The
conventional wisdom is that
Machiavelli, a
career diplomat, wrote The Prince in an effort to gain
employment with the
Medici, who in 1513 were just coming back into power in his native
Florence. However, I believe that it is actually the earliest published
trolling in existence - a
precursor to
A Modest Proposal and similar works.
Consider: Florence was a traditionally republican city-state throughout much of its early history. Machiavelli's experience in diplomacy occurred during an interval (1494-1512) between successive periods of Medici rule, when democratic leanings were at their most pronounced, and he thrived under this form of government. He was an advocate of raising a citizens' militia to free Florence from dependence on foreigners, and even attempted to raise such a militia himself. However, the intellectual Florentines may not have been cut out for warfare, and the militia was ineffective.
When the Medici came back into power, with the aid of a pope friendly to their interests and the foreign power of Spain, and despite the disorganized embryo of the aforementioned militia, Machiavelli was considered enough of a threat to be imprisoned and tortured. When he was released and allowed to retire to the countryside, he wrote The Prince, dedicating it first to Giuliano de Medici, and later to his succesor, "the magnificent Lorenzo de Medici."
If he was aiming for a job with the new regime (and I don't deny that he was) he had too much pride to get his nose sufficiently browned. In this chapter, Machiavelli states (according to my translation, the Norton Critical Edition by Robert M. Adams) that a ruler taking over a city accustomed to republican government (here he has Florence in mind) must either destroy it or be destroyed by it. Citizens of such a city, he advises the Medici, "can always call on the name of liberty and its ancient ordinances, which no passage of time or bestowal of gifts can ever cause to be forgotten...if one does not divide or disperse the inhabitants, they will never forget that name or those ordinances; and, at the slightest incident, they will instantly have recourse to them." If that doesn't sound like a taunt, I don't know what does - especially since the Medici were in no position to destroy their seat of power.
The new pope in Rome (Leo X) was Giovanni de Medici, brother of Giuliano. In writing about the papacy, Machiavelli states that "we may hope that as his predecessors made it great by force of arms, he by his generosity and countless other virtu will make it even greater and more to be revered." This appears to be a case of damning with faint praise. If Niccolo was as eager to get a job with the Medici as is supposed, I think he would have been on his proverbial knees, singing the virtu of the new pope far and wide; he would not have merely hoped that Leo possesed sufficient virtu.
So, after thriving for years under a fairly democratic government, attempting and failing to raise an army to defend it, and being imprisoned and tortured by the new monarchical government, we are to believe that Machiavelli, in true Machiavellian fashion, threw out his long-held democratic beliefs in an attempt to curry favor with the regime; but that despite his well-earned reputation for rhetorical virtu, he was unable to do so with Giuliano - who was not widely regarded as a great intellect. I don't buy it. I think that The Prince is a classic double feint. Everyone knows the old axiom that a ruler who squeezes onto power too tightly will feel it slip out between his fingers. This seems to me a more reasonable explanation for The Prince - he was giving the Medici intentionally bad advice. Although it did not succeed in ridding Florence of the Medici (remember that, at least on the face of it, they did not heed Machiavelli's manifesto) countless rulers - from Napoleon to Mussolini to Peron to Pinochet - have lost their empires, small and large, while acting similarly to those who, like Cesare Borgia, Machiavelli holds up as examples for the aspiring prince.