A Great & Wretched City: Promise and Failure in Machiavelli's Florentine Political Thoughtby Mark JurdjevicHarvard University Press, 2014 Readers who know the Renaissance writer and political operative Niccolo Machiavelli mainly through his standout treatise The Prince - and that's most readers - will be accustomed to associating him with that most singular form of government, the monarchy headed by one powerful individual with the machinery of the state and the police at his disposition. But like most Florentines (the most politics-passionate people of the Renaissance - or perhaps of all time), Machiavelli held that there were three good governmental models: in addition to monarchy, there was also aristocracy and - as a dubious last resort - popular government. And in proper Aristotelian proportion, there were likewise three bad counterparts: tyranny, oligarchy, and anarchy - and as Mark Jurdjevic writes in his vigorously enjoyable new book A Great & Wretched City, "By the 1520s, when Machiavelli was composing the Discourse on Florentine Affairs and the Florentine Histories, the basic question of whether or not Florence would assume the form of a popular republic, close aristocratic oligarchy, or some kind of Medicean principate remained fundamentally unresolved."By the 1520s, Machiavelli was not only a bitter man but literally a broken one: he'd been implicated in a conspiracy against the Medici powers he'd served for virtually his entire adult life, and in addition to being dismissed from his civil duties, he was also tortured - his shoulders were violently dislocated, and although he was released shortly afterward and permitted to retire to his country home, he was never the same again. His world-view darkened, and he experienced the sick-inducing feeling of yearning for something you know is harmful to you: he wrote political histories and commentaries not just to pass the time and fill the mails to and from his friends but also to importune his way back to the cramped hallways of power.It never worked; he died in this near-proximity exile, and Jurdjevic beautifully understands one underlying reason why: "Machiavelli's contemporaries such as Francesco and Niccolo Guicciardini may have shared his doubts about the long-term viability of Medici power in Florence," he writes, "but no one shared Machiavelli's willingness to tell the Medici to plan for a Florentine future that did not include them."Jurdjevic has mastered Machiavelli's writings to such a fine degree that is book bristles with insights, especially about those two great and complex works, the Discourse on Florentine Affairs and the Florentine Histories, so full of galloping humanist inquiry and the comprehensive classical learning and yet so little known to the general reading public (Penguin Classics, bless them, has at least routinely reprinted the Discourses on Livy, another great work about which Jurdjevic has many fascinating things to say, but a fat 800-page popular press Complete Machiavelli is still a thing of dreams). And throughout these analyses, Jurdjevic keeps his eye on the mordant mutability that fills Machiavelli's writings - and is ready at every point with the perfect quote from the theorist himself:

Reflecting on the city's victory over Giangaleazzo Visconti, which had been so providentially celebrated by Leonardo Bruni a century earlier, as well as over the Ladislas of Naples, Machiavelli observed that the sudden unanticipated deaths of those rulers rather than Florentine power or competence accounted for the city's survival: "So death was always more friendly to the Florentines than any other friend, and stronger to save them than any ability of their own." What Bruni saw as God's ideological hand working to privilege Florentine libertas Machiavelli identified as pure and meaningless luck.

"Hence," the brilliant, bitter man once wrote, considering those three forms of good government, "if a founder of a state organizes one of these three governments in a city, he organizes it there for a short time only, because no precaution can be used to make certain that it will not slip into its contrary, on account of the likeness, in this case, of the virtue and the vice."The hard-won complexity of that "no precaution can be used" is the briefest possible precis of the mature Machiavelli who is Jurdjevic's subject, the Machiavelli who could come to stare so clearly at such relativism and yet not be able to abandon it. This is a challenging book, one that requires a fairly sound familiarity with Machiavelli's life and work but that very much repays that familiarity. The many thrilling discussions Jurdjevic provides of that life and work take this much-cited but little-read canonical thinker as far away from "ends justifying means"-type simplifications as he's always deserved to be.