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> One way I'm trying to make sense of is the following: The left is used to being the underdog, the ones fighting for reform against powerful, conservative institutions.

This isn't necessarily true. The Democrats in the US had a near stranglehold on Federal politics from the 1950s through the mid-1990s. The Republican ascendence in the 1990s came about in part because Democrat-oriented institutions; e.g., large blue-chip companies, labor unions, and the Federal government itself were viewed as inefficient and corrupt by a portion of the voting population.

> But we're in a situation where there are pockets of real power occupied by left-leaning leadership. University campuses. Some parts of the media. Large cities.

This also isn't necessarily true. Democratic sympathies != left-leaning. And the actual truth is that, going on voting records alone, people in the US mainly vote based on whether they live in more or less densely populated regions. The institutions you've mentioned are all Democrat-leaning because they are predominantly located in more urban areas. Which makes sense, since the policies that Democrats generally support are all more effective at higher population densities.



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