Drawing on the Jacobin article by Matt Carp, the title of this post I think captures the current political alignment. Why would the working class--especially in this case the white working class--see a political ally in a billionaire real estate developer / serial liar? Partly it's that Trump can mimic signs of tribal membership, like being a class A jerk to women, generally enjoying pissing people off, and that sort of thing.
But also I think the series of tweets by Chuck Wendig, which I found via Daring Fireball, gets at the psychology pretty well, at least for a certain sector of the white working class. Basically, they don't like the poor or professionals, because neither of them want to work for a living.
How do we win enough of these folks back to the Democratic fold in the next four years? Well, some are probably lost causes--deeply bigoted, racist, or otherwise committed to jerkery. The Democratic party can't really appeal to them without damaging its existing coalition, which we don't want to do.
Confronting Trump and the Republicans on policy grounds, rather than trying to participate in the media circus Trumpers thrive on is probably also a good idea. And having policies that truly address the problems of the working class is also a good idea. But I'm not convinced that most voters really know or care much about policies.
What we need is a candidate who can speak like a member of the working class. Not like a jerk, as Trump does, but as someone who can be respectful and still show himself to be a member (or at least potential member) of the working class tribe. As Trump I think has demonstrated, what you say is far less important in American politics than how you say it. Sad, but probably true.
I think it would also help if the party put forward something more than just a set of policies. What we need is a platform calling for larger reforms--a complete overhaul of the political system. My shortlist of needed reforms: 1) abolish the electoral college and elect presidents via national popular vote; 2) run elections for national office through a national governmental agency, and take them away from the parties--the ballot and election regulations would be determined by the national agency, and election districts delineated by the Census Bureau; 3) elections for national office would use an instant run-off voting method instead of first-past-the post.
This might require amending the constitution. Fine. While we're at it, let's also 1) limit terms of Supreme Court members so that every president gets to name at least two justices; 2) declare that constitutional rights apply only to individual human beings, not corporate entities; 3) abolish the Senate; 4) double the size of the House of Representatives.