You are on the money with this one.
My favorite example of this showing through was when Bill O'Reilly interviewed him during the superbowl. He tossed him a softball that most presidents would have whacked at to say the United States as a democracy is more virtuous than countries like Russia[1].
But he didn't. His response was, "do you think our country is so innocent"?
The reason he became popular is the country had also grown cynical. The mainstream media wanted to anoint Jeb "Please Clap" Bush and another Clinton. That was the setup he walked into in 2016. A repeat of Bush v Clinton. America was over it.
He is not dumb. But he is clearly not that intelligent. It doesn't take much to be a cynic. He's not even a particularly good one. He's what he has always been - a salesman, really a con artist. But he's not dumb. To be a good con artist you have to be able to read the room. That is arguably, what he is (or has been) best at. It's why his debate performances especially in 2016, shallow as they may have been, were still a masterclass in dismantling the Republican field. "You'd be in jail" and bringing Clinton's own victims to the debate were more memorable than anything Hillary said. He knows how to win. There is intelligence in that. Cynic may not even be the right word. I think he's more of a nihilist. And given how his wealth has increased while in office, he's accomplishing his goals at pretty remarkable speed. The rest is just set dressing. He'll do on AI whatever whoever at Mar-a-Lago writes the biggest check tells him to do.
The guy watched Citizen Kane and his takeaway was "what a great guy and what an incredible life he lived."