re: Philosophical Discussion: Why does the far left keep winning and winning big?

This is not a comprehensive response, but I believe one element is that the general public is shockingly naive about civics. They could not tell you what the Bill of Rights is if their lives depended on it. A second element is that people have come believe that every single important issue in life is within the purview of government action, and from that comes the reality if a given person sees one issue as important enough, even if that issue really should not be a matter of government at all, the person will ignore all the Marxism in the world to protect that one issue. A third element is absolutely the colleges and media, which are echoe chambers for leftism.