By the winter of 1465–66, Florence was a city divided and all signs indicated that a violent confrontation was imminent. Both Hill and Plain were hurriedly organizing militias in the countryside around Florence and urging foreign powers to intervene on their behalf as soon as the fighting broke out.* These preparations generated their own momentum as an escalation on one side was met by an equal or greater response by the other. Each faction could plausibly claim, and probably sincerely believed, that in calling their partisans to arms they were merely responding to the provocations of their opponents.
The mood of the city was not improved by a disastrous January flood that left the entire quarter of Santa Croce under six feet of water or by the lingering effects of the economic downturn that had begun in the months following Cosimo’s death. In February of 1466, in an atmosphere of growing crisis, Lorenzo set out on another vital diplomatic mission, this time to meet with the two great leaders of southern Italy—the pope and the king of Naples. Piero’s willingness to be without Lorenzo at this critical juncture is one more indication of the decisive role that foreign powers were expected to play in the looming political contest. Marco Parenti reported to Filippo Strozzi in Naples, “everyone knows that Florence has turned towards Venice,” citing “a secret agreement among Luca Pitti, Agnolo Acciaiuoli, and Dietisalvi Neroni…intended to counter Piero de’ Medici.”
Under the circumstances it was important to bring on board or at least neutralize the two southern powers, neither of whom had firmly committed to either side. In each case the Medici had cause for concern. The current pope, Paul II, was Venetian-born and was inclined to favor his hometown as long as its interests did not clash with those of the Holy See. His suspicions of Florence had been aroused when it signed the tripartite treaty with Milan and Naples, which he believed, not without reason, was aimed in part at containing papal ambitions in central Italy. As for Naples, Ferrante had proven himself an unreliable and unpredictable ally. His treacherous murder the year before of the mercenary captain Iacopo Piccinino, Francesco Sforza’s son-in-law, had thrown the whole structure of alliances into doubt.* An additional cause of concern was that Ferrante’s finances were largely in the hands of the Acciaiuoli family, which had ancient ties to the southern realm. Agnolo’s son, Jacopo, had long enjoyed the confidence of the king, a position he was now using to undermine his Florentine rivals.
The gravity of the mission can be gauged by the company Lorenzo kept, which included not only his tutor, Gentile Becchi, who could be expected to keep his young charge focused, but the battle-tested condottiere Roberto Malatesta. Absent were the boisterous companions who so often accompanied Lorenzo on his voyages. Among those left behind was Luigi Pulci, who complained, “So you intend, finally, to leave me in these snow-bound woods, alone and unhappy, while you go to Rome. When shall I join you? when I am old?…How many times have we thought of Rome, and how I should be at your side.”
Another purpose of this southern journey was to round out Lorenzo’s education as a budding merchant prince and statesman. While the trip to Milan had taken him to the source of Medici political power, the Roman journey brought him to the heart of his family’s business empire. Since the days of Giovanni di Bicci, Lorenzo’s great-grandfather, the Medici bank’s most lucrative business had been managing the finances of the papal curia. Nurturing good relations with whoever occupied the throne of St. Peter was thus of vital importance to maintaining a sound fiscal footing. While in Rome, the most pressing task for Lorenzo was to obtain the pope’s signature on a contract naming the Medici bank sole distributors of alum from the papal mines at Tolfa, a deal Piero hoped would pump much needed cash into the Medici coffers.* Pope Paul had agreed in principle to hand over the concession in return for a portion of the proceeds, and Lorenzo was entrusted with finalizing the terms. Paul II’s willingness to expand his already substantial financial arrangements with the Medici bank was welcomed not only for the profits it would generate but as a public affirmation of his continued confidence. With the pope himself consigning his treasure to the Medici bank, who would not feel reassured doing business under the sign of the palle?
Lorenzo and his entourage arrived in the ancient capital at the beginning of March, taking up residence at the Medici headquarters just across the Tiber from the Castel Sant’ Angelo, where his uncle, the corpulent, sour-faced Giovanni Tornabuoni, served as host and guide to the mysteries of the Roman branch.† Under his uncle’s tutelage Lorenzo could study the intricacies of double-entry bookkeeping and delve into the libro segreto, the secret accounts, where the real assets and liabilities of the bank were set down out of sight of the prying eyes of the tax inspectors.* Such a tour was long past due. Business was a neglected aspect of Lorenzo’s education that required immediate remedial attention. Both Cosimo and Piero had been bankers first and politicians second, but Lorenzo, by contrast, seemed to have more talent in spending than in making money. Dipping into his purse to put on lavish entertainments for the cardinals and nobility of Rome, he demonstrated that he had learned the alchemical trick of transmuting gold florins into political capital, but where those florins came from or how to turn one into two or ten into twenty were subjects in which he had shown little interest or aptitude.
Among other things, Giovanni explained that while profits from the Roman branch were vast dealing with constantly changing popes and a venal College of Cardinals brought with it peculiar difficulties.† Tornabuoni was a cautious man and the risks inherent in doing business with the profligate and dishonest men of the papal curia caused him no end of worry. Money and power, rather than prayer and charity, were the twin pillars propping up the Renaissance version of Christ’s holy edifice; the College of Cardinals and the less than saintly men who sat on St. Peter’s throne were acquainted from firsthand experience with the seven deadly sins. A savvy banker could exploit such weakness, but he could also be bankrupted by accepting unsecured pledges from men whose spiritual authority inoculated them against the obligation of most mortals to repay their debts.
Paul II, by no means the worst of his breed, was particularly susceptible to the blandishments of those with ready cash since he was a man less noted for his piety than for his love of jewelry, objets d’art, and fine clothes. His friendliness toward the Medici, as Lorenzo’s uncle pointed out, was directly proportional to his financial need. One benefit the Medici discovered of doing business on the pope’s behalf was that it allowed them to threaten excommunication against those who failed to pay their bills, a spiritual weapon any modern collection agency would be glad to have. “Pope Paul’s head is empty,” wrote an anonymous poet after the pope had himself crowned with a tiara ostentatious enough to throw the papal finances into immediate disarray. “It is then right that it be loaded with jewels and gold.”
On his journey to Rome, Lorenzo had a chance to observe the corrupt heart of the Renaissance church in all its sordid splendor, and the unsavory impression it left only grew over the years. In a famous letter he wrote late in life to his son Giovanni (who had just taken up residence in Rome as a newly minted cardinal), Lorenzo referred to the capital of Christendom as “that sink of all iniquities.” Other aspects of life in the ancient imperial capital he found more to his taste. As Pulci’s letter suggests, the Eternal City loomed large in the collective imagination of Lorenzo and his circle, as it did for all who drew inspiration from the classical past. While contemporary Romans showed little interest in their own history, turning ancient buildings into rubble to be burned in their lime kilns, it furnished more constructive material to the humanists of Florence. Ever since Brunelleschi and Donatello had come here more than a generation earlier to sketch and measure the Forum, the Colosseum, and the Pantheon, Rome had been a site of pilgrimage for those passionate, as Lorenzo surely was, about the vanished classical civilization.
The Eternal City offered a spectacle at once melancholy and sublime. Its greatness was hinted at in the massive, crumbling monuments that still rose above the sheep pa
stures and orchards that over the centuries had encroached upon the neighborhoods of the ancient city. As great as it once had been, in its ruined state it seemed to offer a profound message about the transience of worldly glory. “You may turn all the pages of history,” wrote Lorenzo’s compatriot the humanist Poggio Bracciolini, “but you will find that fortune offers no more striking example of her own mutability than the city of Rome, the most beautiful and magnificent of all those that either have been or shall be…. How much the more marvelous to relate and bitter to behold, how the cruelty of fortune has so transformed its appearance and shape, that, stripped of all beauty, it now lies prostrate like a giant corpse, decayed and everywhere eaten away.”
It was a brief encounter with a young girl, however, that would ultimately have a more serious impact on the course of Lorenzo’s life. He left no account of his meeting with Clarice Orsini, the thirteen-year-old niece of the formidable Cardinal Latino Orsini, but, as his mother later confirmed, his first glimpse of his future bride was sufficient to leave, if not an indelible memory, at least pleasant associations.
Lorenzo, in fact, was unlikely to have had more than passing thoughts of this tall, redheaded girl. True, she belonged to one of the most ancient and influential families in Rome, but her shyness and modesty, perfectly appropriate to her age and situation, would not have captured the imagination or excited the passions of a worldly young man. That he should have remembered her at all two years hence suggests a mild attraction, if nothing else.
In any case more urgent issues soon claimed his attention. Lorenzo’s mission was made more difficult by news, arriving ominously on the Ides of March, that instantly transformed the calculus of Florentine politics and sent shockwaves along the length and breadth of the peninsula. It was on the anniversary of Caesar’s murder that Lorenzo learned of the sudden death of Duke Francesco Sforza, an event that at the best of times would have tested the Medici’s strength. In the current troubled atmosphere, the duke’s demise deepened the sense of impending crisis by depriving the Medici of their most reliable protector and threatening to throw into disarray the system of alliances that Cosimo had built and that had kept Italy relatively peaceful for the past decade.*
“I am in such affliction and sorrow for the sad and untimely death of the Illustrious Duke of Milan that I know not where I am,” Piero wrote to Lorenzo upon hearing the news. (The situation was made worse by the fact that at the time of his death the duke’s heir, Galeazzo Maria, was earning his spurs as an aide in the armies of the king of France. On his return journey he was forced to travel through the hostile territory of Savoy in disguise and arrived in his native city only on March 20). Evidently shaken, Piero urged Lorenzo to meet with the pope once more, to impress upon him the need for statesmanship in these perilous hours and to remind him once again of the devotion of the Medici family. Knowing his son’s inclinations, he also reminded him to “put an end to all playing on instruments, or singing or dancing,” adding “be old beyond your years, for the times require it.” He even contemplated bringing Lorenzo back to Florence to help combat the growing civic unrest. Ultimately, however, he decided that Lorenzo should proceed to Naples in the hope of bringing the king on board and countering the harmful influence of the Acciaiuoli.
Lorenzo left Rome on April 8, arriving four days later in Nola, where the king interrupted his hunting trip to receive him. Gentile Becchi’s report on the meeting was ecstatic. He informed Piero that with all gathered in the room “the King took Lorenzo by the arm and, alone with the Secretary, exited into the antechamber. There I think that Lorenzo satisfactorily discharged your commission to him, spending with His Majesty more than a half hour.” Lorenzo was equally pleased with his reception, telling his father, “I spoke with him, and he replied with many kind words, which I wait to tell you in person.” Even Jacopo Acciaiuoli, who thought his performance awkward at best, was forced to admit that the king had shown him much kindness.* According to Ferrante, his kind reception of Lorenzo was due to “love which we bear towards his Magnificence, your father, to you, and to your house which merits even greater demonstrations,” adding, in words that may have irked the proud adolescent, the paternal advice that he should “strive to follow the example of the revered Magnificent Cosimo and of your father.”
Important testimony on the diplomatic maneuverings in the southern kingdom comes from Sacramoro da Rimini, Milan’s new ambassador to Naples (he was soon to hold a similar position in Florence), who assured Lorenzo that, despite the “crowing” of their opponents, the king was “well-disposed towards his state and opposed to those who are the enemies of your magnificent father,” adding, significantly, that “here you will be received with the same favor as in Milan itself.” As on his earlier trip to Milan, by the time Lorenzo departed from his hosts he had convinced them to stand behind the Medici in the upcoming contest. Ferrante’s tacit support, if not his active involvement, was a welcome boost to Florence’s ruling family, now more than ever in need of powerful friends.
By the end of April, Lorenzo was back in Tuscany. But before returning to Florence he made one final stop in Arezzo, an important client city some twenty miles to the south, where he was honored with a magnificent reception hosted by the city elders. Of all the stops on his journey, it was this one that would pay the most immediate practical dividends. Luca Pitti had long-standing ties to Arezzo, but Lorenzo was able to win the backing of leading citizens so that during the height of the crisis, in late August, the government of Arezzo pledged one hundred troops to the Medici cause.
Passing through the Porta Romana on May 6, Lorenzo and his companions found Florence on the brink of civil war. Two days earlier the Signoria had tried to head off a violent confrontation by demanding that all members of the ruling class twenty years and older sign an oath forswearing violence. The oath also banned all private political associations, a commitment broken so often and so openly that it served merely to demonstrate the impotence of the elected officials. Strong anti-Medici sentiment in the government was confirmed the following week by the defeat of a bill to deliver a promised loan of 60,000 florins to Bianca Maria, widow of Francesco Sforza, a rejection that mortified Piero, who had hoped to demonstrate his loyalty to the ruling house of Milan.
As tensions rose throughout the summer, Lorenzo was called upon to rally the Medici forces. In the countryside around Careggi and in the hills of the Mugello he met with local leaders loyal to the Medici and drilled their militias, while Piero sought to overawe his opponents by inviting infantry and cavalry under the banner of Milan to march to the very borders of Tuscany. Thankfully for the Medici, while Galeazzo Maria got his bearings, the day-to-day running of the government of Milan lay in the hands of Bianca and her capable minister Cicco Simonetta, who made it clear that the powerful Milanese army—even without the promised 60,000 florins—would come to the aid of their friends in Florence.
While Piero met with his supporters behind closed doors, Lorenzo was out among the people. He was, if not yet an equal partner with his father, someone to whom Medici partisans could look for guidance and inspiration. There was no doubt that Lorenzo could now play the part. He had returned to Florence more confident than when he had left it, having proven to himself and those around him that he could hold his own in the world of high-stakes diplomacy. In the space of a year he had held discussions with some of the most powerful men of the age, including a pope, two dukes, a king, and a doge, effectively representing both his country and his family.
Thus when, after a long, tense summer, Dietisalvi Neroni and his fellow conspirators sprang the trap while the family was vacationing at Careggi, Lorenzo was no longer a callow youth more interested in frivolous pleasures than in taking up his responsibilities as the future leader of Florence. But if it was clear to Medici partisans how important Lorenzo had become to the regime, his transformation had largely escaped the notice of their opponents. Perhaps on the morning of August 27, 1466, his reputation for immaturity actually worke
d in his favor because, despite ample evidence of the central role he had come to play, the leaders of the Hill apparently made no provision for his capture, allowing him to warn his father of the ambush that awaited at Sant’Antonio del Vescovo and to return to Florence, where he could launch the Medici counterattack.
Filippo Brunelleschi and Bartolomeo Ammanati, Palazzo Pitti (Garden View), early 15th and late 16th centuries (Art Resource)
VI. GAMES OF FORTUNE
“I am laughing at the games of fortune and at how it makes friends become enemies and enemies become friends as it suits it.”
—AGNOLO ACCIAIUOLI IN NAPLES TO PIERO DE’ MEDICI IN FLORENCE
“Your laughing over there is the cause that I do not weep, because if you were laughing in Florence, I would be weeping in Naples.”
—PIERO DE’ MEDICI IN FLORENCE TO AGNOLO ACCIAIUOLI IN NAPLES
AROUND MIDDAY ON AUGUST 27, 1466, WHILE LORENZO was completing his perilous journey from Careggi to the city, the leaders of the Hill gathered in Luca Pitti’s half-completed palazzo on the slopes of San Giorgio, just south of the Ponte Vecchio. Here, amid the sounds of hammering and the clattering of masons’ carts, Pitti, along with Agnolo Acciaiuoli and Dietisalvi Neroni, anxiously awaited word of Piero’s capture.
In fact, though they did not yet know it, Piero and his men had already slipped through the net. Warned by the horseman sent back by Lorenzo of the trap awaiting him at Sant’Antonio del Vescovo, they had turned off the main road and were somewhere unseen and unheard among the back country lanes. As minutes lengthened to hours with still no word, tensions rose in the cavernous rooms. The bid by leaders of the Hill to seize power had been predicated largely on the assumption that Piero was weak and incapable—a “vile rabbit” Agnolo Acciaiuoli had called him, a man unwilling or unable to take decisive action—but failure to seize the Medici patriarch would turn what was meant to be a swift and decisive coup into a long, drawn-out struggle for which they had not adequately planned.
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