There was an interesting Politico article with an interview of Sharpton (after he had been interviewed about Trump in the NY Daily News back in January), and he made an interesting comment (being a NYer himself) -
<...>
Donald Trump was a Queens guy, says Sharpton, who hails from Brooklyns Brownsville, the citys toughest neighborhood, a collection of housing projects jammed hard between Queens and the Jamaica Bay swamps and the scene of an all-out crack war in the 1980s and 90s.
His father was a successful real estate guy, but they were Queens guys.
They were outer borough [and] had to break into the big Manhattan aristocracy. He was an outsider rich, but an outsider. He was not part of the Manhattan elite. So, he always had this outsider feeling us against them. So, in many ways, when I read people talk about, Well, do you have a billionaire as a populist? He does feel like hes one of the guys who was shut out.
Then, in a hint of a kindred spirit, Sharpton says: On the other side of the coin
I was shut out because of race. He was shut out because of geography and a number of other things. [Its an] unforgiving environment, and a city that could easily swallow you up. Easily.
<...>
http://www.politico.com/story/2016/02/sharpton-trump-is-the-white-don-king-219601
So this "outsider" bit, where Trump has bulldozed his way into Manhattan in garish fashion as a noveau riche, fits with his apparent never-ending quest to not only be accepted by old money NY, but to be "better than them". And so all the massive behind the scenes schemes to present his own manufactured "imagery of wealth" seems to point back to this.
It's literally like the film Citizen Kane - just substitute the Hearst-type/publisher figure with the Trump/real estate figure.
But what he never "got" (as in the reality) was that the true "blue bloods" are not conspicuous consumption types and he is everything conspicuous and more, to the point of tacky. Which reinforces the disdain for him by the very people he is trying to be a part of.