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Authors: Elizabeth Lev

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Caterina had rightly read the papal intent. In 1499 the Borgias were preparing to extend their greedy fingers into Romagna. In May, Pope Alexander VI made his intentions clear with a papal bull in which he declared Caterina
iniquitatis filia,
"a daughter of iniquity."
6
This Old Testament term was used to refer to unjust rulers or tyrants. Even in this case Caterina broke new ground for her era: this was the first time the epithet had ever been used for a woman. The pope, citing tyranny and three years of unpaid tribute, was deposing the Riario rulers in favor of his son Cesare. In response, Caterina immediately dispatched her envoy Giovanni delle Selle to Rome to negotiate and eventually pay the thirty-six hundred ducats owed in tribute, if necessary, but the pope refused to meet with him. It was clear that Caterina could expect to encounter a papal army in the near future.

Caterina would need the friendship of Florence. The king of France was on the move. Now allied with Venice, he was marching toward Milan. Her most powerful ally, Duke Ludovico the Moor, would soon be completely absorbed in repelling this advance and thus unable to come to the aid of Caterina. If the French captured Milan, the city on the Arno would be her only friend. As the French rolled over the Alps and the papal army moved north, the two forces would meet on the strip of the Apennines, the mountains where Tuscany and Romagna were joined. Caterina couldn't afford to antagonize Florence, and Florence couldn't afford to lose Forlì as a friendly neighbor.

Machiavelli arrived at Forlì in the cool morning hours of July 17, but Caterina kept him waiting until the afternoon, when Giovanni da Casale, acting as Caterina's chancellor, received the young diplomat. As the hot summer sun waned, Casale accompanied Machiavelli to the inner sanctum of Ravaldino, Il Paradiso. In the countess's beautifully decorated private apartments overlooking the Apennines, Niccolò first came face to face with the legendary Caterina. She was simply but elegantly dressed, with the white widow's veil concealing her blond hair. In aspect, she seemed anything but the passionate firebrand she was reputed to be. Machiavelli began with an eloquent outpouring of Florence's love for the countess and her family and their appreciation for her loyalty. It was this "affection they had for her and her merits," rather than any real need for her services, that impelled them to offer to renew Ottaviano's contract at a rate of pay applicable to times of peace, ten thousand ducats.

Caterina wryly responded that "the words of Florentines were always so very pleasing to hear."
7
On the other hand, she observed, their actions tended to provoke displeasure. Her "merits," so lauded by the polished phrases of the envoy, had never been recognized in any material way. Throughout Italy, she said, Florence was reputed to be a grateful republic, one that remembered its friends as well as its enemies, but in her case "now showed ingratitude for one who had done more than any other ally."
8
In supporting Florence so staunchly and loyally, Caterina had incurred the wrath of Venice and had been attacked for her fidelity. Closing their interview, she promised to think things over; Machiavelli was escorted from Paradise and left to his purgatory of waiting.

While Machiavelli composed his letter to Florence, optimistically recounting the first meeting, Caterina informed Milan of their encounter. At the same time she enlisted her secretary to entertain Machiavelli and gauge what Florence was really willing to offer.

After two days of waiting, Machiavelli was summoned back to the castle to meet with Caterina. He found the countess at her most charming as she invited him to understand her position. She too loved Florence, and indeed she and her family had been honored with Florentine citizenship as of 1498, but she carried a proud family name and had to consider her honor. Indeed, now that she also bore the name of Medici the question of honoring such exalted lineages was foremost in her mind. She explained that the duke of Milan, pressed for reinforcements against the advancing French, had already offered a
condotta
for Ottaviano at the same pay. Machiavelli parried by turning to another, less pointed subject, a simple purchase of gunpowder, cannonballs, and potassium nitrate for making explosives for the Florentine war against Pisa. Caterina again demurred, apologizing that her supply wasn't sufficient to defend the borders of her own small realm, but she was in the midst of purchasing some from Pesaro that she would be happy to share with Florence. She also had infantry for hire, "well armed, good men and ready immediately," who had been personally trained by her. As the negotiations drew to a close that day, Caterina gently revealed that she would lose face by accepting the dishonorable conditions Florence was proposing, especially if Florence didn't honor the terms of the first contract.

The number of well-placed Florentines in her court, as well as her readiness to offer men and supplies, had convinced the young diplomat that "every day he saw clearly evident signs"
9
of Caterina's friendship toward Florence. As his later treatises would show, he was sensitive to a ruler's fear of losing reputation or face. He recommended that Florence demonstrate its appreciation for the countess in deeds, not words, and championed her request for the back pay due her son and a new
condotta
for Ottaviano at twelve thousand ducats. Machiavelli was hoping that with some cash and an honorable position for her son, Florence could keep Caterina's loyalty without having to formally promise to protect her state, should it be attacked. He suggested a little flattery and a few gifts to woo Caterina as a military bedfellow, but offered no promise of marriage.

The next day Caterina gave the Florentine envoy a glimpse of her dowry. As he watched from the ramparts of Ravaldino, fifty mounted crossbowmen rode in review under the watchful eye of the countess on their way to the duke of Milan. The well-made weapons expertly handled by the crack troops impressed Machiavelli. The following morning, Machiavelli was treated to the sight of five hundred infantrymen marching in perfect formation. These seasoned troops were also on their way to Milan, and Caterina made sure that Machiavelli knew that the duke had already paid for them three days earlier. Machiavelli saw how quickly she could muster her men and how well they were trained, and was duly smitten.

On July 23 Machiavelli hurried to the countess's chambers with the news that Florence was willing to raise Ottaviano's pay to twelve thousand ducats but found Caterina silent and distracted; she abruptly got up to leave five minutes after they had sat down. A perplexed Machiavelli returned to his chambers, confused as to what Caterina had in mind. A messenger arrived shortly after, bearing Caterina's apologies. She was "worried sick" over the illness of Ludovico, her infant son by Giovanni de' Medici. She would be happy to conclude the treaty as soon as possible under the stated conditions; the back pay owed Ottaviano, the new
condotta
at twelve thousand ducats, and a written statement of Florence's obligation to "defend, protect, and maintain her state." Machiavelli balked at the last condition, saying to Caterina's secretary that he could not sign such an agreement without authorization from the Signoria of Florence. He suggested that he could offer a verbal promise, but nothing written. Caterina's closest adviser, Giovanni da Casale, accepted the terms, promising that tomorrow all would be concluded. A confident letter then went from Machiavelli to the Signoria, claiming that the deed was done: Caterina and her state would be at their disposal, but Florence would not need to offer more than the occasional trinket.

The next morning Machiavelli appeared in the countess's chambers for the signing. Arriving at this fourth meeting, Il Machia thought all was settled, but Caterina turned the tables. "After sleeping on it," she decided she required the written obligation of Florence to defend her lands. She was sorry, of course, that she "had indicated other ideas through Giovanni da Casale," but Machiavelli should not be surprised, for "the more things are discussed, the better they are understood."
10
While Machiavelli had thought the seduction of Caterina was complete, she made it clear that the courtship was only beginning. Stung by his misreading of the situation, he showed his shock and hurt through both his words and gestures, betraying his inexperience. Only later would Machiavelli learn to conceal his true thoughts behind a mask of wit and irony. Caterina remained unmoved during his protests and Machiavelli had to inform Florence of his failure. Machiavelli soon left Forlì and Giovanni da Casale traveled to Florence to continue negotiations directly with the Signoria.

Caterina's abrupt about-face was not only a professional embarrassment for Il Machia, but undoubtedly it humiliated him in the eyes of his friends. Later, Machiavelli would take his revenge by denouncing Caterina in all of his famous treatises: as a tyrant in the
The Prince
and as the ribald woman on the ramparts who was willing to sacrifice her own children in both
Florentine Histories
and
Discourses on the First Ten Books of Titus Livius.
But one can glimpse the Caterina he once admired—the alert general, worried mother, and charming countess—in the pages of
On the
Art of War,
where he describes her defense of Forlì against the French: "She would have the spirit to await an army, as neither the king of Naples nor the duke of Milan had done. And though her efforts did not turn out well, nonetheless she earned the esteem her valor deserved."
11

When midsummer 1499 arrived, Caterina was hovering over little Ludovico's bedside. The child was burning with malarial fever, and none of Caterina's remedies could halt its advance. By August 3, she was in despair. The year before she had lost Ludovico's father, and the infant was all she had left of her greatest love. Writing to Ludovico's uncle Lorenzo di Pierfrancesco de' Medici, she intimated that the fever had arrived twelve hours earlier than expected and that it was higher than the last time. "I don't know what else to say"
12
are the simple sad words of a mother on the brink of losing her beloved son. Asking for prayers, the only remedy left to her, she returned to her vigil at her son's bedside. Five days later, her prayers were answered. She wrote a few tentative words of hope to Lorenzo in Florence: "He has recovered enough that if nothing else happens, we hope he may be cured of this illness. Thank God for everything."
13

The boy recovered, and Caterina set about enjoying the waning days of summer. She ordered special sugar confections from Florence and received cases of pomegranates from her friends in the convent of the Muratte. She purchased a new saddle of Florentine leather and began teaching Ludovico her own greatest passion, riding. In these days, Caterina's thoughts rested solely with her family. Her younger sister Chiara arrived in Forlì that summer. Once a cheerful girl lapping up her sister's stories on her bridal route from Milan to Rome, now Chiara was older, sadder, and financially ruined by her husband's mismanagement. Desperate, Chiara had thrown herself on her sister's mercy. The countess interceded with the duke of Milan so that Chiara, who had arrived in Forlì "destitute and derelict," could leave for Milan with the personal assurances from Duke Ludovico that he would see to her needs. Caterina also concerned herself with finding a husband and dowry for Giacomo Feo's sister, who was in her late teens and still unmarried.

Caterina's most serious worry was about the future of her youngest son, Ludovico. Giovanni de' Medici, albeit from the less wealthy cadet branch of the Medici family, had been well-to-do, and as his only son, Ludovico was entitled to his inheritance. As soon as she could leave Ludovico, she traveled with Ottaviano, Luffo Numai, and other important Forlivesi as witnesses to meet with the Medici representatives. Before a notary, she declared the fact that she had hidden so desperately from the duke of Milan. She and Giovanni de' Medici had been married in September 1497, and Ludovico was the child of that marriage. Caterina assumed the guardianship of their son and then gave the equivalent of an exclusive interview with the chronicler Andrea Bernardi, ensuring that her story of the marriage, birth, and guardianship would be recorded. Giovanni's brother Lorenzo di Pierfrancesco, however, was a greedy man, only too happy to take advantage of Caterina's distance from Florence to absorb his brother's inheritance. Lorenzo wanted inventories of the grain business Giovanni had shared with Caterina and the personal possessions left in Forlì. He had already had Giovanni's silver plate packed off to Florence within days of his death. The letters between Lorenzo and Caterina increased in hostility as she took more of an interest in the Medici estate and noted more and more discrepancies in Lorenzo's accounting. The tension would mount for several years until matters finally came to a head in an out-and-out legal battle that would last half a decade.

The arrival of the bubonic plague abruptly halted Caterina's pleasant summer. By the end of August, the illness was raging through Forlì. The bane of the Renaissance era, this terrible disease came from a bacterium hosted by rats, traveling from the infected rodents to humans via fleas. Its onset was marked by a high fever and enlarged lymph nodes, known as buboes, which typically killed victims within three to four days. Europe's first experience of the Black Death had occurred in 1348, when it claimed a third of the population. One hundred and fifty years later, its cause remained a mystery but most well-informed rulers knew of efficacious ways to limit its spread. Caterina had seen the plague before and though she personally feared it little, she knew its capacity for devastation. This time the stakes were much higher. With Cesare Borgia and the French closing in, a plague would weaken the defenses of Romagna; the sickness would have to be defeated in Forlì before it could contaminate other areas. Caterina sealed off her city. No market, no traveling shows, no large assemblies. She brought in special doctors to assist the ill and priests to console the dying. Food and necessities were distributed to the populace free of charge. The city was divided into sectors and subjected to strict rules of hygiene. Those infected were immediately isolated in the Church of San Giovanni while a confraternity of volunteers collected the dead for hasty burial outside the city walls. The clothes, belongings, and even the houses of the incurable were burned, which brought many protests. But these stringent measures saved the region; the casualty count was 179 people, much lower than expected, and the sickness did not reach any of the surrounding countryside.

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