In his essay “Winston Churchill” in Variety of Men, CP Snow says that political judgement means two things, one good and one bad. The good one is “the ability to think of many matters at once, in their interdependence, their relative importance, and their consequences. ” The bad one is more interesting. It is “the ability to guess what everyone else is thinking, and think like them.” He claims Churchill lacked both. I think he’s wrong on both counts. Churchill made lots of wild mistakes, but it was through excess of daring rather than lack of judgement, and he made an extraordinary number of enemies–basically, the entire British Establishment– but that was almost deliberate, because of how he enjoyed tweaking people and dropping the elegant insult, and how he enjoyed being talked about and succeeding. After all, his career was amazingly successful, and a big part of it was that though everybody was nervous around him, he always kept his name and talents in view. The conventional wisdom is that he was a political failure, washed up after stepping down as Chancellor of the Exchequer in 1929 and totally isolated after he opposed the independence process that led to the 1935 Government of India Act. But it isn’t really failure to achieve the number two position in the United Kingdom. For most who achieve it, that is the culmination of their career, and hardly anybody is that successful. People talk as if Churchill was a failure because he was so successful– Chancellor at age 54– and then essentially went into “Third Party” opposition all by himself on grounds of principle over expediency for the country and himself. He took the unpopular positions of being against Indian independence, the abdication of Edward VIII, and Hitler, and got more and more unpopular. Then, of course, it turned out that his strategy, if such it was, was 150% successful– he became Prime Minister in 1940 at age 65, and, more, the greatest Prime Minister in two centuries– at least. So one might better say he was so politically savvy that he knew principle and being right pays off in the end, even in your career. When you’re near the top at as young an age as 54, you can afford to play the long game. And, in fact, there is no way he would ever have become Prime Minister if he had gone along with Tory mainstream opinions. Mainstream Tory opinions + Churchill personality = pick somebody we like better as our party leader. His only chance was to take a chance.
Or, in the twitter version, which may be better:
“…Churchill was savvy; he knew principle pays off in the end. 

When you’re near the top at 54, you can afford to play the long game. 

Mainstream Tory opinions + being Churchill = pick somebody we like better. 

His only chance was to take a chance.”
The memo on writing below is classic Churchill, showing how could lay out an idea whose value powerful and influential people couldn’t deny while at the same time hating him for its pretty much explicit criticism of them for incompetence. It must have infuriated the Civil Service, which Snow describes as hating Churchill more than any other politician. Churchill sacked Hankey, CP Snow tells us how Maurice Hankey detested him— Cabinet Secretary 1916-1938 and then a political member of the Chamberlain War Cabinet of 1939, demoted by Churchill in 1940 and then fired altogether by him in 1942.
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