The very first time Trump’s name was in a major newspaper was in the 1970s when The New York Times reported on the Nixon administration suing Trump and his father for racist housing policies in the apartment buildings they owned in NYC.

Then in the 80s he was the model for Biff Tannen, the villain in the Back to the Future movies. He was parodied by everyone from The Simpsons to MAD Magazine to SNL as the epitome of the sleazy 80s business guy.

No, he was never cool except to a very small slice of people who the sleazy 80s business guy aesthetic appeals to, and nobody thinks those guys are cool.