The Prince

Well, for starters, this book goes well beyond the sentence “Do whatever it takes to win.” Detractors, chiefly those who want morality to rule all dealings, paint this book as advocating stabbing everyone else in the back at the earliest possible convenience. They take the whole book as being the line “It is better to be feared than loved.” In reality, the book is so much more than this.

As has been stated ad nauseum by others, this book is ultimately about realpolitik. Bottom line, others will stab you in the back, so you need to be prepared for it and be willing to stab others in the back yourself. It doesn't advocate breaking alliances but says that there will be times that doing so is necessary, as will be breaking one's word. Anyone who thinks honesty is the best policy at all times is living a fantasy. Anyone who lets their hated boss know what they really think of them is likely to find themselves not working for this boss sooner than they had planned.

Finally, surprisingly, he is a big fan of the people. He states in several sections that it is more important to have the people on one's side than the nobility, if for no other reason that the nobles have more means to depose the prince, while the people outnumber the nobles. Whoa, betide the aristocracy of today if the masses were ever to remember this seemingly obvious fact.

Some criticisms, the thoughts do seem a little swingy in places. He seems to be a fan of republics, but then in portions of the Discourses, included in this edition, he says that republics oppress their people, while claiming that princes do not. In the meantime, in the Prince, he is a fan of republics. When he claims that multitudes are more constant than masses, he seems to jump through quite a few hoops and does quite a bit of cherry picking to “prove” this. and I'll grant that he did this because both of these works had intended audiences and purposes, but one should be aware of this fact as they're reading either one. I also wonder how one would take modern nationalism and mass media into account. Obviously, we can't fault him for not knowing that newspapers, and then radio, and then television, and finally the internet right on portable viewing devices, but these technologies make it very different how the people are impacted. In his view, the people won't care who the ruler is so long as they can prosper, but we see how proud modern people are to be American, or French, or Japanese, or whatever. I think these change the reality from anything he could have discerned from his time.

All in all, this is a must-read. The only thing, I would suggest a different edition. Daniel Donno, the translator of this edition, says he omitted some chapters that related to the military. Presumably, this is because they discuss military tactics and technology, which have obviously both moved on since Machiavelli's day, but I can't tell because they're not in this edition. Donno stated that he felt those chapters would be of little interest to modern (1966) readers, however, I would prefer to make that choice myself. I would also prefer to read the Discourses in their entirety rather than the piecemeal selections included here.