First, I'm citing his most famous book, The Prince, not his Discourses on Livy, which some argue is the greater of his political writings. Nevertheless, it is probably the first book of political science in the modern sense of the term, as opposed to the idealism of his predecessors and his contemporary detractors, such as Erasmus. Also, it is the work with which more are familiar, so it is, some may say unfairly, what people mean when they say "Machiavellian". I will take issue with eight points of the book, though others may argue more, and some of those may have a valid point when they do so.
First, let's discuss Chapter 4 and Chapter 5. When Bush took it upon this nation to overthrow the government of Iraq, he found a situation not unlike the France Machiavelli described, and, in fact, not unlike modern France: various provinces, with their own traditional leaders, each of whom have their own agendas which may or (more frequently) may not necessarily mesh with each other. While, on the surface, it appeared to be similar to the Kingdom of Darius, that which lurked just under the surface made such an undertaking that much more difficult. Next, by gutting the existing government and leaving very little in place, he created a power vacuum which has led to anarchy. Sure, Bush took out the main unifying force in that nation, but he left the lesser "princes" in place, and they have created little other than internecine war and problems for us and for the people of Iraq. Reading further in Chapter 14, the sheer scope of his mistakes in terms of Machiavelli's reasoning become even more obvious. I find it painfully obvious that, in those three, related points, Bush and Cheney have been utter failures.
Second, let's discuss Chapter 7. Bush and Cheney did, in fact, achieve their station by good fortune and have had nothing but problems since. Unlike Cesar Borgia, they have not laid a solid foundation for their power, and have, instead, pretty well united the people of the United States against them through their ineptitude and cronyism. In fact, it is only the sheer difficulty in impeaching sitting presidents and vice presidents that have kept them in their offices, and even that will end some 467 days from today. Read especially that bit on Romagna in that chapter. It's interesting in light of the current administration.
Third, let's discuss Chapter 9. True, Bush has rewarded his greatest supporters among our modern nobility, Congress. However, the nobility are, in turn, hired, retained, and fired by the people they govern, and in forgetting this, Bush has allowed many of his supporters' political careers to come to ruin and has encouraged the election of a "nobility" hostile to his views. We've seen the results over the last several months, and from the perspective of many in the public, that's a good thing, but from Bush's perspective, it's been an unmitigated disaster.
Fourth, let's discuss Chapter 12. Bush has invited ruin, infamy, and an international PR disaster on this nation through his use of mercenaries, most notoriously, those from the right-wing Blackwater Security company. Machiavelli had plenty to say about the use of mercenaries, and none of it was good. Bush and Cheney, therefore, fail also on this point.
Finally, let's briefly discuss Chapter 17 and Chapter 19. Bush and Cheney have developed a reputation for cruelty, yet they are not feared in the sense that Machiavelli uses the term. I know of no one, no matter how much they detest this president, live in the kind of mortal fear of Bush that Iraqis experienced with Saddam Hussein. I happen to be quite grateful for that fact, but the simple fact that they have wielded this tactic so ineptly has caused them great problems with no real benefit. As a result, they are neither feared nor loved, as shown by approval ratings in the low 30s. In fact, Bush and Cheney are hated by a great number of Americans and other nations abroad, and this is precisely what a leader should try to avoid. Indeed, not only have they not avoided being hated, they have appeared to intentionally invite it on multiple occasions. This is yet another failure in purely Machiavellian terms.
It would be much better for this nation if Bush were more Machiavellian, but then again, it would be much better for this nation if Bush were more competent using any governing philosophy the people would tolerate. As sort of a novel idea, I would like to see a president govern by the Constitution they swear, and lie through their teeth as they do so, to defend and protect, but that's not going to happen. It is with this hope that I support Ron Paul for President in 2008.