FLORENCE – 2014 has barely dawned, and I’m standing in a cold, rainy evening at the Piazza della Signoria in Florence, staring at the round plaque on the floor – ignored by the throngs of Chinese tourists – celebrating the hanging and burning of the monk Savonarola in May 23, 1498, accused of conspiring against the Florentine Republic.

Yet I’m thinking – how could I not – of Machiavelli. He was only 29 on that fateful day. He was standing only a few feet away from where I am. What was he thinking?

He had seen how Savonarola, a popular Dominican preacher, had been hailed as the savior of the republic. Savonarola rewrote the constitution to empower the lower middle class; talk about a risky (populist) move. He allied Florence with France. But he had no counterpunch when the pro-Spanish pope Alexander VI imposed harsh economic sanctions that badly hurt Florence’s merchant class (a centuries-old anticipation of US sanctions on Iranian bazaaris).

Savonarola had also conducted the original bonfire of the vanities, whose flaming pyramid included wigs, pots of rouge, perfumes, books with poems by Ovid, Boccaccio and Petrarch, busts and paintings of “profane” subjects (even – horror of horrors – some by Botticelli), lutes, violas, flutes, sculptures of naked women, figures of Greek gods and on top of it all, a hideous effigy of Satan.

In the end, Florentines were fed up with Savonarola’s hardcore puritan antics – and a murky papal Inquisition sentence sealed the deal. I could picture Machiavelli exhibiting his famous wry smile – as the bonfire had burned exactly one year before at the very same place where Savonarola was now in flames. The verdict: realpolitik had no place for a “democracy” directed by God. God, for that matter, didn’t even care. It was only human nature that is able to condition which way the wind blows; towards freedom or towards servitude.

So this is what happened in that day at the Piazza della Signoria in 1498 – in the same year Lorenzo the Magnificent died and Christopher Columbus crossed the Atlantic on his third voyage to “discover” the New World; no less than the birth of Western political theory in the mind of young Niccolo.

Study humanity, young man

Florence is the first modern state in the world, as Jacob Burckhardt makes it clear in his magisterial The Civilization of the Renaissance in Italy, in awe about “the wondrous Florentine spirit, at once keenly critical and artistically creative.”

Florentines spent a long time weaving the proud, patriotic tradition of a self-governing republic; a very Aristotelian set up according to which “the end of the state is not mere life, it is rather a good quality of life.” Very cooperative, with everyone involved, completely different from Plato’s Republic, whose rules were imposed from above.

At the dawn of the 15th century, Aristotle-reading Florentines eager to celebrate their civic and political freedom were busy on their way to carve – alongside their fabulous traditions of pictorial realism and fondness for classical architecture – no less than what became known as the Renaissance.

Why did Florence invent the Renaissance? Vasari’s answer was as good as any: “The air of Florence making minds naturally free, and not content with mediocrity.” It helped that education focused on the studia humanitatis – the “study of humanity” (on the way to oblivion now in the early 21st century), featuring history (to understand the greatness of ancient Greece and Rome); rhetoric; Greek and Roman literature (to improve eloquence); and moral philosophy, which boiled down to Aristotle’s Ethics.

Machiavelli, born in 1469, the same year young Lorenzo de’ Medici, or Lorenzo the Magnificent, his grandfather Cosimo’s favorite, ascended to power after the death of his father Piero, lived for the most part in a Florence under the Medici. So he understood the nature of the (rigged) game; as crack historian Francesco Guicciardini put it, Lorenzo was a “benevolent tyrant in a constitutional republic.”

Machiavelli’s family was not wealthy – but totally committed to the ideal of civic humanism. Unlike Lorenzo, he may not have received the finest humanist education available, but Machiavelli studied Latin and read ancient philosophers and especially historians – Thucydides, Plutarch, Tacitus, and Livius, whose works were found in Florence’s bookshops. In the ancient Greek and Roman heroes he saw examples of great virtue, courage and wisdom; what a sorry contrast with the corruption and stupidity of his contemporaries (we could say the same thing half a millennium later).

While Machiavelli was an Aristotelian, Lorenzo was somewhat a Platonist. Yet it was Cosimo’s protege, the philosopher Marsilio Ficino, the coordinator of the Platonic Academy, who best explained it; Lorenzo did not believe in Plato, he used him. And on top of it he knew how to show off – as in installing Donatello’s spectacularly ambisexual David on its pedestal in the cortile of the Palazzo Medici, and avidly promoting the leading philosopher among his circle of friends, the dashing Pico della Mirandola, known as the “man who knew everything” – or at least the entire range of human knowledge available in the Renaissance since the fall of Constantinople in 1453.

And then, only one month after Savonarola’s burning, the slender, beady black-eyed and black-haired man with a small head and aquiline nose, described by his biographer Pasquale Villari as “a very acute observer with a sharp mind” got a job; and for 14 years he was a loyal servant of the restored Florentine republic, always on horseback on sensitive missions, negotiating, among others, with pope Julius II, the king of France Louis XII, the Holy Roman Emperor Maximilian I, and the unpredictable, larger than life Cesare Borgia, the illegitimate second son of the man who would become pope Alexander VI. Machiavelli was in charge of Florence’s foreign policy; definitely not your usual Beltway think-tank armchair “expert.”

While Machiavelli was hanging out with Cesare Borgia, he became friends with Borgia’s chief military engineer, none other than Leonardo da Vinci. One would need a Dante to imagine the dialogue between the man crafting the new science of politics and the most accomplished scientific mind of the Renaissance; the bifurcation of the humanist spirit, from art, poetry and philosophy into reality – politics and science.

A satire or a living book?

As I sat down in my favorite enoteca in front of the Pitti palace to reread The Prince, I also delved on other sources; there has been a deluge of books on Machiavelli celebrating the 500th anniversary of the writing of The Prince, which was concluded after roughly four months in late 1513. The best happened to be Il sorriso di Niccolo (Editori Laterza), by Princeton’s Maurizio Viroli. Viroli established for good that Machiavelli was never a Medici puppet.

Before he became secretary of the Second Chancery, in June 1498, Machiavelli was admittedly very close to Lorenzo the Magnificent. Soon after the Medicis returned to power in Venice after a period of exile, he had to endure the strappado – the Florentine torture of hands tied behind the back, body lifted to the ceiling by rope and pulley, and dropped straight down – no less than six times (is the CIA aware of it?). Yet he didn’t become a rat: he was left to rot; and after 22 days was set free from his cell at the Bargello tower in early 1513 by the intervention of two Medici supporters.

In the final years of his life, Machiavelli was under various guises at the service of pope Clemente VII, none other than Giulio de Giuliano de Medici. But the bottom line is that Machiavelli was not a Medici follower; he wanted above all for the Medici to follow his advice.

So he left jail, impoverished but not broken, retreated to his small farmhouse, and set out to write. The Prince came out as history – not political theory. Rousseau actually branded it a “satire.” Gramsci called it “a living book” – a celebration of a utopian Prince “via so many passionate, mythical elements that come alive in the conclusion, in the invocation of a really existing prince.” So Machiavelli in fact designed the myth of the founder and the redeemer of a free republic – imagining that the redemption of the state would be at the same time his own redemption after he was stripped of his job of secretary by a laconic communique and later accused of being a conspirator.

It has been a blessing to re-read The Prince alongside The Discourses – which, in time, became the intellectual and political guide of all who cherished the ideal of republican freedom in Europe and the Americas. The Discourses is Machiavelli’s fusion of Polybius and Aristotle. The Romans had found out that a great empire was doomed if it did not keep Aristotle’s balance of monarchy, aristocracy and democracy. Machiavelli went one step ahead; every real republic is actually doomed. In a free republic like in Ancient Greece and Rome, or Florence before the Medici, too much prosperity, success, greed – and overextension – distorts men’s drive towards self-enrichment (or dissolves it into complacency) rather than keep it at the service of the state.

The real rot comes from within – not from an external power. Think of the late Soviet Union. Think of the current decline of the American Empire. But then again, mediocre exceptionalists never got the picture; Leo Strauss, at the University of Chicago in the 1950s, taught that Machiavelli was “a teacher of evil.”

As the rot from within grows, that’s where the Prince steps in. He’s like the Last Man Standing – very far from the idealized figure of a philosopher-king or a Platonic teacher. He’s the ruler who pulls a corrupt society out of its devious, self-destructive ways and hurls it back towards sound political life – and preeminence. (Machiavelli was specifically thinking of someone to save Italy from foreign invaders and its own deaf, blind and dumb rulers).

And if the Prince must resort to violence to defend the republic, it must never be gratuitous, but always subordinated to a well-argued ragion di stato (the 2003 bombing and occupation of Iraq obviously does not qualify). The Prince anyway is not a political messiah; rather a mix of the fox (“in order to recognize traps”) and the lion (“to frighten off wolves”). The most apt contemporary version would be Vladimir Putin.

In that fateful day in May 1498, Machiavelli saw in Savonarola’s burning how religious fundamentalism is incompatible with a successfully commercial and politically viable society (House of Saud princes never read The Prince). And then he displayed to us the wall of mistrust between ethics and the science of government – as if drawing an abridged road map for the future global hegemony of Western civilization.

It’s curioser and curioser how the Medici dynasty rejected The Prince at the time; after all, that was the ultimate handbook on how to become a (political) Godfather, in the post-Renaissance and beyond. In parallel, I always wondered what wise Ming dynasty courtiers would have made of The Prince. Probably, imperially, ignore it.

So this is how I celebrated the half-a-millennium anniversary of The Prince; sharing a few glasses of Brunello, as if we were in a Florentine osteria in the early 16th century, with the spirit of a very distinguished senior civil servant of the Florentine Republic who was thrown out of office exactly as he was admitted; poor, incorruptible and with his dignity intact. I could not but admire his wry smile dying in his lips and barely hiding his pain – but then again, he knew we’re nothing but playing a small part in this whole human, all too human, comedy.