I didn’t find A question of upbringing particularly insightful — it contrasts Churchill and Hitler — but I did love this quote from Churchill about Hitler’s failed invasion of Russia:
He forgot about the winter. There is a winter, you know, in Russia. For a good many months the temperature is apt to fall very low. There is snow, there is frost, and all that. Hitler forgot about the Russian winter. He must have been very loosely educated. We all heard about it at school; but he forgot it. I have never made such a bad mistake as that.
I can hear A.A. Milne giving that explanation to Christopher Robin and Pooh Bear.