy had only four great grandparents out of a possible eight, and only six great-great grandparents out of a possible 16.
In other words: Carlos’s family tree was a dang wreath. And if Philip hoped it would get better, well, it most certainly didn’t.
Given that Philip was just exiting his teenage years when he had Carlos and had a bunch of kingdoms to run on top of all that, perhaps he can be forgiven for some parenting failures concerning his son. But, um, he really did a bad job. By all accounts, Carlos grew up as an arrogant and spoiled brat, leading one dignitary to call him “ugly and repulsive,” though probably not to his face.
Somehow, though, that was just the start when it came to Carlos.
If Philip had an icy streak in him, his son was a whole glacier. The heir’s antics reached truly bloodcurdling proportions. According to lore, he took pleasure in tormenting animals and serving girls alike, once ordering that a housemaid be whipped for his enjoyment at the tender age of 11. Then when a man gave him shoes he didn’t like, Carlos tried to force the man to eat them.
As another ambassador put it, “He wished neither to study nor to take physical exercise, but only to harm others.” But by this time, Philip wasn’t keeping even half an eye on his son—he had his own cruel plans to put into motion.
Philip waited nearly a decade before choosing another bride, but—perhaps fearing his son’s ability to follow in his footsteps—he finally began looking in the 1550s. Once more, his daddy Charles V pulled through: Charles’s cousin was none other Queen Mary I of England, the eldest daughter of Henry VIII and his first wife Catherine of Aragon, and she was looking for a husband.
Charles immediately suggested his son Philip, sending over an attractive portrait of him painted by the master Titian. But right from the beginning, there were serious issues.
At the time, Mary was 37 years old, somewhat sickly, and had never been what anyone would have called comely. Meanwhile, Philip was reasonably attractive, a full decade younger than her, and in the pink of health. It was an instant power imbalance, but that wasn’t all.
Mary quickly grew obsessed at the thought of tying the knot with her Spanish prince, even going against the prevailing opinion of her ministers that she should marry an Englishman and causing insurrections when she insisted on the union. This would be creepy on its own—but Philip’s reaction was ice cold.
For Philip, there was absolutely nothing in his marriage proposal resembling emotion. Although the English government made sure he would only co-rule England alongside Mary, and only as long as their marriage lasted, it was still a position of immense political power—and that’s all it was for him. As one of his aides put it, “the marriage was concluded for no fleshly consideration.”
Well, someone should have given Mary that memo, because it didn’t take long for it all to unravel.
In mid-July of 1554, Mary and Philip finally met for the first time. But again, don’t go picturing anything close to romantic: Philip couldn’t speak English—in fact, he never truly learned—and the so-called lovebirds had to work around the barrier with a hodgepodge of other languages. Then two efficient days later, they made it official in a wedding ceremony at Winchester Cathedral.
Aw, true love, right? In any case, Philip didn't waste any time when it came to wooing his new wife.
In September of that same year, England got word of momentous news. Their Queen Mary had stopped menstruating and was experiencing morning sickness and weight gain to boot. To everyone at court, it seemed like the country was about to get a new heir. Ever the pragmatist, Philip even made sure parliament passed a law making him regent in the event of Mary dying in childbirth. Aw.
But Philip’s next response to the situation was truly surprising.
While all the court doctors fussed over Mary, Philip himself had strange feelings about the pregnancy. Whether his close proximity to Mary helped him see there was something off about her symptoms, or he just had a sixth sense about it, Philip wrote to his brother-in-law during this time expressing doubts about whether Mary’s pregnancy was real.
And as the months passed, the disturbing truth became clear.
In the spring of 1555, Mary was so certain that she was about to give birth, she called her sister Elizabeth to court so she could witness the coming of a new heir. Yet the summer brought devastating developments. Though rumors swirled that she had given birth in secret, the truth was Mary hadn’t given birth at all yet, frustrating Philip and the rest of the court to no end. And then came the final nail in the coffin.
In July of 1555, after 10 months of experiencing certain symptoms of a pregnancy, Mary’s abdomen finally receded, revealing that Philip’s doubts had been justified all along. In fact, the Queen of England had likely just suffered from a phantom pregnancy over her deep desire to have a child with her beloved husband. And darker days were ahead.
Mary had lost all her hopes to give Philip an heir in an instant, so it’s safe to say she was beside herself with heartbreak and grief. More than that, her entire court had been ridiculing her for months, with one courtier sniping that the pregnancy had been as likely to “end in wind rather than anything else." Philip only dealt his wife more betrayal.
As soon as he was sure Queen Mary wasn’t pregnant, Philip up and left England to tend to matters of state in Flanders. Yes, he left his still-recovering wife—who was by one account now “extraordinarily in love” with him—to the vipers in her court. It was a colossal jerk move, even for Philip, and the fallout from it was unimaginable.
One of the reasons Mary’s ministers were hesitant about allowing her to marry Philip was their fear that, as an even more pious Catholic than herself, Philip would push her toward intolerance of other religions, particularly Protestantism. They were right to worry: If his presence didn’t make her so before, his absence did now.
Dejected at Philip leaving, Mary began to believe her phantom pregnancy was a punishment from God because she “tolerated heretics.” Soon enough, she began persecuting Protestants, eventually earning her the infamous nickname “Bloody Mary.” But even though Philip was very much a part of Mary’s villain origin story, he didn’t stop there.
In 1556, Philip finally achieved his destiny. That year, his elderly father Charles V abdicated his throne, and he officially became King Philip II of Spain at last. But even with this good news, he didn’t return to Mary—in fact, he stayed away from his wife for nearly two years, only returning in 1557 when he wanted her to help him raise an army for warmongering.
And just like with any bad boyfriend, Mary should have run away when he showed up on her doorstep.
Things went wrong from the start of Philip’s little jaunt to England. For one, he convinced Mary to enter into a conflict with France…one that went disastrously for her nation. By the end of it, England had lost Calais, its last remaining territory on mainland Europe. Mary was so distraught at this that she was supposed to have said, "When I am dead and opened, you shall find 'Calais' lying in my heart."
Yep, gonna blame Philip for that one too. But his professional ambitions turned out to be the least of Mary’s worries.
Philip’s return to England—which included at least one conjugal visit—raised Queen Mary’s hopes that she was pregnant again. Only, something was different this time. Mary realized her health was failing, and if she did have a child, she likely wouldn’t be around to see them grow up. Knowing this, she drew up documents once more making Philip regent over the child when she passed.
Tragically, Mary’s luck was about to take an even worse turn.
Although Mary had expected to give birth in March of 1558, this again didn’t happen—something much worse did. While Mary had no child to speak of and possibly had gone through another phantom pregnancy, she was experiencing intense pain in her uterus. She lived in agony from May of that year onward, getting progressively weaker.
After the hard realization that she would not have any heirs, she arranged for her sister Elizabeth to succeed her. And when the end came, her husband dealt her two insults, each more biting than the other.
In November of 1558, Queen Mary I passed, probably from uterine cancer or perhaps ovarian cysts. Philip then outdid himself in cruelty. As if to underscore just how indifferent he was to the wife that adored him, he wrote to his sister during the mourning period, coolly saying, “I felt a reasonable regret at her death.” Oh, but he had more barbarous plans.
Philip had spent so long playing political games that everyone knew there was barely a beating heart underneath his doublet anymore. Even so, probably a few courtiers still managed to raise their eyebrows when they found that in the wake of Mary’s passing, Philip had sent a marriage proposal to her sister, now Queen Elizabeth I.
After all, with Mary gone, Philip no longer had access to the throne or the title King of England, and he would have very much liked to keep both those things. But for perhaps the first time in his life, his sliminess caught up to him.
Elizabeth I didn’t go down in history as a fool, and for good reason. Whether she didn’t think Philip would help her in the long run or she was just seriously turned off by his baldly mercenary offer, she took her time answering Philip’s proposal and eventually turned him down. But in the meantime, Philip already had his eye on another powerful bride.
In 1559, Philip found his next wife: Elisabeth of Valois, one of the daughters of King Henry II of France and Catherine de Medici. Although not the beauty of her extremely good-looking family—that title belonged to her sister Margaret of Valois—the icy Philip still seemed to warm to Elisabeth’s plain prettiness, not to mention her powerful lineage. But, of course, it all came with a side of creepiness.
While Philip was 32 years old when they married, Elisabeth was just 14. Just wait, it gets worse.
Philip was nothing if not pragmatic, and he knew that as much as he loved the look of his new wife, a 14-year-old girl was too young even by 16th-century standards to bed and get with child. His solution for his manly urges? He merely took up with another mistress, Eufrasia de Guzman—he had already cast off Isabel Osolio around this time—and bedded her until Elisabeth was old enough.
Still, even Philip’s formidable resolve wasn’t enough, and he eventually slipped into Elisabeth’s chamber just a year later. As he’d find out, it was far too soon.
Over the next four years, Philip and his wife tried to have more heirs together besides his lone son Carlos. It was full of bloody tragedy. First, a 15-year-old Elisabeth gave birth to a stillborn son, and in 1564 she miscarried twins. By this last pregnancy she was a full adult, and Philip was likely getting worried he would never secure his legacy.
He should have worried—because that legacy was a ticking timebomb.
In 1562, Philip’s troublesome son Carlos got a cruel kind of karma. While chasing a servant girl down some stairs (because of course that’s what he was doing) the spoiled prince took a spill and hit his head. For days, he lay on the brink, experiencing severe pain and delusions. Only trepanning his skull—drilling a hole into it—took Philip’s son back from the edge.
Yet when the prince recovered enough to move around, everyone quickly realized they had a huge problem on their hands.
Carlos had never been a model prince, to say the least, but after his head injury, he went from menacing to downright terrifying. All his youthful proclivities for causing harm became completely unchecked, and they forced Philip into a painful decision. The man for whom political legacy was everything had to remove his heir from any positions of power.
Little did he know then, this would come back to bite him in a horrific way.
In 1566 and 1567, Philip finally got some good luck, and his wife Elisabeth gave birth to two daughters in succession, his favorite girl Isabella Clara Eugenia and then Catherine Michaela. Sure, they were “just” daughters, but they were also healthy and showed no signs of Carlos’s complete mental instability.
In fact, the same year little Catherine was born, that mental instability grew to ruinous proportions.
While Philip was rejoicing—as much as Philip could ever rejoice—in the births of his two daughters, Carlos went off the deep end. The prince was so mentally disturbed that one day when someone threw water from a window and it accidentally splashed him on his walk, he demanded the man’s house be set on fire. Though actually, turns out this was Carlos being nice.
Carlos also attempted to throw a servant who displeased him out of a window—oh, and then he tried to kill two of his father’s men. It was the last boundary of sanity for Carlos. Soon, his murderous streak deepened.
In the fall of 1567, Philip faced his most gruesome and harrowing ordeal yet. In a fit of insanity and paranoia, Carlos barged into the rooms of Philip’s half-brother John of Austria and tried to shoot him. When that didn’t work—a wary servant of Carlos’s had already removed the bullets from the gun—he proceeded to try to throttle John with his bare hands.
John survived the attack, but Philip could ignore it no more: He had a full-blown crisis on his hands, and he needed to deal with his son. He proved just how ruthless he could be.
Philip couldn’t have his own son trying to kill other members of his family, and he immediately had the boy locked up and all but isolated from the world. For weeks, Philip kept Carlos from receiving any correspondence, and refused to let anyone but his most loyal men visit the prince. But still, Philip didn’t think it was enough, and early next year, he took it up a whole lot of notches.
In the midnight hours of January 17, 1568, Philip accomplished a brutal coup. He entered his son’s room in full armor and with a full complement of men at his back, then turned Carlos from a virtual prisoner into a complete one. He took away any papers and arms in the room, then boarded up the prince’s windows for good measure.
From Philip’s perspective, he had no other choice. But it didn’t go the way he wanted—not in the slightest.
Instead of these measures mollifying Carlos—wouldn’t you know it?—the prince only grew more agitated. He threatened constantly to take his own life, leading Philip to take away even cutlery from his son’s rooms during meal times. It didn’t stop Carlos; now he merely went on a hunger strike and very nearly succeeded in offing himself.
Philip, meanwhile, had to perform damage control. True to form, he did it incredibly sneakily.
With his only son locked up in his rooms and going loopy, Philip went to desperate measures to protect his good name. He told almost no one about the true state of affairs, lying through his teeth and making excuses for his son’s absences that had nothing to do with his heir going through a violent psychotic break. Maybe he would have pulled it off…if catastrophe hadn’t struck first.
In the summer of 1568, Carlos suddenly passed, likely from complications of his already poor health and his attempts to starve himself. Or that’s what history thinks probably happened—many rumors at the time indicated that Philip had his troublesome son “taken care of,” a narrative many associate with Philip to this day.
Whether there’s any truth to it or not, Philip’s next phase of life was certainly not angelic, either.
Just after his son Carlos's suspicious and brutal end, a bitter twist of fate came once more for the King of Spain. In October of 1568, his wife Elisabeth of Valois, who had been pregnant again, miscarried a baby girl. But the tragedy wasn’t over yet: Elisabeth quickly succumbed to complications of her bloody labor along with the newborn.
Philip was in his 40s now, a widower again after his third marriage, and he had no male heir to speak of. In search of a new bride and a replacement son, Philip really dialed up the creep-o-meter.
Almost as soon as Elisabeth of Valois croaked, Philip knew who he wanted as his fourth wife: Anna of Austria, the daughter of the new Holy Roman Emperor Maximilian II and Maria of Spain. She was more than two decades younger than Philip—but that’s not actually the creepy part. The creepy part is she was his dang niece.
Actually, no, I lied. It’s the next part that’s truly disturbing.
As a matter of fact, Anna of Austria was on Philip’s mind long before their marriage. That’s because he’d already lined the girl up to marry his violent, horrific son Carlos. With Carlos (mercifully) gone and his wife now gone, Philip thought, “Yeah, might as well marry that niece myself,” as one does. In May 1570, they did—and then came the surprise.
Despite their unenviable meet-cute, Philip and Anna of Austria seemed to have a very happy marriage, with some describing her as his favorite wife, and with Philip very likely keeping no mistresses at this time, apparently the highest compliment any Medieval man could pay his bride. But that wasn’t all.
After a lifetime of struggling to sire healthy, mentally-balanced boys, Anna gave him four sons in a row, plus one girl for good measure, over only a decade. Still, all this good fortune was something of a monkey’s paw.
Although Philip got a series of heirs in his marriage to Anna of Austria, he also got a series of tragedies. All but one of the children, the future King Philip III of Spain, made it to adulthood, and Anna of Austria herself caught a vicious bout of influenza—or else suffered from heart failure—and perished in 1580 at just 30 years old.
Philip was staring down the barrel of his mid-50s and alone again. Perhaps that’s why some of his last decisions quickly lit his legacy aflame.
For decades, Philip had maintained cordial, if chilly relations with his ex-sister-in-law Elizabeth I over in England. Well, that didn’t last. See, Philip had spent his reign putting down Protestant insurrections, particularly in the Spanish-held Netherlands, and still viewed himself as the protector of the One and Only True Religion, Catholicism.
So when the Protestant Elizabeth started helping the Dutch rebels in 1585, Philip drastically—and infamously—turned on her.
One of Philip’s biggest, and last, legacies as King of Spain was also his biggest failure. In 1588, desperate to keep Catholic supremacy in Europe, Philip turned his Spanish Armada toward English shores, attacking no less than the iconic English Channel with the express intent of invading England and strong-arming them into putting a Catholic on the throne.
That is not what happened. What happened was one of history’s most embarrassing disasters.
Although much is made of Elizabeth’s army trouncing the Armada and sending the Spanish back with their tails between their legs, the truth is something much worse happened. Right at the place where the Armada was going to strike, an enormous storm hit the channel, destroying many of Philip’s ships without the English lifting a finger.
Philip had to retreat without ever taking a bite of England—and then the whispers started.
In this hefty war of religion, it was extremely bad PR for a natural disaster to stymie Philip’s ambitions so brutally. Indeed, Protestants around Europe cheered at the storm’s destruction of the Armada, believing that it was God showing his will to the people. Philip, for his part, reportedly complained, “I sent my fleet against men, not against the wind and the waves!”
Flabbergasted at his loss, Philip couldn’t let the thought of England go. It would almost be the end of him.
Another little-known fact about the famed Spanish Armada is that there was more than one. Philip kept desperately trying to hammer at England’s shores, and sent further fleets in 1596—when he was approaching his 70s—and then again in 1597. Each of them failed in their missions, and likewise failed to fulfill Philip’s desire of one last golden victory for his golden age.
Unfortunately, these were far from his final disappointments.
By the end of his life, bouts of malarial fever and gout had crippled Philip and turned him into a shadow of what he once was. In order to bear the pain and still govern his nation, Philip took to strapping himself to a chair for the last three years of his life—the years he sent out those two desperate Armadas again. And more upset was to come.
Philip lived long enough to watch his son and heir, Prince Philip, grow into a young man. He was deeply disappointed in what he saw. After the Carlos debacle, he tried to give his son the best, most progressive education the crown could buy. But it was nonetheless clear to everyone—probably Philip most of all—that the boy, while studious, had no political mindset. Once more, the consequences of this were far-reaching.
Philip ruled over what many historians call the “Golden Age” of Spain, thanks mostly to the masses of gold and silver coming in from the “New World” Philip had inherited. Yet when he finally succumbed to cancer in 1598, he might as well have been ruling over a kingdom of ash. In his son, Philip likely saw no glimmer of hope to take Spain to greater heights—and he was right.
The nation declined during Philip III’s reign onward, and Spain lost the Netherlands and their fight with Protestantism within 50 years of the old king’s end. King Philip II of Spain had been a warmonger, an honorary Tudor, a serial husband in desperate search of an heir, and a hero of Catholicism. None of it mattered in the end.
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