Apparently, Ol’ Blue Eyes was another person that thought Donald Trump was ‘Somethin’ Stupid’. According to Eliot Weisman, Sinatra’s former manager’s new book, The Way it Was, Sinatra was so furious at Trump’s attempts to change a deal he had at Trump’s Taj Mahal in Atlantic City, that Sinatra told him to go f’ himself.

Trump felt the deal was way too pricey. In 1990, Frank was supposed to perform for 12 concerts, and Trump felt it was for too much money. Weisman writes that at the time, they had a deal already in place with former casino operator Mark Etess. When he was killed in a helicopter accident, Trump stepped in to finish the deal. Newsweek

Besides lowering the price for Sinatra’s performances, Trump had a few other demands. First of all, he wanted Sammy Davis Jr. out of the shows. At the time, Sammy was dying of cancer, and Trump felt he was just dead weight on stage. He also wanted to yank sixties favorite duo Steve and Eydie. These were all Frank’s dear friends and he took offense at the thought of working without them.

The singer was not amused and Sinatra gave Weisman two choices: to tell Trump he should go f*** himself on Sinatra’s behalf, or to give Trump’s phone number to the American pop singer so he could personally call Trump himself to tell him to go f*** himself. Newsweek

The deal never went through. Trump decided to play the Sands in Las Vegas instead. Like many of Trump’s projects, the Taj Mahal was a failure before the first jack pots rang out. Trump started building it in 1990, for one billion dollars. At the time Trump called it “the eighth wonder of the world”. But that one billion dollar was built on debt. And when the casino failed to bring in money, that debt just got bigger. When Sinatra cussed out Donald Trump, he was just starring at the sky praying for “Pennies from Heaven”.