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  Niccolò Soderini’s debut on the public stage more than three decades earlier was of a kind to leave an indelible impression on his fellow citizens. It came in 1429 when Soderini, then an obscure young man of twenty-seven, was charged with plotting the murder of Niccolò da Uzzano, one of Florence’s most distinguished citizens and a pillar of the reigning Albizzi regime.† Twenty years earlier, Uzzano had played a prominent role in the prosecution and hanging of Niccolò Soderini’s father, Lorenzo, who had been involved in a scheme to defraud his relatives.* Niccolò, his rage at this affront to the family honor undimmed by the passage of time, had hired a bunch of thugs to murder Uzzano in the street, but after inflicting only minor injuries on their intended victim, the men were captured. Brutally tortured, as was the Florentine custom in such matters, they led the authorities back to Niccolò.

  Niccolò was in danger of meeting the same fate as his father when the Medici stepped in like guardian angels to stay the executioner’s hand. Their intervention had nothing to do with the merits of the case; it was simply a cynical attempt to exploit what had begun as a sordid criminal act for their own ends. The rising Medici faction was then engaged in a life-and-death struggle with the ruling Albizzi regime, and they saw in Niccolò’s trial an opportunity to embarrass their rivals. Spreading rumors that Uzzano had fabricated the evidence against Niccolò, they managed to confuse the issue to such an extent that in the end the Signoria was forced to drop the charges.

  Thus Niccolò and his younger brother Tommaso were recruited to the Medici cause. The decades of Cosimo’s ascendance saw the brothers rise to prominence within the reggimento, but political and financial success did not mellow the prickly Niccolò. When he was not employed in running errands for his Medici patrons or attending to his many business ventures—which, now that he was in the good graces of the masters of the city, tended to prosper as never before—he was often embroiled in legal battles. As early as 1432 Soderini had alienated his own brother, quarreling with him over a division of property, and in 1453 Soderini was involved in another lawsuit with his sister-in-law Alessandra Strozzi to seize control of a farm she had inherited. Even among the normally litigious Florentines, Niccolò Soderini stands out for the number and bitterness of his legal disputes.

  The origins of his disillusionment with the Medici date to 1453 when, as ambassador to Genoa, he managed to interject himself into a local political feud, much to the consternation of Duke Francesco Sforza, who resented the Florentine ambassador stirring up the pot in a city that Milan considered within its sphere of influence. After considerable pressure from the duke, Cosimo agreed to find “some honorable excuse” to bring back his hotheaded emissary. Thereafter, Soderini’s career declined. A series of minor appointments, including ambassadorships to Rimini and Pesaro, suggest that Cosimo no longer trusted him. Niccolò’s conviction grew that he could never prosper as long as the Medici remained in power. During the last years of Cosimo’s life, as popular discontent with the reggimento began to grow, Soderini became a natural focus of the emerging opposition. With his election in October of 1465 as Gonfaloniere di Giustizia, Soderini finally had the opportunity to turn the tables on those he believed responsible for stunting his career.

  There is no doubt that Soderini was a gifted and opportunistic politician. One of his first acts upon being named Gonfaloniere was to reduce the tax on wine, for which, according to a contemporary diarist, “the people called down blessings on his head.” It was during his two-month reign that Parenti was convinced that Piero’s star was on the wane. “Piero di Cosimo, at the beginning of [Soderini’s] term, feared him and went along with his proposals, because never had a Gonfaloniere entered office with such support among the people and with such expectations of the benefits they would receive from him.”

  But while Soderini’s rise had been dramatic, his fall from grace was even more spectacular. As Soderini’s reputation soared, his most ardent supporters—including oligarchs like Agnolo Acciaiuoli, Dietisalvi Neroni, and Luca Pitti, who initially thought that Soderini would be useful in helping to trim Piero’s sails—now feared they might be swept away by the indiscriminate tide. They had no desire to rid themselves of the overbearing Piero only to replace him with the domineering and reckless Soderini. The scope of Soderini’s reforms threatened not only the Medici themselves but all who had risen to prominence on their coattails. Perhaps his most controversial proposal was for a new scrutiny—the periodic canvassing of Florentines to determine those eligible for political office—that was to be more democratic and wide-open than any held in recent times.* By including in the purses many names previously left out, the Gonfaloniere threatened to undercut the power base of the leading families by diluting the dominant position they had built up in the electoral rolls.* The head of the Medici household now shrewdly played on those fears. “Piero,” Nicodemo Tranchedini reported to Francesco Sforza, “has well demonstrated to these others not to go along, because many of them will fall from power.”

  By December 1465, it was clear Soderini had overplayed his hand. Many now took a sharper look at the man they had championed just months before, and Soderini’s shady past could not withstand the renewed attention. Even Parenti admitted that Soderini’s noble goals were sabotaged by questionable business dealings that opened him to charges he was using his position for personal gain. “Niccolò went in boldly, but then he lost heart,” his sister-in-law noted with evident relish, “and his brother [Tommaso] said to Giovanni Bonsi, ‘he went in like a lion and will leave like a lamb,’ and so it happened. As soon as he saw the beans† were not in his favor he began to humble himself, and since he left office he goes around with sometimes five and sometimes six armed men nearby.”

  While Soderini’s fall from grace heartened the Medici and their supporters, Piero, too, had emerged from the contest gravely wounded. The diminished authority of the Eight and the closing of the electoral bags deprived him of the controls that Cosimo had built up over the years. Soderini’s overreaching allowed Piero to recoup some of his lost prestige, but it did not alter the fact that the head of the Medici could no longer have things his way in the Palazzo della Signoria.

  The government of Florence was now effectively shared by more hands than it had been in more than a generation. But far from bringing about reconciliation, the new disposition simply added to the mood of suspicion and fear. It was during the summer and fall of 1465 that the emergence of the two factions of Hill and Plain began to push the city toward civil war as the fluid alliances and rivalries typical of Florentine politics hardened during the battle over the closing of the electoral bags and preparations for a new scrutiny. “[I]n this bill one begins to see the emergence of the dissension among the leaders of the city,” recalled Alamanno Rinuccini, “because Messer Luca Pitti was its author and supporter, and this displeased Piero di Cosimo and his followers.” Since Florentine political theory made no allowance for rival parties—assuming instead that men of goodwill naturally agree on what constitutes the common good—differences of opinion led to bitter recrimination as each side accused the other of sacrificing the interests of the republic for private gain.* The tendency to transform small disagreements into epochal battles was increased by ill-conceived regulations that, in a futile effort to abolish the formation of political parties, banned private gatherings of like-minded citizens, forcing men to meet in secret—an outcome that no doubt contributed to the conspiratorial atmosphere. As Agnolo Acciaiuoli described Florence in a colorful turn of phrase, the city had now become “a paradise inhabited by devils.”

  One unintended consequence of the political reforms was that it led to Lorenzo’s first position of real responsibility in the government. At the age of sixteen he was chosen to sit on the controversial and contentious committee tasked with supervising the new scrutiny.† The following year Lorenzo, substituting for his ailing father, participated in his first major public art commission, serving on the board that chose Andrea del Verrocchio to sculpt Christ
and St. Thomas for the niche belonging to the Mercanzia (the board of trade) in the facade of the church of Orsanmichele.* The two appointments, one political, the other cultural, indicate the accelerated pace at which the teenager was being groomed to take his place at the apex of Florentine society.

  More noteworthy to contemporary observers was the sudden rise of the fabulously wealthy Luca Pitti as the leading opponent to Piero. (While initially supporting Niccolò Soderini’s reforms, he had been among those who had balked at the more extreme proposals of the Gonfaloniere.) His growing stature was signaled by the splendid new residence, designed by the great Brunelleschi, he was now building for himself on the high ground on the south bank of the Arno River. Its massive scale was “greater than any other that had been built by a private citizen until that day.” Unlike the palace on the Via Larga, Pitti’s monument to himself stood in haughty isolation on the highest land within the city walls, more like a princely castle than a merchant’s home.† During the winter of 1465–66, Pitti’s half-completed residence had become the meeting place for those disenchanted with the Medici regime. Marco Parenti’s description of the scene at Pitti’s residence in March of 1466* shows that he had now surpassed his onetime ally as the leading citizen of Florence:

  [Piero’s] reputation was much diminished at this time. And messer Luca Pitti held court at his house, where the greater part of the citizenry went to deliberate on matters concerning the state. Messer Agnolo Acciaiuoli and messer Dietisalvi di Neroni, most prominent among the other citizens, though they were thought superior in prudence to messer Luca, nonetheless allowed him to rise in esteem, and that it might rise even further they too attended him at his house. All this they did to obstruct Piero di Cosimo, to whose house men were once accustomed to go to discuss matters public and private, and to deny him the authority he once possessed, which had now become burdensome to everyone. In this way they had brought him down to such an extent that few, and these few of little prestige, frequented his house, and so thought that in little time they would bring him down completely.

  Luca Pitti’s emergence as the leading exponent of reform must have come as a surprise to any Florentine who had followed his career. Only seven years earlier he had been vilified for the harsh methods he had used to push through legislation that strengthened the controls of the Medici regime. Like most of those now in opposition to Piero, Pitti had been willing to do Cosimo’s bidding, but his pride would not allow him to place himself under the authority of his son. This was a generational as much as an ideological conflict, pitting those who felt that they had earned the right to succession through their long years of loyal service to Cosimo against Cosimo’s natural heirs.

  For all his sudden celebrity, however, Pitti could not command the affection of his followers or inspire trust in his compatriots. His main attribute, embodied in his ostentatious palace, was a vanity ill suited to one who claimed to speak for the rights of the ordinary citizen. Cosimo summed up the difference between the two men during the last years of his life, when the two former allies had begun to grow apart. “You raise your ladder to the heavens,” he observed, “while I rest mine upon earth lest I should mount so high that I may fall. Now it seems to me only just and honest that I should prefer the good name and honor of my house to you: that I should work for my own interest rather than for yours. So you and I will act like two big dogs who, when they meet, smell one another and then, because they both have teeth, go their ways.”

  Now in his seventies, with hollow cheeks and the sharp profile of a bird of prey, Pitti had been one of Cosimo’s most effective lieutenants, though, according to Guicciardini, he prospered in Medici Florence only because “he had not sufficient brains that Cosimo need fear him.” In the summer of 1458, when the government was besieged by reformers who wished to abolish the electoral controls that ensured the dominance of the regime, it was Pitti, then serving his two-month term as Gonfaloniere di Giustizia, who led the pro-Medici reaction. At the time, according to Parenti, he was “a man entirely devoted to Cosimo.”

  Since Cosimo’s death, however, Pitti had been angling for the top position in the reggimento, and those electoral controls that had appeared to him so necessary only a few years back were viewed in a different light now that they favored Piero at Pitti’s expense. Pitti’s leadership of the anti-Medici faction was confirmed in May when his signature appeared prominently atop an oath signed by four hundred of his fellow citizens pledging to work toward democratic reforms. One of its stated goals was to ensure that “[a]ll the affairs of the commune should be conducted in the Palace of the Priors,” an attack directed at the sickly Piero, who, even more than his father, was accustomed to doing the government’s business in his private chambers.*

  Both Neroni and Acciaiuoli were content to let Pitti serve as the public face of the rebellion precisely because, as Guicciardini noted, he posed no long-term threat to their own ambitions: “Thinking that Messer Luca Pitti, with his strong following, would be a useful instrument, they entered into negotiations and convinced him that they would make him head of the city—though they are said to have agreed among themselves that as soon as they had deposed Piero they would also get rid of Messer Luca. That much, they thought, would be easy, since he was not a very capable man.” Marco Parenti, who knew him well, shared their low opinion of Pitti, judging both Acciaiuoli and Neroni “superior in prudence.”

  Agnolo Acciaiuoli, like the other leaders of the Hill, was driven to oppose Piero out of motives that were at least as much personal as ideological. At one time Cosimo had counted him among his closest friends. Their affection was based on a mutual passion for classical literature and philosophy that they had both discovered while young men attending learned discussions in the garden of Santa Maria degli Angeli conducted by the great humanist scholar Ambrogio Traversari. Acciaiuoli’s attachment to Cosimo was genuine and cost him dearly when the Albizzi government banished them both in 1433. Having demonstrated his loyalty in this most trying time, Acciaiuoli soon reaped his reward. The following year he returned to Florence in triumph with Cosimo, quickly rising to a place of prominence within the highest circles of the regime.

  For all his skill and erudition, there seems to have been a streak of naïveté in Acciaiuoli that allowed his passions to overrule his better judgment. This naïveté was compounded by the fact that over the years he spent much of his time abroad on important missions for the government, and was therefore ill equipped to engage in the sort of intrigues that were a perpetual feature of Florentine political life. “Now Agnolo had been absent from Florence for a long time,” Vespesiano da Bisticci explained, and “he did not realize the treachery of the democracy of the city so, being strongly importuned, he cast in his lot with Messer Luca.”

  But Acciaiuoli was not just the dupe of shrewder and more violent men; he had his own reasons for wishing to rid the city of the Medici. Vespesiano da Bisticci traces his estrangement from his old friend to Cosimo’s attempts to block the appointment of Agnolo’s son Lorenzo as archbishop of Pisa in order that he might promote his own kinsman, Filippo de’ Medici, for the job. Though Lorenzo was given as consolation the less prestigious bishopric of Arezzo, Agnolo resented Cosimo’s behind-the-scenes maneuvering.

  It was a second betrayal, however, that turned the friends into bitter enemies. When the young Alessandra de’ Bardi wed Acciaiuoli’s son Raffaello, she brought with her the prestige of the ancient Bardi name (Cosimo himself was married to Contessina de’ Bardi) as well as a substantial dowry. Marriages between leading merchant families carried important political and financial ramifications, and though love rarely entered into the equation, this marriage proved more than usually unhappy. Shortly after the wedding Alessandra began complaining to her relatives of abuse at the hands of Raffaello. The complaints grew so persistent that the Bardi dispatched a band of armed men, who showed up at the Acciaiuoli palace in the dead of night to rescue the long-suffering bride. Agnolo, if not Raffaello, might have reconciled h
imself to the loss of the Bardi girl, but to return the dowry would entail not only financial loss but would constitute a permanent stain on the family escutcheon. Cosimo, whether out of a sense of fair play or out of political calculation, ultimately intervened in favor of the Bardi. Agnolo, already less than pleased by Cosimo’s neglect of his family’s interests, saw this as an unforgivable breach of friendship, and from that moment he worked to take his revenge against the family that had wronged him.

  Though all the leaders of the Hill were motivated in part by personal grievances, it would be a mistake to dismiss the revolt as simply the work of a few disgruntled men driven by greed and ambition. Whatever motivated the break, they had tapped into a genuine current of discontent. Few would deny that Cosimo had led the city wisely, but even his loyal supporters acknowledged that his unprecedented power had come at the expense of the traditional prerogatives of the Florentine upper classes. To concede the same authority to his son would be to admit that republican government had been replaced by dynastic rule. With Cosimo in the grave, Piero laid low by illness, and Lorenzo not yet grown, the traditional ruling class saw this moment as perhaps the final opportunity to reclaim its ancient status.

  Among those now frequenting Luca Pitti’s doorstep was Niccolò Soderini. From the moment his government left office—to the accompaniment of celebratory bonfires in the Piazza della Signoria and graffiti on the Palazzo declaring “Nine fools out”—Soderini redoubled his efforts to bring about a change of regime, his hatred for Piero sharpened by the Medici’s behind-the-scenes role in his recent disgrace. To accomplish his goal he would need to mend fences with his former allies. Soderini’s task was made considerably easier by the fact that since his disastrous tenure as Gonfaloniere Piero had once again emerged as the chief threat to their collective ambitions. Sometime between December of 1465 and May of 1466, Soderini and the other dissidents ironed out past differences and forged an alliance powerful enough to bring about Piero’s downfall.