The whole reason he is where he is boils down to the fact that he spent decades building a cult of personality, and he happens to be a world-class, shameless liar. It is the kind of trait you see in high-functioning psychopaths who can look you dead in the eye and invent reality on the spot.

Look at his actual track record. Every single business venture he has touched has cratered because he treats companies like cash cows to bleed dry, taking his cut and running right before the whole thing collapses. The genius businessman myth is total fiction. He is not a visionary operator. He is just a walking billboard for everything broken about American culture, where a massive chunk of the population is genuinely fine lighting their own lives on fire as long as they think the people they hate are getting hurt worse.

His entire M.O. is a constant loop of whining about being the victim while giving everyone else an excuse to be absolute garbage human beings. He built an entire movement out of spiteful, miserable assholes who were just waiting for someone to give them permission to lean into their worst impulses and call it fighting back.

Because winning elections has little to do with what policies you propose. This is something liberals at least struggle greatly to understand. It's what gets the Democrats nominating unlikable unelectable candidates because they have an impressive resume and a website full of consultant-written policy papers. Voters know that no policy proposal survives election day, so what policies you're running on means very little. What matters is your vision and general vibe. That's what actually wins elections, not being the smartest or the most qualified. You can bitch and moan all you want about this reality, but it won't change a damn thing.

Trump beat Clinton even though Clinton had a resume and intelligence that blew Trump's out of the water. He did so because Clinton came across as unlikable and inauthentic. He had a vibe voters liked, Clinton didn't.

He's just really good at working a crowd. You could certainly see that in the beginning. He shamelessly and with great passion just spits out things he heard, be them true or not. Sometimes he gets a boo. That subject is dropped and when a reporter asks he'll just flat out deny it was even mentioned. If something gets a reaction he runs with it. After some time he got a bunch of subjects that he could really hammer to make the crowd go wild and then he takes them national. And if those things don't work in practice that's a worry for another time.