Sinatra and the Jack Pack: The Extraordinary Friendship between Frank Sinatra and John F. Kennedy-Why They Bonded and What Went Wrong

by Michael Sheridan, David Harvey

A New York Times Bestseller

Frank Sinatra desperately wanted to be part of John F. Kennedy, Jr.’s gang. He had his own famed “Rat Pack,” made up of hard drinking, womanizing individuals like himself—guys like Dean Martin, Sammy Davis, Jr., and Peter Lawford—but the guy “Ol’ Blue Eyes” really wanted to hang with was Lawford’s brother-in-law, the real chairman of the board, John F. Kennedy.

In Sinatra and the Jack Pack, Michael Sheridan delves deep into the acclaimed singer’s relationship with the former president. He shares how Sinatra emerged from a working class Italian family and carved out a unique place for himself in American culture, and how Kennedy, also of immigrant stock, came from a privileged background of which the young Frank could only have dreamed.

By the time the men met in the 1950s, both were thriving—and both liked the good life. They bonded over their mutual ability to attract beautiful women, male admirers, and adoring acolytes. They also shared a scandalous secret: each had dubious relationships with the mafia. It had promoted Frank’s career and helped Kennedy buy votes. FBI Director J. Edgar Hoover had, over two decades, compiled detailed and damning dossiers on their activities.

From all accounts the friendship thrived. Then, suddenly, in March 1962, Frank was abruptly ejected from JFK’s gang. This unique volume tells why. It will release shortly after a television documentary inspired by the book airs, is filled with a beloved cast of characters, and is the compelling, untold story of a tumultuous relationship between two American icons.

Skyhorse Publishing, as well as our Arcade imprint, are proud to publish a broad range of books for readers interested in history--books about World War II, the Third Reich, Hitler and his henchmen, the JFK assassination, conspiracies, the American Civil War, the American Revolution, gladiators, Vikings, ancient Rome, medieval times, the old West, and much more. While not every title we publish becomes a New York Times bestseller or a national bestseller, we are committed to books on subjects that are sometimes overlooked and to authors whose work might not otherwise find a home.

Genres: History, Biography, Nonfiction, Music, Audiobook

303 pages, Kindle Edition

First published April 19, 2016

Reviews

[Priscilla · Rating 4 out of 5]

I've read dozens of books on JFK, but have always been curious about his friendship (and its demise) with Frank Sinatra. This book details Frank and JFK's upbringings, their rise to fame/power, how they met, and how their friendship came to a crashing end. This book provides a good introduction to Frank Sinatra's life and legacy. There were several typos throughout the book - one that irritated me in particular, citing Peter Lawford's final marriage in July 1964, only for him to pass away 6 months later in December 1984. Yes it's just one digit, but that one digit makes a huge difference! Aside from that, this was a fascinating book and I would recommend it to anyone interested in JFK and Sinatra.

[Kris Kurk · Rating 3 out of 5]

An interesting book. It mostly went through Kennedy history starting with Joe Kennedy and A little on Sinatra's past, and some mob history. There was very little about the relationship between Sinatra and Kennedy.

[AllBookedUp · Rating 4 out of 5]

Truly a fascinating read. I blew through it because I just couldn’t stop. The friendship started off strong and good but like all things, ego , a woman, and a public meltdown (on Frank Sumatra’s side over Ava Gardner) got involved. That and the mafia.

Sidenote: Frank Sinatra had a problem with Peter Lawford. It stretched back to 1953, despite the fact that they knew each other for at least six years before and had appeared in a number of films together. Peter Lawford is close to the Kennedys.

[Amy Schwartz · Rating 4 out of 5]

I thoroughly enjoyed this! I've read a lot of books on JFK and I'm looking for a good one on RFK, but getting back on this, it was actually quite riveting in parts. I never really knew anything about Sinatra except that he was a singer and played in some movies. I learned a lot about him and even a few things about the Kennedys.

[William Howle · Rating 3 out of 5]

The book was interesting with some history errors. It was apparent that the author was infatuated with the Kennedys. His treatment of Sinatra seemed to be on target. All through the book, I thought he was pandering to the Kennedys as many authors do.

[Joseph Pileggi · Rating 5 out of 5]

Not bad

Book has some errors including calling Nixon ,Eisenhower's son in law. It was not a bad read but nothing new.

[Lloyd · Rating 3 out of 5]

This is a retelling of the relationship (friendship) of John (a.k.a. Jack) F. Kennedy and Frank Sinatra. In the subtitle, it purports to explain why they bonded and what went wrong. The “Jack Pack” was a reference to the inner circle of Jack Kennedy’s friends and associates. Essentially, these two men bonded, according to the author, because they came from immigrant families (each of there grandfathers were immigrants to America) and the families overcame prejudice against the Irish and the Italians to the point where their heirs, Jack and Frank, attained the pinnacle of success. If you’re more cynical you may see that each man associated with the other to further their individual careers. As for overcoming prejudice, in Jack’s case, his father, Joe Kennedy, really broke through the barrier and created the wealth that the Kennedy family enjoyed. The Sinatra’s parents had achieved at best middle-class success. It was Frank’s success as a singer and actor that brought wealth to the Sinatra family. Unfortunately, this book broke no new ground. The stories told are the often-repeated tales over the years about each man’s poor behavior towards women and their supposed connections to organized crime. As for what went wrong with their friendship, once again it is a repeated story and no new information is provided. There are no footnotes in this nonfiction account of their lives. So, as a reader you are left to wonder if the story is true or just the same old often-repeated gossip and conjecture. In addition, the author makes a huge mistake that should have been caught before this book ever went to print. Several times the author refers to Richard Nixon as President Eisenhower’s son in law. That is just plain factually false. However, if you hadn’t heard all of these stories before (like just how did Frank Sinatra get out of his contract with Tommy Dorsey so he could become a solo act) then you may be interested in these stories now.

[William O. Robertson · Rating 4 out of 5]

The book is a fascinating read about John Kennedy and Frank Sinatra and how their careers ran in parallel from their different upbringing, and also how their family's association with shady characters of the underworld almost wreck havoc on their ambitions—one being with entertainment success and the other political success. Especially interesting in the book is the depth of a “Deep State” within the U.S. Government. Although the book does not refer to it as such, one can nevertheless see how the deep state worked – especially with the FBI being headed by J.Edgar Hoover and how the mafia was used by the Kennedy presidential campaign of 1960. Sinatra and Joe Kennedy were a sort of intermediary with mafia connections to bring in votes from West Virginia and Chicago to insure a Kennedy victory to the White House. Nothing new here, since this is well documented how the mob was involved in the 1960 presidential election. The premise of the book details how the Jack and Frank relationship developed and how it eventually ended because of shadowy figures in the background—mainly from Frank's past.

The sexual affairs, the corruption, the influence peddling for votes (and favors). It's all here. What a great movie or mini-series this would make!

[Elena Smith · Rating 5 out of 5]

I never thought I’d read a biography that was a page-turner. Wrong. The title alone suggests a modern mash-up, and it does not disappoint. This creative writer lays out two intertwining stories, well-woven. Clever use of modern cultural terms and concepts made the work fresh and accessible, without overshadowing the nostalgia of the time periods he writes about. There were parts of the historical narrative that I’d never read before. Although Sheridan’s opinion(s) on the men were evident, I felt that he presented the subject matter fairly, even debunking an oft-repeated myth about the Kennedy family.

[Mary · Rating 3 out of 5]

This was a boring, inaccurate history book. 3 times the author said Richard Nixon was Dwight Eisenhower's son-in-law!!! The only things I could actually believe were the extremely numerous quotes the author used from other sources. I would have given it a one star if it had not had some interesting descriptions of Frank Sinatra's pathetic attempts to ingratiate himself with both the Kennedy's and the "mob". I also found the short information of the men who assisted JFK with his elections and his presidential staff interesting. If you lived through these times as I did, don't bother with the book.

[Jason Gillespie · Rating 4 out of 5]

Pretty fascinating read about two of my personal favorite historical personalities. Great insight into the timelines the two men found themselves in and the point in history in which their lives intersected. Great political insight , especially around the time of Kennedy's assassination and during the last years of Sinatra's life. Heartbreaking perspective of a man that lived his life fully in the spotlight facing losing so many friends towards the end of his. Really good read. Enjoyed it thoroughly.

[Steve Hager · Rating 1 out of 5]

I couldn't get very far in this book; I put it down because of so many mistakes not historical and logical. As example, the author makes the case that Frank's mother provided abortion services and refers back to an botched abortion in 1842 in Hoboken that ended in the death of a young woman. That's fine, but the narrative continues to say, "Three decades later, there was still demand for abortion, and Hatpin Dolly was carrying on the long-established tradition in Hoboken." The timeline is seven decades not three. There are several similar mistakes that frustrated me. I gave up.

[Bobby Panichella · Rating 3 out of 5]

I thought this book would be interesting and it was but I don't know what's true or made up. He wrote
about both names but when he got down to Kennedy he wrote about parties with Frank & JFK but didn't really get into his Rat Pack days Dean Martin wasn't mentioned or any of the rest of the gang.He writes about Peter Lawford but he had to JFK sister was married to him.He only mentioned Marilyn Monroe when he was writing about all of Sinatra's friends who died.Thats why I'm not sure what's true & or just made up.Anyway If your a JFK or Sinatra fan read it maybe you would like it more

[Howard Harrison · Rating 5 out of 5]

Bravo. The author adroitly combined the biographies of two of the most famous Americans of the 20th century into an easily digestable 250-page book. No wasted details as these parallel bio's careen toward an historic intersection then split apart again. As a non-fiction storyteller myself, I know it when I see it and this is it. The only negative was a surprising number of typos. But none could diminish my thorough enjoyment of this book

[Erin Hayes · Rating 5 out of 5]

I took a break from The Patriarch (Joe Kennedy biography) to read this and I’m so glad I did. For an Irish woman from Boston I don’t know nearly enough detail about the Kennedy’s (aside from their womanizing ways). This gave great background and story to the friendship and fall out. I read 20% over a period of weeks but the last 80% I tore thru in three days (and I have two young kids and a business so you know I was riveted). Highly recommend.

[LeAnne · Rating 5 out of 5]

Italian immigrants and Irish immigrants arrive in the US

and years later the future for two takes very different routes. Frank has a very strong, very determined mother (Dolly)....Jack has a very strong, determined father (Joe). Each of the two men are products of their parent, become friends but for the wrong reasons. IMO, the Mafia played a large part in how it turned out.

[Frida Dillenbeck · Rating 3 out of 5]

The recount of the two lives is interesting yet disturbing not only because of their terrible exploitation of women, power and political positions but also because total lack of personal accountability and immoral behavior. The recount of each life left me feeling sad for them and their families. I need to read something happy after this sad tale.

[Brenton Smith · Rating 3 out of 5]

I was really hopeful for this book. Kennedy has always fascinated me and I love Sinatra’s voice. Their friendship had so much potential, but this felt more like a brief biography of the two men and how their lives briefly overlapped. I did enjoy learning how their upbringings had parallels with a strong parental figure, but I do wish it’d explored their friendship more.

[Zakariyya Elarbi · Rating 3 out of 5]

Loved reading the history of the relationship between JFK and Frank, but the actual writing of the book was very jarring-- seemed as though two different people were alternating writing chapters, resulting in a weak narrative held together with lots of scotch tape.

[Marilyn · Rating 3 out of 5]

It's a good short history of the two men: where they came from, their personalities (and Herbert Hoover's and Sam Giancana's that affected Frank's and Jack's careers), how they met, what they wanted from their friendship, why Jack cut off Frank and Frank cut off Bobby, the roles of the Mafia and the FBI in the making and breaking of their connection.

If you are interested in either man, or in their relationship, this is a good book. I don't know if it is thorough; but I thought it was a good read.

[Cindy Kasper · Rating 5 out of 5]

Thoroughly enjoyed this book. Well written and fast moving. Did not spend a lot of time on topics, just kept it moving. Interesting information! There were things I learned about people in this book that I never knew. Amazing!

[Marlene · Rating 3 out of 5]

A lot of this book is just retelling what is already known. However, at least 3 times the author states that Nixon was Eisenhower's son-in-law. With such an obvious error, one has to wonder what else in the book was untrue.

[Philip Brown · Rating 4 out of 5]

Half rockumentary/half presidential bio

The author gives an accessible history of the lives of Frank Sinatra and JFK, highlighting the points at which their lives intersected. Fascinating history. Thoroughly enjoyed this.

[Joan · Rating 4 out of 5]

I knew a lot of what happened between JFK and Sinatra from other books I've read but did learn more about his childhood, his early singing career and layer years. Sinatra had a great voice but he sounded like a petty bully with a bad temper if he thought he was wronged. I did enjoy the book.

[Joseph · Rating 4 out of 5]

Man the author has it out for Sinatra. JFK gets a softer touch with the usual historical argument that the old man was doing the dirty work. JFK is a lovable but, politically bold leader who wisely cut his ties with Sinatra on advice from his family. Still a well written book

[Jennifer · Rating 1 out of 5]

Am I the only person who noticed that the cover characterizes President Kennedy as John F. Kennedy JUNIOR? If you can't get the cover right, I don't have much faith in the book.... the son-in-law thing was a bridge too far too.

[Jewels · Rating 3 out of 5]

You learn something new everyday! Why were Nixon, LBJohnson and J Edgar Hoover together in Dallas the day before JFK was assassinated??

[Steve · Rating 5 out of 5]

Gripping and hard to put down. That said, Sheridan is clearly no fan of Sinatra, but despite that obvious bias, an engrossing read.

[Ewa Hammer · Rating 2 out of 5]

Needs good editor

Not much new information. Writing disorganized. Needs a good editor. There are better books out there on these people. Skip this one.

[Lori · Rating 3 out of 5]

Slightly disappointing!