Jump to ratings and reviews
Rate this book

Boss of Bosses: The Fall of the Godfather- The FBI and Paul Castellano

Rate this book
“At least as good as Mario Puzo, with shades of David Mamet or even Arthur Miller.”—New York Daily News

Paul Castellano headed New York’s immensely powerful Gambino crime family for more than ten years. On December 16, 1985, he was gunned down in a spectacular shooting on Manhattan's fashionable East Side.

At the time of his death, Paul Castellano was under indictment. So were most of the major Mafia figures in New York. Why? Because in 1983 the FBI had hidden a microphone in the kitchen of Castellano's Staten Island mansion. The 600 hours of recorndings led to eight criminal trials. And this book.

Agents Joe O’Brien and Andris Kurins planted that mike. They listened to the voices. Now they bring you the most revealing look inside the Mafia ever . . . in the Mafia’s own words.

“Beautifully done, not only strange and fascinating but even touching.”—Robert Daley, author of Prince of the City

382 pages, Mass Market Paperback

First published May 23, 1991

23 people are currently reading
1825 people want to read

About the author

Joseph F. O'Brien

6 books1 follower

Ratings & Reviews

What do you think?
Rate this book

Friends & Following

Create a free account to discover what your friends think of this book!

Community Reviews

5 stars
335 (35%)
4 stars
378 (39%)
3 stars
206 (21%)
2 stars
28 (2%)
1 star
6 (<1%)
Displaying 1 - 30 of 58 reviews
Profile Image for Julio The Fox.
1,718 reviews117 followers
October 1, 2022
'To live outside the law you must be honest."---Bob Dylan

"You can get far in life with a kind word but you can get a lot farther with a kind word and a gun."---Al Capone

This is a cautionary tale for anyone, and not just criminals, who wants to live multiple lives simultaneously while ignoring the killing contradictions that venture entails. BOSS OF BOSSES is based on FBI tapes taken from a bug planted in Paul's house on Staten Island, NYC. Paul "Big Paul" Castellano, head of the Gambino crime family from 1976-1985, ignored both Dylan and Al's dictums and it cost him his life, on December 16, 1985, at the hands of his underling, John Gotti. Castellano had the misfortune of being the Boss who succeeded a criminal genius, Carlo Gambino, Paul's cousin and brother-in-law, (trust me, these things get complicated) and was in turn succeeded, through assassination, by a publicity hound with no brains, Gotti. Paul's control over everything from unions to the garment industry in New York City to loan sharking made him think he was a businessman, not a thug. (He boasted of reading THE WALL STREET JOURNAL every day.) But he forgot that he would not have any of these businesses without the thugs who worked under him. His megalomania knew no bounds. He referred to his mansion as "The White House" and claimed "If the President of the United States needs a favor, I can help him out." In a world where ceremony and earning money mean everything Paul violated both. He regularly received huge cash payments at the White House while letting his street soldiers starve. In La Cosa Nostra private and public lives are supposed to be kept separate. While most mobsters, Italian or others, have a mistress along with a wife, they place them in different parts of town. Not Big Paul. His mistress lived on the same premises as his wife and when he had to choose he threw the wife out! This book is unusual in that it was written by the two FBI agents who surveilled Paul's White House and grew to respect a man who was once a king in his own head and wound up shot to death while Christmas shopping.
Profile Image for Rich Flammer.
Author 1 book6 followers
January 1, 2008
Take an intimate look at one of the most powerful Mafia bosses in US history via a wire tap snug inside his palatial home, add the engaging, colorful ghostwriting of Laurence Shames, and you get a stunning, honest, and poignant ride through the fascinatingly complex humanity of the underworld. Unlike the plethora of books and movies that glorify American mobsterhood, this exposé reveals the mundane, insipid, tedious, fallible, and sometimes pathetic lives of gangsters, while granting deference and reverence when deference and reverence are due.

Rather than either celebrating or loathing the characters and their nefarious pursuits, the writers present a relatively unbiased account of their existence, never denying the Family their humanness nor frailty. And if the authors do err on the side of callousness (after all, they are in law enforcement and writing from the perspective of an enemy camp), they do so, undoubtedly aided by the prodigious literary skills of Shames, in a surprisingly considerate, respectful manner.

The same candor through use of wire taps that makes for such captivating reading left their FBI superiors fuming, and both agents had to leave the bureau in an unwitting deal that allowed them to collect royalties on the book. And despite the often dubious intimacies of Paul Castellano's life the authors share with the reader, the "Boss of Bosses" prestige was inadvertently, but not surprisingly, enhanced by the book, and the Godfather's notoriety has since gone from a relatively unknown, to legendary status. But it's not his legend, but rather his volatility, that provides the book with its biting intrigue and strength.
Profile Image for AC.
2,220 reviews
August 11, 2018
A great read. The ending is a bit strange, since the authors veer slightly into a sort of hagiography. But the first 5/6 of this book are fabulous and capture the authentic voice of the characters — like reading George Higgins’ best work. The real merit belongs to the ghost writer, who just wrote a bang up book.
4.5 stars
Profile Image for Eileen Fireman.
109 reviews7 followers
December 18, 2023
This a very good book about some very bad people. Paul Castellano, the Boss of Bosses, was the baddest—at first. As he grew in stature and maturity he became more remote and business minded than his street thugs. They liked it in the gutter. It was the only thing they knew. In another dimension he would probably be running a Fortune 500 company. As it was he was running the Gambino crime family and forbade his crew getting into the drug trade. They on the other hand were chomping at the bit to get into it anyway. There was just too much money to be made. The average gangster has a bottomless pit in their psyche that there is never enough money and will do anything to anyone to get it. After all the pit has to be filled, the fire stoked. Big Paul, as he was commonly known, had untold riches and it was coming in daily by the barrel. The soldiers started to resent him for his remoteness; his wealth; the controversial way he dealt with his marriage; the no drug edict, and most of all, they just didn't like or relate to him. He lived in a 17-room mansion on a hill facing the Verrazzano Bridge on the exclusive Todt Hill area of Staten Island. The mansion was referred to as the White House because of its resemblance. As time went on he spent less and less time outdoors or meeting with the lower echelons of his troops. He rattled around his mansion in a red silk bathrobe and velvet slippers a lá Hugh Hefner. Big Paul's bunny of choice, and love of his life, was his maid Gloria. A nothing looking, newly arrived immigrant from Columbia. This affair was carried on while his long suffering wife still resided in the home and his daughter and her family lived across the street. I guess the heart wants what the heart wants. His Captains came to him to pay tribute and report in. While this mob business and love affair was brewing, the FBI and then Mayor of New York, Rudolph Giuliani, made it their business to wipe out the Mafia. Those with the most power were the first to go. FBI agents Joseph O'Brien and Andris Kurins (the authors of this book) were on the task force and their priority was to take down Castellano. They managed to bug his house and listened in for months and hours of real time discussions with his men. They also heard everything there was to know about his astounding private life. I believe in time they began to have a Stockholm type symptom of feeling a certain respect for Castellano. Finally a big bust goes down and Paul is arrested. As they take him out of his house he behaves like the consummate gentlemen and they treat him as such by not even cuffing him until they get to court. Big Paul never makes it to trial because John Gotti and Sammy the Bull saw to his end. The two agents didn't realize that writing this book in such detail would put the FBI in a twist by releasing information the FBI thought shouldn't be released. My takeaway is on some level the FBI feared the two agents' respect for Castellano, as well as spilling FBI beans jeopardized the Agency. They are now ex-FBI and I think they couldn't care less. I recommend this book highly not because it dealt with a big shot Mafia boss but because the writing is superb and very smart. Operatic in scope O'Brien and Kurins grew to admire the man warts and all. The curtain is lowered and at the end of the game both the king and the pawn go back in to the same drawer.
Profile Image for Samantha.
155 reviews21 followers
October 14, 2007
This book was excellent! It was written by two former FBI agents whose job was to study Paul Castellano's evey move in order to bring him to justice.

At times poignant, at times funny, this book recounts the efforts to gain intelligence on a man who rarely left his house and held court (as it was later discovered) in the dining room next to his kitchen.

Paul Castellano was the most powerful crime boss at the time, boss of the Gambino family. But he was also human and suffered from the same things that ailed "lesser" people - diabetes, impotence, insecurity, indigestion. He was a man who earned his millions by stealing them, yet desperately wanted to be seen as a legitmate business man. He was also being used by his own mistress, who began as his maid and ended up (for a short time) usurping his wife as woman of the house.

O'Brien and Kurins, the authors and former agents, came to grudgingly respect Castellano despite the fact that he was "the bad guy." What he did was illegal and immoral, but he did it with surprising grace and and stuck to his beliefs with an admirable tenacity, even as his enemies (both inside and outside the family) were closing in.

This was a terrific read and I found it very compelling.
Profile Image for Derrick.
210 reviews132 followers
January 30, 2021
This book turned out to be pretty good. I didn't know very much about the career of Paul Castellano. The main focus of this book is the FBI's investigation of Big Paul and the Gambino family. At first, since this book was written by a couple of FBI agents, I wasn't really digging the law enforcement slant they seemed to put on everything. Then by about the last quarter of the book, I felt like they started to back it off a bit. It was almost like they began to feel sorry for an older and sicker Paul Castellano. I've read so many books about gangsters/mafia/organized crime. This one was definitely enjoyable. On to the next....
Profile Image for Jake.
2,053 reviews70 followers
April 12, 2022
I just finished rewatching The Godfather in honor of its 50th anniversary and I decided to tackle this one because the agents applied the movie title as a sobriquet for Paul Castellano, the mob boss of the Gambino crime family who is perhaps most famous as being the guy in John Gotti’s way that got killed in front of a Manhattan steakhouse.

There’s an abundance of information out there now that shows that mobsters are not the nobless oblige Robin Hood thief-types portrayed by Marlon Brando and Al Pacino. Most of them are lower class humps who had few options in life and decided to take the path of violence. This was not the common understanding of the mob in New York City in the 80s. Castellano was the biggest boss of the biggest family and yet, he was somewhat regarded as “the Howard Hughes of the mob”, living out of the limelight in his massive Staten Island manor. The mystery only added to the mythos but once you look behind the closed door, you see what was at the end of The Irishman: a broken, sad old man.

The book recounts the FBI’s surveillance of Castellano and some of his cohorts. A lot of the information was covered in other spaces but it’s still a compelling look at how the agents hunted down and developed relationships with the don and others. I didn’t care for the grousing about how hard it is to attain search warrants and affidavits, especially since we’ve seen the FBI play fast and loose with the rules amongst people without high profiles and fancy lawyers, but I enjoyed this one almost in spite of myself. It’s eminently readable and gives a portrayal of a sad man at the head of a futile empire that glitters like gold but which is really just gilded trash.
Profile Image for Carolyn M L.
286 reviews
February 5, 2022
This is probably one of the best mob books I’ve ever read - and I’ve read many. I was sceptical at first - I usually prefer to read from the POV of the mobster than from that of law enforcement (which usually contains a lot of back slapping, self congratulatory bluster) but Joseph F. O’Brien and Andris Kurins did a heck of a job with this book. Not much has ever been written about Paul Castellano - he’s most famously known for his demise at the hands of his successor, but in life, he was so much more than that. Reading excerpts from the infamous Castellano tapes as a result of the FBI bug was so very interesting. The man was human. Who knew?

I came by this book after much searching. As an avid true crime reader and an organised crime aficionado, I knew it existed but sadly it no longer seems to be in print (a crime in itself) but I found it. I’m so glad I did. Big Paul Castellano - despite his many faults - now means a lot more to me that being just the guy that John Gotti had whacked outside Sparks Steakhouse. The authors had developed some kind of bond with the man by the end of their investigation and I can understand why. I felt exactly the same by the end of the book. If you can find a copy, I’d highly recommend it.
Profile Image for FDR.
17 reviews1 follower
October 29, 2017
It was interesting to learn about the FBI’s methods, and Castellano as a boss. It wasn’t a tedious read, but they’re not the most modest fellows and it could've been written with less sensationalism. It's also not 100% how things happened.
126 reviews2 followers
July 9, 2021
A fantastic look at the investigation that all but crippled the Gambino Family and the Italian-American Mafia in general.

You'll come to know Paul Castellano the man more than anything else. The American public will always have a fascination with the Mafia and when you read this, you'll see that mob guys are extremely flawed human beings. They're extremely relatable yet seemingly god-like in their exploits.

Mobsters think they're beating the system by not being "working stiffs" but you'll see they deal with the same work-related issues anyone does only with the stakes raised much higher. Your boss in accounting isn't gonna have you shot outside your house, yet everyone can relate to disliking their boss, or being a boss with unruly employees.

The book is an easy and fun read, and if you're an amateur mob historian like me, it's a mandatory part of your mob literature.

The one thing that bugged me while I was reading this is that the agents who tell the story seemed to be enamored with the mob, as anyone would be, but they almost seemed to view themselves as being allowed to "rub elbows" so to speak, and they lament the end of this when Paul is arrested and finally put on trial. I felt like they used Paul so to speak and I didn't feel right about it.

I do however think it's interesting to see the metamorphosis of the relationship between Paul and the agents over the course of about 5 years.

Surprising that this was never made into a movie (that I know of)
Profile Image for TheSlowKenyan.
53 reviews1 follower
December 18, 2024
Unlike my previous mob book "Mob Power Plays", "Boss of Bosses" gives a pretty substantial look into the inner-workings of the American Mafia. It's pretty interesting stuff, even if the book is mostly just the two lead agents who worked on prosecuting the titular Paul Castellano patting themselves on the back.

The book opens with the murder of Paul Castellano (going for that "Citizen Kane" vibe, fellas?) which I don't think was a good move. I think this could have been saved for the end, which felt pretty abrupt. I suppose Paul's ending was abrupt for the agents who spent years building a case on the guy only to have him get riddled with bullets by hitmen, but did we the readers need to feel this in a different sense? I don't think so.

The best part of the book is probably the planting of the bug in Castellano's house and the recordings of his private conversations. The reverse heist is well done and it's where you learn that "The Sopranos" wasn't far off, because being a mobster is pretty damn miserable and empty. The life of constantly watching over your shoulder has some perks, but a hell of a lot of pain as well.

I enjoyed this book quite a bit. I don't think the agents make for the best authors, but it's definitely serviceable writing accompanying a fascinating figure and his organization.

I recommend "Boss of Bosses" if you're interested in the American L.C.N. families, or honestly, I recommend it even if you just enjoyed "The Sopranos".
Profile Image for Marti Martinson.
341 reviews8 followers
April 26, 2021
This is an impressively written book. Although it is filled with persons (not characters, because it's not fiction), they carry the names, descriptions, and titles throughout the text with precision. It has brevity, clarity, and even moments of very witty sarcasm. There is no reason to doubt their dedication or competence as field agents: if the installation of the eavesdropping bug is true, they certainly deserved medals. Their case reports are, hopefully, held up as how-to examples in FBI procedures.

Why did I give it a 1? Their half-assed, pissant apologetic for "FBI resources were more needed to fight communists" than the mob in the 50s, and their taking the newly arrested mob boss to a freaking deli, just like poor Dylan Roof was taken to Burger King after shooting 9 Black church members. RUFKM?

They left the FBI over royalty disputes, and I think they were reprimanded for adding text after FBI approval. Too bad they couldn't have stuck around to incarcerate todays bandits: hedge fund managers, pay day and title loan company CEOs, and day traders.

I still recommend reading the book.
Profile Image for Rumi Bossche.
1,092 reviews17 followers
August 6, 2024
Boss of Bosses by FBI agents Joseph F. O'Brien, and Andris Kurins, tells the story how they caught the capo di tutti capi, the boss of all bosses at the time, Paul Castellano. The beginning of this book really feels like that first season of the Sopranos in a way. Castellano works in the garbage department, lives in a big house outside the bigger city and seems untouchable. Until his house gets bugged. This is a really nice insightfull book as you get to hear the very most personal conversations the gangsters have with each other, and you get to know the certain soldiers and bigger ups. O'Brien and Kurins are relatable guys as you follow them and do funny stuff like send all the big gangsters Christmas cards to rile them up. The story never gets dull, although it gets pretty technical at times. This is a interesting read.
194 reviews2 followers
February 15, 2018
Something so simple as a recording device can lead to a really interesting book. 'The Sopranos' this wasn't [although I'm sure I heard Tony Soprano in my head at more than one point - rest in peace James Galdofini], but a book about the time before the 'Teflon Don', 'Wiseguy' and 'The Sopranos' - a simpler time, but the book doesn't glorify the business either. A really good book that I would recommend.
Profile Image for Anthony.
7,248 reviews31 followers
March 11, 2018
The story of a ten year investigation by FBI agents Joseph F. O'Brien and Andris Kurins, of Paul Castellano, and their crusade to gather criminal evidence to bring, not only him to trial, but all the heads of New York crime bosses, known as The Commission. Not an easy task, due to the low profile that Castellano kept, and his choice to run his crime network from the confines of his well guarded and highly secure home on New York's Staten Island.
Profile Image for Warbotter.
127 reviews
November 3, 2024
Mob Authors are a great read, Maybe it's because the subject matter is so choice with absolutely insane and dark stories. Either way O' Brien tries his best to Make Castellano a person, Not a sympathetic or likeable one mind you, But a fail able human being whose sin is very common, Greed. Wanting it all is taken to a new degree and a price must be paid. THEE Mob story.
Profile Image for Venatici.
102 reviews2 followers
June 2, 2017
Excellent portrait of Mafia godfather Castellano and the agents who brought him down after bugging his home.
Profile Image for Adam.
313 reviews
August 13, 2017
Meh. Not much substance besides gossip and household intrigue. Nothing about the inner workings of the mob or individual crimes really.
42 reviews
May 26, 2018
Sheds a bit more light on big Paulie...very honest, very well written.
Profile Image for Kelly.
320 reviews4 followers
November 26, 2018
Well told. The authors managed to corral lots of characters, lots of events and lots of background information into an easy to read and absorb book.
46 reviews
April 12, 2020
This was OK. In my opinion it did not pick up until the last few chapters. But an interesting read.
Profile Image for Patrick Wikstrom.
370 reviews3 followers
October 28, 2020
Fast read by the 2 FBI guys who brought him down. I love this stuff 3.5***
2 reviews
August 15, 2021
Costa Nosta at its peak
This entire review has been hidden because of spoilers.
Profile Image for Sue Boros.
87 reviews1 follower
June 10, 2023
While growing up in Jersey when Castellano hit the ground, this book reminded me of a lot and insured the stories were true.
5 reviews
December 26, 2023
Fantastic book, great depiction of the investigation and how agents work. Also an interesting view of Paul Castellano the man
Displaying 1 - 30 of 58 reviews

Can't find what you're looking for?

Get help and learn more about the design.