Why Sinatra Told Donald Trump to “Go Eff Yourself”

Posted on: May 9, 2025, 08:31h. 

Last updated on: May 9, 2025, 10:08h.

Corey Levitan Read More
Expertise: Commercial Gaming, Entertainment, Expert Insight, Las Vegas, Restaurants, Las Vegas Myths.
  • When the president of Trump’s Taj Mahal died before the casino opened in 1990, Trump himself took up negotiating a deal to procure Frank Sinatra for its opening residency
  • It didn’t go well

Last month, we told you why Keith Richards of the Rolling Stones pulled a knife to get Donald Trump evicted from his own casino. Turns out, Frank Sinatra had his own casino-related run-in with America’s future president.

Frank Sinatra had some choice words for Donald Trump when he tried dictating the terms of his opening residency at the Trump Taj Mahal in 1990. (Image: Shutterstock and CNN)

Ol’ Blue Eyes was tentatively booked to open the Trump Taj Mahal Casino in Atlantic City with 12 shows in April 1990. Negotiations began the previous year with the venue’s original operator, Mark Grossinger Etess.

But when Etess died in a tragic helicopter crash in October 1989, Trump decided that he now had the power to dictate contract terms to Sinatra.

That’s never a safe thing to assume regarding Frank, whose power derived not only from his worldwide celebrity but from his friendships with some very dangerous characters.

This story comes from “The Way It Was: My Life with Frank Sinatra,” a 2017 tell-all written by Eliot Weisman, Sinatra’s manager from 1975 until the legendary crooner’s death in 1998. It was also verified by Sinatra’s daughter, Nancy, just this week. 

The Trump Taj Mahal operated in Atlantic City from April 1990 to October 2016. Initiated (and named) in the mid-1980s by Resorts International, it was taken over by Donald Trump in 1987 when Resorts International hit a financial rough patch and Trump acquired a controlling stake in the company for $79 million. (Image: Shutterstock)

While meeting with Weisman at Trump Tower in November 1989, Trump immediately took issue with Sinatra’s fee, which Weisman said he characterized as “a little rich.”

Trump also demanded that Sinatra cut his opening acts. They included Liza Minnelli, Steve Lawrence & Eydie Gorme — whose names Trump claimed not to even recognize — and Sinatra’s close friend and fellow Summit member, Sammy Davis Jr.

Davis had just been diagnosed with the throat cancer that would take his life a few months later.

Weisman relayed Trump’s demands to Sinatra.

Ol’ Red Eyes

“You’ve got two choices!” Sinatra told Weisman, according to his book. “Either you go up there and tell him to go fuck himself or give me his number and I’ll do it!”

Weisman chose the latter, as he figured he was supposed to.

“I rode the elevator back up and walked into his outer office,” Weisman wrote. “Before his assistant could stop me, I poked my head in through the door. He looked up at me and we made eye contact.”

Sinatra says go fuck yourself!” Weisman recalls saying as he walked out before Trump could even process the information.

Sammy Davis Jr. in 1967. Sinatra always had his friend’s back. (Image: Milton Greene/GQ)

Before Weisman even left Trump Tower, he called Jay Venetianer, the booker at one of the Taj Mahal’s largest Atlantic City competitors, the Sands. Weisman called a meeting for Florida the next day. He told Venetianer that he had better bring his checkbook.

Venetianer complied and signed an exclusive, $10 million deal with Weisman’s Premier Artists for Sinatra, Davis, Minnelli, and Steve & Eydie.

Reporter David J. Spatz’s unnamed sources were quite good for him to have published the following in his column in Atlantic City’s The Press newspaper on March 22, 1989 …

“For nearly six months, Weisman had been negotiating a package deal that would have put Sinatra, Minnelli, Lawrence, Gorme, and Davis under exclusive contract to the Trump organization. But that deal, which was originally being brokered by the late Taj Mahal president Mark Grossinger Etess, fell apart about a month after Etess and two other Trump executives died in the crash of a chartered helicopter.

Sources inside Trump said the company was concerned about spending so much money on the deal because they felt Minnelli and Davis weren’t particularly big attractions at the blackjack and craps tables. But sources close to the Sands and Premier Artists said clashing personalities — and not money — doomed the deal with Trump.

The Trump Taj Mahal, the largest casino hotel in Atlantic City, opened with Elton John headlining its 6,000-seat Mark Etess Theatre.

Though it would have been just desserts for Sinatra to have debuted at the Sands on that very same night, he didn’t make his first appearance under his new contract until October 5.

Unexpected Call

Eliot Weisman promotes his book about managing Sinatra in 2017. (Image: thewayitwasinc.com)

Weisman never expected to hear from Donald Trump again in his life. (After all that, would you?)

But in 1995, his assistant told him she had Trump on the line.

“Hey, Eliot, how are you doing?” Weisman recalled Trump asking convivially, as though nothing bad had ever happened between them.

“The Mar-a-Lago club is opening and I need some talent,” the future president continued.

I wanted to hang up,” Weisman wrote, “but obviously, I had an obligation to my clients.”

He recalled telling Trump that Don Rickles was available.

“Good,” Trump replied. “Who else?”

Weisman shot back: “You can have Steve and Eydie — if you know who they are now.”

Weisman was having difficulty keeping his temper in check, and Trump could tell.

“What are you upset about?” Trump asked him. “You know, you should be thanking me.”

“Thanking you?” Weisman recalled saying. “For what?”

Trump replied: “If it wasn’t for me, you would have never had that great run at the Sands.”