Caterina Sforza
Known as the “Tigress of Forli“, Caterina Sforza was an ultra-tough, tyrannical ruler who dominated in the 15th century, she refused to back down from any challenge no matter how “impossible”.
Adored and feared in equal measure by her Renaissance contemporaries, Caterina Sforza is most remembered for her political activity in Castel Sant’Angelo in 1484; her tenacious regency of Imola and Forlì, after the assassination of her first husband, in 1488.
Never seeming to register any fear, and went out of her way to ensure that everyone who crossed her wound up suffering slow, excruciating and horrific deaths, by her vengeful hands – a renaissance virago (woman who fights like a man)
In the latter years of the 15th century, up to 1494, were a time of unusual prosperity in Italy. It was Caterina’s grandfather Francesco Sforza, a popular condottiero and ally of Cosimo de’ Medici who would gain the Duchy of Milan in 1450, and Bianca Maria Visconti.
Filippo Visconti. the last Duke of that race, in 1447, without heirs male,had some years before his death, given his daughter Bianca, and the succession to his duchy, to the celebrated soldier of fortune Francesco Sforza.
Galeazzo, was the son of Francesco and Bianca, who succeeded his father.
Caterina was the illegitimate daughter of Galeazzo Maria Sforza, 5th Duke of Milan and Lucrezia Landriani the wife of the courtier Gian Piero Landriani, a close friend of the Duke. (however that worked) .
Caterina was initially raised by her mother’s relatives, but after the death of her grandfather, Galeazzo was in France at the head of a military expedition to help King Louis XI of France against Charles I of Burgundy.
Called home by his mother, Galeazzo returned to Italy under a false name which was necessary to pass through the territories of his enemy, the Duke of Savoy, who made an unsuccessful attempt on Galeazzo’s life.
Of the noble and wealthy cities of Italy, Milan was one of the noblest and wealthiest; now Galeazzo Maria Sforza, was its Duke.
In his first years Galeazzo and his mother ruled jointly, but later his ruthless character pushed him to oust Bianca Maria from Milan.
Galeazzo then brought Catarina , whom he legitimatized at age 8 and her 3 other siblings her parents had sired, to live with him, in his court.
Caterina was most likely acknowledged by her father because noble children were often useful tools for politically advantageous marriages.
Such schemes formed the principal occupation of Italian princes and were a fruitful source of innumerable atrocities and abominations, as any reader of Italian history knows- such ambition found its excuse in the law of self – preservation.
In the perpetually shifting scene produced by alliances, jealousies, leagues, friendships and treason, and a crowd of petty issues, it was near impossible for any family of princely rank to hold its own – the fortunes of each were always on the rise, or decline.
At the time, Italy was preserved only by a careful maintenance of the balance of power between some 4 or 5 of the leading princes of the peninsula.
A large portion of labors and abilities of statesmen, were devoted to perpetually trimming any troublesome balance.
It is interesting to observe how roughly the theory was understood, yet how perfectly practiced by accomplished professors of the art.
The smallness of objects to be weighed against each other, rendered the task of keeping the scales, even in that microcosm, a delicate one – as they were capable of disarranging the balance, only great dexterity could preserve the equilibrium.
Accordingly, checking and counter checking, and far-sighted schemes of attack, and devised means for future defense.
Sixtus IV at Rome, Lorenzo the Magnificent at Florence, Galeazzo Maria Sforza at Milan, and the Republic of Venice,’ were the powers‘ between whom and by whom the peace of Italy, and possessions of each, were preserved.
At the time, united in a common course of policy kept in check the ambitious Queen of the Adriatic, far more powerful than any 1 of the 4, though much less so, with all of them combined.
The rest of Italy, consisted of petty principalities, which served singularly to complicate the game and to increase the interest of its vicissitudes.
If endowed with any military talent, these small princes of a city and its immediate neighborhood become generals of the forces, in the pay of one of their more powerful neighbor -in this way several of them became important elements.
Some, again, would die without heirs male, and leave their female successors, a daughter or widow, a prize to be scrambled for by the royal crowd, always on the look out for such windfalls.
Others were perpetually at feud with their own subjects, which gave an opportunity for some neighbor to intervene on behalf of another party, with the same ultimate result.
Finally, (and this was perhaps the way in which most seriously compromised the tranquility and influenced the destinies of Italy)-—-they formed the material from which each new Pope was made.
Going forward Caterina’s education was under the superintendence of Duchess Bona, a princess of the house of Savoy, whom Duke Galeazzo married.
Three years after Galeazzo’s marriage, he went on a tour of his neighboring states, ending in Medici ruled Florence, where Caterina’s love of art was fostered.
Dazzled by the works of the greatest artists, architects and sculptors, Florence was the center of the world for creativity.
Lorenzo de Medici, admired by the Florentines as their de facto ruler, had amassed the greatest artistic minds and his court was a hive of intelligence.
He, his family, and his city captivated Caterina in a love that would last until her dying day.
Caterina grew up, alongside her father’s children regardless of legitimacy, all being treated the same, and taught to bear the Sforza name with pride.
Galeazzo’s children were raised in beautiful Italian villa surrounded by attendants, lavish luxuries, and dungeons full of those who were being brutally tortured into submission, by her father.
Galeazzo was famous for being lustful, cruel and tyrannical , a trait at times seemed passed down to his daughter, Caterina.
Sforza Castle, Milan
Caterina received an enlightened education to rival the most eminent men of the day, taught by Francesco Filefo, and her father’s court poet, author of Sforzinda, lauding her grandfather’s success in grasping the duchy of Milan.
Her days were filled with Latin, the classics, such as Cicero and Homer with her fathers library, which was the envy of all, as it was filled with over a thousand of the most illuminating and beautiful books money could buy.
The Black Prayer Book, also known as the Prayer Book of Galeazzo Maria Sforza, is one of the richest and most sumptuous examples of its kind. Dated to the 15th century
Galeazzo insisted his children hunt frequently, to hone their bodies and minds and to overcome fear and practice strength, as it was the closest they could get to battle. Few fathers would encourage their daughters in such manly pursuits, thus Caterina, gained an early advantage.
One that would prove vital in the shifting arena of Italian politics.
In later life, this would be a strength she needed to draw on, as it is the true meaning of her name; Sforza…strength. 
In 1473, at the age of 10 Catarina was engaged to Girolamo Riario nephew (though soe claim illegitimate son of the Pope) and known as the “Captain of the Vatican Ship of State” by Pope Sixtus IV.
Their marriage however, was not consummated until she was 14 yrs old, the legal age.
Girolamo was like the Pope’s consigliere, in the “good old days” when excommunication actually meant something, so let’s just say , she was well “connected“
Pope Sixtus IV, also gave Girolamo the Lordship of Imola, already a Sforza city, but at the time a fief of the Riario family.
After a triumphal entrance into Imola in 1477, Caterina went to Rome with her husband, in the service of his uncle, the Pope.
Upon her arrival in May 1477, Caterina found a city full of cultural fervor, with a desire for renovation – the atmosphere a mix of intrigue and power.
At the end of the 15th century, Rome was no longer a medieval city, but not yet the important center of artistic endeavors it would become a few decades later, as one of the most important cities of the Renaissance.
However, things were changing. Galeazzo was beginning to make enemies.
His extravagance was becoming unmanageable, coupled with civic expenditure and his imposition of the “Inquinto” tax on staple foods, the populace became restless.
They were starving and watching Galezzao spend vast amounts on jewels, trappings and projects that were never finished.
The cry for a republic had begun!
Galeazzo was an avid eye-witness of the executions, tortures, and mutilations, which his duty as a sovereign obliged him frequently to inflict on his subjects.
But he held a stranger propensity, he reveled in the sight of death, and human decay.
Some strange touch of insanity, which so frequently develops itself in minds exposed to the poison of unchecked power.
He would witness the suffering, the dying, and dead, for the mere pleasure of witnessing it.
Later, the friends, family, and survivors of the tortured, were able to overcome exact revenge, by murdering her father.
On December 26th 1475, while preparing for mass, he was struck down by 3 assassins.
14 blows mutilated his body, as he lay on the cold stone floor – dead.
The terrible deaths handed to his murderers, did nothing to assuage the grief felt by his children for the loss of an indulgent father.
Caterina’s step mother quickly transformed, declaring herself regent for her step child.
She abolished taxes, took control of the city and became a competent ruler, almost over night.
Caterina watched her in awe, inspired by her fortitude and strength, she became confident in the knowledge that a woman could rule as well as any man and resolved to take her example.
Only a few short weeks after, fearing a possible rebellion within the city, Bona wrote to Caterina’s husband that the time was right for Caterina to join him.
The final ceremony of the marriage was celebrated by the papal legate and the whole court.
Tellingly the only notable absentee was the groom himself.
Despite her husband’s objections, Caterina quickly integrated, due to her extroverted and sociable character, into aristocratic Roman society and became versed in the measure’s of politics.
As evidenced by correspondence from that period, Caterina immediately became admired as one of the most beautiful and elegant among noble Roman women.
She was welcomed everywhere, treated with great respect and lavishly praised by all of society including the Pope,
She soon transformed from a simple adolescent into a refined and powerful intermediary between the Roman court and other Italian courts, especially Milan.
In 1478, Girolamo was one of the plotters behind the Pazzi conspiracy, a plan to assassinate the two most prominent members of the Medici family in Florence.
In addition to conspiring, he was an intended beneficiary, once Lorenzo and Giuliano de’ Medici had been killed.
Riario would have become Lord of Florence. But the plot failed, as only Giuliano was killed.
The attack in the cathedral was extremely violent. Giuliano was stabbed to death while a wounded Lorenzo manages to barricade himself with Clarise and his mother Lucrezia.
“Outside the cathedral, after having occupied Palazzo Vecchio, Jacopo proclaims a new republic.
However, when the crowds see Lorenzo still alive, they rise up against the Pazzi.
Unrest and violence fill the streets. Salviati, Francesco, and Jacopo are hanged from the windows of Palazzo Vecchio, while the people of the city destroy every Pazzi coat-of-arms and effigy!
Lorenzo is furious and filled with pain, but is reminded of love and mercy by Botticelli and Clarice.
It is only thanks to them that he decides to exile and not execute Guglielmo suspected of being aware of the plan to murder them.
“While the crowds applaud Lorenzo, Botticelli starts to paint a new work of art dedicated to Spring…but now the Pope is ready for all-out war.”
The same year, in March 1478, Caterina gave birth to her first child, a daughter named Bianca after Caterina’s paternal grandmother, Bianca Maria Visconti, who was aunt to the French king and rode alongside her husband in battle. She also assisted Girolamo’s early reign.
In 1480 the pope made Girolamo Riario Count of Forlì, but in 1484 Girolao, started a conflict with the Colonna family, whose landed property Sixtus IV wished to take over.
In the course of this feud, Lorenzo Colonna, was arrested and tortured to death, which provoked much enmity against his family in the city.
Riario then erected the fortress of Rocca di Ravaldino, one of the strategically most important strongholds of the Romagna and rebuilt much of the town of Imola, tearing down old and decayed houses.
He also tried to earn the favor of the populace by erecting magnificent public buildings and churches, while abolishing taxes.
Occupation of Castel Sant’Angelo
After the death of Sixtus IV in 1484, Rome was rioting and looting as was often the case, she rode into the city, 7 months pregnant, and took the Castel Sant’Angelo.
With the support of her soldiers, and several well placed cannons she held the Vatican hostage, ensuring they would choose a favorable successor to Sixtus IV.
Girolamo’s residence, the Orsini palace in Campo de’ Fiori, was stripped of its content and almost destroyed.
Castel Sant’Angelo – an Ancient Jewel of Rome, Italy
Meanwhile, the disorder in the city increased.
A militia accompanied the arrival of the Cardinals who did not want to attend the funeral of Sixtus IV and refused to enter into conclave, for fear of coming under the fire of Caterina’s artillery.
Girolamo had his army occupy a strategic position, yet the Sacred College asked Girolamo to leave Rome, offering in return the confirmation of his Lordship over Imola and Forlì, the military post of Captain-General of the Church, and 8,000 ducats ($1,125,000) in compensation for damages to his property.
Girolamo accepted.
In Forlì, law and order had been maintained by Caterina’s uncle Ludovico il Moro Sforza, Duke of Milan from whom the Riarios learned of the election of Pope Innocent VIII, an old rivala, who now refused Girolamo for leaving Ro
Despite the loss of income, Girolamo did not reinstate taxes on the people of Forlì.
This situation lasted until the end of 1485, when the city government completely ran out of money.
Girolamo, pressed by the Council of Elders, was forced to levy taxes, which were deemed excessive by the population and led to Girolamo’s increased unpopularity among all citizens of Forlì.
Girolamo’s enemies began to conspire against him. and wanted to make the illegitimate son of Pope Innocent, lord of Imola and Forlì instead.
So Riario promoted several further plots against the Medici, but they all failed.
In 1488 he was the last of the main Pazzi conspirators left alive.
He was assassinated in a conspiracy led by two members of the Orsi family.
After more than 6 assassination attempts, Girolamo was killed in April 1488.
Checco and Ludovico Orsi entered the government palace.
One of them attacked Riario with a sword!
Despite the presence of the Count’s guards, a total of 9 assassins slashed Riario to death, and flung his corpse out the window of his own castle, where a crowd gathered in support of the assassins who then proceeded to loot the palace.
The lord’s palace was sacked, while Caterina and her children were made prisoners.
The fortress of Ravaldino, a central part of the defensive system of the city, refused to surrender to the Orsis.
Caterina offered to attempt to persuade the castellan (governor of a castle), Tommaso Feo, to submit.
The Orsis believed Caterina because she left her children as hostages, but once inside she let loose a barrage of vulgar threats and promises of vengeance against her former captors.
According to Machiavelli, when they threatened to kill her children, Caterina, standing in the walls of the fortress exposed her genitals and said:
“Fatelo, se volete: impiccateli pure davanti a me … qui ho quanto basta per farne altri!”
(‘Do it, if you want to: hang them even in front of me … here I have what’s needed to make others!’).
The historical record tells that Caterina, in fact, claimed to be pregnant.
Although her statement that she was pregnant is, by most historians, considered to have been a ruse, to rendered worthless any power the conspirators had in holding her children, Girolamo’s legitimate heirs.
These antics pumped up the defenders of the castle and left the rebel leaders with the morale-crushing realization that they’d basically just let their one piece of leverage walk right into the front door of her castle.
Shocked by this response, the Orsis didn’t dare to touch the Riario children.
Although assassinations were not uncommon in Renaissance Florence, they still had repercussions.
Despite writing to Lorenzo de’ Medici, who no doubt approved of the result of the assassination, they received no written support by the Medici family.
Support, both military and popular, eventually sided with Riario’s widow, and the Orsi brothers fled, taking what they could with them.
Their remaining assets and family were soon destroyed by angry mobs.
Riario’s body had been recovered from the piazza by a local friar, and once Riario’s widow proved vindicated, she had the body cleaned up and laid in state for three days in the church of San Francesco.
She ordered that all those involved in the Orsi conspiracy to be imprisoned, along with the Pope’s governor, Monsignor Savelli, all the pontifical generals, and the castellan of the fortress of Forlimpopoli, and also all women of the Orsis and other families who had assisted in the conspiracy. so the soldiers sought out all who had taken part in the conspiracy.
Houses owned by those imprisoned were razed while their valuables were distributed to the poor.
On 30 July news came that Pope Innocent VIII had given Ottaviano Riario the official investiture of his state “until his line ended.”
In the meantime, Forlì was visited by Cardinal Raffaele Riario, officially to protect the orphan children of his late cousin Girolamo but in reality, to oversee the government of Caterina.
The young Countess personally dealt with all issues concerning the government of her city-state, both public and private. To consolidate her power, she exchanged gifts with the lords of neighboring states and involved herself in marriage negotiations for her children.
She decreased taxes by reducing some and eliminating others, and sharply controlled her realm’s spending.
Caterina dealt directly with the training of her militia in the use of weapons and horses.
It was her intention that her cities and towns be orderly and peaceful, and she expected her subjects to appreciate these efforts.
The states of Forlì and Imola were smaller than the great Italian states but, due to their geographical position, had a considerable strategic importance on the political affairs.
In those years, significant events changed the geopolitical situation of Italy.
Lorenzo il Magnifico, whose shrewd policy curbed claims and rivalries of the various Italian states, died on 8th of April 1492.
Pope Innocent VIII also died on 25th of July, and was replaced by Cardinal Rodrigo Borgia, who took the name of Pope Alexander VI.
His election seemed to strengthen Caterina’s rule. While she and her hus lived in Rome, the Cardinal had often been a guest at their home, and he was godfather to Ottaviano.
These events directly threatened the stability and peace in Italy.
With the death of Lorenzo friction between the Duchy of Milan and the Kingdom of Naples, led up to the crisis of September 1494, incited by Ludovico il Moro, King Charles VIII of France entering into Italy to claim Naples as the Anjou heir.
At first Pope Alexander VI gave his support to Charles’ claim, leading to four years of war.
During the conflict of Naples and Milan, Caterina, was placed in a strategic position of passage for anyone who wanted to go to the southand tried to remain neutral. She knew Forlì was exposed to invasion, located in a strategic position on the way to Rome.
On one side, her uncle Ludovico had allied with Charles VIII; on the other side, Pope Alexander VI now opposed France’s ambitions in Italy, and her brother-in-law, Cardinal Riario, argued in favor of the incumbent King Ferdinand II.
Caterina chose to join Naples and the Pope, in defence of Imola and Forlì against the French.
Betrayed by her Neapolitan allies, who at the first French attack didn’t help her, Caterina changed sides and submitted to Charles VIII, giving his army via libera (“free passage”) to Naples; however, he preferred to avoid the Romagna and crossed the Apennines.
Naples was conquered by the French army in only 13 days which frightened the Italian principalities, and they formed the League of Venice against Charles VIII.
The League defeated the French King and he was forced to retreat to France.
This time, Caterina managed to remain neutral. By not participating in the expulsion of the French, she maintained the support of both her uncle Ludovico in Milan and also the Pope.
2nd marriage
Two months after the death of Girolamo, a rumor was spread that Caterina was close to marrying Antonio Maria Ordelaffi, who had started to court her.
This marriage would end the claims of the Ordelaffi family on the city of Forlì.
When Caterina saw how things stood, she imprisoned those who had spread the false news.
These rumors were addressed by the Senate in Venice, which summoned Antonio Maria to Friuli, and confined for 10 years.
In fact, Caterina had fallen in love with Giacomo Feo, the brother of Tommasso Feo, the castellan who had remained faithful to Caterina Sforza after the assassination of her husband.
Caterina married him in 1488, but secretly, to avoid losing custody of her children and the regency of her dominions.
All the contemporary chronicles reported Caterina was madly in love with the young Giacomo.
It was feared she would strip her son Ottaviano of his future lordship, in order to give it to her lover and secret husband.
Giacomo was appointed castellan of the fortress of Ravaldino in place of his brother, and was awarded with an order of chivalry from Ludovico il Moro.
In April 1489, Caterina gave birth to Giacomo’s son, Bernardino, later called Carlo in honor of King Charles VIII, who made Giacomo a baron of France.
She had replaced the castellans of the fortresses of her dominions with her closest relatives: the fortress of Imola was given to Gian Piero Landriani, her stepfather, and the fortress of Forlimpopoli to Piero Landriani, her half-brother, while Tommaso Feo was married to Bianca Landriani, Caterina’s half-sister.
A conspiracy was formed to seize the fortress in the name of Ottaviano, and murder Giacomo and Caterina.
The Countess discovered the plot and imprisoned or executed those who were involved.
Immediately after this conspiracy was foiled, another plot was organized by Antonio Maria Ordelaffi, but this also failed. Giacomo’s power increased, along with his cruelty and he incurred the hatred of all, including Caterina’s children.
On one occasion, in full view of the public, he slapped Ottaviano (the rightful Lord of Forlì), but nobody had the courage to defend the boy.
After this incident, adherents of Ottaviano decided to liberate the city from the domination of Giacomo Feo.
Gian Antonio Ghetti and some of Caterina’s own children formed a conspiracy.
On the evening of 27 August 1495, Caterina, Giacomo Feo, and their entourage were returning from a hunt.
Caterina, her daughter Bianca Riario and some of her ladies-in-waiting rode in a carriage, followed on horseback by Giacomo, Ottaviano and his brother Cesare, and many staffieri and soldiers.
Agents of the conspiracy attacked and killed Giacomo.
The same day, Ghetti went to Caterina, thinking that she had secretly given the order to kill Giacomo.
However, Caterina was unaware of the plot, and her revenge was terrible. She reacted with vindictive fury and was not satisfied with mere executions: their deaths had to be the most cruel and painful.
She not only prosecuted the wives and mistresses of the conspirators, but she also sought out the children, even those in early infancy, and all were summarily tortured and executed.
Her fury blinded her to the politics that inspired the plot.
It had involved almost all the supporters of Ottaviano Riario, who were convinced that Caterina had given her consent to the killing of the man who was considered the “usurper” of the state’s rightful ruler.
They had wanted to uphold the power of the Riario family.
As a result of the massacre, Caterina lost forever the good will of her people.
Third marriage
In 1496, the ambassador of the Republic of Florence, Giovanni de’ Medici il Popolano, paid a visit to Caterina.
The second son of Pierfrancesco il Vecchio, he belonged to a collateral branch of the Medici family.
Along with his older brother Lorenzo, he had been sent into exile because of his open hostility toward their cousin Piero, who succeeded his father Lorenzo il Magnifico in the government of Florence.
In 1494, when Charles VIII invaded Italy, Piero was forced to sign a treaty which allowed the French army to move freely into the Kingdom of Naples.
The people of Florence were liberated, deposed Piero and proclaimed a Republic. Giovanni and his brother were able to return to their homeland.
They renounced the Medici surname and took the name of Popolano.
The Florentine government appointed Giovanni as ambassador to Forlì.
Shortly after coming to Forlì, Giovanni and his entourage were housed in the apartments adjacent to Caterina’s in the fortress of Ravaldino.
The rumours of a possible marriage between Giovanni and Caterina and that Ottaviano Riario accepted the post of Condottiero from Florence threatened by the Venetians, alarmed all the lords of the League and the Duke of Milan.
Caterina couldn’t hide her wedding plans and her own feelings from her uncle Ludovico; she truly fell in love with the handsome, charming, and intelligent Giovanni.
The situation differed from the previous one, as this time Caterina had the approval of her children and she obtained the consent of her uncle.
The marriage of two people from such powerful families, however, was likely to arouse opposition, so they were wed in secret in September 1497.
In April 1498, Caterina bore Giovanni a son, the last of her children. The child was baptised as Ludovico after his mother’s uncle, the Duke of Milan, but later he became known by the name Giovanni dalle Bande Nere.
Meanwhile, affairs between Florence and Venice were getting worse and Caterina, who occupied the main route between the two cities, prepared her defenses.
She sent a contingent of knights to the aid of Florence, led by Giovanni and her eldest son, Ottaviano Riario, accompanied by men she had trained herself.
Giovanni became seriously ill and was compelled to leave the battlefield and return to Forlì. There, despite treatment, his condition deteriorated and he was transferred to Santa Maria in Bagno, where he hoped for a miraculous recovery.
On 14 September 1498, Giovanni died in the presence of Caterina, who had been summoned urgently to attend him.
Giovanni’s death left Caterina alone to face the Borgias.
Defence against Venice
After having returned to Forlì in order to make preparations for the defense of her states, Caterina was occupied by military concerns, especially logistics.
Training the militia was executed by the Countess in person. To find additional money and troops, she wrote to her uncle Ludovico, the Republic of Florence and the neighboring states who were her allies.
Only the Dukes of Milan and Mantua sent a small contingent of soldiers to aid her.
After an initial attack by the Venetians, which inflicted severe destruction, Caterina’s army managed to outmaneuver them. Afterwards, the war continued with minor skirmishes until the Venetians were able to circumvent Forlì to reach Florence.
Because of this staunch defence, Caterina Sforza gained the nickname of “La Tigre” (‘The Tiger’).
Capture by Cesare Borgia
In the meantime, Louis XII had succeeded to the French throne. Louis claimed the rights both to the Duchy of Milan as a grandson of Valentina Visconti, and to the Kingdom of Naples as heir to the House of Anjou.
Before starting his campaign in Italy, Louis XII secured an alliance with Savoy, the Republic of Venice and Pope Alexander VI.
In the summer of 1499, he came to Italy with a formidable army; without having to fight a single battle, he occupied Piedmont, as well as Genoa and Cremona.
He settled in Milan, which had been abandoned the previous month by Duke Ludovico, under the protection of his nephew-by-marriage Emperor Maximilian I.
Alexander VI allied himself with Louis XII in return for the King’s support in establishing Alexander’s son Cesare Borgia, the Duke of Valentinois, as ruler in Romagna.
Alexander issued a Papal Bull in March 1499 to invalidate the investiture of the feudal lords, including Caterina.
When the French army left Milan with Cesare to the conquest of Romagna, Ludovico il Moro regained the Duchy, with the help of Austria.
Caterina sought relief from Florence against the approaching French army, but Florence was threatened by the Pope, so she was left alone to defend herself.
She immediately began to recruit and train many soldiers and began to store weapons, ammunition and food. She reinforced the defences, especially that of Ravaldino where she resided and which was already considered impenetrable. She also sent her children to Florence.
For several days the artillery of both factions engaged in a mutual bombardment: Caterina’s cannon inflicted heavy losses on the French army, but the French artillery damaged the defences of the main fortress. What was destroyed during the day was rebuilt during the night.
Caterina’s solitary resistance was admired throughout all Italy; Niccolò Machiavelli reports that many songs and epigrams were composed in her honor.
As time passed without decisive results, Cesare changed his tactics.
His troops bombarded the walls of the fortress continuously, even at night. After 6 days, they opened two breaches in the walls.
On 12 January 1500, his forces stormed the fortress. The bloody battle -quick and decisive.
Caterina resisted, fighting with weapons in hand until she was taken prisoner.
Immediately she surrendered to Antoine Bissey (the bailli of Dijon) as a prisoner of the French, because there was a law preventing French forces from holding women as prisoners of war.
According to Machiavelli, the defense operations were misdirected by Giovanni da Casale: “The poorly built fortress and the scant prudence of the defender, therefore, brought disgrace to the magnanimous enterprise of the Countess …”
Rome
Cesare obtained custody of Caterina from the French general, Yves d’Allègre, promising he would treat her not as a prisoner but as a guest.
Caterina and her entourage were forced to go with the army preparing to conquer Pesaro, but conquest had to be postponed because Ludovico il Moro returned to Milan, forcing French troops to turn back.
Cesare departed alone with the Papal army for Rome, where he took Caterina to be held in Belvedere Palace.
Towards the end of March, Caterina tried to escape but she was discovered and immediately imprisoned at Castel Sant’Angelo.
To justify Caterina’s imprisonment, Pope Alexander VI accused her of trying to kill him in November 1499 with poisoned letters, as a response to the Papal bull which had deprived the countess of her fiefdoms.
Even today it is not known if the accusation was founded or not. Machiavelli believed that Caterina had tried to poison the Pope, however, an inconclusive trial took place, and Caterina remained imprisoned until June 1501, when she was released by Yves d’Allègre, who had come to Rome with the army of Louis XII for the conquest of the Kingdom of Naples.
Alexander VI alleged Caterina signed documents renouncing all of her fiefs, while his son Cesare, was appointed Duke of Romagna.
After a brief stay in the residence of Cardinal Riario, Caterina embarked from Livorno to Florence, where her children were waiting for her.
Florence
In Florence, Caterina lived in the villas which had belonged to her 3rd husband Giovanni de’ Medici, often staying at the Villa Medici di Castello.
Soon, she complained of being mistreated and living in a straitened financial situation.
For many years she conducted a legal battle against her brother-in-law Lorenzo de’ Medici for the custody of her son Giovanni, who was entrusted to him during her detention.
In 1504, her son was finally returned to her, because the judge recognized her confinement as a prisoner of war was not comparable to the detention of a criminal.
With the death of Pope Alexander VI in August 1503, Cesare Borgia lost all his power.
This reopened the possibility of restoring power to all the old feudal lords of the Romagna, who had been deposed.
Caterina lost no time in sending letters to adherents, and pleaded her case to Pope Julius II in her own name and that of her son Ottaviano Riario.
The new Pope was favorable to restoring the lordships of Imola and Forlì to the Riarios, but the populace of both cities declared that a majority of the people opposed the return of the Countess, so the domain passed instead to Antonio Maria Ordelaffi in October 1503.
After having lost her last chance to return to her former power, Caterina spent the last years of her life dedicated to her children, in particular to her youngest son Giovanni (her favorite and the most like her in personality and character), her grandchildren, her “experiments” in alchemy, and her correspondence with former friends of hers in Romagna and relatives in the Milanese court.
Death and burial
In April 1509 Caterina was stricken by a severe case of pneumonia.
She appeared to have recovered, but had a relapse, after which she made her will and arranged her burial.
At the age of 46, “The Tigress of Forlì“, who had “frightened all of Romagna”, died on 28th of May 1509.
Her body was placed in a small tomb in the chapel of Le Murate in Florence, a convent of nuns whom Caterina had befriended during her time in that city where she kept a cell as a spiritual retreat.
During the 1830s the nuns were forced to leave the property, and in 1845 it was redesigned as a prison.
Sometime during this renovation, Caterina’s body was lost.
In June 1537, 28 years after Caterina’s death, her grandson Cosimo de’ Medici, the only grandson of Giovanni, became the Duke of Florence and in 1569, the Grand Duke of Tuscany.
Through him, Caterina was the direct ancestress of the later Grand Dukes of Tuscany, the Dukes of Modena and Reggio, and the Kings of Spain and France. Notable descendants include Marie de Medici, both King Louis XIV of France and Queen Maria Theresa of Austria, King Charles II of England,
The original ivory silk duchess satin dress, designed by royal couturier Norman Hartnell, for the wedding of Queen Elizabeth featured elaborately embroidered star lily and orange blossom motifs was inspired by Botticelli’s “Primavera.
Diana, Princess of Wales (through illegitimate Descendants of Charles II of England), Prince William, Duke of Cambridge, Prince Harry and Prince George of Cambridge.
