From Celebrity Feuds to Casino Hotel Luxury: Why Sinatra’s Boldness Defines the High-Stakes Lifestyle

When the president of the Taj Mahal passed away before the venues grand opening in 1990, Donald Trump took direct control to ensure his new casino hotel would become a world-class destination. To cement its status, he engaged in a high-stakes celebrity negotiation to book the legendary Frank Sinatra for an inaugural residency. However, the negotiations took a sudden turn and did not end well, leaving the future of the star-studded casino hotel atmosphere in uncertainty.

Last year, we discussed an incredible incident when Keith Richards of the Rolling Stones pulled a knife to have Donald Trump evicted from his own casino. Surprisingly, Frank Sinatra had a similar, albeit more explosive interaction with America’s future president.

Sinatra was set to kick off at the Trump Taj Mahal Casino in Atlantic City with twelve scheduled performances in April 1990. The groundwork for this monumental opening had been laid the previous year by the venue’s original operator, Mark Grossinger Etess.

Tragically, Etess died in a helicopter crash in October 1989, and suddenly, Trump believed he had the authority to dictate terms to Sinatra.

The notion of dictating to Frank Sinatra was, as one might expect, a precarious position. Frank’s influence and power extended well beyond his renowned singing career, thanks to his connections with some formidable individuals.

This entire saga has been recounted in Eliot Weisman’s 2017 tell-all, The Way It Was: My Life with Frank Sinatra, which Weiseman penned after managing Sinatra from 1975 until the Rat Pack icon’s death in 1998. Sinatra’s daughter, Nancy, confirmed the retelling of these events just this past week.

When Trump met Weisman at Trump Tower in November 1989, he immediately criticized Sinatra’s fee, which he deemed “a little rich.” He also insisted Sinatra should cut his supporting acts, which included the likes of Liza Minnelli, Steve Lawrence, and Eydie Gorme—names Trump claimed to not even recognize. He also wanted to eliminate Sam Davis Jr., a close friend of Sinatra’s, who was already battling throat cancer at the time.

Weisman communicated Trump’s unreasonable demands to Sinatra.

Ol’ Red Eyes

In response, Sinatra shot back: “You’ve got two choices! Either you go up there and tell him to go fuck himself or give me his number and I’ll do it!”

Weisman decided to relay Sinatra’s message rather than confronting Trump directly.

“I took the elevator back up and strolled into his outer office,” Weisman recounted. “Before his assistant could stop me, I peeked into Trump’s office, and we made eye contact.”

“Sinatra says go fuck yourself!” was how Weisman exited the meeting, leaving Trump in stunned silence.

Just before Weisman departed Trump Tower, he reached out to Jay Venetianer, a prominent booker at a major competitor, the Sands. Weisman quickly arranged a meeting for the next day in Florida and informed Venetianer that he would need to bring his checkbook.

Venetianer was quick to comply, subsequently signing a lucrative $10 million agreement with Weisman’s Premier Artists for Sinatra, Davis, Minnelli, and Steve.

An unnamed source for reporter David J. Spatz provided further insight and confirmed that Weisman had been negotiating a package deal with Sinatra, Minnelli, Lawrence, Gorme, and Davis for nearly six months under the Trump organisation. However, the deal disintegrated shortly after the fatal helicopter crash that claimed Etess and two other executives.

Staff within the Trump organization expressed concern regarding the financial commitment but attributed the deal’s failure to personality clashes rather than money.

The Trump Taj Mahal opened as the largest casino hotel in Atlantic City featuring Elton John as its inaugural headliner.

Though it would have been an ironic twist for Sinatra to debut at the Sands that same night, he did not make his first appearance under his new agreement until October 5.

Unexpected Call

Weisman never anticipated that he would hear from Donald Trump again after their explosive encounter. But in 1995, his assistant unexpectedly informed him that Trump was on the line.

“Hey, Eliot, how are you doing?” Trump greeted as though nothing had transpired between them.

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

Weisman reflected, “I wanted to just hang up, but I had responsibilities to my clients.”

Weisman suggested Trump could book Don Rickles, to which Trump swiftly responded, “Good. Who else?”

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

Throughout this interaction, Weisman struggled to maintain his temper, prompting a curious Trump to ask him, “What are you upset about? You should be thanking me.”

“Thanking you?” Weisman shot back. “For what?”

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