The Real Reason Frank Sinatra Hated Donald Trump

When Donald Trump took to the podium for his Fourth of July speech at the base of Mount Rushmore on the eve of America's 244th birthday in 2020, he told his audience that he plans to create the "National Garden of Heroes," which will feature the likeness of numerous "giants of our past" (per the Daily Mail). Trump plans to create "a vast outdoor park" that'll be open to the public in time to honor the 250th anniversary of the Declaration of Independence.

"We gave the world the poetry of Walt Whitman, the stories of Mark Twain, the songs of Irving Berlin, the voice of Ella Fitzgerald, the style of Frank Sinatra, the comedy of Bob Hope, the power of the Saturn V rocket, the toughness of the Ford F-150, and the awesome might of the American aircraft carriers," the president said. "We will raise the next generation of American patriots. We will write the next thrilling chapter of the American adventure. And we will teach our children to know that they live in a land of legends, that nothing can stop them, and that no one can hold them down."

Yet, while Trump boasted about America's robust culture, his remarks sparked backlash among Sinatra's surviving relatives. "Frank Sinatra would have loathed Donald Trump," actress Mia Farrow tweeted about her former husband. Nancy Sinatra, the crooner's daughter, replied, "He actually did loathe him." And, as his former manager can confirm, said assertions about the "My Way" singer are right on the money.

Frank Sinatra had his manager tell Donald Trump to 'go f**k himself'

Having managed singer Frank Sinatra from the mid-1970s to the late '90s, Eliot Weisman was intimately acquainted with Ol' Blue Eyes' personal and professional opinions. Thus, when Weisman published 2018's The Way It Was, his tell-all about life alongside Sinatra, he revealed that the crooner's personal opinion of Donald Trump plummeted after their professional deal collapsed.

As Weisman wrote (per Independent UK), Sinatra was scheduled to perform at Trump's Atlantic City casino in 1990. Sinatra had a deal in place with the Taj Mahal's original operator Mark Grossinger Etess, but he died in a helicopter crash before details were finalized. Trump stepped in, but the star's fee for the proposed 12-show residency was "a little rich" for the magnate, so he attempted to renegotiate. In particular, Trump refused to pay for the additional acts involved with the show, which included Sinatra's Rat Pack pal Sammy Davis, Jr. and vocal duo Steve and Eydie.

Weisman called Sinatra to convey the developments and Sinatra apparently gave his manager only two options: tell Trump to "go f**k himself," or give Sinatra the now-president's phone number, so he could do the deed himself. Weisman subsequently told Trump, "Sinatra says go f**k yourself!" and the crooner played at the Sands in Las Vegas instead. While Trump has been known to hold a grudge, he clearly hopes to use the memory of Sinatra to further his latest executive order to erect new statues.