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Challenge: make the Soviet Union transition into a democratic nation like the United States, possibly in the '80s or '90s.

Extra points if you can think of a POD after World War II (IE a timeline where Stalin rules the country during the war still). Something with Trotsky is acceptable though.

The SU seemed already like a kind of allegory to the USA. So, make the Soviet Union a nation that becomes a democratic state. I can imagine that the Communist Party could be a major political party, but there would be others, of course.
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