By William Landon, Northern Kentucky University
There was hope that with Lorenzo de’ Medici having made his peace with God, his eldest son, Piero de’ Medici, would recognize the potential that would mean for the Medici in an increasingly hostile Florence. Their hopes were drowned in the rough seas of Piero’s pride and reckless impetuousness. Piero de’ Medici has come to be known as Piero ‘the Unfortunate’.

Piero, ‘the Unfortunate’
The title was given to Piero in the 16th century by Florentines sympathetic to the Medici. Piero, such Florentines believed, ought not to be blamed for his poor judgment in the lead-up to the collapse of the Medici regime. Rather, he was the victim of circumstances beyond his control.
The biting Florentine sense of humor, on the other hand, especially when wielded by a republican, could also refer to Piero as ‘the Unfortunate’, but with a wry cynicism. When we peel away these later descriptions of Piero—who immediately assumed his father’s position after Lorenzo’s death—we find a young man of only 21 who had been raised with all of the accouterments of wealth and familial finery.

He had been given an excellent humanist education, and he took after his father by being a lover of poetry, literature, and platonic philosophy. Like his father, grandfather, and great grandfather, Piero was also a collector of manuscripts and books. The starkest point of contrast between Piero and his recent ancestors was that while he possessed the trappings of wealth, he no longer had access to liquid capital.
The Medici Bank Lacked Funds and Piero de Medici Lacked Talent
Lorenzo de Medici had not personally managed the family bank, leaving it in the control of individuals who mismanaged it. By the time Piero inherited the bank, it was bordering on bankruptcy.
He could not use personal wealth to coax bickering nobles into agreements, and perhaps more importantly, he was unable to distract the populace of Florence with public spectacles as his father had done. He simply could not afford to fund horse races, feasts, or carnival parades.
More disastrously, Piero did not possess his father’s uncanny ability to read people and predict their actions—talents that allowed Lorenzo to manage the ever-bickering factions in Florence’s aristocracy and in its government more widely. Where Lorenzo would spend hours in thoughtful contemplation, analyzing the possible outcomes of his actions, Piero was spontaneous.
At other times in Florentine history, spontaneity was essential, but in the aftermath of Lorenzo’s death, prudence and patience were necessary. Piero had neither. We might be tempted to blame his youth for these situational defects, but Lorenzo had faced many crises while still a very young man. And we cannot suggest that Piero was inexperienced. His father had made certain that Piero was involved in Medici and Florentine political activities since his early teens.
This article comes directly from content in the video series How the Medici Shaped the Renaissance. Watch it now, on Wondrium.
Family Squabbles Led to Political Ones
Piero was young, but he was thoroughly known by Italy’s powerhouses. Perhaps the ease with which he slid into his father’s role at Florence—a transition that had been agreed upon before Lorenzo’s passing—lulled him into a false sense of security.
Plus, with Lorenzo gone, Piero’s mother and his wife—both members of the Orsini family—pushed him to prioritize Florence’s relationship with Naples. This is exactly what Piero did—with immediate and horrible consequences. The balance of power between Milan, Naples, Florence, and Rome that Lorenzo had so artfully constructed broke down within weeks.
The peace that Lorenzo had authored was washed away in a flood of bloody war. By the following summer—1493—the regent of Milan, Ludovico Sforza had begun plotting to take the Dukedom of Milan from his nephew, Gian Galeazzo Sforza.
Gian Galeazzo had been only seven years old when his father, Galeazzo Maria, was assassinated in 1476. Ludovico Sforza—his uncle—became the regent of Milan and remained regent as Piero de’ Medici began to shift Florence’s balanced alliance between Milan and Naples firmly in the Neapolitan direction.
Enter King Charles VIII

As the Milanese and the Venetians had done on numerous occasions in the 1480s, Ludovico Sforza made yet another overture to the French, hoping they could be convinced to shore up Milan militarily while making their way to Naples to reclaim its throne. While the previous kings of France had been cautious and relatively moderate, the new French king, Charles VIII, was young and spontaneous—just like Piero de’ Medici.
In fact, King Charles VIII of France and Piero de’ Medici were alike in many ways. But, when we widen our view and consider the power at each man’s disposal, we are forced to conclude that the Medici, while powerful among the other families and dukedoms in Italy, were almost insignificant compared with the monarch of a united nation-state.
Charles could field tens of thousands of his own well-trained men. He had horse and cannon and siege engines—all of which could be mobilized swiftly. And, if he decided to heed Ludovico Sforza’s call for assistance, he and his armies could cross the Alps and wash over Italy within a matter of weeks. The world had changed.
Common Questions about Piero de’ Medici’s Problems
From the point of view of those who were sympathetic to the Medici family, Piero de’ Medici gained control of the family in unfortunate circumstances which got worse since it was out of his hands. On the other hand, a biting sense of humor can also be sensed in the nickname when it was used by a republican.
Lorenzo de’ Medici had not managed the Medici bank himself. He had left it in the control of different individuals and by the time Piero needed money, the bank was on the brink of bankruptcy.
As people in charge, both Piero de Medici and King Charles VIII made spontaneous decisions and were not as careful as their predecessors. The difference lay in the power that they possessed. Charles VIII was the monarch of a nation-state that had various military capabilities compared to Piero de’ Medici was only in control of a city-state.