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Authors: Elizabeth Lev

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The marriage offers continued; in 1497 Lorenzo di Pierfrancesco de' Medici offered his daughter and in 1498 the Gonzaga offer was renewed. But Caterina held out for a military career for her firstborn. In June 1498, Ottaviano's long-awaited
condotta
arrived. He would be employed by Florence in the war against Pisa for the amount of seventeen thousand ducats. The contract had been negotiated by a new friend of the countess, Giovanni de' Medici of Florence. Caterina proudly prepared one hundred light cavalry and one hundred infantrymen to accompany her son on his first steps toward glory. Ottaviano returned in August after a modest success, although reports revealed that he ran a disorderly camp and was incapable of disciplining his soldiers. Nonetheless, the proud mother celebrated her son with a commemorative medal. The papal bull by which Sixtus IV gave Forlì to the Riarios permitted the family to mint their own coins. Girolamo had used this privilege only once or twice during his reign, but Caterina had struck several coins since his death. In the earlier medals, Caterina, invariably represented in profile, wore a low-cut dress and her uncovered hair tied back, with a single loose strand framing her face. A diadem of pearls crowned her brow, indicating her status as sovereign. On the recto of two of the surviving coins the words
TIBI ET VIRTUTI,
"to you and to virtue," frame a figure of Fortune, while another from 1493 shows winged Victory riding in a two-horse chariot encircled by the motto
VICTORIAM FAMA SEQUETUR,
"fame follows victory." In 1496 Caterina minted another set of coins in which the figures of Victory and Fortune made way for mention of Ottaviano. Caterina still appeared on the front, but now tightly cloaked in a widow's veil, older and more sober than in the earlier medals and taking her first steps back from the throne to prepare the way for her son. The medal commemorating Ottaviano's Pisa campaign was designed by Niccolò Fiorentino, who made no attempt to idealize the nineteen-year-old. With an empty expression and heavy jowls, Ottaviano already looked like an old man.
16

Caterina's maternal attentions were not limited to Ottaviano, the heir to Forlì and Imola. Her second born, Cesare, had been destined for a career in the church since his childhood, and on February 19, 1492, at the age of twelve, he was given his "first tonsure," the shaving of the hair from his crown, leaving only a ring of locks encircling his ears, nape, and forehead. Now Caterina endeavored to ensure that he collected the benefices and titles customary among Renaissance prelates. Her relations with Cardinal Raffaello Riario had soured since the death of Feo because Caterina was certain that Cardinal Riario had encouraged, if not personally sent, the assassins. Despite Cardinal Riario's many displays of assistance through the years, Caterina complained about him ceaselessly to Duke Ludovico in 1496. "I don't know if he thinks he is dealing with a child here or if it is because I am a woman that he thinks he can beat me with his words," she railed in a letter dated April 11, 1496. "If I told you all the anguish and troubles he has made me suffer: I would seem like more than a martyr for his behavior and continual fabrications about me."
17
This time Caterina got her revenge through diplomatic channels. In the fall of 1496, as the cardinal lay seriously ill, Caterina convinced the duke of Milan to transfer his abbeys and benefices in Milan to Cesare upon his death.

Bianca Riario, Caterina's only girl, was growing up to be as lovely as her mother. Fifteen in 1496, Bianca had been intended for Astorre Manfredi of neighboring Faenza since she was eight. The official engagement was several years in the making, as the political consequences were significant for both Florence and Bologna. The Medicis were hesitant to allow Caterina a foothold in Faenza, and Giovanni Bentivoglio of Bologna, Astorre's grandfather, had long dithered about the match, sometimes supporting and sometimes opposing it. In 1495, during those last happy days before Feo was murdered, the engagement was finally made official, and ten-year-old Astorre paid his first visit to Forlì. He rode with an honor guard of thirty men, impressing the townspeople with his horse and handsome clothes. Caterina struck another medal for the occasion, but the festivities were short-lived. In December 1495, Ottaviano Manfredi, Astorre's cousin and pretender to the rule of Faenza, attacked the little town to wrest it from the child Astorre. Caterina joined forces with Giovanni Bentivoglio to subdue the attack, but the scuffles caught the eye of Venice, which was looking for a foothold in the heart of Romagna. Venice offered itself as "protector" of Faenza, openly interfering in local politics. Soon Faenza appeared to be slipping into the hands of Venice and the future rule of Astorre seemed irreparably compromised. Venice worked tirelessly to oust the town's loyal castellan and replace him with one of their own collaborators. Caterina, recognizing the hostile maneuver, immediately warned the duke of Milan. But Milan's lingering fear of the French gave precedence to the duke's tenuous alliance and he remained silent. In the midst of the overbearing Venetian presence in Faenza and Caterina's own misgivings about Giovanni Bentivoglio's intentions, Bianca's wedding was soon called off.

By 1496 the towns of Romagna realized that they had little protection from the nibbles and scratches inflicted by their larger neighbors. Venice raided Caterina's lands with alarming regularity, stealing livestock and ruining crops. Finding her uncle unwilling to assist her in obtaining justice, she assembled her own standing force of eight thousand soldiers ready to deter the Most Serene Republic. Some of the men were her own citizens looking to defend their homes, while others were soldiers of fortune hoping to make a little money in eternally war-torn Romagna. In 1496 only one other large northern state remained hostile to Venice, and so Caterina turned her attention to her neighbor Florence.

With the expulsion of Piero the Unlucky and his family, Florence had appointed more representatives to the governing body, expanding the popular voice in the republic after years of Medici oligarchy. The driving influence behind this reform was a Dominican friar from Ferrara, Girolamo Savonarola. The forty-four-year-old had gaunt features honed by an ascetic life and dark eyes that blazed from under the black hood of his habit; his dynamic preaching had mesmerized the Florentines. His prophecy that Italy's sinful ways would have dire results had presaged the arrival of Charles VIII of France. Nobles and peasants, old and young, and men and women flocked to his sermons and turned their minds to repentance.

Giovanni and Lorenzo di Pierfrancesco of the cadet branch of the Medicis had also reaped immense profits from Piero's disgrace. They had changed their names from Medici to Popolani, meaning "of the people," shamelessly pandering to anti-Medici sentiment while greedily appropriating Medici villas, jewels, and art. Giovanni "Il Popolano" began frequenting Forlì in the summer of 1496. A wealthy businessman, he went there to hire some of Caterina's well-trained troops for an imminent war with Pisa, which had taken advantage of Charles VIII's departure to declare independence from Florence. However, political observers in the know suspected that his real motive was to lure the countess of Forlì to the side of Florence and France in the latest arrangement of Italian political divisions.

The young Medici was thirty when he first met Caterina. With flowing light brown hair, warm eyes, and aristocratic features, Giovanni paired physical beauty with a splendid education. Many a woman in Florence had already succumbed to the boyish charm of this lover of art, literature, and brilliant conversation. At thirty-three, Caterina was still renowned as a beauty, and at long last, her excellent schooling at the Sforza court found an appreciative admirer in Giovanni Popolano.

As an honored guest, the Medici was lodged inside the official residence at Ravaldino, but before long Caterina offered him rooms in Il Paradiso. In mid-October, Francesco Tranchedini, Ludovico the Moor's eyes and ears in Forlì, warned the duke of Milan that Giovanni was living in the fortress and that he had seen Caterina "caressing him." The envoy concluded that Caterina would be "willing to go so far as to marry him to satisfy her lust."
18

Ostensibly, other business concerns had protracted Giovanni's stay. The winter, a war, and internal disorganization had caught Florence with no stores of food for its people. By contrast, Caterina had reaped a modest harvest in Forlì and had put away huge grain stores to ensure that her people had food throughout the winter. Late in 1496, Giovanni and Caterina officially became business partners. In the spring of 1497, 130,000 bushels of grain were shipped from Forlì to Florence, garnering considerable income for Caterina, food for Florence, and frayed nerves for the duke of Milan.

Duke Ludovico pelted Caterina with endless demands for clarification regarding Giovanni and her position toward Florence, as the rumors increased. Caterina coolly denied any intimate relationship with the Florentine businessman, even going so far as to gently taunt the duke when she was confronted with a recent report that she had tried to obtain permission for the marriage from the king of France. "According to some chatterboxes, I have had any number of husbands," she pointed out before flatly denying a marriage to Giovanni. "I am no longer at that age when others should think that these youthful appetites reign in me; foremost on my mind is my duty to govern these states."
19
Patently untrue, but Caterina had no intention of being tethered by her uncle. To him, she consistently maintained that she was eternally loyal and grateful to Milan, Giovanni was just a welcome guest, and Ottaviano would be willing to accept his
condotta
to fight for Milan at any moment. The duke, no stranger to political deceptions himself, was not completely fooled, but all that the frustrated Ludovico could do was lament that she sold so much grain to Florence.

Meanwhile, within the walls of Il Paradiso, Caterina had finally found a soul mate. No arriviste like Girolamo or stable boy like Feo, Giovanni was her equal. They shared similar interests: Caterina had remained a voracious reader all her life, and with Giovanni she could discuss literature. Like all Florentines, he had a scientific bent and took an interest in Caterina's botanical experiments, assisting her in obtaining the more exotic ingredients. Despite his reservations about the relationship between Caterina and Giovanni, Tranchedini acknowledged in a letter to the duke of Milan that Caterina's household seemed tranquil and her children appeared to get along well with the Florentine. As a member of a ruling family from a greater state, Giovanni would pose no threat to her sons, and at long last Caterina knew peace with a man whom all her children, from Ottaviano to little Bernardino, respected and admired.

Giovanni's arrival also brought considerable economic improvement. With their grain business flourishing, he helped Caterina to get her jewels out of pawn. He brought exquisite Florentine luxury goods to Caterina and her children. She put aside her widow's wear and soon returned to her stylish ensembles. The Forlivesi were well aware of the relationship between Caterina and the young Medici; loose tongues claimed that the countess was "afraid of a cold bed." Unlike previous occasions, she ordered no beatings for rumormongering.

Happy and confident, Caterina began to find the will to look inward again. Busy months had bolstered her strength, and at last, as the first fruits of June ripened in her orchard, she turned to mending her spiritual troubles. She had heard much about Girolamo Savonarola from Giovanni. Caterina's old acquaintance Sandro Botticelli had become one of his followers, known as the
piagnoni,
and had been renewed through repentance. The friar arranged "bonfires of the vanities" in Florence, helping citizens rid themselves of the lures and temptations of the sinful life. Women brought clothes, makeup, and ribbons; artists brought their more erotic drawings; men brought cards and dice; they all looked to start anew on a steady path toward Heaven.

The horrible massacres following Feo's murder weighed heavily on Caterina's conscience, especially now that she had found a greater, richer love than her earlier blind passion. The Holy Year was now only three years away. In 1500 she would be able to travel to Rome to obtain remission for all of her sins by praying at the shrines to Saint Peter and Saint Paul. But the troubled times in Italy and the ever-present specter of death had Caterina concerned about the welfare of her immortal soul. She wrote to Savonarola in the summer of 1496. Her letter has been lost, but the friar's response has been preserved. Savonarola exhorted her, telling to her to pray but also to ensure that others prayed for her as well. Understanding her active character, he also counseled her to do good works and to donate generously to the needy, because "charity extinguishes sins, as water puts out fire. Above all," Savonarola advised, "employ every care and attention to dispense justice to your subjects."
20

Caterina followed the friar's advice and dedicated herself to charitable works in Forlì and Imola, supporting shrines and organizing confraternities. She also took an interest in a Florentine community of nuns known as the Muratte. The convent, founded in 1424, sat at the end of the Via Ghibellina, by the city walls. The convent had enjoyed Medici protection for many years and had been substantially rebuilt by Lorenzo the Magnificent after a fire in 1475 had nearly destroyed the structure. The sisters lived by the rule of Saint Benedict, dedicating their days to manual labor, which they did while reciting constant prayers. Caterina bestowed generous gifts on the sisters. Whenever they in turn sent her sweets or other fruits of their labors, Caterina always thanked them kindly but insisted that they should not worry about acknowledging her donations. Their holy prayers for her soul were recompense enough.

It was also probably the friar's influence that persuaded Caterina to grant pardons to her most hated enemies: the Tartagni family and Giovanni Brocchi. As she sought her own forgiveness, it was her duty to offer the same, as Savonarola certainly would have reminded her.
21

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