It's not rocket science:
1. Donald Trump knows the incentives of corporate media and how it operates. He has been in the public eye for over 50 years.
2. Donald Trump has an understanding of class consciousness, which is to say that he knows billionaires will support him if he offers favorable legislation for them.
3. Donald Trump understands that white people perceive their position of power is under threat, and that whenever white people feel threatened, they will get activated and defend white supremacy with everything they have. They've already done this multiple times in America. The existence of the KKK was a backlash to the south losing the civil war and black people participating in political and economic life.
The Democrats are a large party that is largely funded by billionaires and has a majority of white voters who are not as wedded to white supremacy as the less educated--a demographic which continues to grow as education costs grow, and advertising infests all form of affordable or free media. Conservative millionaires are also buying up local news and other media outlets to make their perspective and needs a priority.
The only way to get out of this is for the democratic party to be taken over by working people. Unions were the backbone of that party in the past but with globalization and the offshoring of jobs, many of those unions were weakened. Reagan and his privatization and anti labor perspective hurt those unions too. Now a sizeable part of the party is supported by big business. With automation increasing, unemployment will increase. This is an opportunity for the party to gain voters that are victims of the wealthy, unemployed and angry about it.
They can't vote for someone who reminds them of the boss that laid them off or who is receiving campaign donations from the company that fired them.
There are a lot of laid off tech workers, drivers, factory workers, etc. Who will also get their welfare slashed when Trump is in office. If someone who refuses wall st money, is not a fukking lawyer or business owner like 90% of democrats it feels like, he's going to get a lot of support if he speaks to these issues that people are feeling. Especially if he himself can say "hey, on the salary I make I can't buy a house either. I'm not okay with that and we are both tired of being told that it isn't that big of a deal or that the economy is improving. Yeah its improving, for the people who bought stocks before many people were even old enough to vote"
Promise people free education
Promise to raise taxes on the wealthy and cut government waste.
Promise people jobs
Offer to NEGOTIATE better deals with China. Not threaten, not bully, negotiate. People are stupid but if he says
"everybody watching RIGHT NOW look for 5 items you can hold in your hand that you bought from the store. Now tell me how many of them have a 'made in America' label on them? Exactly. They're making our stuff, the last thing we should be doing is telling them to stop when we don't have the people to copy their manufacturing ability. We have robots, sure, but I don't want robots doing the work that anyone listening or watching wants to do, and wants to do for a fair wage like the old days"
That shyt will resonate with a LOT of voters.
Couple that in with telling people that the ultra wealthy could fund Medicare for all without seeing a change in their lifestyle and that ngga will get people activated. Especially with how fukking FURIOUS they are at health insurance companies. It's possible. If Donald Trump could win in 2016 with most of Hollywood and tons of donors against him, a liberal who speaks to the same concerns, is younger, and doesn't have the stink of the professional managerial class on him gets going, his charisma will be enough to dominate any room he's in and make establishment democrats look out of touch and completely untrustworthy. Couple that in with Trump's failures he can highlight, that's a slam dunk.
The next president is out there, he just hasn't been radicalized yet. It's going to happen within the next 4 years. A lot of people are going to have that "fukk it what do I have to lose" energy and will try to get into politics.