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Vengeful Facts About Alessandro De Medici, The Tyrant Of Florence

Brendan Da Costa

The Medici family struck fear into the hearts of their enemies for centuries, so it’s no wonder Alessandro de’ Medici’s life was full of backstabbing, secrets, and bloody vengeance. As the last of the main Medici line, Alessandro more than followed in his dysfunctional family’s footsteps—in fact, his exploits and infamous end wrote the book on “scandal.”


1. His Family Was Infamous

The Medici family was a powerful dynasty in Florence during the Italian Renaissance. Well, everybody knows that absolute power corrupts absolutely, and the influential clan produced some notoriously bad apples. Alessandro de’ Medici was born in 1510, and the future Duke of Florence may very well have been rotten to his core.

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2. He Had a Distinctive Look

Alessandro de’ Medici was famous during his time for some of his “distinguishing” features. The Florentine had tight, curly hair, a broad nose, and a dark complexion. Alessandro’s appearance was so noteworthy, in fact, it earned him the nickname, “Il Moro” or “The Moor.” But these features have produced controversial speculation today…

3. His Enemies Spread a “Dark” Rumor

Back in his day, people could not keep the name “Alessandro de’ Medici” from their mouths, and his allies and enemies alike whispered about his parentage. Was this Florentine nobleman really a Black, African man? Some experts dismiss these rumors as mere insults from his foes, but his true parentage may be much different.

4. He Had a Controversial Heritage

Although we’ll never know for sure, there’s evidence that the rumors about Alessandro being a Black man were cold, hard truth. Around the time of his birth, an African servant named Simonetta da Collevecchio was working in the Medici household, and she could have very well been Alessandro’s mother. Oh, but it gets so much more twisted than that.

5. His Father Was “Magnificent”

As if the mysteries of Alessandro’s mother weren’t juicy enough, his father’s side was somehow even more dramatic. Most people from Alessandro’s time believed the young boy’s father was Lorenzo the Magnificent, who must have taken a liking to poor Simonetta while she was in his house. Yet there’s another, more scandalous theory. 

6. He May Have Been Sinful

According to some historians, Alessandro’s father was actually Giulio de’ Medici. Why’s that scandalous? Well, Giulio eventually became the freaking Pope, AKA Pope Clement VII. As you might know, Holy Fathers aren’t supposed to go around making illegitimate children with serving wenches. Maybe that explains Alessandro’s many, many issues.

7. He Was Forced to Flee His Home

In 1527, the teenaged Alessandro was baptized into tragedy. The Medicis had never been popular, but by the time Alessandro was born, their power was waning—and the wolves were closing in. That year, the Medicis’ Republican enemies ousted them from the city, forcing Alessandro to flee for his life. He would soon plot a brutal revenge.

8. He Was a Teenage Tyrant

If there was one thing Alessandro knew how to do, it was survive. He bided his time in exile until 1530, when the Medicis made a triumphant return to Italy alongside powerful allies. In this second Age of Medici, Alessandro made sure he got what was his. The 19-year-old became the vaunted Duke of Florence…and his reign of terror began.

9. He Married Young

With all of the scandal surrounding his own birth, you might expect that Alessandro strove to walk the straight and narrow when it came to his personal life. Well, you’d be very, very wrong. In 1536, when he was 26 years old, Alessandro married the wealthy Margaret of Austria…and “gnarly” doesn’t even begin to describe their union.

10. He Was Mercenary

First and foremost, Alessandro did not marry Margaret for love. Like pretty much everything else the Medicis did, the marriage was a soulless political power move. Margaret was the illegitimate daughter of the mega-important Holy Roman Emperor Charles V, and Alessandro just wanted that sweet, sweet Holy Roman support. And there was a more chilling detail.

11. He Had a Child Bride

As if it weren’t disturbing enough that poor Margaret was being used as a pawn in a game of thrones, get a load of this: She was a child bride. When Margaret and the very adult Alessandro tied the knot, she was just 14 years old. Here’s the real kicker, though…Charles V had been arranging the marriage for years before it was finalized. Yeesh.

12. He Was Debauched

Was Alessandro a kind, loving husband to his “baby” girl Margaret? Um, no. He committed the ultimate betrayal. Before their marriage, Alessandro took up with a beautiful mistress named Taddea Malaspina, and he wasn’t about to let a little thing called “the sanctity of marriage” push him into monogamy. Instead, what Margaret got was humiliation.

13. He Had a Strange Romance

Alessandro wasn’t just playing around with Taddea, he was absolutely infatuated with the woman. In fact, some say she was his only mistress, and he was as devoted to her as a married man can be. Honestly, I can’t tell if this is the one good quality about Alessandro, or just an extra slap in the face to his wife. Don’t worry, though, it gets soapier.

14. He Kissed His Cousin

In case you need more “ew, gross” for your reading pleasure, let it be known that Alessandro and his beloved Taddea were actually distant cousins. Though, well, with Alessando’s uncertain parentage, the illicit love birds might have been even more closely related than that. You never can tell with these Medicis.

15. He Was a Baby Daddy

Taddea wasn’t just Alessandro’s prized side-piece, she was also the mother of two of Alessandro’s illegitimate children, Guilio and Giulia de Medici, who were born just before or just after he got hitched. Aw, isn’t that sweet? But although Alessandro was apparently a one-woman philanderer, as we’ll see, this may not be quite true.

16. The People Hated Him

Alessandro de’ Medici was powerful, feared, cunning….and very, very unpopular. There are constant complaints from his lifetime that he was a despotic ruler who loved absolute power and didn’t want to give a shred of his influence as the Duke of Florence away to anyone else. This flaw would eventually prove fatal.

17. His Marriage Was Barren

While Alessandro was running around fathering illegitimate children, his marriage bed was getting mighty cold. Tragically enough, Alessandro and Margaret of Austria had no children together. Sure, this was partly because Margaret was still barely a teenager…but it’s also because Alessandro suffered a tragic twist of fate right after the wedding.

18. He Had a Family Feud

The Medici family in-fighting makes the Lannisters from Game of Thrones look like The Brady Bunch. Although Alessandro was raised alongside his younger cousin Ippolito, it wasn’t exactly all hand-holding and shine theory in the Medici household. The two cousins had a steady rivalry, and in 1530, that rivalry exploded.

19. He “Betrayed” His Cousin

Ippolito was one of the favorite Medici sons, but that all changed when the upstart Alessandro came back to power in 1530 and was chosen as the Duke of Florence…over Ippolito. Naturally, Ippolito felt that this was his rightful claim, and he did not take well to watching his cousin get all his glory. It was a slight Ippolito wouldn’t soon forget…

20. He Made a Powerful Enemy

As a consolation prize for his “stolen” Dukedom, Alessandro’s cousin-slash-rival Ippolito got a cushy job in the Catholic Church, and he almost immediately started using his power to wreak vengeance on “The Moor.” Proving that blood was not thicker than water, Ippolito swore to depose Alessandro by any means necessary. Fate, however, had other plans.

21. A Twist of Fate Saved Him

In the summer of 1535, Ippolito was traveling through the southern Italian province of Lazio, presumably plotting his next move against Alessandro. Well, let this be a lesson to you: Don’t mess with the Duke of Florence. As if by an act of God, Ippolito succumbed to a fatal fever, and just like that, Alessandro’s enemy was gone. But a dark theory about that day persists.

22. He May Have Been an Assassin

Florence found the holy man’s vicious end more than a little suspicious. Many claimed that Alessandro had orchestrated his cousin’s end by way of poison, which, given his absolutist and despotic rule, didn’t seem too far-fetched. The next time a family member plotted against him, however, Alessandro wouldn’t be so lucky…

23. He Had an Arch-Nemesis

The Medici family tree was as twisted and rotting as a witch’s broom, but nothing beats Alessandro’s distant relative—and soon-to-be arch-enemy—Lorenzino de’ Medici. Tellingly nicknamed “Bad Lorenzo,” Alessandro’s clansman was bitter and jealous of The Moor’s success, and was all too happy to pick up where Ippolito left off. This time, he was terrifyingly successful. 

24. Madness Ran in His Family

Lorenzino more than earned his nickname “Bad Lorenzo.” Before becoming involved in his vendetta with Alessandro, Lorenzino’s most infamous act was when he snuck into the near-sacred Arch of Constantine and mutilated the heads of the ancient statues there, just for kicks. Is it any wonder he rose to one of the most infamous acts of the 16th century?

25. He Was a Libertine

Alessandro and Lorenzino weren’t always mortal enemies, or at least Lorenzino hid his hatred well. The winsome pair were notorious around Florence for indulging in debauched escapades together, and Alessandro placed a certain amount of trust in his kinsman. Too bad Lorenzino threw that trust right back in his face.

26. He Was Oppressive

You don’t get to be a Duke of Florence by being nice to people, so it’s no surprise that Alessandro made some big enemies during his time at the top. Some of his most hated foes were republicans, who didn’t want any of the Medicis to have power. Obviously, this meant Alessandro was Public Enemy Number One…and they came up with a cruel plan to topple him.

27. People Claimed He Killed His Mother

Though scandalous rumors flew about Alessandro’s true maternal heritage, an even worse whisper abounded among his enemies: That he’d slain his own mother Simonetta just to prevent his mixed-race status from coming out. There’s no evidence to suggest that Alessandro was this debauched, but that doesn’t mean he was a saint…

28. He Wasn’t Born Free

16th-century Italy wasn’t exactly progressive, and any mixed-raced child had to assume the social status of their mother. So how did Alessandro rise to become a powerful, megalomaniac duke? He got very, very lucky. In a fit of benevolence, his father freed his mother so that his son could reach his full, sociopathic potential.

29. He Incited a Jealous Rage

In case you need another reason to root against “bad Lorenzo,” he was from the “Junior” branch of the family, which in Medici-speak was “the wrong side of the tracks.” Is this a valid way to judge someone’s character? Absolutely not. But it certainly didn’t help Lorenzino’s seething grudge against his more powerful cousin Alessandro.

30. He Sent a Political Message

When Alessandro came marching back into Florence and became Duke, he wasted no time at all becoming one of the most hated nobles in the city. One of his first acts was to remove the bell from the Palazzo della Signoria—a symbol of his republican enemies—and have it melted down into money and arms, AKA his two favorite things.

31. He Was a Famous “First”

Barack Obama took the oath of office on January 20, 2009 and became the first Black president of the United States…but someone had him beat. Almost 500 years earlier, Alessandro de’ Medici became the first black head of state in the western world as the Duke of Florence. To Obama’s credit, though, he was elected to office, not appointed.

32. He Insulted the Wrong Man

In 1536, Alessandro de Medici made a fatal error. One of Lorenzino’s relatives had just passed, and all of the old man’s money was up for grabs. Acting as a mediator in the estate, Alessandro sided against Lorenzino getting the money, nearly ruining the “bad” Medici in the process. Note to self: Don’t tick off a bona fide psycho.

33. He Fell Into a Trap

Lorenzino had already raged out on some inanimate statues just for fun, so his fury over this actual slight was white-hot and filled with hatred. As far as he was concerned, it was time for Alessandro to go down. On January 6, 1537, Lorenzino lured Alessandro over to his private apartments—and he did it with a diabolically scandalous method. 

34. Women Were His Greatest Weakness

“Bad Lorenzo” had a famously beautiful sister named Laudomia, a widow with no husband to speak of. Lorenzino was also well aware that the married Alessandro still liked a nice roll in the haystack. So he told the Duke that if he came over that very night, sultry Laudomia (or perhaps another woman) would be there, ready and willing. That’s…not what happened.

35. He Made a Fatal Error

When Alessandro arrived at Lorenzino’s house, everything seemed in order. Bad Lorenzo made his cousin comfortable, and then told him he was just going to fetch the woman for a night’s “entertainment.” This is where Alessandro made his second mistake. He sent away his guards, got comfy on the couch, and fell asleep…for the last time.

36. He Had a Rude Awakening

When Alessandro woke up groggily, it was to the flash of steel. Lorenzino had crept back into the room with his faithful servant Piero di Giovannabate, and both men were fully armed with swords and daggers. They hacked at the Duke of Florence with all their might, and like their lives depended on it—because they did.

37. He Met a Gruesome End

Alessandro de’ Medici was a fighter until his very last breath. Even caught with his pants almost literally down, he fought back his attackers and tried against all hope to save himself. It was all in vain. In the wee hours of that winter morning, Alessandro succumbed to his wounds. But somehow, his story wasn’t even over yet.

38. His End May Have Been Senseless

To this day, we still can’t know for sure why Lorenzino offed his own cousin. Some historians argue it was petty revenge, while others say it had to do with a long-standing family feud. It also could have been simply because “Bad Lorenzo” was, well, a really abhorrent sociopath. But Lorenzino himself confessed a much different motive.

39. He May Have Died for a Reason

According to Lorenzino, Alessandro’s own sins condemned him to his brutal end. In his formal confession Apology, written a few days after the horrific act, Lorenzino claimed he’d done it because the power-hungry Alessandro had overstepped his boundaries and needed to be brought down to make way for a new Florentine Republic. If so…he failed miserably.

40. He Got a Lasting Tribute

Holy Roman Emperor Charles V hated the thought of his son-in-law Alessandro decaying in an unknown grave, and he tried to make things right. When news of Alessandro’s demise reached the Emperor, he held a full funeral service that paid homage to Alessandro’s true might and influence. But paying his respects wasn’t enough. You see, blood calls for blood.

41. He Haunted His Killer

Lorenzino spent much of the next 11 years of his miserable life looking over his shoulder. But you can’t outrun justice: In 1548, two hired men finally caught up with “Bad Lorenzo” and gave him an even worse end, executing him with extreme prejudice in Venice. For years, historians wondered who orchestrated the hit. The answer surprised them.

42. He Had a Secret Avenger

Alessandro’s ignominious end sent shockwaves through Florence, and any one of his vengeful relatives could have masterminded Lorenzino’s assassination. But a new study shows that the culprit was none other than Holy Roman Emperor Charles V. Charles just couldn’t let his son-in-law’s death go, and lay in wait for a decade before making bloody amends. Now that’s metal.

43. He Had a Long-Lost Child

A little less than year after Alessandro was slain, a “miracle” happened: He had another illegitimate daughter. The girl, Porzia de’ Medici, was born to an unknown mother—Alessandro, you naughty boy—when her father was already rotting in his grave. I guess Alessandro really wasn’t that loyal to his beloved Taddea after all. Except it gets creepier.

44. He Had Disturbing “Appetites”

According to some sources, the depiction of Alessandro as desperately in love with his one true mistress Taddea Malaspina is downright naive. Alessandro didn’t just mess around with multiple women, he may have, er, kept it in the family. Certain accounts say the Duke took up with Taddea’s sister Ricciarda, too. I, for one, am shocked that Alessandro de’ Medici is a problematic man.

45. He Was Incredibly Vain

The paintings we have of Alessandro show a good-looking man, but this Duke’s narcissism knew no bounds. He was constantly commissioning portraits of himself from Florence’s master painters, and even once produced a coin with his face on it that depicted himself as a Roman emperor. Okay, Alessandro, we get it. But he didn’t stop there.

46. His Mother Met a Tragic End

I’d like to say that Alessandro never forgot his mother’s struggle…but I can’t. Their relationship was heartbreaking. After knocking her up, the Medicis didn’t want anything more to do with Simonetta, and the woman lived in absolute poverty while her son grew up in the lap of luxury. Thing is, that’s not even the worst part.

47. He Abandoned His Own Family

We know from existing letters that Simonetta frequently wrote to her son Alessandro, by then one of the most powerful people in Florence, desperately asking him for money. What’s less clear is if he ever sent his own mother any financial aid back. I don’t know why I expect a bloodthirsty duke to have a conscience, but c’mon Alessandro.

48. He Gave a Bizarre “Gift”

When Alessandro’s mistress Taddea gave birth to their daughter Guilia, Alessandro wanted to do a little something to thank the new mom. So he gave her an unsettling “present.” To commemorate the moment, Alessandro gifted his side-piece with a portrait…of himself. Because what communicates, “You just pushed an entire child out of your body” better than a selfie?

49. He Was Part of a Massive Cover-up

Even from the grave, Alessandro caused a scandal. His allies in Florence didn’t want his assassination getting out and starting riots in the streets, so they went to desperate measures to conceal the truth. They snuck into Lorenzino’s apartment and wrapped Alessandro’s lifeless body in a carpet to remove it from the scene. And then they doubled down on the indignities.

50. His Burial Was Humiliating

Alessandro de’ Medici got a humble carpet instead of a burial shroud, but this humiliation was nothing compared to his funeral. Once the Medici operatives had successfully removed Alessandro’s body from the apartment, they hurriedly buried him in little better than a pauper’s grave. But just desserts were on the horizon…

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24


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