December 10, 2013, marks the five hundredth anniversary of Niccolò Machiavelli's announcement in a letter to his friend Francesco Vettori that he had composed a small work entitled De principatibus (On principalities). Machiavelli wrote Vettori that he was still “fattening and polishing” it, but his description of the subject matter—what a principality is, of what kinds they are, how they are acquired, how they are maintained, why they are lost—largely corresponds to the book we now know as The Prince.

Although neither The Prince nor his Discourses on Livy was published until 1532, five years after Machiavelli's death, manuscript copies circulated not merely in Florence, but in northern Europe. As Giovanni Giorgini shows in his survey of five hundred years of Italian scholarship, from the very beginning the reception of Machiavelli's work has been extremely mixed. Some readers have decried his evil teachings and advocacy of tyranny, whereas others have celebrated his republican political principles and Italian nationalism. Some have understood him to be a hardheaded advocate of “raison d'état” whereas others have found his presentation of “the prince” and culminating call for the liberation of Italy to be incredibly romantic.

In contrast to the enduring popular view of Machiavelli as a “Machiavellian” teacher of tyrants, most scholars in the late twentieth and early twenty-first centuries have understood him to be a republican, if not a kind of democratic political theorist. Scholarly attention has consequently shifted away from The Prince to his Discourses on Livy. By publishing this special issue in honor of the five hundredth anniversary of the composition of The Prince, we hope to remind readers of the paradoxical character and, partly for that reason, enduring fascination of what remains Machiavelli's most famous and widely read work.

The authors of the essays included in this collection include some of the best-known scholars working on Machiavelli today. They represent the wide range of disciplines—history, politics, literature, rhetoric, and philosophy—for which Machiavelli remains a seminal figure. As their essays demonstrate, learned commentators continue to disagree markedly about the character, content, and contemporary relevance of Machiavelli's work.

In “Dating The Prince” William J. Connell presents new documentary evidence to show that, although Machiavelli had drafted most of his little treatise in 1513 and initially planned to present it to Giovanni de' Medici, he completed it in the spring of 1515 and actually presented it to Lorenzo. Machiavelli's gift did not impress the young Medici prince, however, and his hopes of advancement were crushed.

But what did Machiavelli want to teach Lorenzo or persuade him to do? In “Alexander the Great as ‘Lord of Asia’ and Rome as His Successor,” “Cesare Borgia and Machiavelli,” and “Revisiting Agathocles,” Vickie Sullivan, John M. Najemy, and Victoria Kahn lead readers to reconsider some of the reasons Machiavelli has been called a “teacher of tyrants.” Did he really or unambiguously praise these generals? And if he did praise them, for what exactly did he praise them, and why?

The prominence of Alexander and his legacy in The Prince has been little noticed; but, Sullivan argues, Machiavelli suggests that the example Alexander set of world conquest and solitary rule provided a model for later ambitious Romans to imitate—Julius Caesar, first and foremost. Alexander conquered and ruled the kingdom established by Cyrus. So by imitating Alexander, the Roman emperors subjected Europe to the despotic form of rule that originated in Persia. However, in conquering Europe, Rome surpassed Alexander. He conquered and then ruled peoples who were accustomed to being slaves whereas Rome subjugated those who were accustomed to being free. Rome no longer dominated Europe politically at the time Machiavelli wrote, but the Roman Church continued to claim universal jurisdiction. Machiavelli's deployment of both the Romans and Caesar as examples that ought to be imitated thus has ominous implications. Is Machiavelli encouraging the emergence of a new Caesar, as Mussolini later thought? Or is he pointing to a more subtle form of world domination?

Cesare Borgia has often been taken to be the model Machiavelli sets for his princely reader, if not the “hero” of the work as a whole. Machiavelli introduces him as an example of a man who acquired a principality through good fortune and the arms of others, but who subsequently “established great foundations for his future power” (Prince 7). However, Najemy reports, the dispatches Machiavelli sent back to Florence after his three encounters with Borgia in 1502–3 show not only that Borgia never overcame his dependency on the arms of others, but also that Machiavelli knew full well that Borgia had not. In chapter 7 of The Prince, Najemy concludes, Machiavelli reproduces Borgia's empty claims about what he intended to accomplish in order to show “that a new prince must not believe that bravado alone can bring success” (554).

Kahn suggests that “Agathocles the Sicilian” may provide the most telling example—or set of alternatives—that Machiavelli puts before Lorenzo. Machiavelli's paradoxical judgment that Agathocles rose to power by his own virtù, but that it cannot be called virtù to massacre one's fellow citizens, and that a man can acquire empire this way, but not glory, not merely raises questions about what exactly he means by virtù. It also constitutes a kind of “metadiscourse” about the relation between Machiavelli and “Machiavellianism,” virtue and success, the use of violence and the need, ultimately, to obtain popular approval and consent.

Nathan Tarcov documents the importance of belief and opinion in Machiavelli's Prince. Because Machiavelli states not only that where there are good arms there must be good laws, but also that princes must learn to fight like foxes as well as lions, many readers have concluded that he preaches nothing but the use of force and fraud. Tarcov shows, on the contrary, that Machiavelli explicitly recognizes the political importance of the beliefs and opinions of both the people and the prince. Indeed, Machiavelli also states some distinctive beliefs and opinions of his own. But, Tarcov cautions, “Only insofar as Machiavelli defends his opinions with reasons can his readers have faith and trust in him” (586).

In The Prince Machiavelli famously opposes virtù to fortuna. But in “Farewell to Fortune” Anthony Parel argues that Machiavelli's understanding of “fortune” was based on outmoded Ptolemaic cosmology. Since this cosmology has long been discarded, Machiavelli's analysis of the ways and extent to which human beings can resist fortune in chapter 25 is also outmoded. It should not be studied as political philosophy, but as part of the history of political philosophy; and that history should include the history of natural science as well as ethics and politics.

Chapter 26 of The Prince has long puzzled commentators, since Machiavelli appears there to shift from a hardheaded, if not amoral analysis of politics to a passionate call for the liberation of Italy. Instead of the instrumental use of religion he recommends elsewhere, Miguel Vatter observes, in chapter 26 we see Machiavelli proposing to use political means to achieve the providential will of God. To determine who Machiavelli's God is, however, we need to find a conception of God who fosters the ferocious aspects of politics he finds in both the Roman historians and the Hebrew Bible. That conception is not to be found in the republican Christian tradition reconstructed by Maurizio Viroli, but in Arabic and Jewish politicophilosophical reflections on prophets, philosophers, and kings.

In “Five Hundred Years of Italian Scholarship on Machiavelli's Prince” Giorgini shows that some of Machiavelli's contemporaries continued to prefer a more traditional understanding of the virtues of the prince and a mixed regime. At the end of his life Machiavelli was reportedly despised by all parties in Florence; and his impious, immoral teachings were regularly condemned by representatives of the church. However, republican interpreters soon began arguing that in appearing to recommend expedient policies to rulers, Machiavelli was, in fact, informing the people about the cruel and immoral practices of Italian princes. Taking the Discourses to reveal more of Machiavelli's true thought than The Prince, Italian Enlightenment authors went even further in emphasizing his patriotism as well as his republican sympathies. Nineteenth-century commentators began stressing Machiavelli's analysis of the political use of religion and the independence of politics from morality, emphases also to be seen in the two most powerful and influential interpretations of Machiavelli in Italy in the twentieth century by Benedetto Croce and Antonio Gramsci. In Italy, Giorgini concludes, Machiavelli continues to be studied by practicing politicians as well as historians of political thought and Italian literature.

Harvey Mansfield suggests, however, that Leo Strauss's Thoughts on Machiavelli has changed the contours and questions of scholarly debate. Strauss has not merely exposed and explained Machiavelli's esotericism. Strauss practices some of the same “tricks,” and thus establishes “a parallel between Machiavelli's troops of Machiavellians and his own school, known … as Straussians” (642). But Strauss does not make it easy to see what the parallel is or what exactly his thoughts about Machiavelli are. He maintains that Machiavelli was a philosopher, but not a philosopher who wanted to stay in his “ivory tower” and contemplate. He wanted to have an effect—and he did.

The essays included in this special issue thus not only reopen old questions about Machiavelli's Prince; they also point to new avenues of inquiry: What does it mean to contend that Machiavelli was a “philosopher,” rather than merely a “political thinker” or “political theorist”? Did he have a “political theology”? How was his understanding of human nature related to his understanding of nature as a whole? What exactly did he think about the relation and relative political importance of force and opinion, efficacy and honor? What are we to make of his knowing misrepresentation of historical fact? Both the intention and effect of Machiavelli's Prince have been debated for five hundred years; it looks as if they will continue to be debated for many more.