I'm waiting for the Area 51 files!
Say what you like about the man, he's got a great sense of showmanship. And maybe the best deadpan comic delivery since Leslie Nielsen. It was really weird seeing him work the fryer at McDonalds, because he was simultaneously totally sincere - the man loves McDonalds and you could sense his childlike joy at being there - and also in on the joke.
A savvy Bill Clinton era Democrat might have pulled the same stunt and made it work, but I'm not sure there are any of them left. Try imagining Gavin Newsom doing it and not looking like the world's biggest fake.
If you listen to Trump voters, which most lefties don't - yes, he has enthusiastic fans, as you'd expect with someone who was a celebrity for decades before he was a politician. But lots of his voters are very transactional and many think he's kind of an asshole. They're just prepared to hire an asshole to do some work for them, like you would hire a sleazy lawyer to handle your messy divorce.
The question might be - which is easier, push the Republicans to moderate their unpopular stances, or hope that the Democrats start to acknowledge material reality? Team-based thinking is maybe not helpful here.