It seems that Trump’s art of dealing often included threats and/ or the reality of bankruptcy and stiffing the people he owned money to. I was present at the conclusion of a Frank Sinatra dealing. Like Sinatra himself, it was the Epitome of Cool.
There’s a new book out by a former manager of Frank Sinatra. In it, Eliot Weisman tells of having brokered a deal to have Sinatra open Trump’s Taj Mahal Casino in Atlantic City; but before the contract was actually signed, Trump’s Casino Manager was killed in a helicopter crash.
Trump, fresh from hitting it big in his ghost-written book, THE ART OF THE DEAL, decided to renegotiate himself with Sinatra’s agent.
Weisman came back to Sinatra with Trump’s new deal demands. He would pay Frank less money. Sammy Davis Jr., who had just been diagnosed with cancer at the time, would not be on the bill; nor would Steve and Edyie, who Trump said he never heard of.
Sinatra gave his agent two choices. Tell Trump to go @#^@ himself, (an act which is anatomically impossible even for Trump), or just give Trump’s phone number to Frank so Frank could tell Trump himself.
Sinatra played The Sands in Vegas those dates and Trump opened his casino without Sinatra.
Eventually, Trump did something nobody thought was possible. He butchered the running of his casino to the point where he declared it bankrupt and closed it down. How can anybody with first count on the money ever go broke running a casino? Maybe the juice off the top demanded by his partners was too exorbitant, you think?
Like most performers, Sinatra didn’t have much time for promoters. The promoter that booked Sinatra in the Minneapolis Auditorium tried to do some late fast shuffling on Frank and almost lost the event.
The promoter’s rep, who didn’t like the promoter anymore than we did, told us the outcome of the promoter’s finagling. Sinatra told the promoter that not only would the deal stand as verbally agreed to, there would be one additional clause added to the rider. The promoter would have a new baby grand in the in the dressing room next to his, or Frank would go with another promoter for the Minneapolis gig.
‘No problem’, the promoter told Frank.
‘And’, added Sinatra, ‘At the end of the show, the piano belongs to me’.
The promoter sputtered and stammered, pointing out how much a baby grand piano costs.
Sinatra pointed out the original deal should have been honored, and if there was anymore arguing, it will be a concert grand instead of a baby grand.
It was a sell out performance. Even with the additional cost of the piano, the promoter still came out okay. Sinatra gave a full concert and encore after encore after encore.
We were breaking down the show when Sinatra came on stage, as he did in the smaller venues. He shook our hands, thanked and tipped us. And, unlike most entertainers, Frank never believed in having a roadie throw us a T shirt as a tip. He was a one of the last holdouts to the old school of giving cash for a for a tip.
Then he handed Mark, the house carpenter, a piece of paper. ‘The piano movers will be in first thing in the morning,’ Frank explained. ‘Here’s the address where the piano gets delivered to.’
‘Wow!’ said Mark said, reading the address out-loud. ‘The St. Joseph’s Children’s Orphanage in St. Paul. okay!’
‘And remind the movers not to tell the Orphanage where it came from,’ Sinatra said. ‘Just tell the good sisters they owe the donor a Rosary or two.’
He thanked us again and walked off the elevator to the garage.
Sinatra had a reputation of being one of the most generous celebrities around, even though he tried to keep his giving a secret.
Trump, on the other hand, brags about his charity giving; but there are a lot of organizations that he said he gave to are still waiting for the first dollar.
And that’s a wrap.
Don Ostertag: Off Stage 
I always thought of Sinatra as a jerk and loudmouth which seems expected if one is going to do it “my may”. This is a fine story about him I enjoyed hearing. Thanks for that, Don. I love your stories.
Thank you Cindy. I feel the same about MY WAY. And so did Sinatra. He did not like the egotistical lyrics Paul Anka put to an olad French melody, but recorded as a favor to Anka. The acceptance by the fans surprised him.
Sinatra fought for civil rights also. Was responsible for breaking the color line in the Vegas Casinos among other things. A song i identify with him is THE HOUSE I LIVE IN (THIS IS AMERICA TO ME}. Great clip of the documentary on UTube.
I always look forward to your fascinating insights. What a great story.
Thank you Gwen. Believe me, we have a mutual admiration.
Frank was a character. He could be very gracious and generous – and the opposite a bit later.
I admired him as a entertainer to ber sure. A good actor – a great song stylist.
I sometimes think people who give generously should tell. I know that seems unhumble, but I believe it encourages others to give also.
Good point about encouraging others to give.
Wouldnt it be fabulous to know if any pianists out there started their lessons on this piano :).
Cool thought, Charlotte.
There’s always sorts of stories about Sinatra, some horrible and some really cool. No doubt horrible people would do these kinds of deals to make word get out that they’re really an alright type of guy but plenty more wouldn’t bother. I think the truth is somewhere in the middle but whatever it was a great story and one I can take your word for. Thanks for sharing Don.
Makes sense, Lloyd