Machiavelli, The Prince
Much ink has been spilled. Here a philosopher, unschooled in political science, takes a look. What would a philosopher say? Well, here's what this one says.
Machiavelli analyzes quite adeptly certain concepts pertinent to rulership that might slip by in their inchoate and misleading guises. He lays out for us fortune, power (virtue), good, evil, political stability, and so forth, showing us the surprisingly cynical entailments that flow from them when the viability of the state and its subjection by another are at stake. Genius analyst though he is, however, he doesn't push his account forward into the more nuanced terrain that might weaken and make his claims less startling. He assumes that the looming probability of the fall of the state and its being conquered by its foes is enough to license his most strident recommendations of treachery and evil. He draws a false dichotomy between the impotence of Savonarola and the brutality of Cesare Borgia who sliced his lieutenant in two for his subjects to see.
Machiavelli attempts to place caveats on his exhortation to cruelty and evil. He says in ch. 8 that the ruler should do these things only to secure himself and as much as possible for the good of the people, while not persisting in doing them. He becomes confused as to whether Agathocles was virtuous for using heinous crimes to secure power; he is not equipped to understand that he is confused. He denies in ch. 18 that he advises the ruler not to do good, but he points out that the state will require that the ruler do evil. But these attempts at facing the real trade-offs between the stability of the state and other moral obligations are fleeting and inchoate. There is no sign of the possibility that one will need to accept an elevated risk of instability and insecurity in favor of some other moral value. And yet we know that such cases in which other moral values override stability and security do exist. This is why Machiavelli's The Prince has a certain unreal aura about it. It isn't that Machiavelli countenances the obligation to do of evil which causes this effect; it is that he is not equipped to present this obligation in the context of other obligations. Not the jaded cynic he is known for being, Machiavelli is naive, evincing not the foggiest notion of the difficult moral trade-offs that any serious political philosophy must grapple with.
Even if we take Machiavelli's point seriously that evil is sometimes necessary in order to secure the state, Machiavelli never shows that certain of his examples are cases in which great evil was required. He doesn't acknowledge the obvious objection that in many of these cases there may be alternatives to slicing adversaries' throats or cutting lieutenants in half that would also result in security to the state. Also, he ambiguates over securing one's own power and securing the state. For at times he slides from the wholesome security of the states as the goal of his political advice to the prince's own desire to maintain power as the goal. The two are not the same.
The case of Cesare Borgia illustrates Machiavelli's failings well (and indeed Borgia is Machiavelli's favorite case of the scores and probably hundreds which he adduces in illustration of his views.) Borgia, Machiavelli says, was a great example of a ruler, exhibiting pleasantness, liberality, magnanimity, as well as the darker virtues. The examples of the former three virtues are unsatisfying. Borgia makes friends in Rome and the College of Cardinals because these are useful friendships, and he removes the overly brutal law enforcer Remirro de Orco from Romagna. Yet, we know that there are cases in which pleasantness, liberality, and magnanimity have moral weight in spite of their not being in the interest of the ruler. So, again, Machiavelli fails to deal forthrightly with moral constraints, even where he seems to do so.
By the way, Machiavelli is most certainly the Western Han Feizi (280-233 bc).