This is a couple of years old, but I just stumbled across it. It is a lecture by Andrew Sullivan on Oakeshott.
I love the way that Sullivan captures the experience and feeling of reading Oakeshott, the richness of the Oakeshott reading experience. Consider this passage:
Oakeshott loved Shakespeare. In all the odd and quirky characters–from Falstaff to Bushy, from Benedik to Hamlet and Macbeth–he saw what a free society could create, not in terms of projects or goals or abstractions, but in terms of the human beings that are allowed to flourish with all their idiosyncrasies and faults and character traits.
This was for Oakeshott a wonder to behold. Every person he met was a character, or at least a potential character. And he saw the point of liberal democracy as giving individuals the ability to more fully become themselves, to ripen and mature in all their idiosyncrasies and differences.
All of life, Oakeshott argues, is an adventure. Let’s see what I can become. Let’s see what I can make of my life. Let’s greet life and its difficulties and exigencies and unpredictable nature as an opportunity.
In writing my article on “The Rule of Law, Freedom, and Prosperity” a few years ago, in the end I finally decided that Oakeshott holds the key to understanding what the rule of law is all about. I think there is something going on in Oakeshott that is complementary but richer than Hayek’s views on the rule of law. On the other hand, most readers don’t fully understand Hayek’s views on the rule of law either, resting their critique on Hayek’s views as expressed in The Constitution of Liberty, rather than the fully developed views that come out in Law, Legislation, and Liberty. (I elaborate on this observation in the second half of this article).
You can find an excerpt from Oakeshott’s classic essay “On Being Conservative” here.
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