In a soon to be released book, The Way it Was, written by Eliot Weisman, it is clear that there was no love lost between Frank Sinatra and Donald Trump. Weisman, who was Sinatra’s manager from 1975 until the singer’s death in 1998, tells the story of a deal gone bad. Apparently, back in the '90s Sinatra and good friend Sammy Davis Jr. had a deal to perform at Trump's soon to be opened Taj Mahal casino in Atlantic City, but when Mark Grossinger Etess, the Trump executive of the Taj Mahal, died in a helicopter accident, Trump reneged on the deal, wanting to pay less money and drop Davis from the act.
Sinatra's response to the lesser deal?
Tell Trump to go fuck himself.
Sinatra then went on to perform for the competition, The Sands Casino.