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The Tigress of Forlí

The Renaissance was considered the Golden Age of Bastards. It was extremely common, at the time, for powerful men to take a litany of mistresses, father children with them, raise them, and watch as those children grew up to take on the world. Petrarch, Boccaccio, Leonardo da Vinci (who actually had seventeen half-brothers and sisters) and even Francesco Sforza, our heroine’s own grandfather, were all illegitimate. Caterina Sforza was no different. And in this golden age, she stormed the Castel Sant’Angelo without spilling any blood while heavily pregnant, wrote a book on alchemy, trained and led numerous armies, and even managed to turn her captor, Cesare Borgia, into her lover. 

Portrait of Galeazzo Maria Sforza by Piero Benci — Presumed portrait of Lucrezia Landriani by Piero del Pollaiuolo
Uffizi Gallery, Florence — Gemäldegalerie, Berlin


Caterina was born in 1463 to Galeazzo Sforza, Duke of Milan, and Lucrezia Landriani, the wife of Count Gian Piero Landriani, a courtier at the ducal court and a close friend of the Duke’s. 

Like his father, Galeazzo was condottieri (a mercenary military leader), and when he succeeded to the dukedom of Milan, he had all his children join him at court. There, they were entrusted to their grandmother, Bianca Maria Visconti, a formidable woman in her own right. Bianca ensured Caterina and her siblings received a humanist education, learning Latin, the classics and dance as well as nurturing their warrior heritage through lessons on governing, warfare, and hand-to-hand combat.

Fresco depicting silverware offered as a gift for the wedding of Girolamo Riario and Caterina Sforza
Museo Nazionale Romano, Rome © GKSihat 2022


By the age of ten, Caterina was married to Girolamo Riario, the nephew of the then pope, Sixtus IV. Riario was, it’s safe to say, an absolute prick. He was tyrannical, a terrible leader who constantly imposed high taxes, and tried (and failed) on numerous occasions to assassinate the Medici, the de facto rulers of Florence. 

Despite over a year of searching, I haven’t been able to find a single good word about him. On Caterina, however, there are plenty. 

As useless as her husband was, Caterina was brilliant. She made several political alliances in Riario’s name, raised an army and trained them, and played the role of papal niece perfectly, all while managing her wifely and motherly duties. 

But when Pope Sixtus IV died in August 1484, Rome turned chaotic. Sixtus, himself, had made many enemies, and they all showed up in full force. 

Caterina’s response? 

She rode to Rome, crossed the Tiber, and stormed the Castel Sant’Angelo, seizing it without a single drop of blood shed… all while seven months pregnant. Several attempts to get Caterina to give up the fortress failed. In the end, it was the culmination of a bad deal her husband made (which, naturally, angered Caterina) and her uncle, Cardinal Ascanio Sforza’s intervention which had her give up her position. 

Map of Forlí


1488 saw the assassination of Riario. The conspiracy was led by the Orsi family of Forlì, supposedly over a financial dispute. Caterina and her children were taken prisoner, and the City of Forlì all but lost to her. 

Or so the Orsi believed. 

Tommaso Feo, one of Caterina’s most loyal guards, still held the Rocca di Ravaldino, a fortress located inside Forlì’s walls, and he refused to back down. Though they kept her children hostage, the Orsi sent Caterina to convince Feo to surrender. What they hadn’t expected, once set free, was Caterina turning on them. 

It was from the top of the Rocca di Ravaldino’s battlements where the most famous of Caterina’s stories (which may or may not be a rumour) is said to have happened. The Orsi threatened to kill her children, so Caterina climbed atop the wall, lifted her skirts, and cried out: “Hang them in front of me if you want. Here, I have what is needed to make others!” 

The Orsi surrendered. With her eldest son, Ottaviano, still only nine years old, Caterina assumed power of Forlì as regent. Her first act? To have all those involved in the plot to assassinate Riario killed alongside the Orsi. 


Over the next few years, Caterina negotiated marriage deals for all her children, made new alliances with neighbouring states, decreased the taxes imposed by her late husband, and trained a new militia. She was trusted, beloved. 

During this time, Antonio Maria Ordelaffi – who came from a family who believed they had claims over the City of Forlì – began to spread rumours that he and Caterina were to marry. Though there are some claims that he was courting Caterina, the betrothal was a blatant lie, and Caterina’s anger led her to imprisoning him for a decade alongside anyone who dared spread the rumour. 

Caterina had actually fallen in love with Tomasso Feo’s younger brother, Giacomo. They married in secret, but their infatuation with each other soon had others worrying that Feo would strip Ottaviano of his birth right, especially after Caterina bore him a son. As Feo’s power increased, he became increasingly cruel. When he slapped Ottaviano in public, an assassination plan was put in place. Distraught by the murder of her husband, Caterina had the assassins and their families (including their mistresses and illegitimate children) slaughtered in retaliation. 

The people of Forlì lost faith in her. 

Detail of Botticelli’s Primavera, possibly Caterina Sforza
Uffizi, Florence


Caterina was lucky enough to fall in love a second time. Her third husband was Giovanni de’ Medici, aka Giovanni delle Bande Nere. Giovanni was what is commonly referred to as the ‘secondary branch of Medici’. That is to say, his family weren’t descended from Cosimo the Elder. 

In 1492, Lorenzo il Magnifico, the grandson of Cosimo the Elder, died. In his life, Lorenzo had brought stability to the warring states of Italy. His death not only brought an end to the Golden Age of Florence, but also had a knock-on effect that led to the catastrophic end to a decade of peace in Italy. Florence turned to his eldest son, Piero, as their de facto ruler. Unfortunately, even with the new Borgia pope and his son, Cesare, as allies, Piero was… let’s say, ill-suited to the role. So much so, that Giovanni and his brother stood against their cousin. 

Piero had them exiled.

A few months later, Florence had Piero exiled.

These brothers from the secondary branch of Medici were allowed to return. Giovanni took the surname Popolano and was appointed ambassador to Forlì where he met and fell in love with Caterina. They wed soon after. 

During their marriage, Florence and Venice’s already tense relationship grew worse. Realising that Forlì stood between the two cities, Caterina returned to prepare for attack. As she defended Forlì against Venice, stopping a number of their attacks until they were eventually forced to retreat, Giovanni contracted pneumonia and died, leaving Caterina to face what was to come alone. 

Portrait of Cesare Borgia
Palazzo Venezia, Rome


While all this was going on in Italy, Louis XII had succeeded to the throne of France. The story here is complicated with lots of moving pieces, so for the sake of this post, let me simplify it to this: the Borgias were preparing to conquer. 

Pope Alexander VI’s notorious son, Cesare, had given up his Cardinal’s hat, travelled to France, became Duke of Valentinois, married a French noblewoman, fathered a daughter whom he named Louise in honour of his new royal ally and then returned to Italy with an army. The Borgias were meant to be allies of Caterina – in fact, the Pope was Ottaviano’s godfather – but their aim was uniting the Romagna under the banner of the Borgia Bull. 

Cesare took Imola first. When he turned his attention to Forlì, Caterina admirably asked her people whether they wanted to capitulate or fight. They chose the former. Cesare took Forlì without bloodshed. I wonder, had she not retaliated against the assassination of Giacomo Feo, would Forlì have chosen Cesare so easily?

Caterina, however, was not ready to give up. She sealed herself in the Rocca di Ravaldino and refused all offers of peace. On 12th January 1500, almost a full month after the start of the assault, Cesare’s army captured the fortress and took Caterina prisoner. When they entered Rome, Caterina was not pulled along in a cage, defiled or degraded. She rode by Cesare’s side, wearing his colours. It’s unclear what happened between the two headstrong figures on the road, but it’s believed Caterina had the younger, famously handsome, Cesare as her lover.   

At first, Caterina was held in the Belvedere Palace in the Vatican, treated as the Pope’s guest – unwilling, but guest all the same. After she tried to escape, her fortunes changed and she was moved to the Castel Sant’Angelo, the very place she had stormed years before in her first husband’s name. Eventually, she conceded to the Borgia’s wishes. Having signed over her lands, she was allowed to retire in Florence, where she spent the rest of her life. 

Medal of Caterina Sforza
The Wallace Collection, London


Caterina’s last years were sad ones. 

Her brother-in-law, Lorenzo (of that confusing secondary branch of Medici), had taken custody of her son, Giovanni (named after his father), and she had to fight a long legal battle to win him back. Though Ottaviano had followed in his maternal grandfather’s footsteps for a brief while, employed twice by the Florentines as a condottieri, he ended up entering the church after being deposed by Cesare Borgia. Even when Pope Alexander VI died and Cesare (who had become a surprisingly beloved ruler) had lost his hold over the Romagna, Caterina had no chance of regaining her usurped power. 

She spent her days, instead, writing. Experimenti contained 454 recipes; 66 of which were cosmetic, 358 medical, and 38 alchemical. 

She died in 1509 aged 46 years old. Her body was laid to rest in a convent of nuns whom she had befriended. Sadly, by the 1830s, the nunnery was turned into a prison, and her remains disappeared. To this day, we don’t know where she is. 

La Dama dei Gelsomini by Lorenzo di Credi
Pinacoteca Civica di Forlí


Caterina Sforza was a force to be reckoned with. 

She was altruistic, spending her time and resources tending to the poor and sick when plague broke out, taking them food and medicine of her own making and braving the worst hit districts. She was vengeful, rumoured to have plotted against Borgia Pope by contaminating cloth with plague and sending it to him. She was a brilliant leader, lowering taxes and spearheading military training. She was even blind at times, loving so deeply that she occasionally followed her emotions rather than her intellect.  

But for all her greatness, her faults and her passions, there’s one important thing we should remember: 

Caterina Sforza was not a woman to be swept aside and ignored. 

She was a free woman in a man’s world. She thrived as a thorn in their side. Not only is she one of the few women to ever be mentioned in the works of Niccolò Machiavelli, a feat in itself, but 513 years later, we’re still sitting here talking about her.  

The Tigress of Forlì.

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