This story was funded by our members. Join Longreads and help us to support more writers.

Anne Thériault | Longreads | September 2018 | 18 minutes (4,588 words)

From the notorious to the half-forgotten, Queens of Infamy, a Longreads series by Anne Thériault, focuses on badass world-historical women of centuries past.

* * *

The year was 1519. Henry VIII was king of England and still (mostly) happily married to Catherine of Aragon. The throne of France was held by Francis I, also known as “Francis of the Large Nose,” which may or may not have been a dick joke. Charles I of Spain had just become Charles V, Holy Roman Emperor. Martin Luther was stirring up shit in Germany. And in Florence, a couple whose union represented a last-ditch coalition between France and the Pope against the ever-expanding Holy Roman Empire welcomed their first child, a daughter they named Catarina Maria Romula de’ Medici (hereafter referred to as Catherine).

Looking for a Queens of Infamy t-shirt or tote bag? Choose yours here.

I like to think of the Medicis as the Kardashians of Renaissance Europe; at the very least, they had the same intuitive understanding of how to create and exploit a personal brand. Just the mention of the Medici name conjures up images of vulgar opulence, moral decay, and murderous treachery. Machiavelli’s The Prince — the so-called “textbook for tyrants” — was dedicated to Catherine de’ Medici’s father, and it was rumored that each of her children carried a copy with them at all times. Catherine herself inspired such nicknames as the Serpent Queen, the Black Queen, the Maggot from Italy’s Tomb, and (more flatteringly) the Mother of the Modern High-Heeled Shoe. She was also called the Merchant’s Daughter, a dig at her family’s nonaristocratic origins.

Whether or not Catherine was a basilisk who covered her shimmering scales with silk and velvet is up for debate, but it’s true that the Medici dynasty had decidedly common roots. In fact, a little over a century before Catherine’s birth, the Medicis were little more than casually wealthy textile traders. I mean, they had money, but not in mind-boggling amounts. That all changed in 1397, when they started a bank and discovered a latent talent for money management. By the mid-1400s, the Banco dei Medici was the biggest bank on the continent, and the Medicis themselves were the richest family in Europe.

Money can’t buy you happiness, but it sure can get you just about anything else, including various titles, marriages into noble families, a couple of popedoms, and the de facto lordship of the entire city-state of Florence. Also: a tomb designed by Michelangelo! The only problem with the Medici family’s scheme to dominate Europe was that supply couldn’t keep up with demand; even as they acquired all these positions of power, their ability to produce heirs veered into a steep decline. By the time Catherine was born, she was the only legitimate heir of the main branch of the family, and it soon became clear that she was quite possibly the last.

I like to think of the Medicis as the Kardashians of Renaissance Europe; at the very least, they had the same intuitive understanding of how to create and exploit a personal brand.

Catherine’s parents were Lorenzo II de’ Medici, Duke of Urbino and ruler of Florence, and Madeleine de la Tour D’Auvergne, a member of France’s noble (later on, royal) Bourbon dynasty. Their union represented an alliance between Francis I of France and Pope Leo X (Lorenzo’s uncle, born Giovanni de’ Medici) against the Holy Roman Empire (which was happily trucking along in its mission to Fuck Shit Up in Europe). Lorenzo and Madeleine’s marriage had a fairytale-like quality; both were young, beautiful, and, by all accounts, deeply in love. The wedding, hosted by Francis, involved ten days of banquets, masques, balls, jousts, and tournaments. When, just a few months later, Madeleine announced that she was pregnant, the pope and the king of France were beyond delighted that all their schemes were panning out.

FRANCIS I: fuck their fucking empire

LEO X: yes, fuck it

FRANCIS I: fuck England and Spain, also

LEO X: lol

LEO X: isn’t Spain … a part of the holy roman empire?

FRANCIS I: yes, but fuck it especially

Sadly, their gloating would be short-lived.

Lorenzo fell ill in the autumn of 1518, and was bedridden by the time Catherine was born on April 13, 1519. Madeleine’s health also plummeted shortly after her daughter’s birth. She died on April 28, and Lorenzo soon followed on May 4. Their causes of death are unclear — in Lorenzo’s case, it’s speculated that he died from tuberculosis, syphilis, or a combination of both, and Madeleine is thought to have suffered from puerperal fever, the plague, or possibly also syphilis. Whatever the cause, Catherine was left orphaned at just three weeks old.

* * *

The people of Florence quickly warmed to their tiny orphan overlord and gave her the nickname Duchessina, although the fact that Catherine was a girl all but guaranteed that she would never inherit her father’s title. But even if hot gender nonsense meant that Catherine couldn’t fulfill Francis and Leo’s plans, she was still a valuable pawn. (The rule of Florence would eventually go to Alessandro de’ Medici, who contemporaries considered to be Lorenzo’s illegitimate son, although modern historians think he was the son of Cardinal Giulio de’ Medici, later Pope Clement VII; Alessandro’s mother was Simonetta da Collevecchio, a woman of African descent who is variously described as a servant or slave in the Medici household, and Alessandro was the first Black head of state in modern Europe).

Francis wanted to raise Catherine in the French court but Leo strongly disagreed, mostly because he was about to burn that bridge by allying himself with the Holy Roman Empire. Quel scamp! Leo brought Catherine to Rome and put her in the care of her grandmother, Alfonsina Orsini; after Alfonsina’s death, Catherine went to live with her aunt Clarice de’ Medici. Things were stable for approximately one year before Leo died and was succeeded as pope by Adrian VI, a pious hardliner with strong ties to the Empire. Cardinal Giulio de’ Medici, who had expected to win the papal election, hurriedly left Rome for Florence, bringing Catherine and her cousins Alessandro and Ippolito with him. It was the fourth time her life had been completely uprooted in as many years.

You can only coast on charm for so long before real life catches up with you and you have to pay all the angry peasants you’d hired to fight out all your petty grudges.

Adrian VI died in 1523 (“live hard, die fast” apparently being the motto of most 16th-century popes), and Giulio finally acceded to the papal throne as Clement VII. The Medicis, whose position in Italy had been somewhat precarious under a non-Medici pope, breathed a sigh of relief. Everything was going to be cool again, right? Well, no, not exactly — Clement had shifted the papal alliances once more and formed a league with France, England, Florence, and Venice against the Holy Roman Empire. Some shit was about to go down.

In 1527, the Empire defeated France in Northern Italy, and shortly thereafter realized they didn’t have enough money to feed or pay their troops. This is why charismatic leaders need meticulous employees to crunch their numbers for them! You can only coast on charm for so long before real life catches up with you and you have to pay all the angry peasants you’d hired to fight out all your petty grudges. The upshot of all this was a bunch of hungry, furious soldiers on the road to Rome, many of whom were Lutherans who had a personal beef with the pope.

People who want you to commit to long-term projects will tell you that Rome wasn’t built in a day, but you know what? It wasn’t sacked in a day, either. The Imperial forces really took their time to get the murdering and desecrating exactly right. I mean, if you’re going to destroy a metropolis nicknamed The Eternal City, you’d better give it the ruin it deserves. For seven months Rome was systematically flattened into the world’s largest outdoor toilet. Eventually hunger and a plague epidemic drove the occupying forces from the city; from there, they headed north to Florence, where a revolt against the Medici rule of the city was already underway. Sackings for everyone!

As the violence mounted, Ippolito and Alessandro de’ Medici were spirited out of the city, leaving Catherine behind with her aunt. Nothing says “boys are assets and girls are liabilities” quite like saving the young male heirs in your family and leaving the girls and women behind to face a murderous mob.

Catherine was taken hostage and placed in the Santa Lucia convent, an institution famous for its hatred of the Medicis. She was deeply unhappy there, although apparently not quite unhappy enough to suit her captors, who soon moved her to the convent of Santa Caterina of Siena, a place contemporaries described as a “disease-ridden hovel.” After a bit of a fuss by the French ambassador (France, after all, still had a vested interest in the Duchessina), Catherine was relocated to the Murate Monastery, where she would live in relative comfort and happiness from the time she was 8 until a few months after her 11th birthday.

Help us fund our next story

We’ve published hundreds of original stories, all funded by you — including personal essays, reported features, and reading lists.

At some point after joining the Florentine insurrection the Imperial army had gone home, but in 1528 they were back in Italy, trouncing the French once again. By this point, Clement VII realized that he had badly miscalculated which horse to bet on, and quickly switched his allegiance back to the Holy Roman Empire. In 1529, Clement VII and Holy Roman Emperor Charles V signed a treaty in which the pope promised to crown Charles emperor in return for his help restoring his family to power (Charles was already the Holy Roman Emperor, of course, but being crowned by a pope gave him that extra sheen of divine respectability). Which is how the Imperial army wound up besieging Florence in 1529 in order to restore the Medici family to power just two years after participating in the revolt against them. Truly, time is a flat circle or something.

From some perspectives — namely those of the Imperial Army, Charles V, and the pope — the siege went pretty well! Others — the citizens of Florence, and also probably Catherine — didn’t think quite so highly of it. The hunger and disease that the siege brought with it only heightened the existing hatred of the Medici family, and the Florentines increasingly found a vector for their outrage in their young Duchessina. Some people called for her death. Some said that Catherine should be placed naked outside of the city walls, where she would either halt the Imperial barrage or else accidentally be killed by her own allies. One extremely charming suggestion involved her being left in a military brothel, where she would be raped by soldiers and thus no longer of marriageable value to the pope.

Nothing says ‘boys are assets and girls are liabilities’ quite like saving the young male heirs in your family and leaving the girls and women behind to face a murderous mob.

Eventually the rebel council decided to send Catherine back to the Santa Lucia convent, at least for the time being, since the Murate convent was a pro-Medici establishment that would likely allow the Imperial forces to rescue the girl. Certain that this latest move was an elaborate cover for her execution, Catherine cut off all her hair and put on a nun’s habit in a last-ditch effort to save herself. She thrashed and kicked at the man who had been sent to transport her before screaming out, “Let us now see what excommunicated wretch will dare to drag a spouse of Christ from her monastery!” As she was taken through the streets of Florence, a furious crowd gathered to scream abuse and death threats at her. It was a terrifying experience, one that Catherine would relive several times during her long and eventful life.

* * *

After the Imperial Army defeated the rebels in Florence and lifted the siege, Clement VII brought Catherine back to a (newly refurbished and Imperial Army-free) Rome in hopes that a few years in the Papal court would give her the polish she needed to hook a noble husband. Although she was frequently described as bright, witty, and well-mannered, many contemporary observers made a point of remarking that Catherine wasn’t conventionally attractive, proving that the brand of dude who loudly declares that he would never stoop to marry Rihanna has always existed. Much to the dismay of all the men who pooh-poohed Catherine’s “protuberant eyes,” the pope managed to make an extremely advantageous match between her and Francis I’s second son, Henri.

FRANCIS I: I’m confused

FRANCIS I: are we still in a fight?


CLEMENT VII: but listen, I put together a pretty exclusive dowry package

CLEMENT VII: it includes several cities that have cheeses named after them

The wedding took place in Marseilles on October 28, 1533, and it was a Whole Thing. Francis and Clement were intent on out-lavishing each other — at one point, the pope presented the king with a unicorn’s horn mounted in gold, and Francis gifted Catherine’s cousin Ippolito with a live lion. Catherine’s hair and velvet robes were encrusted with gems. Francis wore a white satin robe and a cloak of cloth of gold, embroidered all over with fleurs de lys and pearls. On a scale of one to ten, Catherine’s wedding was a Level Eleven Medici Event. It was some Deep Medici Shit. In astrological terms, it was a Medici sun with a Medici moon and also Medici rising.

On their wedding night, Catherine and Henri — both 14 years old — retired to a sumptuously decorated bed for their coucher, which is french for “first boning.” Francis decided he should stick around and watch because he was a weirdo pervert he wanted to make sure they consummated their marriage. He stayed until he was satisfied that “each had shown valor in the joust,” which is a weird metaphor because as far as I know, sex is not a contest where partners ride around on horses and try to violently knock each other down with pointy sticks. On the other hand, who knows what Francis does in his personal life?

CATHERINE: things are finally looking up!

CATHERINE: I’ve more than fulfilled my obligations by marrying an actual prince

CATHERINE: no one wants to dangle me naked in front of a besieging army

CATHERINE: God has at last granted me peace and stability

GOD: lol

GOD: sorry, I shouldn’t laugh, but

GOD: lol

On September 25, 1534, Clement VII died after several months of illness. This posed several problems for Catherine. No longer the niece of a pope, her status at the French court plummeted. To make matters worse, her dowry was only partly paid and the new pope, Paul III, refused to make good on the rest of it. Francis, who had been excitedly making plans for all the Italian territory he was about to acquire, now had to come to terms with the fact that he would own none of it. Catherine, once the sole heir to the wealthiest family on the continent, was now worthless, at least from a political standpoint. The French were furious.

Catherine knew that the best way to secure her future in France was to have a child with Henri. Francis I’s eldest son, also named Francis, was as yet unmarried; this meant that if Henri had any sons, they would be directly in the line of succession. A child would also have made it much more difficult for Henri to have his marriage to Catherine annulled, as some people suggested he should do. Yet try as she might, Catherine couldn’t seem to get pregnant. Part of the problem was that Henri wasn’t all that interested in his new bride — in fact, he was in love with another woman, Diane de Poitiers, widow of the Grand-Sénéschal of Normandy and 19 years Henri’s senior.

On a scale of one to ten, Catherine’s wedding was a Level Eleven Medici Event. It was some Deep Medici Shit. In astrological terms, it was a Medici sun with a Medici moon and also Medici rising.

Let us pause here and have a brief word about Henri, who, like his wife, had experienced a deeply traumatic childhood. Things had started out well enough, but in 1525, when Henri was 6, shit went sideways. During the same war with the Holy Roman Empire that had led to the sacking of Rome, Francis I was captured during the Battle of Pavia. The French king didn’t feel that he could serve his people well as a prisoner, so he offered up two of his sons as hostages until the ransom could be paid. Henri was 7 and his brother Francis, the Dauphin (heir to the French throne), was 8 when they were sent to Spain in exchange for their father. There, they would spend the next four and a half years in a series of increasingly bleak prison cells. Unsurprisingly, the experience affected the young boys profoundly.

When Henri and the Dauphin returned to the French court, everyone remarked on how changed they both appeared. Whereas before they’d been spirited and outgoing, now they were sombre and aloof. After his initial joy over his sons’ return had passed, Francis I quickly grew impatient with them, saying he had no time for “dreamy, sullen, sleepy children.”

FRANCIS I: would it kill you to smile once in a while?

FRANCIS I: what’s your problem?

HENRI: what’s my problem? are you fucking kidding me?

FRANCIS I: look at your younger brother Charles! So happy! So carefree!

FRANCIS I: why can’t you be more like him?


FRANCIS I: looks like someone caught a bad attitude while he was out of the country!

Since it was still several centuries before the invention of psychotherapy, Henri tried to work through his issues by throwing himself into activities like hunting, jousting, and other sports that involved physical violence. Also tennis, which the French called jeu de paume. (The nobility were all really into tennis at the time; it was an obsession that would end badly for them when the Third Estate, some two and a half centuries later, discovered the tennis court at Versailles.)

In spite of Henri’s efforts to channel his feelings into traditionally masculine pursuits, he couldn’t seem to win his father’s approval. Among other perceived slights from his son, Francis lamented that Henri just wasn’t French enough. The years in prison had marked Henri in more ways than one, and his accent, manners, and taste in clothing were all notably Spanish. In an effort to combat this, Francis put Henri under the care of Diane de Poitiers, a member of the queen’s household who was renowned for her style and beauty — you know, French things. It wasn’t long before Henri was deeply smitten with her.

Henri was not particularly good at any form of deception, and he was as artless about his love for Diane as he was about any other feeling — including his complete indifference toward his wife. It wasn’t long before everyone at court knew what was going on. Catherine, meanwhile, publicly kept up the appearance of wedded bliss while privately cherishing a grudge against Diane. She knew that her situation was too shaky to make any kind of move against her rival, but she also knew that there would be a day when she could have her revenge.

* * *

Life continued in this holding pattern for a few years — Catherine pursuing Henri, Henri pursuing Diane, and Diane pursuing the lifestyle of a chaste court widow — until 1536, when the Dauphin collapsed after a game of tennis and died shortly thereafter. The Valois family immediately suspected that poison was responsible, since the Dauphin had drunk a glass of water brought to him by his secretary, Sebastian de Montecuculli, just before falling ill. There were a few other facts that made Montecuculli seem especially guilty: he had formerly been employed by Charles V, a book about poisons was found in his room, and also he was Italian. Everyone knew Italians were famous poisoners.

And how did Montecuculli wind up working for the Dauphin in the first place?

He had been in Catherine’s retinue when she had come to France.

It’s like they always say: hug your loved ones today, because tomorrow they might be poisoned by agents of the Holy Roman Empire.

The French already disliked Catherine, and the news about the Dauphin’s death brought their hatred to a fever pitch. After all, they reasoned, who stood to benefit the most from the Dauphin’s death? None other than Henri and Catherine, the new Dauphin and Dauphine of France.

Francis was utterly destroyed by his eldest son’s death, his grief compounded by remorse for his poor treatment of the princes since their return from captivity in Spain. It’s like they always say: hug your loved ones today, because tomorrow they might be poisoned by agents of the Holy Roman Empire.

The king, hell-bent on vengeance, decided to bring Montecuculli in for questioning (read: torture). Montecuculli was savvy enough to know that denying the charges meant that he would be subjected to hours of pain; he confessed almost immediately, saying that he had been hired by the Emperor to kill both the king and the Dauphin.

FRANCIS I: case closed!

FRANCIS I: not only am I a great king and a great father

FRANCIS I: I am also a great detective

FRANCIS I: is there anything I can’t do?

FRANCIS I: the other day I drew a pretty decent-looking horse, so

FRANCIS I: I think it’s pretty clear that I’m great at everything I try

Even though Montecuculli later recanted, Francis went ahead and had him executed. Fortunately for Catherine, her name hadn’t come up during the confession, and Francis chose to ignore the rumors that she was behind the murder — probably in part because that would have meant implicating Henri, who was the one who stood to secure the most from his brother’s death. Catherine had not gained much out of the whole affair other than a new reputation for treachery and increased pressure to bear Henri a child. Since Henri’s brother Charles was still unmarried, the entire future of the House of Valois rested on Catherine’s ability to produce an heir.

Catherine wanted nothing more than to conceive a child, but this proved difficult, as Henri left the country almost immediately after his brother’s death. Francis had decided to assuage his grief by launching yet another military campaign against the Empire, and Henri begged to be allowed to fight. Francis at first refused, saying that it would be too great of a risk to his son’s life, but eventually relented once Henri pointed out that it was the right of the Dauphin to serve in the field. Catherine must have been especially affronted by the fact that, while he was in Italy, Henri conceived a child with a woman named Filippa Duci. Being the kind of person who wants to make sure the salt is rubbed nice and deep into the wound, Henri pointed out that this meant that the lack of royal heir was all Catherine’s fault. He also christened his new daughter Diane, after Diane de Poitiers, and gave the child to his favorite to raise.

DIANE DE POITIERS: thank you for this … baby?

HENRI: you’re welcome!

HENRI: I know how much women love babies

HENRI: so it’s, like, a symbol of my love for you

DIANE DE POITIERS: truly, every young girl dreams of someday growing up to raise the natural child of a man who claims to be in love with her

HENRI: that’s what I heard, yeah

Henri and Diane’s relationship had been outwardly chaste (if extremely passionate, at least on Henri’s side) before his departure for the war. It was when he returned, 18 years old and a seasoned fighter, that things started to heat up. Diane discarded any pretense of being a celibate widow and lived openly as the Dauphin’s mistress. Henri, who was constitutionally incapable of doing anything by half measures, began to dress in Diane’s colors and covered everything he owned with a special monogram that interlaced H and D. He also chose a crescent moon (a reference to the goddess Diana) as his device and “Until it fills the whole world” as his motto.


CATHERINE DE’ MEDICI: you two can have your cute in-jokes

CATHERINE DE’ MEDICI: I have my own motto and I don’t need yours

HENRI: you mean that line about being a happy little ray of sunshine?

CATHERINE DE’ MEDICI: it actually says “I bring light and serenity” under a picture of a rainbow

CATHERINE DE’ MEDICI: because I am an incredibly happy person

HENRI: babe, your nails are digging into your palms so hard that you’re bleeding

CATHERINE DE’ MEDICI: so. fucking. happy.

In spite of her misery, Catherine managed to settle into an outwardly comfortable relationship with Diane. This arrangement was mutually beneficial: Diane knew that another woman in Catherine’s place would put up much more of a stink about her husband’s mistress; Catherine was terrified of displeasing Henri and losing what little affection he showed her.

* * *

The uneasy balance between the Dauphine and the favorite solidified when a lesser royal faction, the House of Guise, began a not-so-secret campaign to have the young Dauphine replaced by the beautiful and young Louise of Guise. The Guises claimed descendancy from Charlemagne and were infamous intriguers and social climbers; they’d already managed to marry their way into the house of Bourbon and the crown of Scotland. With Catherine at the nadir of her powers — seemingly barren, ignored by her husband, eclipsed by the Dauphin’s favorite — it must have seemed like the perfect opportunity to place their relative on the throne. This plan was supported by Francis’ mistress, the Duchess of Étampes, who felt that Diane was gaining too much power at court. Like Diane, the Duchess knew that to unseat Catherine would threaten her rival’s position.

As for the Dauphin, at first he didn’t much care whether Catherine stayed or went; he was in love with Diane, and assumed he would figure out a way to be with her no matter who he was married to. So it was up to Catherine and her nemesis to figure out how to save the former.

It was a do-or-die situation, and Catherine decided to gamble everything.

Diane came out swinging in Catherine’s defense, enumerating the Dauphine’s many sterling qualities to anyone who would listen. She emphasized Catherine’s youth and the many years of fertility she might have in front of her. She convinced Henri to finally take his wife’s side by implying that to do otherwise was to play right into the hands of his father’s mistress, whom he loathed.

But having Henri on Catherine’s side was not enough. The final decision rested with the king himself. With his mistress set against the Dauphine, it would be hard to talk Francis into siding with his son’s wife.

It was a do-or-die situation, and Catherine decided to gamble everything. She collapsed at Francis’ feet, tears streaming down her face. She wailed that her husband deserved a queen who could bear his children, and asked only that she be allowed to serve as the new Dauphine’s lady-in-waiting. Please, wouldn’t the king just replace her but let her stay in France in the lowly position that was her due?

Catherine knew that there was nothing left for her in Italy — no uncle-pope, no place as Duchess of Florence, and certainly no advantageous marriage to make. She also knew that if Louise de Guise became Dauphine, she would almost certainly dispense with Henri’s former wife as soon as she could. If the king took her at her word, she would be ruined. Her entire future rested on Francis’ reputed soft spot for young women’s tears. Would he come through? Or had she gravely miscalculated?

Read Part Two: The Reign of Catherine de’ Medici

Queens of Infamy: Joanna of Naples
Queens of Infamy: Anne Boleyn
Queens of Infamy: Eleanor of Aquitaine

* * *

For further reading on Catherine de’ Medici:
Leonie Frieda, Catherine de’ Medici: Renaissance Queen of France
Christopher Hibbert, The House of Medici: Its Rise And Fall
Mary Hollingsworth, The Family Medici: The Hidden History of the Medici Dynasty

* * *

Anne Thériault is a Toronto-based feminist killjoy. She is currently raising one child and three unruly cats. If she has a looming deadline, you can find her procrastinating on Twitter @anne_theriault.

Editor: Ben Huberman
Illustrator: Louise Pomeroy