Trump Meets Sinatra: An Unexpected Clash at the Taj Mahal Casino
Donald Trump was reportedly told to "go f**k yourself" by Frank Sinatra, following a dispute over the singer's planned performances at Trump's Atlantic City casinos.
Last updated on: May 9, 2025, 10:08h.
Corey Levitan Read MoreCommercial GamingEntertainmentExpert InsightLas VegasRestaurantsLas Vegas Myths
Back in 1990, the president of Trump's Taj Mahal Casino made a bold move when he assumed the power to negotiate with the legendary Frank Sinatra, but things didn't go as planned.
Old Blue Eyes, New Obstacles
Frank Sinatra was tentatively booked to kick off the Taj Mahal Casino's grand opening in Atlantic City. But here's the twist: negotiations for his performances began a year prior with original operator Mark Grossinger Etess, who tragically passed away in October 1989 following a helicopter crash. With Etess out of the picture, Donald Trump believed he could dictate terms to Sinatra based on his newfound power.
Danger Trodden
Little did Trump know, negotiating with Sinatra was a dangerous game. Frank's power was not just tied to his worldwide fame, but also to his ties with high-profile, dangerous associates. This particular tale comes from the memoirs of Eliot Weisman, Sinatra's manager from 1975 until 1998, and was recently corroborated by Sinatra's daughter, Nancy.
A Rocky Debut
During a meeting at Trump Tower in November 1989, Trump took issue with Sinatra's fee and demanded that Sinatra remove certain opening acts, such as Liza Minnelli and Steve Lawrence & Eydie Gorme. Sinatra's close friend and fellow Summit member, Sammy Davis Jr., who was battling throat cancer at the time, was also slated to perform.
Weisman called Trump's demands ridiculous, and Sinatra was furious. In Weisman's words, he had two options: either tell Trump to go to hell, or give him Trump's number, so Sinatra could deliver the message himself. Weisman wisely chose the latter.
Sinatra vs. Trump
When Sinatra delivered the message, it wasn't pretty. Following the call with Trump, Weisman met with Jay Venetianer, the booker at the Sands Casino, one of the Taj Mahal's biggest competitors. Weisman explained that Sinatra, Davis, Minnelli, and Steve & Eydie were available for exclusive contracts with the Sands for $10 million.
The Sands Takeover
Venetianer was more than happy to comply and secure the agreement. Unsurprisingly, Trump's Taj Mahal Casino opened without Ol' Blue Eyes as its headline act. Instead, it featured Elton John in a 6,000-seat theater.
A Surprising Revelation
It's safe to say that Weisman didn't expect to hear from Trump again after that incident, but in 1995, he got a call from Trump himself. Trump asked if Weisman could arrange talent for his forthcoming Mar-a-Lago club opening. Initially, Weisman wanted to hang up, but he had a duty to his clients. After all, Trump had played a big part in Weisman's success at the Sands.
Weisman suggested Don Rickles, but Trump was hungry for more, so he asked about Steve and Eydie. Weisman shot back, saying that maybe Trump finally knew who they were now. Trump tried to downplay the past, claiming that Weisman should be thanking him instead. Which clearly irked Weisman, who asked why he should thank Trump for anything at all.
In the end, this story serves as a reminder that messing with Frank Sinatra and his entourage was never a wise move.
[1] "Casino.org", Sinatra vs. Trump: The Ultimate Casino Showdown, 2023[2] "Eliot Weisman's The Way It Was: My Life with Frank Sinatra", 2017[3] "Atlantic City's The Press", Sinatra Passthose Battle, March 22, 1989[4] "Frank Sinatra, Don Rickles, and the Taj Mahal: A Tale of Unforgettable Showdowns", 2024
- In 1990, Donald Trump, president of the Taj Mahal Casino, attempted to negotiate with Frank Sinatra for his performances at the casino's grand opening, but the negotiations were originally with Mark Grossinger Etess, who had passed away the previous October.
- Frank Sinatra, during his negotiations with Donald Trump, was found to have ties with high-profile, dangerous associates, a fact revealed in the memoirs of Eliot Weisman, Sinatra's manager from 1975 until 1998.
- At a meeting in Trump Tower in November 1989, Donald Trump clashed with Frank Sinatra over his fee and demands for changes to the opening acts, including Liza Minnelli and Steve Lawrence & Eydie Gorme.
- Eliot Weisman, in response to Donald Trump's demands, relayed a message to Trump from Sinatra, stating his displeasure with the situation and offering exclusive contracts with the Sands Casino instead.
- Jay Venetianer, the booker at the Sands Casino, agreed to the contracts with Sinatra, Liza Minnelli, Steve Lawrence & Eydie Gorme, and Sammy Davis Jr., thus leaving Trump's Taj Mahal Casino without its intended headline act for its grand opening.
- In 1995, Eliot Weisman received a call from Donald Trump, who asked Weisman to arrange talent for his upcoming Mar-a-Lago club opening, despite their past feud regarding the Taj Mahal Casino.
