Kelly Ross who I think is the deepest of all philosopher and the widest.
And he also is not much of an authoritarian. 

I call him deepest because he seems to be always able to zero in on the flaws of philosophies that are considered rigorous and logically exact . For some reason he always finds the major flaw. And he is politically a libertarian or more exactly he goes with the American Constitution.

The other thinkers that are important are Karl Popper (The Open Society and its Enemies), Michael Huemer (The essay which destroyed Marxism.). I mind include Allen Bloom (The Closing of the American Mind) (Closing of the American Mind) and Harold Bloom (The Lucifer Principle) (howard_bloom___the_lucifer_principle).

The thing about all these people are they are not authoritarians. But they are different in many ways.

The most encompassing and systematic is  Kelly Ross.

The question that comes up then is how to reconcile this with Torah. If Torah was solely a issue of personal morality then there would not be  any question. But it is public law also in the sense that the only authority anyone has in Torah is to enforce the laws of the Torah. The Torah gives some legitimacy to a Sanhedrin and to a king  and even to prophets but not one of these can change or modify or reinterpret a single law. They can only deal with the questions what is the law and how does it apply and also to solve contradictions based on the 13 principles.

The best interface between Torah and libertarian ideas I think is Kelly Ross. At least he was reading his material that helped me organize my own ideas into a cohesive system.