Frank Sinatra and Donald Trump had a brief, tense business encounter in the late 1980s/early 1990s, but Sinatra reportedly disliked Trump and never considered him a close friend or ally.

How They Were Connected

Trump and Sinatra crossed paths in the world of casinos and entertainment in Atlantic City, New Jersey. In 1990, Trump was preparing to open the Trump Taj Mahal casino and wanted Frank Sinatra to headline the opening shows. Sinatra’s manager, Elliot Weisman, was negotiating the deal, which included a series of performances and appearances by other Rat Pack–era stars like Steve and Eydie and Sammy Davis Jr..

The “Go F*** Yourself” Incident

According to Sinatra’s former manager Elliot Weisman in his 2017 memoir The Way It Was: My Life with Frank Sinatra , Trump tried to renegotiate Sinatra’s fee after the original deal was nearly done, calling the cost “a little rich”. Trump also wanted to cut out the opening acts, including Sammy Davis Jr., who was seriously ill at the time.

When Weisman told Sinatra what Trump had said, Sinatra’s reported response was blunt: he told his manager he had two choices — either tell Trump to “go f*** yourself,” or give Sinatra Trump’s phone number so he could say it himself. The deal was then canceled, and Sinatra never performed at the Taj Mahal opening.

Sinatra’s Daughter on Their Relationship

Frank Sinatra’s daughter, Nancy Sinatra, has publicly stated that her father “loathed” Donald Trump. She made this comment in 2025 on social media, responding to actress Mia Farrow (who was once married to Sinatra) saying that Frank would have hated Trump.

Nancy clarified that her father actually did loathe Trump, not just that he would have. She later added that she hoped Trump would do his best as president, saying she didn’t believe anyone set out to be a bad president, but that didn’t change her father’s feelings about him.

Trump’s Later Use of Sinatra’s Image

Despite Sinatra’s reported dislike, Donald Trump has often invoked Frank Sinatra’s legacy. At his 2017 inauguration, Trump used Sinatra’s signature song “My Way” as the soundtrack for his first dance at the inaugural ball.

In 2020, Trump gave a speech at Mount Rushmore where he praised Sinatra and suggested he should be included in a future monument to American heroes. That’s when Nancy Sinatra and Mia Farrow made their comments about how much Frank would have disliked Trump.

Sinatra’s Own Words (via Trump)

On the Howard Stern Show in 2014, Trump told a story about dining with Sinatra in Monte Carlo, describing him as a volatile, intimidating figure when drinking. Trump recalled that Sinatra had a huge fight with his wife at dinner, then later angrily told a young fan who asked for a photo, “Get this guy out of here”. Trump used this anecdote to paint Sinatra as a tough, old‑school star — not as a personal friend.

Summary of Their Relationship

  • Business clash : Trump tried to renegotiate Sinatra’s performance deal for the Trump Taj Mahal, calling the price “a little rich”.
  • Sinatra’s reaction : He reportedly told his manager to tell Trump to “go f*** yourself” or give him Trump’s number so he could say it himself.
  • Personal feelings : Nancy Sinatra has said her father “loathed” Trump, and there’s no evidence they had any real friendship.
  • Trump’s use of Sinatra : Trump later embraced Sinatra’s image and music (especially “My Way”) for his own events, despite Sinatra’s reported disdain.

So, while Trump has often referenced Sinatra as a symbol of American success and swagger, the historical record suggests Sinatra himself had little respect for Trump and considered him a difficult, lowballing businessman.

Information gathered from public forums or data available on the internet and portrayed here.