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Frank Sinatra and the Mafia Murders

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It was said of the young Frank Sinatra that he came across as "St Francis of Assisi with a shoulder holster." 

Mike Rothmiller and Douglas Thompson draw on previously secret LAPD intelligence files, a cache of FBI documents released to the authors in 2021, and extensive interviews with prime sources, including many who worked with Frank Sinatra and many more who tracked his long and fatal association with the American Mafia, notably his ongoing connection, after his original godfather was assassinated: Sam 'Momo' Giancana, who shared a lover with President John F. Kennedy.

Sixteen days after the assassination of John F. Kennedy on 30 November 1963, while the singer was 'consoling' the president's widow, nineteen-year-old Frank Sinatra Jr. was kidnapped at gunpoint from his hotel room in Lake Tahoe, Nevada. A $240,000 ransom was demanded from his father. While the FBI and Nevada and California law-enforcement agencies sprang into action, Frank secretly contacted his Mafia friends for help. The Mafia believed they could free young Frank much more quickly through their underworld connections. In the end, nine people died, having been beaten for information.

Revealed here as never before is the extent to which Sinatra was adopted by the Mafia. They promoted his career and 'watched his back' and, in return, Sinatra danced to their tune.  New information disclosed here shows that Sinatra also offered to spy for the CIA. Inside sources say Sinatra wanted the CIA to intercede to stop an investigation into his gaming license in Las Vegas. But the CIA declined because they were already working with the Mob and were concerned Sinatra would learn of the Mafia's connection to the CIA and leak it.

256 pages, Paperback

First published September 15, 2022

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Mike Rothmiller

43 books19 followers

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5 stars
229 (37%)
4 stars
223 (36%)
3 stars
123 (20%)
2 stars
27 (4%)
1 star
10 (1%)
Displaying 1 - 30 of 52 reviews
4 reviews
October 16, 2022
Good info; brutal editing

I’d been looking for a book on this very topic. This was the first and only one I’ve come across. The authors provided interesting information. However, as good as that was, it all took a backseat to the nonexistent editing for the entirety of the book. I’ve never read a book that lacked so much punctuation. Often, I had to go back and read sentences over, so I could try to understand what was being said. More often than not, it was missing periods or commas, making it a confusing read. If you can get by that, it’s a worthwhile read.
Profile Image for Stephen.
2,117 reviews449 followers
June 22, 2023
Interesting book but nothing really special though
Profile Image for Valerity (Val).
1,082 reviews2,765 followers
September 1, 2022
This was quite an eye opening read. I’ve learned bits and pieces of some parts of this book in other books thru the years, including Rothmiller's. But nothing like this more detailed look behind the scenes, thanks to the release of many previously withheld documents of several law enforcement agencies. Sad to say, it just makes me feel even more hopeless for the situation our country has ended up in today, as you can see where some of it started way back. A good read for Sinatra fans, and those who enjoy revealing mob books.
Profile Image for Naomi's Bookshelf.
153 reviews73 followers
October 26, 2022
Who knew what the real Frank Sinatra was like? I had heard that he wasn’t a great guy but this book was a real exposé of the man. I was fascinated with every single page and I couldn’t believe some of the stories. I was hooked from the beginning and I didn’t stop until the end. The book starts with a kidnapping of Frank’s son and suddenly goes back to the beginning of his time connected to the mob. I felt every kind of feeling as I learned about his life and criminal connections. This is a great nonfiction about a man who had the world in his hands and back covered by the mob.

I received an arc via Netgalley in exchange for a honest review.
Profile Image for CrabbyPatty.
1,702 reviews193 followers
February 2, 2023
The book uses the kidnapping of Frank Sinatra, Jr. in 1963 as a framing device to show Sinatra's relationship with the Mafia; whereas publicly Sinatra was willing to let the FBI find his son, in reality he turned to his life-long friends in the Mafia to do whatever they needed to do to find Frank, Jr.

Through extensive research and interviews, the authors have put together a fascinating story. There's an Italian saying la famiglia e tutto meaning "family is everything" and in the case of Sinatra and the Mafia, his found family was everything - support for his singing and acting career, money and status, muscle to handle his disputes and disagreements - and Sinatra reveled in the perceived power it gave him. 

Sinatra is revealed to be a petty bully with a massive anger / inferiority problem - there was little about which he didn't explode and used his Mafia "cred" to solve pretty much any dispute or perceived slight.  Along the way, we get the inside scoop on the Rat Pack days in Vegas and Hollywood, Marilyn Monroe, Bugsy Siegel and Virginia Hill, Sam Giancana, Judith Exner, Carlos Marcello, Johnny Roselli, Pat and Peter Lawford, and so many more.

The authors' detail how "the boys" weren't too happy with the making of The Godfather and the careful negotiations to never mention "the Mafia" in the film.  However, once the movie was made .... "the boys" loved it.  Sinatra, on the other hand, deplored the weak, spineless depiction of himself in his alter ego Johnny Fontaine (which for the most part seems pretty much accurate). 

Especially noteworthy is the authors' take on the Kennedy family, starting with Joe using the Mob to get JFK elected, and how promises were made and not kept, RFK's mission to take down the Mafia, and the resulting assassination of JFK in Dallas in 1963.  The story seems pretty plausible, IMHO. 

The content of the book is 4 to 5 stars, but the editing (dear gawd, the horrible editing) and run-on sentences make reading the book a challenge. Also I wearied of the casual sexism, racism, homophobia.  One small example - Judith Exner is described as brainless "little Judy" running from JFK's bed to Sam Giancana's.

Rating:  3.5 stars - strong content marred by weak editing.  

I received an ARC from the publishers, via NetGalley, in exchange for an honest review. 

Visit my new blog "I Love True Crime Books"
Profile Image for Nate.
49 reviews
January 21, 2024
While I have no doubt that the authors did countless hours of research to compose this, the book was utterly disappointing and frustrating to read. It opens in an interesting way, but the pseudo-Martin Scorsese tone is slowly dropped until the narrative reads like any other nonfiction. No big deal there, but the lack of consistency in narration style quickly grew annoying after that point. The editing was horrible overall: run-on sentences, missing commas, and improper formatting of em dashes were some of the main offenders.

To make matters worse, the narrative itself was all over the place. Transitions were downright missing between most of the paragraphs. The story line jumped around without warning, dropping names galore and wasting pages upon pages on characterizations of people that just were not relevant. Frank Sinatra was hardly mentioned at all in Part I. That's not even taking into account the fact that the actual kidnapping of Sinatra Jr., the marketing basis of this book, is completely abandoned until it's revisited for around 30 pages near the end of the book. And, just to top things off, the book included many instances of interjected sexism and misogyny.

There was a lot of good and interesting information buried within this book, but I can't help but think that the premise of this narrative should have been reevaluated to more accurately reflect its contents. It probably would have been beneficial to hire some better editors, too.
Profile Image for ♥Milica♥.
1,734 reviews678 followers
Want to read
August 24, 2022
I see Douglas Thompson, I click "add to tbr", simple.
Profile Image for Maggie.
134 reviews
September 1, 2022
Whew! This one’s exciting! I read it in a flash. Highly readable and interesting.

I’m game to read anything about Sinatra, and was thrilled to see a new selection. This is a rare case when the galley phrase “revealed here as never before” is absolutely true. It’s long been known that while Frankie enjoyed being a benefactor, his alter ego was dark and sometimes cruel. This book is NOT about his good side. Mike Rothmiller and Douglas Thompson delve into the darker pieces of his personality with depth and novelty.

For those interested in the Kennedy’s, Lana Turner, Sammy Davis, Jr., Ava Gardner, Marilyn Monroe…(the list goes on and on!), you’ll find plenty to drop your jaw. There’s a lot of interesting stories about most everyone in Mr. Sinatra’s circle.

Big thanks to NetGalley and Ad Lib Publishers for granting access to a digital ARC in exchange for a review.
28 reviews
October 2, 2023
Interesting subject matter, but this has to be the most poorly written book I’ve ever encountered in my life. Sentence structure is horrible to the point of making the reading experience awful. Sentence fragments. Long, convoluted run on sentences meandering all over the place covering enough topics for several paragraphs. Awkward phrasing, inconsistent use of names, lack of coherent narrative structure. I often had to reread sentences just to try to understand what they meant.

I can’t understand all the high ratings for this book. If I had known what a slog it is I wouldn’t have bought it. I rarely ever DNF, and even now I’m not sure if I definitely will, but I am putting it aside at least for now. Perhaps I will try it again when I’m in the mood to bang my head against a wall.
Profile Image for David Orgel.
14 reviews
December 28, 2024
There’s plenty of information here, but the writing and editing are so clumsy that it’s a labor of OCD to make it all the way through. Especially annoying (besides the execrable copyediting) are Scot/Brit Douglas Thompson’s lame efforts to try to use an American, quasi-hardboiled style while British spellings are used throughout, not to mention the significant number of British idioms scattered around. Still looking around for a good book about Sinatra and his relationship with the Mob.
Profile Image for Sandra Frey.
273 reviews5 followers
June 20, 2024
I listened to the audio, and judging by some of the reviews of the hard copy's editing, it sounds like I dodged a bullet (rim shot).

My experience with this book was sort of split in half. The first half focused substantially on mafia and mafia-adjacent figures, and while the general arcs of what was going on in and around Sinatra's life were interesting, it felt a lot like name salad. This sense was likely boosted by the fact that I wasn't seeing the names written or setting my own pace, and the fact that I was not previously familiar with many of the names (though obviously I knew some).

By the second half, Frank was ensconced in fame, and the narrative began to focus more on fellow celebrities and political figures for whom I already had a lot of mental context, so the events all became more clearly cut. I appreciated what were technically tangents to focus more intently on surrounding figures like Mickey Cohen, Lana Turner, the Kennedys, and Judith Exner, all of which fleshed out the general culture of corruption, dysfunction, and game-playing Sinatra was afloat in (and contributing heartily to).

One mistake of mine that got cleared up: I always knew Sinatra loved rubbing elbows with the mob, but I had casually assumed it was a consequence of his fame, rather than a lifelong association to which he owed much of his fame. The ultimate image of him that one comes away from this read with is not at all impressive, but I was already pretty unimpressed when I started the book.
Profile Image for Ray Campbell.
945 reviews6 followers
May 18, 2023
This is an enjoyable, fast-moving, well written book. Rothmiller gives us an outline of Sinatra's life with few details except where it came to the mob. When Sinatra's life crosses paths with a mob boss, gangster, Mafia member... Rothmiller fills in the back story of that individual. Thus, this is less a book about Sinatra and more about the Mafia.

I did enjoy this perspective. It's almost quaint to read in Sinatra's biography that he hung out with gangsters in Cuba. One imagines drinks, prostitutes, and a command performance. The support they gave in return for his company and performance may have been an introduction or protection. However, when Rothmiller explains who these men really are, one realizes that there is nothing quaint about these relationships. These were the top people, and they did really bad things.

We've all heard rumors about the mob killing Kennedy and/or Marilyn Monroe. Or, that Kennedy won the presidency with the help of the Mob in Chicago. Rothmiller explains why this is not so far-fetched. I am not a conspiracy theorist kind of guy. However, Rothmiller's sources are FBI and other government records as well as published interviews and writing. It's not that I didn't know this stuff, but knowing names isn't the same as looking at police records and the details of crimes. This book fills in blanks I didn't know I had. Very well done.
Profile Image for Marcus Coles.
Author 8 books1 follower
May 17, 2025
Despite a lifetime of denial, Frank Sinatra was as close to the mafia as one could be without being a ‘made man’ himself. They made him though, protected him, watched over him, fought his battles and guarded his public image. They secured his role in From Here to Eternity for which he won an oscar. He was bosom buddies with some of the most notorious gangsters of the twentieth century, such as Roselli, Giancana, Frattiano, Costello and Gambino. His business interests included casinos and nightclubs in Vegas which were notorious for being run by the mob. As one of the most famous entertainers in the world he rubbed shoulders with Hollywood legends such as Marilyn Monroe, Ava Gardner and the Rat Pack. From the world of politics, he was part of the Kennedy inner circle until his ties with the mob became an embarrassment to the new President. He lived a fascinating life and was often at the centre of colliding worlds. Despite his public persona and the fact that he was adored by millions, he definitely wasn’t the kindly, warm heartthrob of his fans’ dreams. This book provided an interesting look into the private life of a man who lived a fascinating life.
Profile Image for patrick Lorelli.
3,724 reviews39 followers
June 16, 2023
The author has used unsealed files to revile classified secrets about Sinatra and the Mob. He opens with the tale of Frank Jr. being kidnapped and will go into detail about and the total outcome later in the book. The book itself is good and for some parts I had known about so the author using unsealed files just proved those. Another item was interesting that though he and Dean Martin were good friends Martin did not want in on his deals because Martin knew the men Sinatra was dealing with having grown up around that lifestyle in Ohio. The relationship with the Kennedys has been talked about in other and older mob books once again this has just proved that along with an interview with actor Lawford and how because he was associated with the Kennedys by marriage Sinatra dumped him from their group and he was no longer welcomed around anywhere. There is much more in this book and was a good read. I received this book from Netgalley.com
Profile Image for Janalyn, the blind reviewer.
4,446 reviews136 followers
September 3, 2022
Frank Sinatra was back by the mafia early in his career when he sang for cheese sandwiches in the pack of Lucky’s cigarettes. This association with scar his life but also benefit him tremendously in the long run and that is what this book is about and what an interesting book it was. It even discusses the time the association with the mafia helped his girlfriend get out of the murder charge in Cuba. I found this book so interesting and so revealing and learned so much I didn’t know about Frank Sinatra I thoroughly enjoyed it and totally recommend it. If you love all Hollywood and tails out of school you love this book. I received this book from NetGalley And the publisher but I am leaving this review voluntarily please forgive any mistakes as I am blind and dictate my review.
Profile Image for Joe.
135 reviews1 follower
May 23, 2024
This was a surprisingly captivating book. It greatly details Sinatra’s long involvement with the mafia. It has an almost gossipy and morbid tone throughout it as it celebrates the many affairs that both Sinatra and key members of the mob had and almost celebrates the literal body count left in the mafia’s wake. The only regret is I’ll never be able to think of Sinatra as being “cool” again. He was a temperamental child who had no control over his emotions and who was lucky the mob allowed him to live out his life and die of natural causes. It’s better to know the truth, than celebrate false idols….still, that guy could deliver a line!!
35 reviews
November 21, 2024
Fascinating and eye-opening read

This book was certainly an eye-opening, interesting and oftentimes an annoyingly confusing read. In many places the sentence structure was very awkward and had a “wiseguy” feel to them. I was definitely surprised that this was written by two bestselling authors.

Considering the book is about Sinatra, the authors veer off into the lives and times of many, MANY other people. Some of whom had a tiny connection with Sinatra.

My opinion of Sinatra has completely changed. I had already read about his bullying behavior in a book about reporter Dorothy Killgalen. This story really brought to light many things, especially about JFK.
Profile Image for Beth.
267 reviews7 followers
August 25, 2022
Thank you to Netgalley and the publisher for this advanced readers copy.

Frank Sinatra and the Mafia Murders is rather a juicy story that relies of recently released records from LAPD and the FBI.

Sinatra was clearly involved with the mafia and they had a very transactional relationship.

This book offers a glimpse into the side of Sinatra not generally known. The historical moments are good to read - back to President Kennedy's assassination era.

If you are a fan of the Mafia in that era or Sinatra in any era - you should read this book.
Profile Image for Lydia Granda.
270 reviews4 followers
Read
July 30, 2023
This book is all over the place, it jumps from one character to the next, Frank Sinatra is more of a minor character who occasionally jumps back into the story. It was eye opening to read what he was really like but no surprise. The proofreader should not have been paid foe this jobs, there was a multitude of misspellings and missing punctuation that leads the reader to having to re read sentences in order to understand what was being said. I'd rate this as okay but not worthy of a recommendation to anyone.
Profile Image for Genevieve.
70 reviews
March 27, 2025
This book provided a serious deep dive into the double life of Frank Sinatra and his mob ties. I listened to it as an audiobook, so I didn’t have the negative experience with the punctuation and sentence structure which others have mentioned. I think that the author did a great job of citing other sources to provide the reader with an even more detailed look at Sinatra’s controversial life off stage. Within its pages, several other A-list celebrities and politicians are not immune from having their seedy pasts exposed as well. Pop some popcorn and enjoy. 4/5
Profile Image for Lady.
1,081 reviews17 followers
January 31, 2023
Wow, this book was certainly very shocking reading and quite unexpected for me anyway. I have loved Frank sinatras music, but I knew nothing about his past. Let's say very eye-opening. I can't believe how bad he really was as a person. Arrogant doesn't seem to sum it up enough. It was shocking what he was able to get away with. There certainly was never a dull moment in this book. It definitely had me turning the pages. It was well written and obviously well researched. It kept my attention throughout. I found it funny how he was served. It's definitely a must-read book if you want to learn more about Frank. I am sure this book will rock a few boats as it doesn't hold back.

So much praise goes out to the authors and publishers for bringing us this extremely shocking story.
Profile Image for James Greenwood.
3 reviews
November 21, 2024
For how Frank and the Mafia tie together, it’s really interesting with some great quotes and information gives you a great insight into the relationship.

However, talk any negative chat about Sinatra with a bucket of salt. Author clearly despises him and makes claims which he himself can substantiate. Shame if he hadn’t used a 4th of the book doing this and stayed on topic, could have been 5 stars.
Profile Image for Troy Sonnenfeld.
65 reviews3 followers
January 11, 2025
The authors provided interesting information. However, as good as that was, it all took a backseat to the poor editing for the entirety of the book. Often, I had to go back and read sentences over, so I could try to understand what was being said because of the lack of punctuation. More often than not, it was missing periods or commas, making it a confusing read. If you can get by that, it’s a worthwhile read. If not, don't pick it up.
Profile Image for Jade Star.
36 reviews
March 30, 2025
I feel i cant express really if the writing skill is bad or not, because it's just an info dump. I will rate it on how fun it was to read though! Maybe I would love this book more if I wasn't rushing to read it the day before it was supposedly due.
Lots of people left complaining about how this good isn't true, but it 100% is! You can go on the fbi archives website, it's all true! Maybe it's just too crazy to believe such a public figure would be apart of all that
Profile Image for Amelia Maness-Gilliland.
114 reviews10 followers
October 6, 2022
This is a good one! I grew up listening to Frank Sinatra music playing in the background, My parents loved him. I remember hearing speculation regarding his ties to the mafia but never really knew what to think. This book lays it all out there! Sinatra’s background with the mafia and all the juicy details! I couldn’t put it down!
Profile Image for Lorraine.
1,472 reviews40 followers
July 15, 2023
If your interested in organized crime, Frank Sinatra or the Kennedy years don’t miss this compelling book. I listened to it from Hoopla, from my local library and found it incredibly interesting. It certainly offered a different view point of Frank Sinatra and the Kennedy’s then the popularly held view held by the public.
17 reviews
April 2, 2024
While the book reveals many interesting aspects of how organized crime worked in its heyday and Sinnatar's connection to much of it, the narrative was way too rambling. It jumped from one story to another often with no relation between the two. Many of the tales were repeated as nauseum. There should have been much better editing.
Profile Image for Mortisha Cassavetes.
2,840 reviews64 followers
April 11, 2024
I really love Frank Sinatra's music but the more I read about his life, the more I am shocked about his lifestyle and violence. This book tells the story of how Frank is connected to many Mafia murders and his ways of staying out of the spotlight. I definitely recommend this book to all who love the music behind the madness.
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