Ruthless Facts About Charles V, Emperor Of Europe

Charles V, Holy Roman Emperor was born into the twisted world of Medieval royalty—and his dramatic life rivaled that of his contemporary, Henry VIII. Though Charles became maybe the most powerful person on Earth, his life was anything but classy. With his scandalous affairs and vicious feuds, the twisted life of Charles V proved one thing: Absolute power corrupts, absolutely.


1. He Had A Handsome Father

Charles of Habsburg (yes, those Habsburgs) was born in February 1500 to some truly wild parents. His father, Philip the Handsome, was an Austrian prince. With the Holy Roman Emperor Maximilian and the fabulously-wealthy “Mary the Rich” as his grandparents, Charles must have felt pretty darn good about the genes coming from his dad’s side.

And how about his mom’s genes? Well, that’s another story…

2. His Genes Weren’t Perfect

Charles V’s mother was Joanna of Castile, AKA Joanna the Mad. Though she stood in line two inherit the thrones of Aragon and Castile, Joanna was also infamously, well, mad. Her mental health was questionable even before her son was born, but as Charles grew into a young man, things would get so much worse—and Charles had to pay the price for it.

3. His Birth Wasn’t Glamorous

For a man who rose to the height of power and luxury, Charles V came from some pretty darn humble beginnings: He was born on the floor of a bathroom. When momma Joanna went into labor, she wasn’t about to let that ruin her evening plans, so despite her contractions, she still dressed up and went to a glitzy ball. But she couldn’t keep Charles in forever.

Near the end of the night, Joanna was forced into a bathroom, where she gave birth to Charles right next to the toilets. From the beginning, it seemed like Charles’s parents didn’t want him getting in the way of their social life—and that didn’t change as the boy grew up.

4. He Had A Tragic Childhood

Charles’s childhood was cripplingly lonely. Apparently, “parenting” wasn’t very high on his mom and dad’s list of priorities. Not long after his birth, Philip and Joanna dumped Charles off with his aunt and went cavorting off to Spain. They barely ever came to visit after that. Maybe they thought they’d have plenty of time to spend with little Chucky when he grew up—but fate had other plans.

5. His Parents Abandoned Him

While his parents were off in Spain or Austria—basically, anywhere Charles wasn’t—the boy lived out his lonely childhood in the Netherlands. He may have hated his parents, but he loved his homeland. Even when he came to rule some of the most powerful countries on earth, Charles’s heart always lay in the Low Countries.

And speaking of Charles’s heart: The boy was growing up fast, and that could only mean one thing. Sure, he was still a child, but it was high time to find this little prince a wife.

6. His First Engagement Was Gross

We all have that one friend who got engaged way too young—but medieval royals put those friends to shame. Charles’s parents betrothed him to England’s Princess Mary (Henry VIII’s sister) when he was just seven years old and Mary was only 11. See, Charles’s family had their thumb in just about every single one of Europe’s royal pies, except for England. They hoped Charles and Mary’s marriage would fix that.

It seemed like a good plan, but that didn’t stop it from going up in flames.

7. He Suffered Rejection Early

OK, so maybe royals used to get engaged waaay too early, but at least they didn’t marry until they were teenagers. Unfortunately, in this case, that gave the King of England lots of time to get cold feet. In a move that infuriated Charles’s parents, he called off the betrothal and instead set his girl Mary up with the King of France instead.

Their grand plans gone up in smoke, the Habsburgs were forced to find another bride for little Charles—but if you think they were going to forget this betrayal, you’ve got another thing coming.

8. His Parents’ Power Grew

In 1504, Charles’s grandma suddenly passed, making his mother the Queen of Castile. Since everyone figured she was totally insane, they also made sure that his dad became king as well. It was the most power Charles’s parents had ever seen, but they didn’t get to enjoy it for long. Soon after they took the throne, tragedy struck.

9. He Knew Loss From A Young Age

Being handsome didn’t save Charles’s dad Philip from a sudden and painful death. Typhoid claimed the newly-crowned king less than a year after he took the throne. Though Charles, who barely even knew his father, probably couldn’t have cared less, the news absolutely devastated his mother. But Philip’s death was only the beginning—things were about to get so much worse.

10. His Mother Went Off The Deep End

Joanna was mentally unstable to begin with, but the loss of her husband pushed her to her breaking point. Now the sole Queen of Castile, she completely lost control of her people, and the country quickly fell into chaos. It was a dark and frightening time for Castile. Plague and famine ravaged the land, and the country seemed on the brink of complete collapse.

But this is where our boy Charles comes into the picture.

11. He Was A Savior

By this point, Queen Joanna had basically become a recluse. While her country fell apart around her, she took her husband’s corpse and fled to the isolated town of Tordesillas. Some nobles set up a regency to try and rule in her absence, but things didn’t get much better. The country needed an actual monarch—but don’t worry. One was coming. And his name was Charles.

12. He Wanted Power

Castile floundered with effectively no monarch for nearly a decade. Then, to make matters worse, in 1516 Joanna actually inherited the crown of Aragon as well. That made her the Queen of all Spain, but as we’ve heard, she was in no state to rule. However, by now, her boy Charles was 16 years old and ready to take the reins himself.

Charles had himself proclaimed King Charles I of Spain and took control of the country—but not everyone was happy about it.

13. His Own Granddad Hated Him

Charles was just 16 years old and had spent almost his entire life hidden away in the Netherlands, yet he still had enemies. Even worse, those enemies were his own flesh and blood! His maternal grandfather, Ferdinand II of Aragon, absolutely hated the idea of Spain falling into the hands of a foreigner—even if that foreigner was his own grandson.

He did everything he could to make sure the throne of Aragon went to anyone other than Charles V. But he was in for a rude awakening.

14. Rivals Tried To Keep Him From The Throne

Ferdinand hated the idea of Charles becoming the King of Spain, and he had one extremely important ally on that front: Cardinal Jimenez de Cisneros, the regent of Castile. As regent, Cisneros hoped to rule Castile with an iron fist, and he didn’t want this kid from the Netherlands coming in and spoiling all his fun. But even at just 16, Charles was clever, and there was nothing Jimenez could do to stop him from taking the throne.

If only Jimenez had fallen in line quicker—because people who crossed Charles had a strange habit of winding up dead.

15. His Enemy Met A Suspicious Fate

Cardinal Jimenez finally backed Charles as king, but by that point, it was too late. When Charles finally arrived in Spain, the Cardinal rushed to meet him to pay respects—but he never made it. He fell suddenly ill on the trip and passed before he ever laid eyes on the new king. Does that seem a little suspicious to you? You’re not the only one. From the moment Jimenez gave his last breath, people started to wonder.

Who knows how Jimenez really died, but everyone assumed it was poison—revenge for challenging Charles’s rule.

16. He Couldn’t Be Stopped

Charles’s grandfather Ferdinand passed in 1516, and he could do nothing to stop Charles from swooping in and taking his throne. Forced to see the writing on the wall, Ferdinand finally accepted Charles as his heir. But shortly before his end came, Ferdinand wrote to his grandson and made one final, desperate request.

17. His Grandpa Made A Last Request

Though he could be a shrewd political manipulator, Ferdinand was still a big softie at heart. He deeply loved his queen, Germaine of Foix, and shortly before passing he wrote to Charles and begged him to make sure that Germaine was taken care of. Well, Charles did indeed make sure that Germaine was taken care of—but probably not in the way that Ferdinand had in mind…

18. He Needed A Wife

OK, so now Charles was the King of Spain. That could only mean one thing: He needed heirs to continue on his legacy. So, years after his first engagement went up in flames, Charles hit the town again looking for a wife. Pretty soon, his advisors settled on someone: Isabella of Portugal. Sure, she was his cousin, but if you’re a Habsburg, being a blood relation is basically a requirement.

Isabella was perfect, but there’s one thing those advisors didn’t count on…

19. He Was Uncontrollable

The first time people picked out a bride for Charles V, he was basically a toddler. This time he was a full 18 years old, and the new King of Spain wasn’t one to be pushed around. He was enjoying single life too much to settle down and marry. Charles undoubtedly caused plenty of hand-wringing when he refused to marry Isabella and live that single life instead.

The way Charles saw it, he was the king, so he could do whatever he wanted—but quickly, he’d come to regret turning down Isabella. He didn’t know how good he had it…

20. His Next Engagement Was Seriously Messed Up

Charles couldn’t outrun his advisors forever. He had a kingdom to run, and that meant he needed to secure a wife. But by 1521, the Isabella ship had sailed. So they picked out a truly disturbing bride-to-be instead. Remember when Charles was engaged to an English princess at seven years old? Turns out, these royals could get a lot weirder.

This time, the 21-year-old Charles became engaged to a six-year-old English princess: Mary, Henry VIII’s daughter. Oh, and of course, she was also his cousin. Yes, Charles’s love life was a total mess. But don’t worry—the rest of his life was a total mess too.

21. He Fought Rebellion

Throughout his rise to power in Spain, Charles also had his lands back home in the Netherlands to keep an eye on, and almost as soon as he left, things went south fast. A peasant’s revolt threw the region into conflict for several years. But the rebels were about to learn that while Charles was young, he was still someone you didn’t want to cross.

22. He Made A Chilling Statement

After nearly a decade of fighting, Charles’s forces finally put down the peasants’ rebellion. So, do you think Charles was a “forgive and forget” kinda guy? Not even close. He rounded up all of the rebellion’s leaders and beheaded them to make an example. The message was clear: If you crossed Charles, you were going to pay the price.

He was already that ruthless at 20 years old—and he’d only get worse as he grew older.

23. He Played Dirty

In 1519, Charles added Austria to his ever-increasing empire. That meant he was Lord of the Netherlands, King of Spain, and King of Austria. It was only a matter of time before he added an even greater title to his repertoire: Holy Roman Emperor. Though names as powerful as King Francis I of France and Henry VIII of England challenged him for the spot, nothing was going to stop Charles from claiming the power he craved.

Charles became Holy Roman Emperor in 1519. So how did he manage to beat out both the kings of France and England? Simple: He bribed the pants off of the entire electoral committee. Easy as that.

24. He Had An Infamous Deformity

Austria isn’t the only thing Charles inherited from his grandfather. A member of the Habsburg royal family, Charles got land, influence, and power…and the Habsburg jaw, a congenital deformity that years of inbreeding ensured stayed in the Habsburg family line for generations. But the jaw was just the start of Charles’s health problems.

25. He Had A Painful Illness

Charles V, Holy Roman Emperor, was one of the most powerful men in history—but he was still a man. On top of his deformed jaw, he suffered from epilepsy throughout his life, but that wasn’t so bad compared to a far worse ailment: Gout. Believe it or not, a medieval king’s diet wasn’t exactly great. He pretty much only ate red meat, which left him with excruciatingly painful, swollen joints.

Eventually, this agonizing sickness would come back to bite him, but for now, Charles had an empire to run—and his newfound power brought some extremely dangerous enemies.

26. His People Revolted

Running an empire is no picnic, and Charles learned that almost immediately. His grandfather wasn’t the only one who didn’t like the idea of a foreigner ruling Spain. So, when Charles raised taxes so he could go off and fight wars across Europe, the obvious happened: People revolted. But this time, unlike the revolt in the Netherlands, the rebels had a secret weapon…

27. They Used His Mother As A Pawn

Remember Charles’s mom, Joanna the Mad? She was still kicking around throughout all of this. Living in seclusion in the Spanish countryside, no one thought her fit to rule—but the rebels preferred a mad Spanish Queen they could control to a ruthless Dutch King they could not. But the rebels made a mistake they hadn’t counted on: They made it personal for Charles.

By bringing his mother into the picture, the rebels made sure their fate would not be pretty.

28. His Response Was Brutal

Spanish rebels fought against the king’s forces for the better part of a year, but in the end, the iron will of Charles V was too much for them to overcome. Charles’s men absolutely crushed the rebels at the Battle of Villalar and took their leaders captive. And we know what Charles does to rebels at this point. He had all three of the leaders beheaded, and just like that, the rebellion fell apart.

But they had revealed a serious weakness in Charles’s rule: His mother. So Charles took drastic measures to make sure it never happened again.

 29. He Gave His Mother A Chilling Fate

After a lonely and isolated childhood, Charles held little affection for his parents. Still, what he did to his mother was ice-cold. He locked her up and threw away the key. Sure, her “prison” was the Royal Palace in Tordesillas, but she was a prisoner nonetheless. If you thought Joanna the Mad was unstable before, she really went off the deep end when her own son made her his prisoner.

30. Her Madness Got Much Worse

Joanna became intensely paranoid, utterly convinced that the nuns who looked after her were secret assassins coming to take her life. She barely ate, struggled to clothe herself, slept fitfully, and almost never bathed. She was still Queen Joanna in name, but she had fallen just about as far as anyone could fall. You’d hope that maybe, Charles would hear what had become of her and find some level of mercy.

Nope. Not even close. When Charles V heard about his mother’s state, his response was chilling.

31. His Response Was Cruel

When caretakers wrote to Charles and updated him about his mother’s condition, his heartless reply was cruel, even for him. He wrote, “It seems to me that the best and most suitable thing for you to do is to make sure that no person speaks with Her Majesty, for no good could come from it.” He doomed his own mother to a life of utter isolation and madness so he could go off and play emperor.

But some historians claim the story of Joanna the Mad is even more twisted than it appears.

32. It All May Have Been A Lie

Queen Joanna of Castile’s madness has echoed through history even to today, but some historians think it was all a terrible lie. Reports claim she was keenly intelligent in her youth, and rumors of her insanity only began after she married. It’s possible that Joanna was merely a threat to her husband and son’s rule, so they each claimed that she was mad so they could cast her aside and rule alone.

If that’s the case, it makes what Charles did to her so much more disturbing.

33. One Man Changed Everything

Maybe it was just a “right place right time” thing, but Charles was emperor for some of the most important events in modern human history. Chief among them was the matter of a certain monk named Martin Luther. Luther’s Ninety-five Theses threatened to completely upend Christianity as the world knew it, and they came out just around the time that a youthful Charles came to power.

Charles was still a teenager at the time, but even he realized this probably needed addressing. Unfortunately, he only succeeded in making a horrible mess of things.

34. Charles Made A Plan

To deal with Martin Luther, Charles did something no one expected: He invited Luther to come have a chat. While thousands across Europe were calling for Luther’s blood, Charles thought he could discredit the man. He invited Luther to come to the city of Worms and make his case. Charles even promised that no harm would come to him, and he could leave a free man.

Luther couldn’t pass up a deal that good, so he agreed. Charles didn’t realize it yet, but he’d made a terrible mistake.

35. It Blew Up In His Face

Charles hoped that Luther would simply renounce his Theses and call it a day. Instead, Luther gave an impassioned defense of his work, denouncing the Pope and mainstream Christianity. Even though his plan completely backfired, young Charles was still forced to keep his word and let Luther walk away from Worms a free man.

Charles hoped that he’d nip the Protestant Reformation in the bud with this conference—instead, he only made it stronger. And you know it would come back to bite him in the end.

36. He Looked Incredibly Weak

Even though Charles let Martin Luther go free, he still issued the Edict of Worms declaring Luther and anyone who shared his views a heretic. Still, it’s hard to call the whole fiasco a success. Charles had given Luther a platform and lent his preaching legitimacy. His allies considered the whole thing a disaster—and some of them decided to take matters into their own hands.

37. His Own Man Disobeyed Him

The local lord, Frederick of Saxony, was particularly furious that Charles had let Luther go free. Against Charles’s wishes, he had his men kidnap Luther and lock him away in an isolated castle. Sure, Luther ended up surviving the ordeal, but the whole mess made Charles look absolutely terrible. Not only had he completely failed in his attempt to stop the Reformation, but now his own lords were disobeying his direct orders, making him look weak and ineffective.

It seems like Charles learned a valuable lesson though. For the rest of his reign, he made one thing frighteningly clear: If you cross Charles V, Holy Roman Emperor, you’re going to pay a terrible price.

38. He Was Behind Atrocities

For most people, locking up your mother for years would probably be the worst thing you ever did. For Charles, that was nothing. What about Hernan Cortes and the conquistadors‘ utterly horrific domination of the Americas? Yeah, they did all of that in Charles’s name. Charles was completely OK with the massacre of thousands as long as it meant he could add more territories to his ever-expanding empire.

But the conquistadors weren’t the only ones in the New World on Charles’ orders.

39. He Loved Gold

Charles V is proof that no matter how rich you are, you could always be a little richer. In 1529, Charles funded an expedition by a German banking family to find a legend: The mythical El Dorado. Enticed by legends told by Indigenous peoples, Charles hefted over a huge chunk of change in the hopes his men would find the city of gold and make him rich beyond his wildest dreams.

Sure, they didn’t find it, but I don’t think Charles had to worry too much. He was doing just fine without El Dorado—though for a despicable reason.

40. He Caused Untold Suffering

We have Charles V to thank for the Atlantic Slave Trade, one of the most evil enterprises in human history. Charles was the first ruler to authorize his men to transport slaves directly from Africa to the Americas. The charter made him unbelievably rich—and caused unspeakable human misery for generations. I bet that Charles liked to think of himself as a pretty good guy, but his legacy speaks for itself.

41. His Empire Was Like No Other

People usually connect the phrase, “The empire on which the sun ever sets” with the British Empire, but they just stole that title from Charles. With lands stretching across the entire globe, Charles V’s Holy Roman Empire was the original empire under the sun. It was an amazing accomplishment—but it couldn’t last forever. Before long, Charles would see everything he built start falling apart around him.

42. He Spent His Life Fighting

Charles V had enemies in every corner of the globe, but one foe was greater than the rest: France. See, with territories in Germany, Austria, Spain, and Italy, Charles’s empire completely surrounded France. Understandably, that made the French nervous—and it led to a fierce rivalry. Charles would spend nearly his entire reign struggling against France, with each side resorting to truly twisted measures to try and gain the upper hand.

43. He Had A Mortal Enemy

Charles started his reign by putting down some petty rebellions, but in 1521, he hit the big time: War with France. Specifically, with King Francis I, the man who would become Charles’s mortal enemy. To say they hated each other would be an understatement. These two kings utterly despised one another, and it would take them to some dark and disturbing places.

44. He Wanted A Fight

Charles V hated King Francis I of France so much that he actually challenged his nemesis to single combat many, many times. Don’t get me wrong, I’d absolutely love to see two pompous kings awkwardly take up swords and swing them at each other, but maybe that wouldn’t be the smartest decision.

Obviously, Francis refused Charles’s ridiculous challenges every time, but don’t worry—Charles would find plenty of ways to make his rival suffer.

45. He Took His Nemesis Hostage

Charles V and Francis were the two most powerful monarchs in Europe for many years, and they made Italy their battleground. The Italian Wars became the focal point of their rivalry, and soon enough bloodshed broke out all across the country. Then, in 1525, the Battle of Pavia changed everything. Not only was it a massive victory for Charles, but there was an extra cherry on top:

Charles managed to take Francis, his mortal enemy, captive. Oh, you know this is going to be good.

46. He Rubbed It In Francis’s Face

Sure, Francis wouldn’t duel Charles face to face, but at least Chuck got to utterly humiliate his rival. Charles eventually let Francis go free—but you know he didn’t release his rival for nothing. First, Charles forced Francis to give up Burgundy, one of the richest and most important French territories. But that was just the tip of the iceberg. Charles’s other demands were far more brutal.

47. He Took His Rival’s Sons

Burgundy wasn’t enough for a man as ruthless as Charles V. No, he needed a way to make sure Francis didn’t back out of their deal. So, he hit Francis where it hurt most: Charles let Francis return to France…in exchange for his two sons, who became Charles’s prisoners in his stead. He hoped that would make sure Francis would stay in line—but Charles underestimated just how heartless Francis really was.

48. His Enemies Wanted To Destroy Him

In the end, King Francis wasn’t about to let something as small as his children’s safety get in the way of his rivalry with Charles V. The second he made it back to France, he announced his deal with Charles was bogus and refused to give up Burgundy. But that was just the beginning. Next, he formed a massive alliance with the Pope, England, Venice, Florence, and Milan.

This alliance, the League of Cognac, had a single goal: Destroy Charles V, Holy Roman Emperor. If the fighting had been bad before, it was about to get so much worse.

49. He Still Wasn’t Married

Keep in mind, all of this happened before Charles was even 25 years old. He was fighting rebellions left and right, challenging kings to duels, and taking mistresses who were far older than him. His life seemed plenty busy, but there was one huge problem he’d put off for too long: He still didn’t have a wife. He was still technically engaged to Princess Mary of England, but between her being a child and him being at war with England, there wasn’t much of a “spark.”

He called off the engagement and set his eyes on a different wife—someone no one expected.

50. He Married The Woman He’d Rejected

After many affairs and failed engagements, Charles finally settled on a wife. The lucky lady was…Isabella of Portugal! Don’t remember her? She was actually the woman he was supposed to marry when he was 18 and living that bachelor life. Apparently, she didn’t take that first rejection too hard, because she agreed to marry him. I guess the fact that he was the freaking Holy Roman Emperor didn’t hurt his chances.

But there was one problem: They hadn’t actually met yet. But that was about to change.

51. He Loved Her So Much

After years of “will they/won’t they,” Charles and Isabella finally decided they would. They met for the first time in 1526, and nobody, not even the couple themselves, expected what happened next. The marriage was almost entirely political in nature, but when Charles and Isabella first laid eyes on each other, the sparks flew. It was love at first sight.

Most political marriages at the time were cold and calculated, but Charles and Isabella actually loved each other. Unfortunately, that only made what happened to them all the more devastating.

52. He Went On Vacation

So far, Charles V’s reign had been anything but relaxing. Beheading rebels, searching for gold cities, capturing kings, it could really take it out of you, ya know? Well, after his marriage, Charles decided he’d earned a well-deserved vacation. He and Isabella traveled to Granada for a long and lavish honeymoon. It was a blissful time in an otherwise exhausting life, but it couldn’t last forever.

Though Charles V left a legacy of destruction, pain, and scandal behind him, at least his marriage was a bright spot. He and Isabella loved each other deeply for their entire marriage, and they both remained faithful the entire time. In a world of Kings like Henry VIII, that’s almost unheard of. But marital bliss or no, Charles still had an empire to run.

Soon after his marriage came one of the darkest moments of his entire reign.

53. He Ignored His Empire

As much as Charles would like to enjoy his honeymoon and pretend the world outside didn’t exist, it was a fantasy. The Italian Wars were still raging, and things were only getting worse as Charles and his wife vacationed. In fact, his negligence ended up having disturbing consequences. His soldiers in Italy went months without being paid, so is anyone surprised that they eventually snapped?

Since Charles wasn’t paying them, they took matters into their own hands, and the fallout was brutal.

54. His Men Committed An Atrocity

Charles’s men mutinied and directed their anger at the holy city of Rome. Thousands of men descended on the capital, massacred the troops inside, then ravaged the city. They pillaged churches and monasteries, looted palaces, and slaughtered civilians. It was one of the darkest days in Roman history. It’s safe to say, the Italian Wars had gotten out of hand, and it was high time someone put a stop to it.

So who finally got Charles and Francis to bury the hatchet? Why, their mommies of course.

55. The Ladies Had To Step In

This phase of the conflict came to a close with the “Ladies’ Peace.” Why do we call it that? Because Francis’s mom and Charles’s aunt negotiated the truce. Apparently, it took a feminine touch to get the two pouty kings to finally lay down their swords. And after all that bloodshed, what did Charles and Francis accomplish? Basically nothing, really.

Charles and Francis had fought over Italy for years. Thousands perished. And in the end, pretty much nothing changed. Wonderful.

56. He Couldn’t Stop

So Charles spent almost a decade fighting a pointless conflict that claimed thousands of lives and accomplished nothing. What’s the only thing he could do that was even stupider? Do it all again! It turns out, just because mommy and auntie told them to play nice, Charles and Francis weren’t about to set aside their hatred that easily. In 1536, they started fighting in Italy yet again, this time over Milan.

Thankfully, this conflict wouldn’t last quite as long as the earlier one, but there is one notable thing about it: It ended in the most awkward way imaginable.

57. He And His Rival Were Incredibly Childish

In 1539, Charles and Francis signed a peace treaty ending hostilities once again. So what made it so awkward? Well, Francis hated Charles so much that he literally refused to be in the same room as him! Though at the end of the day, both of them signed the treaty, the pouty Francis made Charles sign it in a different room, then had a servant bring the paper to him to seal the deal.

These were two of the most dangerous men in all of Europe, and they fought like 10-year-olds.

58. He Started Fighting Again

As always, the truce between Charles V and Francis didn’t last long. In 1542, the two of them started fighting yet again, but this time, things were different. Though Charles and King Henry VIII of England had been enemies plenty of times before, they both decided they hated Francis more, so they teamed up. The enemy of my enemy is my friend, as they say.

It seemed like Francis was completely outgunned, but Charles wasn’t the only one who found new allies. Francis teamed up with someone too—a more dangerous enemy than any Charles had faced so far.

59. He Faced An Enemy Unlike Any Other

This time around, Francis joined forces with Suleiman the Magnificent, Sultan of the Ottoman Empire. With the combined strength of the French and Ottoman Navies, the two of them made major gains along the Mediterranean. But Charles wasn’t about to go down without a fight. Realizing that Francis had made himself vulnerable, Charles decided to hit him where it hurt most.

60. He Entered Enemy Territory

In 1544, the combined forces of Charles V and Henry VIII attacked France itself. After years of fighting proxy battles across Europe, Charles was finally done messing around. He personally led the forces as they ravaged across the French countryside. With Charles in Northern France and Francis winning in the Mediterranean, the two of them had reached a stalemate.

Once again, after years of fighting and thousands of casualties, Charles and Francis called a truce. By now, the truth had become abundantly clear: This was a game to them, and the lives lost meant little.

61. He Started Losing

Charles V had spent most of his reign outdueling his enemies at every turn, but the tide was starting to turn. Not only was Charles a shell of his former self after losing Isabella, but there was a new figure on the scene: Suleiman the Magnificent. The Ottomans and their corsairs had been devastating the Spanish and Italian coasts for years, but after his alliance with Francis, Suleiman saw his opportunity and took it.

Maybe Charles was just too beaten down to keep fighting, or maybe Suleiman was simply too smart for him, but either way, the Sultan would deliver Charles one of the most devastating losses of his reign.

62. He Suffered A Humiliating Defeat

Suleiman and his corsairs pushed Charles V to the breaking point. It was only a matter of time before something had to give. Charles was at least smart enough to realize that Suleiman could destroy everything he’d built, so in 1547, he waved the white flag. He was forced to give Suleiman complete control of Hungary—but that was just the beginning.

Charles also had to pay Suleiman a massive tribute in gold every single year.  This sent a message to the world: The ruthless Charles V was no longer the man he used to be. It was the beginning of the end.

63. His Old Sins Came Back To Bite Him

Remember when Charles was young and he made a complete mess of things with Martin Luther and the Protestant Reformation? Well, decades had passed, and it was finally time to pay the piper. Protestantism had only grown and grown, and by now, it was a serious political and military force. In 1552, Protestant lords teamed up with the new king of France, Francis’s son Henry II, and went to war with Charles yet again.

For Charles, fighting with France was nothing new, but this time was different. Charles was old and tired—and a devastating betrayal all but sealed his fate.

64. His Ally Betrayed Him

Duke Maurice of Saxony had been an invaluable ally for Charles in his conflicts with France, but even he could tell that Charles was not the man he once was. So, he did the unthinkable: He stabbed Charles in the back and joined the Protestant cause against him. His forces turned and cornered Charles in the city of Innsbruck.

The turncoats had one goal: Capture the Emperor. For the first time in his life, Charles V found himself in genuine danger—and it couldn’t have come at a worse time.

65. The Betrayal Came At A Terrible Time

Charles suffered from gout for most of his life, but by now, it left him almost completely unable to move under his own power. With Maurice of Saxony’s men knocking on his door, the ailing Charles was forced to desperately flee the city. He barely made it out alive, his men carrying him in a litter as he fluttered in and out of consciousness.

He survived, but he couldn’t keep doing this forever. Charles was finished.

66. He Called It A Day

Charles had spent the last 40 years jet setting across Europe, fighting battles and scheming against his enemies, but it was time to go home. He retreated back to the Netherlands and did something absolutely no one expected: He retired. After playing the game of thrones so ruthlessly for so long, Charles decided he’d rather fade away than burn out.

The reign of Charles V, Holy Roman Emperor, was finally at an end, but he was at least going out on his own terms.

67. He Gave It All Away

Thoroughly defeated, Charles began the humiliating process of dividing up his massive empire. He gave territory to his sons, cousins, and brother, then retired to a monastery to live out the rest of his days. Say what you will about Charles, but he knew when to fold them. While many kings leave crises of succession when they pass, Charles settled all of his affairs and lived out his final years in comfort and luxury.

At first, it honestly seems like a pretty classy move—but as always, the truth is darker than how it appears.

68. His Final Speech Was…Something

Charles’s abdication speech has gone down in history. Here was a man who had ravaged the world for decades, and when he finally called it quits, he had this to say: “I know that I made many mistakes, big mistakes, first because of my youth, then because of human error and because of my passions, and finally because of tiredness. But I deliberately did no wrong to anyone, whoever it was. Should injustice have arisen, it happened without my knowledge and only out of inability: I publicly regret it and ask forgiveness to everyone who I might have offended.”

Allow me to remind you, this is the guy who beheaded rebels, locked up his mother, funded the conquistadors, and created the Atlantic Slave Trade. Sorry if we don’t forgive you that easily, Chuck.

69. He Left Things In A Terrible Place

By the end, Charles had to give up his throne because he could no longer pretend that he was doing a good job running his empire. He let the Protestant revolution tear Germany apart, he’d pretty much bankrupted Spain, and he’d lost countless men in his unending feud with France, which, we should point out, he was now on the losing side of.

Yeah, things were pretty bad, but when his son Philip took over the reins, he realized they were even worse than they appeared on the surface.

 70. It Was Worse Than Anyone Realized

Everyone knew Charles played it pretty fast and loose with his royal funds, but Philip was in for a rude awakening when he became King of Spain. Charles had left the country in debt to the tune of 36 million ducats, and they were losing another million every single year. In fact, Charles’s mismanagement of money in Spain led to over half a century of economic turmoil.

At the end of the day, I think I would have tried my luck with the “mad” Queen Joanna over her spoiled son.

71. He Was A Smart Aleck

Give Charles V one thing: He could talk the talk. Literally. He could speak French, Dutch, Spanish, Basque, German, and a little Italian. In fact, Charles allegedly once said, “I speak Spanish to God, Italian to women, French to men, and German to my horse.” We see what you did there, Charles.

72. His Life Was A Journey

The last thing Charles V ever said in public was this: “My life has been one long journey.” Certainly, no one could argue that point. With his Empire stretched across the continent and beyond, Charles spent almost his entire life on the road. But all journeys must come to an end—we can only hope that we don’t cause as much damage along the way as Charles.

73. He Lived In Agony

Charles V lived out his final years in luxury, surrounded by paintings of his wife Isabella. It seems too good for a man who caused so much strife, but at least we can say that Charles’s end wasn’t comfortable. His gout had become completely crippling, and he spent pretty much every day in agony. He couldn’t walk, and had to have servants carry him around in a sedan chair everywhere he went.

Within just a year of giving up his throne, the end drew near—but Charles still had one utterly bizarre act left in him.

74. He Threw His Own Funeral

Sure, Charles knew his time was coming—everyone knew that—but what he did is still completely bananas: He held his own funeral while he was still alive. Maybe he just wanted to hear people say nice things about him, but he planned out the whole shindig. He even sat in his own coffin while friends and family eulogized him, before rising and withdrawing to his room as the end.

If nothing else, at least Charles had a flair for the dramatic.

75. His Slept With His (Step)Grandma

Charles had many affairs and mistresses in his youth, but his first was by far the most twisted. In 1517, Charles finally left the Netherlands behind and landed in Castile. In accordance with his grandfather’s final request, he brought his stepgrandma Germaine over from Aragon to live with him. The two of them hit it off immediately—as in, they almost immediately started an affair.

That’s right. When Charles was 17, he had an affair with his own grandma. Let that sink in.

76. He Flaunted His Affair

Ok, fine, maybe Germaine of Foix was only Charles’s stepgrandma, and yeah, she was only 29 at the time, but still, it was weird. The two (understandably) tried to keep their fling on the down-low, but they couldn’t keep their secret under wraps forever. The fact that Charles kept throwing lavish banquets and tournaments for his hot grandma didn’t help either.

But if people thought those were scandalous, just wait til they saw what came next.

77. He May Have Had A Scandalous Child

Germaine of Foix didn’t marry for years after her husband Ferdinand died. So obviously, it raised a lot of eyebrows when she gave birth to a child just two years after he passed. It raised even more eyebrows when she named her girl, “Infanta Isabel,” a title that usually would have been reserved for the daughter of the King of Spain.

And who was the King of Spain? Oh right, Charles, her stepgrandson. Awkward.

78. His Wife Got Sick

Sure, Charles took a long time to choose a wife, but you can’t say he didn’t pick a good one. He and Isabella loved each other madly, and as soon as they were married, they made like bunnies and started popping out little princes and princesses. It seemed like the rare happy royal marriage—but then, in 1539, tragedy struck.

Isabella came down with a fever while pregnant with their seventh child. Even with modern medicine, such a complication can be extremely dangerous. But Isabella didn’t have modern medicine. Charles’s wife had medieval soothsayers who could do nothing to help her. Yet still, the result was even more devastating than they ever imagined.

79. Everything Fell Apart

In 1539, a deteriorating Isabella miscarried, losing the child. The couple was devastated, but even still, they had more pressing concerns. Isabella continued to get worse and worse, and nothing the doctors tried seemed to have any effect. Everyone knew when it was coming, but still, nothing could have prepared Charles for the inevitable.

Isabella succumbed to her illness at 35 years old. Charles loved his wife more than anyone else in the world—so obviously, his reaction to her loss was utterly deranged.

80. He Spiraled Downward

The loss of Isabella sent Charles into a horrible spiral. Though he had a massive empire to run, he shut himself away in a monastery for two whole months. He grieved alone while his empire fell into chaos. Even when he finally emerged, he had changed. He never stopped mourning Isabella, and wore grim, black clothing for the rest of his life.

Losing his wife would be a turning point in Charles’s life. While his youth had been spent crushing his enemies and amassing his power, once Isabella was gone, he was never the same again.

81. His End Finally Came

Maybe holding your own funeral is bad luck? Just a few months after the brutally awkward ceremony, Charles contracted malaria. He gave his last breath in the early hours of the morning on September 21, 1558. He was 58 years old. In his very last moments, he paid a heartbreaking tribute to the love of his life, Isabella, who he’d been mourning for nearly 20 years.

82. He Made A Tribute To His Wife

When Charles finally left this world, he was carrying a cross. This was pretty normal for any good Christian of the time, but this wasn’t just any cross. It was the exact same cross that his beloved Isabella had held when she passed, all those years earlier. Charles had kept it with him all that time, in the hope that he could finally join her when the end came.

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14

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