For many years I have walked the streets of Italian cities like Florence and Venice. I don’t mean as a tourist—I’ve been there as a historian who felt the need to imagine the settings of the bloodiest conspiracies (mostly enacted inside of churches or in crowded piazzas), involving the Medici family, gutsy popes, and self-promoting condottieri with a passion for book collecting. Lately, I have been thrown back in those same settings when playing the New York Times 2009 Best Videogame, Assassin’s Creed II, which recreates with eerie accuracy the architectural beauties of Renaissance Italy. I keep wondering: why are these cities (or city-states) so attractive for so many people, from high-brow to pop culture? Is it the unique combination of art and violence, refinement and brutality, civic awareness and political unrest?

Early modern Italy is considered by many scholars to be the cradle of modern Western political thought and the birthplace of civic freedom. In the 1960s and 70s, Hans Baron, a historian of German-Jewish descent who moved to the United States, came to wield a strong influence on the ways in which Italian history was understood. In his book The Crisis of the Early Italian Renaissance: Civic Humanism and Republican Liberty in an Age of Classicism and Tyranny he argued that Florence was a beacon of Western freedom, whereas Milan, ruled by the tyrannical Visconti family, was an ultimately perverse power. In the heated post-World War II debate and in the wake of its ideological trauma, Baron had unconsciously traced back the battle between the Allied forces against the Axis powers led by the Nazis. While his provocative view had a deep impact on early modern studies, its historical accuracy was far from being incontrovertible—and it has been vigorously questioned in the last fifty years. However, the commonplace of Florence as a beacon of freedom has been much harder to dispel, as are its implications for Western liberal-democratic culture in general.

Italy during the Renaissance was not a united nation but a patchwork of city-states. Each city-state was controlled, with varying degrees of tyranny and liberty, by one dynasty: the Visconti and then the Sforza in Milan, the Medici in Florence, the Aragon in Naples; Venice was an oligarchy ruled by rich merchant and noble families, and of course there was Rome, under the eternal but ever-changing aegis of the popes and their family clans.

De facto rulers of the Renaissance had a hard time justifying their power de jure. Might and right clashed bloodily in these times of great patronage of art and culture. These leaders’ tough and rough attempts at self-legitimacy were not very different from any of those enacted even today by some worldwide statesmen trying to legitimize their position using all the legal and illegal tools at their disposal.

Ethical and theoretical issues on legitimacy were fearlessly raised by Niccolò Machiavelli in works such as The Prince and The Discourses, whose views are only superficially at odds. The rise of civic culture as expressed in the Italian medieval “Comune” and later in the Renaissance “Signoria,” as well as the symbolic construction of authority by local warlords, kings and popes, are at the root of our contemporary idea of polis or body politic. We can still learn a lot from the challenges faced by these early modern city-states, and how they relate to modern republics.

In his Discourses on Livy, Machiavelli drew parallels between the early Roman Republic and the Florentine Republic. He was fully aware that Florence’s pretensions to empire over other Tuscan cities were ably disguised as a fight for freedom against tyranny. The art of political propaganda was perfected, if not invented, by Renaissance humanists who in their political roles as chancellors of republics and secretaries of princes composed elaborate praises of their cities. Leonardo Bruni’s Laudatio of Florence and the brilliant response to it, Pier Candido Decembrio’s Panegyricus of Milan, are great examples of this fortunate genre that opened the floodgates of civic and nationalistic rhetoric. Before them, the arguments between Florentine humanist Coluccio Salutati, whose pen the Duke of Milan feared more than cavalry, and Milanese chancellor Antonio Loschi still echo debates about world hegemony and supremacy. Loschi opened his punchy Invective Against Florentines (1401) by saying, “We will see—and how will we see—your so boastful constancy and Roman tenacity in defending your most hateful liberty, or rather your most cruel tyranny. You are used to showing off this name and to declaring yourselves to everyone descendants of the Romans.”

In all these fiercely opinionated clashes, ancient Rome remained the model of the perfect city that rose to universal preeminence. At first, the revolt against unjust rulers and the healthy struggle between the patricians and the plebeians created a long-lasting and successful alliance based on military virtue and civic honesty. Then the slow erosion of the city’s founding principles brought about a looming autocracy. Richard Sennett, in his masterful sociological study Flesh and Stone: The Body and the City in Western Civilization, captured the moment when the Roman Republic was reduced to an empty pantomime:

When Julius Caesar moved the old Rostra to a new site in the Forum Romanum, from the side in to the northwest end, he meant this new speaker’s stand to be a place for ceremonial declaration rather than participatory politics. The speaker no longer spoke surrounded by people on three sides; instead, he was placed like a judge within the earliest basilicas. Outside, his voice now projected poorly, but no matter. The orator was meant to appear, to point a finger, to clutch his breast, to spread out his arms: he was to look like a statesman to the vast throng who could not hear him, and who had lost the power to act on his words in any event.

Caesar’s unnamed polemical target was his arch-enemy Cicero, whose oratorical skills and institutional shrewdness had saved the Republic from the mad ambitions of Catiline, the bloodthirsty plotter who had been driven from Rome. Catiline then was stationed in nearby Tuscany where he tried to raise an army of desperados threatening to raze the city, before being annihilated by a punitive expedition. Catiline’s failure, however, opened a wound that would drain the lifeblood from the Roman Republic.

“The discontented shade of Catiline, dressed in the consular toga, haunts Florentine history,” remarked Mary McCarthy in The Stones of Florence Observed, picturing the rebel’s restless soul wandering eternally on the Tuscan hills. Renaissance conspirators explicitly modeled themselves on Catiline. When Girolamo Olgiati, one of the three killers of the Duke of Milan in 1476, proudly confessed to his deed, he claimed to have rid the city of a tyrant, quoting lines from Sallust’s Catiline’s War.

The subsequent attack on the Medici brothers on April 26, 1478, was meant to look like liberation from unfair oppression. After the furious slaying of Giuliano de’ Medici in the Duomo, and the failed stabbing of Lorenzo, the plot’s ringleader Jacopo de’ Pazzi rode into Piazza della Signoria at the head of hired mercenaries shouting, “Hail to the people!” and “Freedom!” But the people took up their weapons and cried “Palle, Palle!” (Balls, Balls!, a reference to the Medici coat of arms) and “Arme, arme!” (To arms! To arms!) The staircases of the Palazzo della Signoria soon became a battleground. The Medici party triumphed and slaughtered the self-appointed liberators.

Machiavelli associated the love of liberty in small republics with “the public buildings, the halls of the magistracy, and the insignia of free institutions.” The tone of this statement was admittedly nostalgic by the middle of the fourteenth century. These appeals to republican symbols sounded all the more outdated and hollow with the irresistible rise and the ambivalent role of the Medici, who eventually turned the republican city into their own fiefdom. Cosimo the Elder gained for posterity the honorable title “Father of Fatherland”—a title that he shared with Cicero, on whom it had been conferred just a few years before the empire of Caesar took over. Famous patron of the arts, Cosimo threw his weight around and gradually gained control of the electoral and administrative system. The Florentine participatory model was based on the Roman Republic’s frequent selections of short-term positions, and was devised over a couple of centuries to prevent the devastating effects of a long history of factional struggles. Dante had famously been one of the victims of these factions and ended up being exiled from Florence for the last twenty five years of his life—for his readers’ enjoyment, he never lacked fodder for invectives against the city and its corrupt citizens.

Slowly but surely, Cosimo turned a majority of the citizenry into Medici clients. But Cosimo’s political stroke of genius was his stealthy and staunch support of condottiere Francesco Sforza, who had married an illegitimate daughter of the last duke of Milan, Filippo Maria of the dreaded Visconti family. Filippo was the epitome of the paranoid tyrant who terrorizes his population and the neighboring countries. For decades he lived barricaded inside of his heavily fortified castle on the outskirts of Milan. When Filippo died in 1447, the Milanese rose in spontaneous rebellion, established the Ambrosian Republic, and destroyed the hated stronghold that was the Visconti castle, symbol of their subjugation. Soon they were squabbling among themselves over the control of the magistracies, but most worryingly they were surrounded by the Venetians, who smelled the Milanese weakness and thought they could easily seize the wealthy city and its fertile plain. So the republican government called on Francesco Sforza to defend them against the immediate threat. Francesco readily obliged but eventually turned against them: aiming to become the city’s next leader, he blockaded its gates and literally starved Milan into surrendering to him, while keeping the Venetians at bay. By early 1450, he entered triumphantly, unarmed, as a liberator from internal dissidence and external threat, while his soldiers distributed breadbaskets. Throughout this cunningly staged pageant, which Machiavelli could not help but grudgingly admire, Francesco received steady financial support from Cosimo de’ Medici. The investment paid back, with huge returns.

As the husband of the former duke’s daughter, Sforza achieved his ambition and was hailed the new Duke of Milan. Francesco offered military protection to his longtime friend Cosimo, using his significant military might to repress or prevent internal rebellions. And after some shrewd political maneuvering, Francesco struck the Peace of Lodi (1454), starting in earnest the golden age of the Italian Renaissance. The solid alliance between Milan and the Medici lent an axis of relative stability to the restless Italian peninsula and enhanced patronage of the arts and letters, leading to an explosion of artistic creativity and humanistic culture.

The other side of the idealized, high-minded Renaissance public life was the rise of strong, ruthless individuals. The first chapter of Jacob Burckhardt’s Civilization of the Renaissance in Italy (1860) is aptly titled “The State as a Work of Art.” City-state chanceries developed sophisticated bureaucracies and diplomatic networks, issuing resident ambassadors who would dispatch coded and highly detailed reports. Three of the modern state’s founding characteristics were now at work: effective policy-handling, systematic information-gathering and impenetrable secrecy-holding.

But the aspect that Burckhardt emphasized like no historian before him was the invention of individualism. The highly competitive environment of Italian politics led to an implosion of the earlier status quo. From quiet medieval subject, the Renaissance individual left faith and pursued ambition—striving for self-reliance and personal success. This mix of ruthlessness and creativity released untamable new energies. The Italian city turned out to be the cradle of the Renaissance man, embodied by multi-talented individuals like Leon Battista Alberti, who served as a model for Leonardo da Vinci’s “universal man,” as Anthony Grafton shows in his biography of Alberti, Master Builder of the Italian Renaissance.

Alberti traveled from court to court, gracing each prince or republic he visited with his literary wit and engineering talent. He was involved in the creation of “ideal cities” such as Pienza, humanist Pope Pius II’s native village in the Val d’Orcia, which he transformed into a perfect architectural jewel. And condottiere Federico da Montefeltro, a worthy colleague of Francesco Sforza who had equally managed to gain the coveted title of Duke, built with Alberti’s likely supervision a fairy-tale palazzo in Urbino. Such small-scale experiments were successful, but not long-lasting politically; once their patrons died, these ideal cities sooner or later lost their magnetic or military power and were swallowed by bigger and stronger city-states.

I left the reader with the picture of the bloodshed in Piazza della Signoria in the aftermath of the Pazzi conspiracy. The collapse of a republican government, which soon lapsed into autocracy, was symbolized by that battle in the Palazzo della Signoria. Most of the anti-Medici plotters were hanged from the upper windows of the palace. To eternalize their shame, Botticelli drew sketches of the corpses left dangling and reproduced them in life-size frescoes, so that anybody passing by the Piazza could not miss the sinister sight. Botticelli’s frescoes angered Pope Sixtus IV, who was the mastermind of the attack in the Duomo, and who requested—as sensitive as ever to visual propaganda—that the portraits of the clergy members who had been caught in the act of subverting the Florentine government be removed at once.

A war of words ensued, with an excommunication of the city of Florence and a counter-excommunication in the fiery, sacrilegious Florentine Synodus, a supposed meeting where all the Tuscan bishops had gathered and attacked the pope as an arch-assassin, “Vicar of the Devil,” and “Pimp of the Church.” After two years of war, the interdict was still having dire effects on Florentine commerce. Lorenzo de’ Medici knew he had to extend a formal apology to the pontiff in order to obtain a repeal. Twelve Florentine ambassadors from the most notable families were finally dispatched to Rome. They were received on December 3, 1480. They justified their “Christian” disobedience by describing it as political self-defense, reminding the pope that they had been desecrated and violated in their own cathedral and government palace.

Sixtus IV did not respond straightaway to the apologetic oration delivered by the chief envoy. He retired into his chambers until the next day, when he summoned the delegation and delivered a wordy reply: “Which kind of patriotism are you invoking? What does it mean to be fighting for your fatherland?” he asked, adding that one should respect the law and honor religion. It is in this context that he formulated what is known as the most eloquent definition of liberty up to that time: “What greater servitude could there be, o sons of mine, than to have no one in Florence able to say, ‘This is good,’ ‘I want this,’ ‘I like this,’ ‘This suits me’?” In other words, the pope was deriding the propensity of Florentines to embrace relativistic judgments of value: their rejection of the absolute moral rules embodied by the Church made them less, not more free. The attack on the individualistic opportunism here masked fittingly the pope’s own will to power.

Rome itself, after the rise and fall of the empire, became the centerpiece of the popes’ domination (except for a displacement of the papal court to Avignon throughout the fourteenth century). Some attempts to restore the republican rule failed miserably. Distinguished citizens brought about short-lived revolutions and pathetic plots: Cola di Rienzo (1347) was ambivalently celebrated by Petrarch in his poem “Spirto gentil” as well as Stefano Porcari (1453), who claimed to be Cola’s poetic heir and whom Machiavelli sarcastically portrayed as a lofty idiot, though he deemed the Church not strong enough to control Italy and not weak enough to be eradicated.

For a few centuries thereafter, the Eternal City kept aggrandizing itself with immortal monuments, and governing a small state in central-northern Italy. The Church’s ecumenical reach aimed at extending its spiritual realm into the whole Catholic world, while gobbling up in the process other cities like Bologna, the medieval high towers-laden town, or Ferrara, the birthplace of epic poets such as Matteo Maria Boiardo, Ludovico Ariosto, and Torquato Tasso, who inspired themselves with Arthurian and Carolingian legends to celebrate the Este, a shiny dynasty of patrons of art. These cities fell under the control of more or less despotic cardinal-legates and lost their independence along with their creativity.

One great exception was Venice, whose bustling mercantile activities were accompanied by ambitious military enterprises. The most successful oligarchic city-state, thanks to her maritime empire, Venice outlasted all her peers. Her final capitulation was signed by none other than General Bonaparte, a Corsican who claimed to have Florentine origins, in 1797. By then, the age of city-states had been long replaced by national warmongering, although the dynamics and the rhetoric of power did not change altogether. Freedom and propaganda are inextricably entangled. Freedom fatally contains its tyrannical counterpart: fighting the neighbor outside of the city often implies a restriction of liberty within the city.

Renaissance Italian cities, fraught with violent contradictions, are still a microcosm worth studying to gauge the limits of contemporary politics. Their spirit lives through the art and architecture of the cities, even if their landmarks are now reduced to meccas of mass tourism.