A couple weeks before the 2016 election Michael Moore (who I’m typically not big a fan of) had one of the best reads on why Trump would and ultimately did win that election.
I've been politically homeless for a while now but still registered Republican as is almost all of my family. Moore's points directly map to my conversations with them better than any other explanation I've seen on the Internet.:
I think it's important to keep in mind that Trump winning the primaries in 2016 was essentially a repudiation of the entire Republican incumbency by a good portion of their base.
Just about every general "reason Trump would win" for last election looks pretty dumb with this election.
Because basically all those arguments remain true - yet Trump didn't win. These aren't argument for why Trump would win. They were arguments for why Trump has some purchase. The reason Trump won was the elites go so sloppy they let him win, they let their garbage boogieman alternative become the choice because they were addicted to having that kind of creep as their opposition.
And Michael Moore's argument in particular is crap among these. Homeless factory workers aren't Trump's base, family construction companies are his base - I see them regularly. The well-off but not college educated.
https://youtu.be/vMm5HfxNXY4
I think it's important to keep in mind that Trump winning the primaries in 2016 was essentially a repudiation of the entire Republican incumbency by a good portion of their base.