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Two ideas I'm thinking about. Churchill becomes PM before the war starts, say in the aftermath of the Germans taking over Czechia, maybe in April 1939. I'd imagine him calling for more extensive British rearmament, and not dilly dallying about in terms of getting a Soviet alliance, at least making a full fledged effort at doing so, unlike Chamberlain.
If he takes over after the war starts, say January 1940, I'd imagine him being more aggressive in trying to get Britain and France into the Finland war, also wondering about him trying to get an accelerated BEF commitment into France. Also, some kind of backdoor dealings with the European neutrals, maybe some kind of deal with Mussolini in the months before the German invasion of France?
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