I was taking on the role of husband the second time around, with renewed hope and enthusiasm. I was determined to spend as much time as possible with my bride, despite a rigorous travel schedule. When it was feasible, Maria joined me on tours and became part of the extended traveling family. My personal life changed and my professional life was about to undergo a major alteration as well.
The Italian tour was considered a tremendous success. The concerts were sold out, the reception was warm and welcoming everywhere we went, and the audiences were enthusiastic. What more could we want? At least that’s what I thought. The change in our accommodations from the villa to the Hotel de Paris, the move, and travel distances all added up and the tour was in the red. When Sinatra discovered that he did all that work and lost money, he was furious. Rudin never even paid me.
While trouble brewed between Sinatra and Rudin, I was focused on our next stops, most notably at New York’s Carnegie Hall. The hall is among the most prestigious and famous concert halls in the world and is a reverential space for many performers. Frank Sinatra was awed by the history of Carnegie Hall. “Do you know how many ghosts live there?” he would say, referring to the many great artists who had performed on that stage. I wondered whether he ever stopped to think about the history he made, but he was too busy making it to properly reflect on its significance.
Carnegie Hall is an intimate space. There are only 2,804 seats in the main auditorium, spread out over five levels. For an artist who is used to performing in large arenas, standing on what is now called the Ronald O. Perelman stage, in the Isaac Stern Auditorium, is like singing in someone’s living room. The audience can see you sweat.
Carnegie Hall was built by Andrew Carnegie in 1891, on Seventh Avenue between Fifty-Sixth and Fifty-Seventh Streets, in what at the time was an underdeveloped section of upper Manhattan. As he placed the cornerstone, Carnegie said, “It is built to stand for ages, and during these ages it is probable that this hall will intertwine itself with the history of our country.”
Some of the world’s greatest musicians have performed on its stage, including Gustav Mahler, Leopold Stokowski, and Maria Callas, not to mention Louis Armstrong, Billie Holiday, Judy Garland, and the Beatles, the greatest artists across all genres. Woodrow Wilson, Mark Twain, and Booker T. Washington also appeared at Carnegie Hall, putting it at the heart of America’s intellectual past. With its soft white walls, red seats, and superb acoustics, many performers have dreamed about gracing its stage.
Sinatra was honored to perform along with pianist Vladimir Horowitz and conductor Leonard Bernstein at the reopening of Carnegie Hall in 1986 after a $30 million renovation effort. The hall had been returned to its former glory but with modern improvements.
Sinatra loved the renovated space and was looking forward to his eight days of concerts in September 1987. So I was surprised to see him nervous and edgy on opening night. Watching a man who didn’t flinch at flying in a plane with a faulty engine tense up before a performance had me completely perplexed. Was it his respect for the venue? Did the thought of taking the stage in this special space make him nervous? I had never seen him like this before and wasn’t sure how this was going to go.
To make matters worse, we were all on edge. Barbara wanted Sinatra to stop smoking, so a week or so earlier, while we were sitting in his dressing room at Bally’s Grand in Atlantic City, he had announced that he was quitting and no one could smoke around him. I passed on the edict and everyone in proximity to him tried to quit, at least for short stints. The whole orchestra and crew, including myself, went cold turkey when he was nearby, which wasn’t easy for anyone, especially me, considering I had been smoking since the 1950s. It became obvious that the combination of nicotine withdrawal and his respect for the hall was weighing on him.
Sinatra wanted to change into his tux early, so I kept him company in his dressing room. I watched as he carefully took off his pants and turned them upside down to hang them. I heard something drop so I looked to the floor. And what do I see there? A pack of Camels and a Zippo lighter that fell out of his pants pocket. Today I think it’s funny, but at the time we were all suffering with the Boss’s no-smoking rule and I was cranky.
“What? Are you kidding me?” I said.
He gave me a look like a kid caught with his hand in the cookie jar. As you can imagine, that was not a look that frequently made its way across his face.
“You’re making us all crazy and you’re still smoking?” I said.
“I really don’t smoke that much anymore,” he said. “I’ve really cut back.”
For his whole life Sinatra had loved to smoke, but from that point on, he smoked only on very rare occasions and not in front of Barbara or when we were with a group. I eventually quit cigarettes as well, though I still enjoy an occasional cigar.
Meanwhile, he couldn’t have picked a more stressful time to give up an old habit. His unhappiness with the results of the Italian tour was the constant undercurrent of all that was going on. On top of it, there was no love lost between Barbara and either of the Rudins. After all, it’s one thing when your wife doesn’t like your lawyer; it’s another when she doesn’t like your lawyer’s wife. Barbara Sinatra and Rudin’s wife, Mary Carol, had known each other for years and always seemed to be in competition. Barbara was a stunningly beautiful woman and Mary Carol was very attractive. Both were well known in the best Hollywood circles. They had the finest jewels and clothes, though few could outdo the baubles Sinatra bought Barbara.
They ran in different social circles, as much as that’s possible among the small cliques of Hollywood’s elite, and neither seemed to make an effort to include the other. Mary Carol was Beverly Hills establishment and treated Barbara as a newcomer. Barbara, for her part, was Mrs. Sinatra and ruled the roost wherever she went. While I never heard Barbara speak ill of Mary Carol, whenever her name came up, she never spoke well of her, either.
Mickey had his own opinions of Barbara, and would say the marriage, the fourth for Frank, would never last. Not only did he believe it to be true, but he also seemed to want it to be true. In various phone conversations we had, whenever Sinatra’s family affairs came up, he always aligned with the kids. It was well known in intimate circles that the children didn’t think the former showgirl was good enough for their father and they wanted Frank to go back to their mother, Nancy Sr.
Rudin, meanwhile, was working with Sinatra’s accountant, Sonny Golden, to have Sinatra transfer some key assets to Nancy Jr., Frank Jr., and Tina. Specifically, Rudin told Golden to initiate the process of transferring Sinatra’s “name and likeness” to the children as well as some of his recordings. My understanding is that the plans to do so had been discussed between Sinatra and his children much earlier on, but it was a long and gradual proposition to work out all the details.
One afternoon when I was in Beverly Hills, I dropped by Rudin’s Camden Drive office. He was in a meeting with Golden and the three of us talked about the bookings I had coming up for Sinatra. The conversation turned to Frank and Barbara’s finances and Rudin again made a point of defining his alliances.
“Barbara has enough with all the jewelry Frank has given her. She doesn’t need anything else,” he said to Golden and me.
Barbara knew that Rudin was siding with the Sinatra kids against her, so she was understandably suspicious of anything Rudin did that affected her financial security. Likewise, Rudin and the kids were always leery of Barbara’s motives. Years earlier, there had even been talk of Frank adopting Bobby, who was already an adult. That proposal was audacious enough to be shut down within a day or two, and while it was said to have been Sinatra’s idea, it served to fortify their mistrust of Barbara.
Given the history, it wasn’t surprising that when Golden told Barbara about the proposed asset transfer, it launched a firestorm. At some point she hired Arthur Crowley, who was famous for, among other things, securing a $20 million divorce settlement for Johnny Carson’s third wife.
While all this was going on, to my knowledge Sinatra stayed quiet, preferring to let the confrontation play out until he had all the information and was prepared to make a final decision. He trusted his advisors, of which Rudin had always been the most important. As much as Sinatra hated being personally embroiled in conflict, he was happy to have Rudin, who seemed to thrive on showdowns, handle disputes for him, such as in 1986, when Rudin sued Kitty Kelley to stop the unauthorized biography of Sinatra and then sued Barron’s for calling him Sinatra’s mouthpiece. Both lawsuits were dismissed.
People have often wondered what caused Sinatra and Rudin to part after thirty-three years together. In my opinion it was three things: Rudin maneuvering against Barbara, the clashes between the wives, and finally, the tour. Nasty letters were exchanged between Sinatra and Rudin and finally Sinatra sent him a letter that said, “We have to part ways.”
I called Rudin and begged him to go to Palm Springs and talk to Sinatra. As much as I was angry at Rudin for not paying me for the Italian tour, there was another part of me that was grateful to him for helping me arrive at my position in life. So I felt a sense of loyalty to him. I had no expectation of taking over for Rudin, and in my mind they had been together too long to let the relationship dissolve over a failed concert tour.
“Mickey, how can you just let it go? You’re friends. You’ve worked together forever. I’ll fly out and we’ll drive to the Springs together. You can work this out.”
“No. I don’t need him,” he said calmly. “I’ll work for my other clients and make more money. What are you going to do?” Rudin said.
I had been working for Frank all this time, but it was through Rudin’s office. Now he was asking me to choose between the two of them. I was not about to dissolve my relationship with Sinatra. I had way too much going on.
“I’m working on a Frank, Dean, and Sammy tour,” I said.
“That’s never going to happen. The best you’ll ever get out of him is ten shows a year at a gambling venue. You will make a big mistake if you go with him. He’s a has-been.”
To me, that was the statement of a bitter, angry man. We had come off a sold-out tour and Rudin should have known better than most that Sinatra was still standing despite having been counted out before in his career. We both knew about the failing health of the aging star, and while I’m sure Rudin knew more than I did, I believed that if handled the right way, Sinatra still had some good years left. I was determined to prove Rudin wrong.
That phone call was the last friendly conversation I ever had with Rudin. The end of the Sinatra-Rudin relationship was about to mean a new beginning for me. After a decade of working with Sinatra, I went from receiving 5 percent of Sinatra’s earnings to 10 percent overnight. Then Bobby Marx called my office.
“I spoke with Mom and she feels the two of us should come to Palm Springs. We’re all happy the Rudin relationship is done, but Frank is worried about what’s next. He asked Sonny, ‘So who’s going to book me now?’ and Sonny told him you’ve been doing it since 1978,” Bobby said.
True, I had been handling nearly all of Sinatra’s bookings, with the exception of the gambling venues, for years, but those statements made me realize that Rudin had never told Sinatra about the scope of my work. Bobby and I met in New York and took a direct flight to Los Angeles on MGM Grand, a superluxurious commercial airline owned by Kirk Kerkorian, with a first-class section that rivaled most private jets. We drove directly to Palm Springs to meet with Frank and Barbara.
The four of us spent the afternoon discussing the management of Sinatra’s career, as well as the tour that Mort Viner—Dean Martin’s agent, from ICM—and I were working on for Frank, Dean, and Sammy, which was slated to kick off in a few months. They asked questions about my career strategy for Sinatra, as well as for details about my accounting and financial background. It was pretty intense but the occasional smile on Sinatra’s face told me he was satisfied with my answers. I knew this job was as much about refereeing the family boxing match as it was about managing Sinatra. I made it clear that I would not take sides and would advise them on what I believed was in Sinatra’s best financial interests. Toward the end of the conversation, with Frank sitting there, Barbara was confident enough in Sinatra’s approval that she said, “Eliot, we would like you to be in charge of Frank’s business affairs.”
Of course, I said yes. I didn’t know whether this would be a short-term situation or a long-term one, but I hoped for the latter and was very happy to be involved. It was agreed that from that day on, Sinatra would be my priority and I would travel on every tour with him. In the process, I would be brought fully up to speed on all of Sinatra’s finances.
That evening, as we sat down to dinner in their home, Bobby started the conversation.
“My mom and the Boss wanted me out here with you to help them put together a plan to make sure everyone is protected,” he said.
“Darling, is that correct?” Barbara said to Frank.
“Absolutely,” Sinatra said.
That meant that while I was now in charge of managing Sinatra’s career, they also wanted my input on the proposed transfer of assets. Barbara was understandably nervous that Sinatra’s key assets were being given away and Sinatra was still waiting for final word from his advisors, which now included me along with Golden, before giving the green light to the deal.
Over the coming months, as I delved into the details of his finances, I was disappointed to see that Sinatra was cash-poor. He spent a lot of money and gave a lot of money to his kids. By far the most valuable assets he owned were the rights to his name and likeness, and the royalties from his Capitol recordings as well as a 20 percent ownership of Reprise Records, all of which were slated to go to the kids as part of the transfer.
Sinatra founded Reprise in 1961, when he left Capitol Records to allow himself more artistic freedom. That’s the genesis of the nickname “Chairman of the Board.” He sold the label Reprise to Warner Bros. in 1963 but retained a 20 percent stake. So, unlike most singers of the day, who only received the royalties for singing, Sinatra earned royalties as owner of the music and label, which grew to include other artists, such as Arlo Guthrie, Frank Zappa, and Fleetwood Mac.
As I gathered the necessary information, I never spoke directly to Sinatra about it. He had told me on several occasions when we were alone how much he hated confrontation between his wife and kids.
“I can’t understand how everyone in this family always thinks they are being mistreated,” he frequently said. So I spared him the details until I had a firm recommendation.
This gift meant that the kids would own his name and likeness, as well as his portion of Capitol royalties, Reprise Records, and his master recordings. Despite my initial reservations, on closer analysis it looked like a good idea. The valuation Sonny had obtained from the IRS was very low and my guess was that it would produce a gift tax that would be substantially lower than the eventual estate tax if they waited until his death. The larger estate tax would pose a huge liability for everyone when he died. I knew I had to convince Barbara that trying to stop the transfer would not be wise. I called her in Palm Springs.
“Barbara, I think you should let this go,” I said.
“What happens to me?” she said. “Am I protected?”
“Let’s focus on income he can earn now, that you can benefit from. He can make personal appearances, commercials and things like that, that won’t be included in the transfer. Of course, he will continue singing and keep selling out.”
With no guarantees, she was reluctant. Again, I wasn’t sure if I would be in this advisory role for the long term, but in the back of my mind I knew that if the kids were being given the rights to his music catalog and name and likeness, I could make a good case for almost everything else going to Barbara, which I believed was fair. Barbara dropped her objections and the kids were poised to be firmly in charge of the Sinatra legacy, though some of the income would continue to belong to Sinatra until his death.
That night I went to bed worried about the future. I knew why she was reluctant. Heck, even I could see it. Everyone was concerned about Sinatra’s health. His vision and hearing were on a downward slide and he was having memory problems. I honestly didn’t know how many shows he could handle a year. On top of that, he had been on an antidepressant for as long as I had known him, and I was convinced it was contributing to his difficulties.
There were more than a few false starts and mishaps. Nonetheless, we kept forging ahead. I’m happy to say that not only did Sinatra go on to make a lot of money, but he went on to make the two biggest-selling albums of his career, all of which irked Rudin no end.