The Underboss: The Rise and Fall of a Mafia Family

by Gerard O'Neill, Dick Lehr

On February 26, 1986, Mafia underboss Gennaro Angiulo was convicted of racketeering and sentenced to forty-five years in prison. In The Underboss, bestselling authors Dick Lehr and Gerard O'Neill tell the story of the fall of the house of Angiulo. The Federal Bureau of Investigation, aided in part by the Irish Mob's Whitey Bulger, entered the Boston Mafia's headquarters in Boston's North End early one morning in 1981 and began to compile the evidence that would lead to the entire upper tier of one of the most profitable and ruthless criminal enterprises in America.

Originally published in hardback by St. Martin's in 1989, The Underboss became a national bestseller. Information uncovered during the course of Lehr and O'Neill's Black Mass investigations adds new dimensions to the story and the authors include this new material-including Whitey Bulger's cagey manipulation of the FBI-in The Underboss's revised text and in a new preface and afterword.

Genres: True Crime, Nonfiction, History, Crime, Biography

260 pages, Mass Market Paperback

First published January 1, 1989

About the author

Gerard O'Neill was an American journalist, newspaper editor, and writer.

Reviews

[Doreen Petersen · Rating 5 out of 5]

Outstanding book!! Would highly recommend this one!!

[Stevie · Rating 5 out of 5]

One of the best La Cosa Nostra book's I have read The Underboss details the rise and fall of Boston's most powerful Italian mobster, Gennaro "Jerry" Angiulo. Angiulo and his brothers controlled the city's gambling and loansharking rackets from their stronghold in the city's close-knit North End. Jerry Angiulo has to be one of the vilest creatures in the history of the American Mafia ruling with an iron-fist and continually berating his underlings which included calling his son Jason a "cocksucking motherfucker" to his face on regular basis for his constant mistakes. Angiulo was a multi-millionaire and huge money-maker for New England crime boss Raymond Patriarca, he wasn't considered a tough-guy but his power was backed up by the formidable Caporegime Larry Zannino, who along with Jerry's brother Danny, handled the murkier side of things gleefully murdering and maiming anyone who got in the Angiulo's way. The story details the FBI's attempts to bring down the Angiulo's by bugging their office on 98 Prince Street, no-mean feat in a neighbourhood constantly on the lookout for suspicious activity from law-enforcement. Through sheer hard work, resourcefulness and dedication the agents successfully bugged the inner sanctum of the Boston Mafia which proved to be a gold mine due to Jerry Angiulo's constant bragging and penchant for strategising out loud. He was brought to trial and convicted under the RICO act and sentenced to life in prison, with his brothers and underlings receiving varying sentences. This was one of the FBI's finest hours but unfortunately some of the agents who helped bring down LCN in Boston then compromised themselves by giving Irish Mob boss Whitey Bulger a license to kill while taking brides from the psychotic mobster in one of the darkest chapters in the history of law-enforcement. The Underboss is an incredible tale and I would highly recommend it, it's one of those books that you don't want to finish.

[Genna · Rating 2 out of 5]

I was genuinely concerned that this book would never end. I give it two stars because it is obviously well researched. But no more than that because they didn’t do anything interesting with the information they got. I think they were trying too hard to make a long book when they are only used to writing articles. It was unorganized and I’m not entirely sure that I learned anything substantial about the Boston Mafia. I was thinking about reading Black Mass, but I think I’m all set. Their shameless plug of Black Mass in their “conclusion,” was cute though.

[Joe Rodeck · Rating 3 out of 5]

Probably better if you're from Boston.

[William Connolly]

Quite informative, very interesting, a good insight into the Mafia outlook on life. The Whitie Bulger situation could have been updated but other than that an excellent true crime book!😎😎

[liz · Rating 3 out of 5]

The true story of Gennaro "Jerry" Anguilo, who ran the numbers racket for the Boston Mafia (and all mob actions for the city).

There was no way I could not love this book; Jerry lived in the town where I grew up. Jerry's still in prison, but we'd go trick-or-treating to his house (where his wife still lives) every Halloween (because they give out full-size candy bars). My family gets Christmas cards for the Anguilos. And I also recognized some places in the North End; Cafe Pompeii (an Anguilo hangout that they owned) is where my brother ate pizza with the cheese on for the first time! Loved it.

[Mark · Rating 5 out of 5]

This terrifying book refutes the notion that the preponderance of organized crime in the Northeast is confined to New York City. From Boston to Providence to Hartford, few in "the life" could afford false steps under the paranoid eyes of Jerry Angiulo, especially given his ties to the legendary Whitey Bulger. After you read this book, you'll be forgiven a case of the willies as you walk Boston's North End of Providence's Federal Hill. For those morbidly fascinated by organized crime, this is a page-turner.

[George · Rating 3 out of 5]

I grew up outside of Boston and went to high school with some of the Angiulo family, so I had a personal interest in this book. The book filled in a lot of the "gaps" concerning the Angiulo's and organized crime in the area. For this alone, I enjoyed the book and would recommend it highly to people like me, who know the area, and have an interest in organized crime. For those whose interest is purely the "true crime" genre, I would say it's "pretty good".

[Lee · Rating 2 out of 5]

I got this book because of how much I enjoyed Black Mass, this author’s book about Whitey Bulger. This book follows the investigation into Gennaro Angiulo who ran Boston for the Patricia family. It was okay but the Boston mobsters just aren’t as interesting as NY or Chicago or even their Irish counterpart Bulger in the same city. Interesting that John Morris and John Connolly who were brought down in the Bulger investigation.

[Sarah Bykowski · Rating 2 out of 5]

The Underboss was an okay read. There was no driving plot, and it jumped around too much for my taste. It also seemed that a lot of the info was restated a few times, as if simply to make the book longer. Now, I know that it is a work of non-fiction, but that doesn't mean they have to be confusing and well...boring with it. Definitely not a book I'd pick up again.

[Matt · Rating 3 out of 5]

The full Rise and fall of Jerry Anguilo and Family. Outlines the Boston and new England Italian Mob origanizations from the 30's through the 80's. Outlines the Patriarcha(providence Rhode Island) Family relationships. Anguilo ended up in Jail for lfe in the 80's. Made room for the Winter Hill/Whitey Bulger era in Boston.

If you are into Boston Mob History, this is a decent read.

[Mila Pool · Rating 4 out of 5]

If you want to read about the FBI and their investigation into Jerry then this is the perfect book. It has information about Jerry and his life but not as much as I hoped. I was hoping it would get deep into the boston mob war and Jerry's using it to get even with some people but I was a little disappointed there.

[Stefanie Robinson · Rating 4 out of 5]

This book is about Gennaro Anguilo, who was a prominent member of the Boston area Mafia. The FBI was aided by Whitey Bulger and his underhandedness, thus able to compile a pretty good case against the upper echelon of the Boston mob. This book was very interesting, and I enjoyed reading it.