Back again with the philosophy questions? This one is a bit more in my wheelhouse than Hegel at least.

But first, who exactly are you referring to as an "enlightenment" philosopher? I know Rousseau makes brief mention of Machiavelli in "On the Social Contract" but I can't remember anyone who engaged substantively with him (although I haven't finished my coffee yet, so that might be the problem).

This is a question that seems to get brought up a lot, the question of "Is The Prince satirical"? Now this gets into interpretation, because I don't think you can say that there is a strict historical answer, just means of interpretation. However, I don't think so.

But, I do not think that Machiavelli means everything he says in The Prince to be taken at face value, if you are the proper reader. But it isn't a satire like Gulliver's Travels is a satire.

I think this case can be made by appealing to several points. First, by looking at the dedicatory letter, it becomes obvious that Machiavelli has a goal in writing The Prince. He wants a job from the Medici. When he's writing The Prince he has been banished, and is living out in the countryside, basically chopping wood for his fireplace all day (now he was previously tortured and banished by the Medici, but he still wants to get back in their good graces.) So on the one level, he wants to get a favorable reception by them. But on another level, he does have some critiques of their rule. This is where the confusion begins. And this is where the interpretive controversy starts.

There was a political philosopher in the 1950's named Leo Strauss, who took up this question of writing under pressure, and wrote a book called Persecution and the Art of Writing, in which, he claimed that most philosophers of history (Plato, Aristotle, Maimonides, and notably Machiavelli) practiced an art of "Esoteric Writing" where they wrote their philosophies on multiple levels, one level for the "masses" (or in Machiavelli's case for the Medici) and another level for the "attentive philosophers." The reason for doing this is to say your true, radical beliefs, without getting prosecuted for them.

You can see how the confusion could start.

However, this overall Straussian doctrine is not without its critics, if you google Strauss or Strassian you will see that there is an equal mix of people talking about him in a philosophic way, and equal parts people calling him the conservative devil. I'm not trying to say he is right, but that he was influential in a number of political circles and this could cause this interpretive confusion. If you want a good book that works through this argument Arthur Meltzer just published one called "Philosophy Between the Lines," Meltzer, while not a self-professed Strassian, he does find (and provides considerable evidence for) this type of writing. His online appendix of esoteric-hinting quotes is impressive.(http://www.press.uchicago.edu/sites/melzer/index.html) Strauss himself did write a book on Machiavelli called "Thoughts on Machiavelli" where he makes this argument as well.

So overall, my answer to you is...ummm, that it's complicated? I think it is clear that Machiavelli has more going on than he lets on.

Also, satire is supposed to be funny. The Prince isn't funny.

Because during the Enlightenment, Machiavelli's magnum opus, The Discourses on Livy, was extremely popular. I'm having a bit of trouble digging up the Big Book that argues this, but if you look at Montagne to Diderot to Frederick II to Thomas Jefferson, there is an enormous appreciation for Machiavelli, particularly his ethical philosophy (incidentally this continued, such that the 1911 Britannica portrays Machiavelli as a misguided patriot). Dismissing The Prince as satire, as Diderot and Rousseau did, was a relatively easy way to ignore the sharp differences between Machiavelli's prince and the Enlightened Despot.

Incidentally, the real problem with Machiavelli's prince that many contemporaries like Guicciardini had was not his ruthlessness but rather his populism. In the modern world we are accustomed to think that republic=democracy-popular=good, while monarch=unpopular=oppressive=bad, but in reality the populist dictator was the real specter of political thought, from Pisistratus to Julius Caesar to Savonarola to Lenin. Machiavelli's prince is unabashedly populist, constantly seeking validation from the people and largely acting as guarantors of its will. And not only does Machiavelli say this is a path to success, he says this produces better governance and laws. The idea that "mob rule" is a good thing is one of the most striking arguments in Machiavelli's works, despite its comparative neglect in favor of, say, the republic vs prince debate that entirely misses his point. The recent Machiavellian Democracy by John McCormick (a hybrid scholarly work and political treatise) does a good job of highlighting this thread.

To deal with the question of whether they were right to do so, however, I'll let the man speak for himself. In a letter to his friend Francesco Vettori, he has this to say about his composing of the work:

When evening comes, I return home and enter my study; on the threshold I take off my workday clothes, covered with mud and dirt, and put on the garments of court and palace. Fitted out appropriately, I step inside the venerable courts of the ancients, where, solicitously received by them, I nourish myself on that food that alone is mine and for which I was born; where I am unashamed to converse with them and to question them about the motives for their actions, and they, out of their human kindness, answer me. And for four hours at a time I feel no boredom, I forget all my troubles, I do not dread poverty, and I am not terrified by death. I absorb myself into them completely. And because Dante says that no one understands anything unless he retains what he has understood, I have jotted down what I have profited from in their conversation and composed a short study, De principatibus, in which I delve as deeply as I can into the ideas concerning this topic, discussing the definition of a princedom, the categories of princedoms, how they are acquired, how they are retained, and why they are lost. And if ever any whimsy of mine has given you pleasure, this one should not displease you. It ought to be welcomed by a prince, and especially by a new prince; therefore I am dedicating it to His Magnificence Giuliano. Filippo da Casavecchia has seen it. He will be able to give you some account of both the work itself and the discussions I have had with him about it, although I am continually fattening and currying it.

If you read the letter as a whole, although there is some humor throughout it is quite obvious that he is being deadly serious here. And in fact Machiavelli has a quote voluminous correspondence, but there is nothing within that hints that he was joking. In another letter to Vettori, incidentally, he also speaks of his sincere desire to be employed by the Medici, which gives a problem to anyone who thinks he secretly hated them (was contemptuous on the other hand, sure). The other main point people raise in arguing that it was satire is that Machiavelli was a staunch republican. This point is true, as the Discourses show he absolutely believed that a republic was the best form of government. But he also has little bits scattered throughout like this (from I.IX):

But this must be assumed, as a general rule, that it never or rarely occurs that some Republic or Kingdom is well organized from the beginning, or its institutions entirely reformed a new, unless it is arranged by one (individual only): rather it is necessary that the only one who carries it out should be he who on whose mind such an organization depends. A prudent Organizer of a Republic, therefore, who has in mind to want to promote, not himself, but the common good, and not his own succession but his (common) country, ought to endeavor to have the authority alone: and a wise planner will never reprimand anyone for any extraordinary activity that he should employ either in the establishment of a Kingdom or in constituting a Republic.

Republics are ideal, but not all republics are created equally. The corrupt republic lead by the few is to Machiavelli just as bad as a corrupt and weak king, while a good republic requires the proper institution of virtue. The early sections of the Discourses largely deals with this process, and is incidentally a really masterful examples of exegesis.

It is difficult to produce direct proof that Machiavelli was not writing satirically--except if course that letter--but I think in general the main takeaway is that the arguments for it being satire are really weak. In the end they boil down to people today finding the text just as disturbing as people did five hundred years ago.

Honestly it's worth a read!