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Authors: Miles J. Unger

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Instead of a peaceful interlude in which to prepare his soul for its final journey, Piero’s last days were troubled by dissensions within and the rumblings of war without. In Machiavelli’s account of Piero’s final days, the dying leader brought together his most powerful associates and chided them for their pursuit of selfish ends:

I would never have believed that the time would come when the modes and customs of my friends would make me bitter and desire enemies, and victory make me desire defeat; for I thought I had in my company men who had some limit or measure to their cupidity and for whom it would be enough to live safe and honored in their fatherland and, besides that, to have had revenge on their enemies. But I know now how greatly I have deceived myself as one who knew little of the natural ambition of all men and less yours…. You despoil your neighbor of his goods, you sell justice, you escape civil judgments, you oppress peaceful men and exalt the insolent…. I promise you, by the faith that ought to be given and received by good men, that if you continue to carry on in a mode that makes me repent having won, I too shall carry on in a manner that will make you repent having ill used the victory.

This speech is largely Machiavelli’s invention, but it reflects the very real divisions between the leader of the party and his various lieutenants who took advantage of his debility to pursue their own agendas. The very thoroughness of the victory of the Plain in 1466 had fostered corruption. In the time-honored fashion of Florentine politics, one faction, having swept all opposition before it, used its authority to tax and spend to enrich friends and ruin enemies, thereby consolidating its hold on power. So distraught was Piero over dissension and mismanagement among his associates that he contemplated allowing the return of some of the exiles—particularly Agnolo Acciaiuoli, with whom he was said to have met secretly at his villa in Cafaggiolo—to act as a counterweight to the more arrogant and ambitious members of the
reggimento.

But Piero was ultimately too crippled in mind and body to effect the necessary reforms, and the threat to recall the exiles was too weak a club, and too uncertainly wielded, to frighten those grown fat on the spoils of victory. Adding to his dismay was the fact that dissension within the
reggimento
came at a particularly inopportune moment. Even as Piero tried to rein in his unruly lieutenants, ominous clouds had begun to gather in the ever tempestuous Romagna.

The Romagna, a region bordering Tuscany to the north and east, made up part of the territory under the nominal rule of the leader of the Church known as the Papal States.
*
Here in central Italy the decay of the Holy Roman Empire in the Middle Ages had left a patchwork quilt of petty states and competing jurisdictions; the removal of the papacy to Avignon in the fourteenth century had further eroded centralized authority. But with the restoration of the popes to their traditional capital in Rome at the beginning of the fifteenth century, successive occupants of the throne of St. Peter sought to reassert their authority over vassals accustomed to treating their territories as hereditary possessions. Each successful extension of papal authority, however, threatened the fragile balance of power within Italy, which was predicated in part on depriving Rome of her traditional role as the mistress of Italy. This was particularly problematic for Florence, surrounded as she was by territories claimed by the pope.

The current crisis originated in Rimini, a city on the Adriatic coast some sixty miles east of Florence. The despot of Rimini, Sigismondo Pandolfo Malatesta, had died in October of the previous year, leaving behind him his widow, Isotta, and an illegitimate son, Roberto. In theory the Malatesta ruled Rimini only as the vicars of the Holy Father, but like many of their colleagues they treated the city as their private domain, leading lives of violence and dissipation and virtually ignoring their titular overlord.

Paul II’s predecessor, Pius II, had been so fed up with his vassal’s wayward behavior that he took the unusual step of burning him in effigy and condemning him to the deepest pits of hell: “Until now, no mortal has been solemnly canonized in Hell. Sigismondo will be the first man worthy of this honor. By edict of the Pope, he will be condemned to the infernal city where he will join the damned and other devils. He is hereby condemned, while still alive, to Orcus and eternal fire.”

Following Sigismondo’s death, Paul went in search of a more pliant servant. He found just such a candidate in Isotta, Sigismondo’s widow, and stiffened her resolve by installing at her side a Venetian commissioner. Not surprising, Sigismondo’s bastard son, Roberto, who had inherited his father’s temper if not his title, reacted to this attempt to disinherit him with vehemence. With the secret backing of the duke of Urbino, he raised an army and proceeded to march toward Rimini with the intention of reclaiming his patrimony by force. On October 20 he entered the city and proclaimed himself
signore.

This petty squabble would hardly have been worth notice except for the fact that, as in the Balkans on the eve of the First World War, the slightest tremor in this fractured corner of the globe threatened to drag the regional powers into the maelstrom. The Venetian-born Paul naturally turned to his native city to help him assert his feudal rights, while Naples, Florence, and Milan, wishing to chastise the arrogant Venetians and fearing the pope’s ambition, came in on the side of Roberto Malatesta. (It didn’t hurt Malatesta’s prospects that he was currently employed as a general in the pay of the triple alliance).
*

For Lorenzo, the pressures of war added to the uncertainties of his succession. An already difficult situation was made infinitely more complex when disagreements broke out among the allies over the war’s prosecution and ultimate aims—disagreements that soon split the Florentine
reggimento
into quarreling factions. At a time when Piero needed the government to come together, its leaders were too busy attacking each other to think about rallying behind his chosen successor.

With his mind thus troubled and his body wracked with pain, Piero, like his father before him, had himself carried to his villa at Careggi. Outside his window the bare branches rasped in the chill autumn breeze, and as the nights grew long and bitter, Piero tried to free his mind of earthly cares. Stories of the blessed saints and of the equally stoic philosophers provided more comfort than the potions of doctors. Friends and family kept a constant vigil at his bedside. Here, far from the noise and distractions of the city, he would compose his soul for its final journey, trusting in God, if not his feckless colleagues, to care for his wife and children.

Lorenzo, however, was trusting his fate to powers nearer at hand. Grieved by his father’s suffering and oppressed by the difficulties he faced, he turned to those who had been his family’s most stalwart patrons in times of trouble—the Sforza of Milan.
*
Unfortunately for Lorenzo, now desperately in need of friends abroad, he could no longer count on their automatic support. Differences arising over the prosecution of the Rimini War between Naples and Milan left Florence caught awkwardly in the middle and the Florentine government seriously divided.

In August, allied forces under Federico da Montefeltro and King Ferrante’s son, Alfonso, duke of Calabria, routed the combined armies of Venice and the pope and succeeded in lifting the siege they had placed on Rimini. But no sooner had this victory been won than the divergent aims of the allies became apparent: Galeazzo Maria Sforza, harrassed by his northern neighbor Savoy, hoped to conclude a quick peace with the pope so he could attend to business closer to home; Ferrante, by contrast, wished to use the recent momentum to achieve a more decisive victory, believing that a weakened papacy would permit Neapolitan expansion in the south. Milan needed a strong ally in the
Palazzo della Signoria,
but it was just this kind of forceful leadership that the ailing Medici patriarch was unable to provide. Trying to steer a middle course between the two quarreling parties, Piero managed to displease both. The extent to which Piero’s authority had slipped is revealed by an exchange between the
Signoria
and Luigi Guicciardini, the republic’s ambassador in Milan. Guicciardini was instructed to abandon Milan should the duke persist in pursuing a policy of appeasement, a policy that placed Piero, who wished to maintain amicable ties with the Sforza, in an untenable position. Filippo Sacramoro, the Milanese ambassador to Florence, spoke ominously of secret meetings “of the enemies of Piero and…those who favor Venice.”

The rifts were so pronounced that Agnolo Acciaiuoli, Dietisalvi Neroni, and the rest of the exiles of 1466 seemed ready to pack their bags for a triumphal return to the native land. Neroni in particular was full of grandiose plans, writing to his son that upon Piero’s death the pope should hurry an ambassador to Florence with an offer of peace as soon as they resolved to mend their wicked ways and “to live in a manner in which they would no longer be the cause of every scandal in Italy, and that their citizens would live freely as citizens, and not as despots.”

In October, the Milanese ambassador confided to the duke that he feared the ailing Piero was losing his grip. Given this crisis of confidence in his leadership there was a real danger that Milan would look for a more reliable ally within the city. It was up to Lorenzo to prove to the duke and his ambassador that the Medici could still be counted on,
*
a strategy that required him to distance himself from his father’s policies and to demonstrate that, whatever Piero’s failings, he was still fully behind the Milanese alliance. It must have been painful for Lorenzo to so openly question his father’s judgment, particularly when Piero could do little to defend himself. But the strategy apparently worked, for Sacramoro shortly wrote to the duke predicting that Lorenzo “will show himself to be of a different nature from his father.”

 

By early December it was clear that Piero’s illness had entered its final phase. A flurry of letters back and forth between Florence and Milan records Lorenzo’s anxiety for his own future. Over the course of three days, from December 1 to 4, 1469, Lorenzo wrote three letters to Galeazzo Maria Sforza (the final one signed as well by Giuliano), each one more fawning than the last. “I would like to declare myself as the devoted servant of Your Excellency, and to recall the ancient devotion of our house and myself in particular toward Your Illustrious Lordship,” he wrote on December 1. This reminder of past friendship became all the more urgent the following day when Piero’s health took a sudden turn for the worse: “My Most Illustrious Lord. Yesterday I wrote to Your Excellency of the illness of my father. Subsequently he deteriorated to such an extent that I have little hope for his recovery, and again assure Your Illustrious Lordship that all my hope resides in you, and that I pray you know, as I already said, that my preservation derives from Your Excellency alone, to whom I humbly recommend myself.”

At the same time as he was stroking the vanity of the duke, Lorenzo was trying to shore up domestic support. “[W]hile certain of having here the support of many good friends,” he explained to Galeazzo, “it seems to me it would do little good without the favor and aid of Your Illustrious Lordship.” Fortunately, the Milanese ambassador was now fully behind Lorenzo. “I can report,” wrote Sacramoro to the duke on December 1, “that [Lorenzo] has so arranged and secured his affairs in the city in regard to the leading citizens, that he seems to be squarely in the saddle.”

But was Lorenzo as fully in control of the situation as both he and Sacramoro implied? Despite their bold predictions, the situation was still volatile. Niccolò Roberti, the Ferrarese ambassador to Florence, was far less certain of Lorenzo’s success, predicting that after Piero’s death the old oligarchy would reassert control and that “all business will once again return to the palazzo [Publico].” In truth, the government was split, the normal divisions exacerbated by the lack of a strong leader and by the growing dissension between Florence’s two principal allies over the conduct of the Rimini War. Both Naples and Milan had their adherents in the
reggimento,
while others hoped to overthrow the triple league altogether in favor of a rapprochement with Venice.

Much would depend on Tommaso Soderini, now the most powerful man in the state. Despite Soderini’s long service both to the Medici and in promoting the interests of Milan, Sacramoro distrusted the wily Tommaso, whose relations with the duke had been strained in recent months by the marriage of his son Piero to the daughter of a nobleman who was a rival of the Sforza. Among other things, this marriage into foreign nobility bespoke vaunting ambition; perhaps Soderini hoped through this connection to outshine the Medici themselves. Also troubling was the fact that at the very same time Soderini was protesting his loyalty to the ruling dynasty of Milan he was expressing admiration for their Venetian rivals.

On the morning of December 2, Soderini—who had been following the course of Piero’s illness so closely that he seems to have been as well informed as Lorenzo himself—called for a meeting of 150 of the leading friends of the
reggimento.
Even before they had a chance to assemble in the small hall they had reserved near the butchers’ guild, news reached Soderini that Piero was only hours from death. Given the gravity of the situation Soderini thought it prudent to transfer proceedings to the more commodious convent of Sant’Antonio, conveniently located a few blocks west of the
Palazzo Medici,
so that all those “well respected but of varying views” might attend the extraordinary nighttime meeting.
*

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