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I am interested in reading controversial opinions about democracy, especially coming from well-educated philosophers. I am not sure if I ever heard of philosophers being fervently against democracy, most philosophers seem to be actually its biggest proponents, so I am curious to know if anyone went against the current on this.

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Thoreau

The argument (if I get it right) is in Civil Disobedience

And it's gist is: In a community if I am a bad member its results are manifest. Whereas in a (large enough) country no such effects are palpable.

And so, the vote once in 4-5 years is a soul degrading "free lunch" since there is no commitment from my side and I can ask/demand anything.

Aside: My gpa used to say: What kind if system do you expect when those who would rule start as beggars for votes?

Speaking of philosophers against democracy surely you've heard of...?

Plato

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I believe Socrates and/or Plato believed that Greece should be led by a "philosopher king."

I argue that Plato believed democratic governance to be erratic and dysfunctional and that the democratic ruler is led by unnecessary appetites and passions.

Plato and Machiavelli on Democracy

Jean Paul-Sartre was a huge fan of Che Guevara and the Cuban revolution, which, according to one's perspective, can be regarded as the antithesis of democracy or one of the greatest democratic coups in modern history.

His [Sartre's] preference for mass movements and bottom-up social organization suggest that he would favor radical participatory democracy.

Sartre's Political Philosophy

These are just a couple examples to get you started.

Of course, philosophy is a huge part of political "science," so you should take a look at Karl Marx and other political thinkers.

I've often heard democracy disparaged as "mob rule." I think this is largely a right-wing attitude, though I'm not certain.

However, as a political activist, I've come to largely agree. In particular, I'm struck by the fact that some of history's most inspirational leaders were dictators.

Which isn't to say democracy is a lost cause; it's just a very difficult thing to create and sustain. If a chain is only as strong as its weakest link, then a democracy is limited by the intelligence and selflessness of its citizens.

Also, note that governments typically become more authoritarian in response to perceived threats (typically war) and as corrupt elements take control of governments.

It has been observed that a pure democracy, if it were practicable, would be the most perfect government. Experience has proved that no position is more false than this. The ancient democracies, in which the people themselves deliberated, never possessed one good feature of government. Their very character was tyranny; their figure deformity. -- Alexander Hamilton

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Aristotle’s definition of Democracy can’t be more controversial:

In our original discussion about governments we divided them into three true forms: kingly rule, aristocracy, and constitutional government, and three corresponding perversions- tyranny, oligarchy, and democracy. Of kingly rule and of aristocracy, we have already spoken, for the inquiry into the perfect state is the same thing with the discussion of the two forms thus named, since both imply a principle of virtue provided with external means. We have already determined in what aristocracy and kingly rule differ from one another, and when the latter should be established. In what follows we have to describe the so-called constitutional government, which bears the common name of all constitutions, and the other forms, tyranny, oligarchy, and democracy.

It is obvious which of the three perversions is the worst, and which is the next in badness. That which is the perversion of the first and most divine is necessarily the worst. And just as a royal rule, if not a mere name, must exist by virtue of some great personal superiority in the king, so tyranny, which is the worst of governments, is necessarily the farthest removed from a well-constituted form; oligarchy is little better, for it is a long way from aristocracy, and democracy is the most tolerable of the three.

He considers democracy as a perversion of constitutional government, also known as Politeia.

Although everything needs to be read in context http://classics.mit.edu/Aristotle/politics.4.four.html

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