The New Yorker Magazine has a very good article about Winston Churchill. I don't necessary agree with all his conclusions but it is very interesting. To read it click on the title for a link. Some quotes from the entice to entice you to read it:
In American conservative circles, he is still El Cid with a cigar, hoisted up on his horse to confront the latest existential threat to Western civilization (though his admirers tend to censor out the champagne or cognac glass that this ferocious Francophile kept clamped there, too). In Britain, it’s a little different. Just as J.F.K. is adored abroad and admired at home—where by now he’s seen as half liberal martyr, half libertine satyr—Churchill in Britain is revered but quarantined, his reputation held to the five years of his wartime rule.
Churchill, asked once what year he would like to relive, answered, “1940, every time, every time.” It really was his finest hour.
Churchill’s real legacy lies elsewhere. He is, with de Gaulle, the greatest instance in modern times of the romantic-conservative temperament in power. The curious thing is that this temperament can at moments be more practical than its liberal opposite, or than its pragmatic-conservative twin, since it rightly concedes the primacy of ideas and passions, rather than interests and practicalities, in men’s minds. Churchill was a student of history, but one whose reading allowed him to grasp when a new thing in history happened.
Again, to read more click on the title for a link to The New Yorker Magazine