Frank Sinatra

Frank Sinatra photographed at the Columbia Recording studio.

William Gottlieb/Redferns

For three wild decades, Eliot Weisman managed one of the most iconic names in American entertainment. Frank Sinatra, whom Eliot referred to either as "Mr. S" or "The Boss," kept Weisman on his toes throughout the Chairman of the Board’s twilight years, navigating Sinatra’s career from his 1970s comeback to his resurgence in the 1990s.

For Weisman, who also managed the likes of Liza Minnelli and Sammy Davis, Jr., the experience was a 24/7 rollercoaster ride and juggling act full of hectic days and late nights, right up until Sinatra’s death in 1997. As a result, Weisman has accumulated countless stories about his time with the boss, the basis of which makes up his book The Way It Was: My Life with Frank Sinatra (Hachette Books), out today (Oct. 24), a revealing look at the man behind the legend that chronicles everything from dates with Jackie Kennedy to fights with Donald Trump.

Here, Weisman discusses his time with Sinatra, from fruitless attempts to reel in his lavish spending, to the balancing act of planning the Chairman’s life on the road -- and exactly why his former client’s music will "last forever."

Billboard: Everybody knows Frank Sinatra as this larger-than-life figure. What was he like as a person?

Eliot Weisman: If you had Frank Sinatra as a friend, you didn’t need any other friends. He was a special person and as loyal as the day is long. He hated bigots and he was always interested in trying to help people. As far as working for a man like that, I never called him "Frank." I called him "Boss" or "Mr. S." I never had the respect for anybody that I had for this man and I miss him every day.

This was one of the most successful people in all of music. Was managing Mr. S a 24/7 job?

It was, but I think what made me successful in negotiating my way through those years is that I tried to stay ahead of him. I knew what he liked and didn't like. There were not many times that he was aggravated, except from stupid little things. He hated the ride from the airport to the venue and he used to break my chops and say, "It has to be no more than 20 minutes." But in a lot of cities, that's impossible. I’d get very involved with his "problems," whether it be with negotiating, or his kids, or his wife. I tried to stay ahead of everything and keep the pressure off of him.

Of all the people I've managed, he was the easiest, because if you got it right he never complained. There were some moments, though, when we’d go to a city and the string section wouldn't be that great. As he’d walk off the stage, I’d throw him a towel and he'd say, "Where’d you get these guys? Lose them for next time or we’re not coming back." One of his favorite things to say was, "You got a camera? Take a picture because we’re never coming back here."

Frank was known for having a good time; what was your most memorable dinner or night out with him?

They were all memorable. He’d hang out after a show, especially if it was in a casino, which he liked the best because then he’d eat in the restaurant and go in the lounge and hang out there until three or four in the morning. Just hanging around, telling stories or talking about current events. He was a hell of a sports fan -- loved baseball. I remember there was a time when I was trying to conserve some money when he was getting older. He used to fold up 10 $100 bills into little squares and put them into his change pocket and that’s what he’d use as tips. I said to [his wife] Barbara, “You know, it’s crazy. That’s $1,000 a night and if we’re out there for 100 nights a year, that’s $100,000.” So we changed them to $20s, which worked for about three or four months. We were in a lounge one morning at around four and he reached into his pocket and looked at the square and saw it was $20. He looked at me and said, “You didn’t tell me we were broke. Don’t ever do this again." I cleaned that up.

What was it like setting up his extensive touring schedule? How did you plot out when and where to go?

If you take everyone else I managed and put them together, he gave me the least amount of problems. But he’d get on my case sometimes. When we’d be out on the road, we’d be gone for three, four, five days and he’d say, “We must be broke, how come we’re out here for so long?” I said, “You told me you wanted to go out.” So he’d have enough of being on the road and go back to [his home in] Palm Springs and I’d come back to [to where I live in] Florida. Then I’d get a call from him and he’d say, “Hey, I’m looking at the calendar. Did I retire and not know that? There’s not a lot of dates coming up.” I said, “You told me you had enough for a while.” He’d say, “Yeah, it’s been a while, I gotta get outta here.” Depending on what was going on with the rest of his life, [that] was how fast he wanted to get out of Palm Springs and get on the road again. We had a good time.

Was there anything Frank was asked to do that never materialized?

Just about the time I was getting involved, [Sinatra’s close friend] Jilly [Rizzo] had a deal with Finlandia Vodka for him and it was turned down, which was insane. At the time, Mickey Rudin, who was his attorney, said, “Well, he doesn’t need to be in the booze business.” It died and it shouldn’t have. On the other side of it, the Duets deal [his 1993 comeback album] was a struggle to the end. This was 10 years after his last time in the studio [in 1982], and there’s no question that his voice was not the same as it was 10 years before. But technology, with tuning, made up for that.

When I got the master and listened to it myself, I knew it was a hit. I called Barbara and had her play it for him. My heart was in my mouth, because there was no obligation to release it; if he didn't like the master, there was no deal. I was on pins and needles and at 2:30 in the morning I got a call from Barbara. She said, "I have good news and bad news. The good news is that he thinks it’s fantastic. The bad news is, if he had a good manager he would have done this years ago." It turned out to be one of the biggest albums of his life.

What made you want to write this book?

This goes back to 2003 or 2004. I met [co-author] Jennifer Valoppi, who I knew through Sinatra. We got to be friendly and we went out to dinner several times and we’d sit around telling Sinatra stories. One thing led to another and she said, “We oughta do a book.” I said, “Who's’ gonna write it?” She said, “Me.” We set up several meetings and put together an outline and it was exciting. She got a meeting in New York with a publisher. We showed the gentleman what we had, and he said, “All of this stuff is great, but what about all of the women?” I said, “I beg your pardon?” I started in 1977, the Boss got married in 1976 to Barbara, and I never saw another woman around, except before he got married he had a dinner date with Jackie Kennedy. The gentleman [pressed me] and I said, “I believe nothing of what I hear and half of what I see and this meeting is over, because that’s not what this book is about.” I was pissed and was turned off by the conversation.

I sort of forgot about it and didn’t think anything would ever come of it again. In the years since, everyone was still telling me to get it down on paper, all of the stories, and my daughter came into my office last July and said, “Dad, you really should do this book.” I said, “Well, you get me a book deal, I’m all in.”

Sinatra is still regarded as one of the greatest entertainers of all time. Why do you think his legacy is still strong today?

It’s how good the music was and how it applies, in one way or another, to everybody. It’s also the persona. Even youngsters who never saw him realize who he was and what he meant to the entertainment business. It’s hard to explain other than that when you look at the lyrics and the swing, his music will last forever.

      Courtesy of Hachette Book Group