To be fair Trump has always played into the rich villain character with the media even in the 1990s… well before his formal entry to politics in the 2000s when the media realized they had a wall-to-wall supervillain story on their hands.
But before he was president he was uncontroversially pretty popular in NYC. Even when playing the villain to the local gov/media. It’s difficult or impossible to disconnect this reality from national perceptions well beyond NYC. He was a president of the United States after all. He’s not just a local. That changes the stakes 1000x fold.
