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Portrait of Piero de' Medici by Agnolo Bronzino.

Piero de' Medici, called the Unfortunate (February 15, 1471 – December 28, 1503) was lord of Florence from 1492 until his death.

Born in Florence, he was the oldest son of Lorenzo de' Medici (the Magnificent) and Clarice Orsini. He was also an older brother of Pope Leo X.

He was educated to succeed his father as lord of Florence, under notable figures like Angelo Poliziano. However, his feeble, arrogant and undisciplined character was to prove unsuited to such a role.

Shortly after he took over as leader of Florence in 1492, Charles VIII of France entered Italy in 1494 with a large army, in part on his way to Naples to assert his claim to the throne there, but also to support Ludovico Sforza, il Moro, ex-Regent of Milan, who wished to eject his nephew Gian Galeazzo Sforza and replace him as Duke, and had lured Charles to Italy to help him in this endeavor.

After settling matters in Milan, Charles moved towards Naples, and needed both to pass through Tuscany, as well as leave troops there to secure his lines of communication with Milan. Piero attempted to stay neutral, but this was unacceptable to Charles, who invaded Tuscany. Piero attempted a resistance, but did not receive much support from Florence, which was suffering from the influence of Girolamo Savonarola; even his cousins defected to Charles.

Piero therefore quickly gave up as Charles' army neared Florence, giving Charles everything he demanded, without making any attempt to negotiate better terms. The resultant fury in Florence led to the Medici family fleeing, after which the family palazzo was looted, the substance as well as the form of the Republic of Florence was re-established, and the family were formally exiled, to wander through the states of Italy and Europe.

Some years later, in 1503, as the French and Spanish continued their struggle in Italy over the Kingdom of Naples, Piero was drowned in the Garigliano River, while attempting to flee the aftermath of the battle which the French (with whom he was allied) had lost.

Piero married Alfonsina Orsini in 1488. She was a daughter of Roberto Orsini, Count of Tagliacozzo and Caterina Sanseverino. They had two children:

• Lorenzo II, Duke of Urbino (September 12, 1492 - May 4, 1519).
• Clarice de' Medici (1493 - May 3, 1528). She married Filippo Strozzi the Younger (1488 - 1538).