> We would be greatful if some of you more knowledgeable savants on this
> List would be good enough to explain [why] ...David Brooks [calls]
> Michael Oakeshott a "big thinker" who is "one of the most most important
> philosophers of the 20th century"
Conservatives consider him one of the most important philosophers of the 20th century because he's one of the only ones they've got. There are lots of conservative political philosophers, but very few of them are explicitly theorists of conservatism -- unlike Classical Liberalism or the socialist tradition, where self-examination runneth over. So basically if you're a conservative intellectual, and you want a Big Text that you can use as a starting point to define what you believe in; and which can make a fair claim to being an addition to the canon of political philosophy; and which wasn't written around the time of the French revolution; then your choices are Strauss or Oakeshott. And if you pick Strauss you have to join a cult.
I'm exaggerating, but not too much.
There is also Nozick, but he's not really part of the canonical explication de texte tradition. When it comes to tradition, he's more of a break than a scion -- more like a radical liberal than an inheritor from Burke.
If you feel like reading something by a smart but fair lefty summarizing Oakeshott and explaining what he means to conservatives today, you might try Robert Devigne's _Recasting Conservatism: Oakeshott, Strauss and the Response to Postmodernism_.
As for searching for the deeper meaning of Brooks, I think Dwayne's right: it'd be liking fishing in a puddle.
Michael