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  By most measures the Medici were ill prepared for the coming contest. Piero’s poor health had thrust Lorenzo into a position of responsibility at an age when his companions were still completing their studies or were apprenticed in the family business. He had already served as his father’s envoy on crucial diplomatic missions, including the wedding of a king’s son and an audience with the newly elected pope. A few weeks earlier he had returned from a trip abroad to introduce himself to Ferrante, King of Naples, “with whom I spoke,” he wrote his father, “and who offered me many fine compliments, which I wait to tell you in person.” The importance for the Medici of such contacts with the great lords of Europe is suggested by Piero’s hunger for news of the meeting. Lorenzo’s tutor and traveling companion, Gentile Becchi, wrote an enthusiastic report of Lorenzo’s performance before the king. Referring to this account, Piero confessed, “Three times I read this for my happiness and pleasure.” Consorting with royalty provided this family of bankers much-needed prestige, though such social climbing if too vigorously pursued could also arouse the jealousy of their peers who believed that they were thus being left behind.*

  The looming crisis would demand of Lorenzo a set of skills different from those he had recently practiced in the courts of great lords. The retiring Piero needed Lorenzo to act as the public face of the regime, the charismatic center of an otherwise colorless bureaucracy. As preparations were made for the coming battle, it was often to Lorenzo, rather than the ailing Piero, that men turned to pledge their loyalty. Marco Parenti, a cloth merchant of moderate means whose memoirs provide an eyewitness account of the events of these months, tells how the countryside was armed in the days leading up to the August crisis. “Thus it was arranged,” he wrote,

  that there were 2000 Bolognese horsemen loyal to the duke of Milan. These were secretly ordered to be held in readiness for Piero; the Serristori, lords with a great following in the Val d’Arno, arranged with Lorenzo, son of Piero, a great fishing expedition on the Arno and many great feasts where were gathered peasants and their leaders, who, wishing to show themselves faithful servants of Piero, met amongst themselves and pledged themselves to Lorenzo. These pledges were accepted with much show as if it had not already been planned, though many were kept in the dark, to send them a few days hence in arms to Florence in support of Piero. And so it was arranged in other places, with other peasants and men who, when called on, would quickly appear in arms.

  The fact that those bending their knees were often rude peasants and their lord a banker’s son gives to the proceedings a distinctly Florentine flavor, but it is clear that Lorenzo had already begun to take on some of the trappings of a feudal prince.

  Lorenzo’s prominence, however, was actually a sign of weakness in the Medici camp. Florentines regarded youth as an unfortunate condition, believing that these giovanni—a term attached to all young men, including those in their twenties who had yet to assume the steadying yoke of marriage—were, like the entire female sex, essentially irrational and in thrall to their baser instincts. So far Lorenzo had given little indication that he was any better than his peers, having acquired a well-earned reputation for fast living. For the leaders of the Hill a trial of strength now, when the father was crippled and his heir not yet mature, was to their advantage. Jacopo Acciaiuoli, son of Agnolo, who had attended the meeting of King Ferrante and Lorenzo, reported to his father, “And returning to the arrival of Lorenzo, many fathers spend to get their sons known who would do better to spend so that they were not known.” Beneath the spiteful jab there is a more substantive message—that neither the ailing father nor his awkward son would put up much of a fight. The next few days would put this judgment to the test.

  Indeed there was nothing in the biography of either Piero or Lorenzo to strike fear in an opponent. “[Piero] did not, to be sure, possess the wisdom and virtues of his father,” commented the historian Francesco Guicciardini (1483–1540), usually a fair judge of men, “but he was a good-natured and very clement man.” A kind heart, however, was not necessarily an advantage in the cutthroat world of Florentine politics; in the centuries of bloody strife that marred the history of the City of the Baptist, men of saintly disposition were notable by their absence.

  Despite the rising tension, August 27 dawned in an atmosphere of deceptive calm. Elections for the new Signoria were scheduled for the following day, and Florentine citizens, the great majority of whom wished only to go about their daily lives undisturbed by the quarrels of their masters, were cautiously optimistic that the leaders of the opposing factions had pulled back from the precipice. Only the day before, Piero and his family had left Florence for their villa at Careggi, something he would never have contemplated had he believed a confrontation imminent. In a crisis anyone who found himself outside city walls could quickly be marginalized. It was just such a blunder that, thirty years earlier, almost cost Cosimo his life. Taking advantage of his temporary absence from the city, the government, led at the time by the Albizzi family, decided to move against their too-powerful rival. Upon returning to Florence, Cosimo had been arrested, threatened with execution, and ultimately sent into exile. The lesson could hardly have been lost on his son that leaving the city at a time of strife was a recipe for disaster.

  Curiously, it was Dietisalvi Neroni, one of the leaders of the Hill, who had persuaded the Medici leader to take this vacation, promising that he, too, would retire to his villa, thus lessening the chances of a violent clash breaking out between their armed supporters. It was an apparently statesmanlike gesture that would allow the democratic process to go forward without interference.

  Piero’s agreement suggests a misplaced confidence that the situation was moving in his direction, and there were in fact indications that the fortunes of the Medici party, which had reached a low ebb in the winter, were on the rebound. But the decisive factor may simply have been the poor state of his health; a few days earlier a flare-up of gout had confined him to his bed, making it almost impossible to conduct any serious business. Thus when Neroni held out an olive branch, Piero was only too happy grasp it.

  Piero had failed to take the measure of Neroni, whose powers of dissimulation were apparently so highly developed that he was able to maintain cordial relations with the man whose destruction he plotted. Piero, not necessarily an astute judge of men at the best of times and now distracted by the pain in his joints, allowed himself to be taken in by Neroni’s conciliatory gestures. “[I]n order to better conceal his intent,” explains Machiavelli, “[Neroni] visited Piero often, reasoned with him about the unity of the city, and advised him.” Though Piero was aware that his onetime colleague had at least flirted with the opposition, Neroni was able to convince him that he was a man of goodwill who could act as a moderating influence on his fellow reformers.

  Machiavelli portrays Neroni as an unprincipled schemer who set out to destroy his old friend in order to further his own career, but with him, as with all the leaders of the revolt of 1466, it is difficult to disentangle motives of self-interest from genuine idealism. Neroni does seem to have possessed some republican instincts, though it is uncertain if these were born of principle or sprang from a practical calculation that he could rise further as a champion of the people than as a Medici lackey. As Gonfaloniere di Giustizia (the Standard-Bearer of Justice, the head of state) in 1454 he was already an advocate of democratic reform, winning, according to one contemporary source “great goodwill among the people.” And in 1465 he had written to the duke of Milan that “the citizenry would like greater liberty and a broader government, as is customary in republican cities like ours.”

  For the most part, however, Neroni prospered as a loyal servant of the Medici regime. It is unclear when ideological differences combined with frustrated ambition to turn him against his former allies, but as early as 1463 the ambassador from Milan reported to his boss that “Cosimo and his men have no greater or more ambitious enemy than Dietisalvi [Neroni].” In spite of these warnings, at the time of
Cosimo’s death in 1464 Neroni was still one of Piero’s closest advisors.

  Neroni’s first line of attack, recounts Machiavelli, was to engineer Piero’s financial collapse. He describes how Piero had turned to Neroni for advice following Cosimo’s death, but “[s]ince his own ambition was more compelling to him than his love for Piero or the old benefits received from Cosimo,” Neroni encouraged Piero to pursue policies “under which his ruin was hidden.” These policies included calling in many of the loans granted by Cosimo—often on easy terms and made for political rather than financial reasons—a move that caused a string of bankruptcies and added to the growing list of Piero’s enemies.

  Despite his rival’s best efforts, however, Piero weathered the financial crisis, and by 1466 Neroni was growing impatient with half-measures. Guicciardini gives to Neroni the decisive role in the attempted coup: “[It was] caused in large part by the ambition of messer Dietisalvi di Nerone…. He was very astute, very rich, and highly esteemed; but not content with the great status and reputation he enjoyed, he got together with messer Agnolo Acciaiuoli, also a man of great authority, and planned to depose Piero di Cosimo.”

  While Piero and his family headed to Careggi, Neroni and his confederates prepared to seize the government by force.

  For generations, Careggi, with its fields and quiet country lanes, had served the Medici household as a refuge from the cares of the city. Cosimo had purchased for the philosopher Marsilio Ficino a modest farm close by at Montevecchio so that his friend would have the leisure to complete his life’s work, the translation of Plato from Greek to Latin. “Yesterday I went to my estate at Careggi,” Cosimo once wrote to Ficino, “but for the sake of cultivating my mind and not the estate. Come to us, Marsilio, as soon as possible. Bring with you Plato’s book on The Highest Good.…I want nothing more wholeheartedly than to know which way leads most surely to happiness.” Lorenzo, too, enjoyed the philosopher’s company, and later in life would convene at Careggi those informal gatherings of scholars and poets that historians dignified with the somewhat misleading label “the Platonic Academy,” finding the country air a suitable stimulus to deep thought.

  Today, however, the villa at Careggi could provide no escape from the troubles of the city. The family had barely begun to settle in when the peace of the morning was shattered by the arrival of a horseman at the gates.* The messenger, his horse lathered from hours of hard riding, his clothes and skin blackened with dust, announced that he had come from Giovanni Bentivoglio, lord of Bologna, with an urgent message for the master of the house.

  The messenger’s point of origin was sufficient to set off alarm bells. The ancient university town of Bologna was strategically placed near the passes through the Apennines to keep a watchful eye on anyone coming from the tumultuous Romagna; from here, an army descending on Tuscany from the north would easily be spotted. Bentivoglio was but one of many trusted allies of the Medici scattered throughout Italy and beyond who kept their eyes and ears open for any scrap of information that might be useful to their friends in Florence.

  This morning’s letter brought news that Bentivoglio’s spies in the village of Fiumalbo had observed eight hundred cavalry and infantry under the banner of Borso d’Este, Duke of Modena and Marquis of Ferrara, setting out in the direction of Florence. To the startled Piero, their objective was clear—to join with the Medici’s enemies in the city and topple them from power.

  Though Bentivoglio’s message has not survived, its contents are summarized by a letter written that same day by Nicodemo Tranchedini, the Milanese ambassador to Florence. In it he informs his master, Galeazzo Maria Sforza, Duke of Milan, that Piero had “received letters from the regime in Bologna, from D. Johane Bentivogli,” and that soldiers of the marquis of Ferrara were “already on the move to come here on the invitation of Piero’s enemies, with horse and riders of Bartholomeo Colione.”

  For months the leaders of the Hill had been in close communication with Borso d’Este, a northern Italian lord whose schemes for self-aggrandizement were predicated on a change of government in Florence. In November 1465, the Milanese ambassador had reported to his employer that Borso’s agent, Messer Jacopo Trotti, “every day meets M. Luca, M. Angelo [Agnolo Acciaiuoli] and M. Dietisalvi [Neroni].” Given the fact that Piero was kept well informed of these machinations by Tranchedini, it is remarkable that he allowed himself to be lured from the city at this critical time.

  If the motives of the Florentine rebels were a mixture of idealism and self-interest, those of Borso d’Este were unambiguous. Described by Pope Pius II in his memoirs as a “man of fine physique and more than average height with beautiful hair and a pleasing countenance,” Borso d’Este was also “eloquent and garrulous and listened to himself talking as if he pleased himself more than his hearers.” In his inflated self-regard he was little different from any number of petty princes who sold their military services to the highest bidder, nor did his taste for costly jewelry, his arrogance, and deceitfulness—other qualities noted by Pius—set him apart from his peers.

  Technically a vassal of the pope, Borso was always looking for ways to expand his family’s territories at the expense of his neighbors. An important step in his campaign was the removal of the Medici, who were closely linked with his chief rival in the north, the powerful Sforza family of Milan. In June his representative in Florence had contacted Luca Pitti to suggest that “Piero be removed from the city.” It took almost two months of negotiation, but by late August the leaders of the Hill had decided to team up with the mercenary adventurer, inviting “the marquis of Ferrara [to] come with his troops toward the city and, when Piero was dead, to come armed in the piazza and make the Signoria establish a state in accordance with their will.”

  Piero had grossly underestimated his enemies’ resolve, but he now moved swiftly to correct the situation. First he dashed off an urgent letter to Sforza, asking him to send his troops, some 1,500 of whom were stationed in Imola in Romagna, about fifty miles to the north, to intercept those of d’Este. Desperately seeking friends closer to home, Piero dictated a second letter to the leaders of the neighboring town of Arezzo, pleading that “upon receiving this you send me as many armed men as you can…and direct them here to me.”

  Even more important was the task of mobilizing the pro-Medici forces within the city. Foreign armies could throw their considerable weight behind one faction or another, but victory and defeat would be determined largely inside the city walls. Here the rebels had a great advantage. Piero, in so much pain from gout that he could travel only by litter, would not arrive back in the city for hours, time the rebels could use to prepare the battlefield and set the terms of the engagement.

  So it was that Lorenzo found himself this August morning hurrying back to Florence, accompanied only by a few companions as young and inexperienced as himself. It was Lorenzo’s mission to ride out ahead of the main party and to raise the Medici banner in Florence, ensuring as well that the gates remained in friendly hands long enough to permit Piero’s safe return. As the head of the household made his slow, painful way to Florence, the fate of the Medici regime would rest in the hands of a seventeen-year-old boy.

  From the moment he left the fortified compound of Careggi, Lorenzo was on his guard. The countryside through which he passed was as familiar to him as the streets near the family palace in the city, the rolling hills and game-filled copses, destination of many a hunting expedition, a constant source of delight. Today, however, the landscape he loved felt menacing. Every low stone wall and ramshackle farmhouse provided a place of concealment, every patch of shade an opportunity for ambush.

  Nothing disturbed the heavy air as the horsemen picked their way cautiously down the winding road. Tiny lizards darted through the underbrush, while hawks circled high overhead. Having completed most of the journey without incident, and with the walls of the city looming before him, Lorenzo brought his small group to a halt. Ahead lay a tiny hamlet known as Sant’Antonio (or Sant’Ambrogio) de
l Vescovo. Little more than a few buildings shimmering in the summer heat, there was nothing ominous in the rustic scene. But Lorenzo had reason to be wary. The village took its name from the archbishop (vescovo) of Florence, whose summer residence was attached to a small chapel there. The reigning archbishop of Florence was Giovanni Neroni, Dietisalvi’s brother. (His sacerdotal office could have provided little comfort: a bishop’s robes in Renaissance Italy were more often the costume of a political intriguer with a dagger in his belt than those of an unworldly man of God.) With Neroni’s recent treachery in mind, Lorenzo knew that to pass through the hamlet, his usual route from the villa to the city, he would have to place himself squarely in the lion’s den.

  It was at this moment Lorenzo signaled to one of his party to remain some distance behind while he and the rest of his companions spurred their horses into motion and continued along the road to Florence. As the riders passed between the first of the buildings, armed men rushed out from behind walls and doorways, surrounding the riders, the points of their halberds glinting menacingly in the sun. Horses reared as Lorenzo and his companions unsheathed their swords. In the shadows men cocked crossbows. In the commotion apparently no one noticed the lone figure who turned his horse around and sped back along the road in the direction they had come.

  The ambush at Sant’Antonio del Vescovo remains one of the more mysterious episodes in the annals of Florentine history. It is a puzzle that must be assembled from bits and pieces, the missing portions filled in with sound conjecture, since no contemporary report gives more than a brief, tantalizing mention. The most detailed account is that of Niccolò Valori, who included it in his biography of Lorenzo, written some thirty years later. But even this narrative raises as many questions as it answers: