On one reading of Plato, he advocates rule by philosopher kings.* He might be right, but you’ve got to be suspicious, given that he's a philosopher.
On one reading of Aristotle, he thinks the best form of life is philosophical, and even God is a kind of philosopher (eternally thinking of perfection). Aristotle might be right, but you’ve got to be suspicious, given that he's a philosopher.
Certain (but not all) deliberative democrats and some other political theorists think society would be much better if most people began acting like political theorists at a colloquium. They might be right, you’ve got to be suspicious, given this is coming from political theorists.
Now, when Rawls and various other high liberals try to determine which liberties matter the most—which are really important for people to develop their moral personalities—they just so happen to come up with the liberties that make the most difference in the life of a typical philosopher. So, freedom of speech is in (good thing for us book writers!), freedom of personal property is in (we like our Subarus, Macs, bicycles, and nice houses), but freedom to own productive property is out. (Who has time to run a pizza shop on the side, anyways?)
This is a touch snarky, but there’s a more serious point here. It may well be that political philosophy is parochial—that it reflects the concerns, values, and (rather limited) life experiences of philosophers at the expense of understanding the concerns, values, and life experiences of non-philosophers. For Rawls, the liberties that are supposed to be respected (by his first principle of justice) are those that are vital for citizens to develop their sense of justice and conceptions of the good life. (I'm not sure this is a good way to determine what liberties people are owed…) Yet he happens to come up with just those liberties your typical philosophy professor would care most about, and his arguments for why it should be those liberties and not others are quite thin and unsustained.
I’m hoping John Tomasi will join us in blogging here, and in particular explain his argument for why Rawls is mistaken to lower the moral status of the economic liberties. If not, I’ll expand upon this point later.
*See Julia Annas’s criticism of the common reading of Plato’s Republic.