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Something that I had a thought about was how parts of the libertarian ideology would have been quite so amenable to the Democratic Party during its battle for its soul over the matter of civil rights v. states' rights in the 1950s & 1960s.

Your challenge, with a POD no earlier than 1900 (That would give you enough room for creativity!), is to create an American political system in which libertarianism is one of the major, if not the major, driving ideology of the Democratic Party whilst the Republican Party has conversely becoming dominated with big-government policies.
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