Want to know the difference between the Renaissance and present-day society? If Machiavelli had written The Prince today, it would be called Ruling Principalities for Dummies. In the fifteenth century, manuals for prospective rulers took the form of profound philosophical treatises. In the twenty-first century, they're bullet-point lists bound in bright yellow covers with a cartoon on the front. Part history and part philosophy, The Prince is a glimpse into the mind of a Renaissance thinker. As much as it is an exploration of politics, it is also an exploration of personality, a fact that becomes much clearer when it's held up next to Machiavelli's other works, such as The Life of Castruccio Castracani and Discourses on Livy.
If one wants to be reductionist, one can boil down The Prince to a manual on how to keep power. Machiavelli focuses in particular on princes who are new to their principality, as hereditary princes simply need to continue the practices of their predecessors that made the people content enough not to revolt. New princes must establish control over their state, whether it's one they have recently conquered or one they've seized in a coup.
I think it's a mistake to reduce The Prince though. What sets Machiavelli apart is his style, the way he articulates his arguments and advances his philosophy for ruling a principality. He draws on specific cases, both from ancient (usually Roman) history and recent events in 15th-century Italy. Consequently, I've learned more about Italian history from The Prince than any other source. Fifteenth-century Italy was one fucked up place, and it's no wonder that Machiavelli felt the need to write The Prince.
In both The Prince and Discourses on Livy, Machiavelli makes heavy use of examples from ancient Rome. In comparing contemporary Italy to the times that preceded it, Machiavelli usually finds his own time lacking. Although he's a staunch republican, if you read only The Prince, you probably wouldn't know it. Maybe Machiavelli wrote it only as an attempt to get into the good graces of the Medicis. From the way he speaks wistfully of Rome—both republic and empire—I couldn't help but get a sense that Machiavelli's outlining what he sees as the qualities Italy needs in a leader who will restore the country's former glory. As a student of history, Machiavelli knows that Italy was once strong—and unified. Even in Discourses, Machiavelli says that only a single man can found a republic (Chapter 9: "How It Is Necessary for a Man to Act Alone in Order to Organize a Republic Anew. . ."). The Prince, then, is a programme for good leadership of a state. More than just keeping power, The Prince is about being great (a condition that Machiavelli never conflates with morality).
For those of us who live in democracies, we don't always have a clear understanding of exactly what duties occupy the mind of a prince. Machiavelli's writing has certainly been eye-opening and educational for me, simply because he comments on matters that I would never think about. Nevertheless, I have no doubt that some aspects of Machiavelli's pragmatic advice still apply. For example, chapters 17, 18, and 19 elucidate the difference between applying necessary cruelty and engendering contempt or hatred. Machiavelli is, if anything, meticulous in his reasoning. He has no scruples about "misremembering" history or, as is the case in his biography of Castruccio Castracani, outright fabricating it. But when it comes to his arguments, each one is carefully constructed and advanced in order to convince.
I have nothing but praise for this particular edition as well. It's a serendipitous Christmas gift from a friend. I had to read a few chapters of The Prince for a philosophy class, so I took the opportunity to read the entire book (and the "other writings" included here). This edition has notes at the end of every chapter that explain historical references, possible translation problems, and most importantly, mistakes made by Machiavelli. The introduction, timeline, and brief biography of Machiavelli were also helpful in providing context—as previously mentioned, I found this book an informative source of Italian history as well as political philosophy. The inclusion of both The Prince and excerpts from Discourses on Livy provides a contrast of Machiavelli's work that's quite useful. I found The Prince more comprehensive (although this could be bias, as the book only has excerpts from Discourses), but Discourses is a fascinating look at Machiavelli's republican sensibilities, as well as his thoughts on the use of religion in republics.
The Prince is essential for anyone interested in political philosophy. Machiavelli's work has retained its fame for a reason: it is both a philosophical and a rhetorical masterpiece. It's a mistake to write it off either as satire or as some sort of dark endorsement of immoral deeds. That scholars more intelligent and more knowledgeable than I still debate some of the meaning behind Machiavelli's words attests to the their complexity. As for me, while I don't think I'll be acquiring a new principality any time soon, now I feel more prepared should that happen.