Once you realize he's stupid, it all makes sense.
When he built Trump Tower back in the 1980s, Jackie Kennedy was New York City's most beloved resident. She was famous for her efforts to save Grand Central Station and her love of great old buildings.
Trump personally promised the head of the biggest museum in New York that he'd preserve the façade of the building he was demolishing to put up his Tower. He lied and razed the place to the ground.
The most desperate ass kisser on the planet threw away a chance to get in good with America's living Queen because he was greedy and stupid.