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The Way It Was: My Life with Frank Sinatra

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A candid and eye-opening inside look at the final decades of Sinatra's life told by his longtime manager and friend, Eliot Weisman. By the time Weisman met Sinatra in 1976, he was already the Voice, a man who held sway over popular music and pop culture for forty years, who had risen to the greatest heights of fame and plumbed the depths of failure, all the while surviving with the trademark swagger that women pined for and men wanted to emulate. Passionate and generous on his best days, sullen and unpredictable on his worst, Sinatra invited Weisman into his inner circle, an honor that the budding celebrity manager never took for granted. Even when he was caught up in a legal net designed to snare Sinatra, Weisman went to prison rather than being coerced into telling prosecutors what they wanted to hear. With Weisman's help, Sinatra orchestrated in his final decades some of the most memorable moments of his career. There was the Duets album, which was Sinatra's top seller, the massive tours, such as Together Again, which featured a short-lived reunion of the Rat Pack--until Dean Martin, having little interest in reliving the glory days, couldn't handle it anymore--and the Ultimate Event Tour, which brought Liza Minelli and Sammy Davis Jr. on board and refreshed the much-needed lining of both their pocketbooks. Weisman also worked with many other acts, including Steve Lawrence and Eydie Gorme, and an ungrateful Don Rickles, whom Weisman helped get out from under the mob's thumb. Over their years together, Weisman became a confidant to the man who trusted few, and he came to know Sinatra's world his wife, Barbara, who socialized with princesses and presidents and tried to close Sinatra off from his rough and tough friends such as Jilly Rizzo; Nancy Jr., who was closest to her dad; Tina, who aggressively battled for her and her siblings' rights to the Sinatra legacy and was most like her father; and Frank Jr., the child with the most fraught relationship with the legendary entertainer. Ultimately Weisman, who had become the executor of Sinatra's estate, was left alone to navigate the infighting and hatred between those born to the name and the wife who acquired it, when a mystery woman showed up and threatened to throw the family's future into jeopardy. Laden with surprising, moving, and revealing stories, The Way It Was also shows a side of Sinatra few knew. As a lion in winter, he was struggling with the challenges that come with old age, as well as memory loss, depression, and antidepressents. Weisman was by his side through it all, witness to a man who had towering confidence, staggering fearlessness, and a rarely seen vulnerability that became more apparent as his final days approached.

321 pages, Kindle Edition

Published October 24, 2017

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Eliot Weisman

2 books2 followers

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5 stars
241 (45%)
4 stars
194 (37%)
3 stars
67 (12%)
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17 (3%)
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Displaying 1 - 30 of 39 reviews
326 reviews2 followers
February 16, 2018
Is it possible that there is any more to say about Frank Sinatra?
Yes, as it turns out. His last manager, Eliot Weisman, writes a mostly loving take on the Chairman of the Board's last few years. Frank was in decline, so there isn't a lot of crazy stuff going on, but it's still a welcome addition to the staggering volume of material about Old Blue Eyes. Also in the mix is Liza Minelli, Sammy Davis Jr., Dean Martin, Don Rickles and many others.
And, there's even a little bit about Donald Trump which I'd like to share.
When Trump was about to open his Trump casino in Atlantic City, he and Weisman made a deal to have Sinatra open the casino. Weiseman was also the manager for Sammy Davis Jr., and had arranged to have Davis perform at the casino. Sadly, Davis had been diagnosed with throat cancer. When Weisman asked if Trump would still agree to let Davis perform, Trump said: "What are you worried about Sammy for, he's going to die anyway."
Nice guy, that future president.
Profile Image for Susan.
887 reviews5 followers
July 4, 2019
I loved Frank Sinatra, still do. I have more of his music on my iTunes than of the Beatles, even though I'm of the Beatles generation (well, Monkees generation actually). The stories in the book were good, Frank was one of the people I would have like to have met. 1962 Frank though. What was distracting were all the errors in the book. "Frank, that's you're toupee!" And talking about famous musicians - Barry Oakley Sr of the Allman Brothers Band. That was an easy check - his name was Berry, not Barry. I seem to be running into errors like this more and more in books. Not sure why but I am beginning to think I missed my calling in life by not becoming a fact checker or proof reader.
Profile Image for Haya Akbik.
20 reviews1 follower
May 7, 2021
great insight on life with Frank Sinatra. Well written, takes you through the later half of his life. Great read if you're a Sinatra fan.
Profile Image for James.
594 reviews9 followers
January 14, 2018
This portrait of the artist as an old man is a fine book to read over a weekend or waiting at the dentist's. Weisman's story is about how he "took a man who was well past his prime and allowed him to live up to the potential that wouldn't go away." Fair enough, and while the book is wholly laudatory (not a speck of dirt anywhere), there are enough anecdotes to keep a reader interested. It's reminiscent of Henry Bushkin's book about Johnny Carson, but this is a little better. One irritating feature is that Weisman alludes repeatedly to the tensions and rifts between Barbara and Sinatra's kids, but never says anything about how the rifts began. Less irritating but odd is Weisman's tendency to include very general descriptions of Sinatra in the middle of stories. For example, if you read this alone--

He was loved, feared, and admired by people who knew him. He was hated by some as well. He was tempermental, unpredictable, generous, loving, passionate, and the best friend anyone could have.

--you'd think it came at the beginning or end of the book. But no, it's in the middle of a passage about the Ultimate Event.

These are small quibbles, however, and Weisman presents the older, faltering Sinatra with compassion. He also spends ten or so pages settling a score with Don Rickles, which really has no place in the book.
Profile Image for Laurie Hoppe.
313 reviews3 followers
November 8, 2022
I wish I liked this book more, for the times when Mr. Weisman knew Sinatra -- his last 20 years -- are very interesting to me. What was life like for this lion in winter? How did someone who personified machismo deal with declining physical power and prowess? How did he calibrate his performances once his instrument -- that magnificent voice -- began to falter? Those questions are answered, and I appreciated the poignant glimpses of a man, a human being, facing the end with as much courage and dignity as he could muster.

It's just that this book is a memoir, not a biography, and that means that, by definition, there's an awful lot of Eliot Weisman in it. And I wasn't crazy about Eliot Weisman. He uses this book to settle some scores, with snarky swipes at Tina Sinatra, Liza Minnelli and Don Rickles. It's Weisman's book, Weisman's story and so it was Weisman's right to do it on these pages. I just didn't give a darn. (I did enjoy his pages-long takedown of Donald Trump, though. Hearing about how Trump did business back in the old days makes it even less surprising that the SDNY is currently interested in Trump's money matters.)
Profile Image for Martin Burrows.
131 reviews2 followers
January 12, 2022
This is a book about Frank Sinatra, written by Eliot Weisman who was his manger for the later years of Sinatra's life until his death. Although it's not great literature, and is co-written by another person, it seems like a very honest portrayal of what Sinatra was truly like and Eliot Weisman's relationship with him. You can tell from this book that Weisman was not only Sinatra's manager, but also truly respected him, and maybe even loved him. The book is mostly a collection of somewhat disconnected stories and remembrances, but it also full of amazing revelations about the "boss", like that he carried a loaded gun with him on stage, and that in his later years, because he was becoming somewhat confused and disoriented, they filed down the firing pin so he wouldn't shoot anyone. What stands out in this book is the honesty, and the inside information about Sinatra, and his family, including details about his will and infighting between different factions of his family after his death. Even if you are not particularly interested in Sinatra, this is an interesting read, and a window into a very exclusive world that no longer exists.
Profile Image for Tami Baker.
500 reviews5 followers
April 4, 2025
I really enjoyed this book. Had it not been for a few issues, I might have considered 5 stars. First, the good - well-written, obviously with a lot of heart. Some new and fresh information about Sinatra’s life. I have read so many books about him and thought I knew alot about his life, but this was a fresh perspective. The bad - the authors “skimmed over” some information which left me with unanswered questions. I also found it strange that Weisman could surmise how negatively Sinatra would feel about Trump when it was obviously Weisman who had a problem with Trump. Ironically and hypocritically, Weisman embraced Bono. It bothered me that the author felt the need to interject his own political views in such a way that he thought he could assume what Sinatra would have felt. Sinatra had, in fact, met Trump, and they got along. Not friends, but the truth is they didn’t dislike each other. It was a good book, and I would still recommend to anyone who enjoys learning a little more about Sinatra.
346 reviews1 follower
June 29, 2018
A different view of Sinatra

I have read several books on the life of Frank Sinatra. This book addresses the later years of his career up until his death. It reveals a more mature side of the singer told from the perspective of his business manager. The Rat Pack years are behind him and he has settled down with a devoted wife. If you are looking for dirt or wild stories, this is not for you. But it is an intriguing and engaging story of the artist as he enters the September of his years.
2 reviews
November 14, 2017
Great book about the chairman

Hi Brenda number of books about his life but this is the latter stages of his life and I think it was terrific I didn't know the interesting parts that was just described in this book

I have read a number of these books about Frank Sinatra throughout the years but this is a factual account of later in his life and I was very fascinated the way the book was put together well done well received



4 reviews
November 22, 2017
Frank Sinatra A legend in his own time

I chose this read because I was always interested in his life and his music. I saw him years ago in Providence. I was much younger . He was great and the audience was yelling "We love you Frankie.. in the audience was Jackie Onassis. What a night that was. The book gives me more detail into his personal life and was very informative.
Profile Image for Dona.
1,348 reviews12 followers
April 19, 2018
I saw Frank Sinatra perform in around 1993 and reading this book confirmed my suspicions that he was slipping badly by that time. It was really a heartbreaking performance as it was obvious he was having difficulties remembering the words to his songs. The author explains a lot of that and also goes into more about the bitter relationship between Sinatra’s wife Barbara and his children. Interesting read.
Profile Image for Kathleen Blakely.
23 reviews
February 15, 2019
Sinatra.

I grew up with his music, my dad played music by ear, my mom sang like an angel. Music, especially Sinatra, was ingrained upon us. I know all the songs, words, and befall to cry with My Way, even had it played on my dad's passing. Sinatra. Loved him then, love him now. Wonderful to read about how this incredible talent continued and will continue forever. Th a no you for a glorious read. Sinatra.
Profile Image for Keith CARTER.
405 reviews10 followers
May 27, 2019
A great read, in fact, a must read for any Sinatra fan, this book gets into the "nitty-gritty" of the man everybody called Boss. It shows his fallibilities along with his exceptional talents. This book does not hold back, it is told by the person who knew him as well as anyone, his manager of many years. I have read quite a few books on the Boss but this one I found streets ahead of the others.
Profile Image for Simone Bocedi.
Author 1 book21 followers
December 3, 2018
Sinatra is one of the greatest artist and personalities that ever existed. The fact that in New York they’re still playing his songs at every occasion is a testament of what he has meant to the city - and the country - and the world. This book does “the boss” justice and even if I wanted to know way more about him, I’m happy there wasn’t, and he’ll live as a legend forever.
Profile Image for William O. Robertson.
265 reviews1 follower
October 10, 2019
I love a read like this! Reading this perspective by Sinatra's agent during his final years as an entertainer, transports one back to what was happening during Sinatra's tours and recording engagements in the 1970s and 80s and even into the early 1990s. Any Sinatra fan that hadn't read this book will undoubtedly discover things about Old Blue Eyes they hadn't known or heard before.
Profile Image for Lori.
389 reviews1 follower
July 3, 2021
I picked this up at my local Dollar Tree. I figured for $1, if I hate it, I wouldn't feel bad about donating it. Turns out, I actually really enjoyed this book.

I can't imagine what working with The Chairman was like. This book gives a unique insight into a complex man in the twilight of his career.
Profile Image for Eric Benjamin.
168 reviews
March 20, 2023
I loved learning about Frank Sinatra, through his long time manager Eliot Weisman. This book is an absolute gem. The people, with their talents, faults and foibles come alive through Weisman’s writing. Learning about Eliot is also very interesting, as his story is one of overcoming extreme adversity to achieve the highest successes.
4 reviews
December 9, 2025
I don’t typically enjoy a book about someone so well known from such a specific perspective, but Eliot Wiseman was more qualified than most to be able to share what he does about Frank Sinatra. It was a little sad to learn about his limitations and deteriorating condition during these last years of performing and recording. A nice glimpse into the later years of an American icon.
3 reviews
August 7, 2019
Fantastic read!

This is a must read to any Sinatra fan! This book is an honest account of an exceptional man who was “ Sinatra “! Eliot takes you on a fantastic journey through the career and personal life of a true legend!!!
Profile Image for Mick Meyers.
611 reviews2 followers
December 25, 2021
The book gave a favourable view if frank Sinatra, different to the usual anecdotes wheeled out and touched more in the business side.it is a shame that at the end the families fell out over his estate.iter then that a good read .
1 review
April 19, 2022
A fascinating book. I could not put it down.

I enjoy Sinatra music verse much. His devotion to his work is excellent. I was fortunate to attend a concert in Cincinnati in his later years. Now I enjoy him on Sirius XM radio every day.
279 reviews1 follower
August 25, 2024
While there was a little too much self-promotion in this book and a little too much taking credit for just about every success of every star he managed, I enjoyed the inside look at Sinatra. But then, I love reading anything about Sinatra.
Profile Image for Joyce Donahue.
62 reviews
January 22, 2018
Perfect!

Great, well written insider memoir... and a must-read for any Sinatra fan. Oh, the stories! I couldn't put it down.
38 reviews1 follower
June 27, 2018
Amazing story!!

Couldn't put it down. Every chapter kept me wanting to read on. We written and very easy to read. One of the better books I've read.
Profile Image for Nick.
402 reviews9 followers
December 7, 2018
Truly fascinating. A look at the later years of Frank Sinatra.
Profile Image for DEBORAH G.
157 reviews2 followers
March 21, 2019
Great celebrity inside info, I love that. I reccomend it as good reading for anyone over 50, who remembers Franks Sinatra.
Displaying 1 - 30 of 39 reviews

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