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In 1941 when Winston Churchill visited the USA after Pearl Harbor and gave a speech to the assembled Congress, he said something to the effect of that while his mother was American and Father British, if it had been the opposite he very well could have been a person attending the US Senate. So, what if that did occur?
Ok, granted this is ASB, but what if Churchill's actually father ends up marrying a British women, and it is one of Churchill's aunts, say Lady Sarah Churchill who marries a American man, maybe someone slightly famous or into Politics. Then they end up having a son who has Churchill's exact personality, just obviously a different name and has a parallel life adapted to American history. How would this work?
Edit: Damnit! I screwed the spelling in the title! Who will take this seriously!