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Whitey: The Life of America's Most Notorious Mob Boss

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From the bestselling authors of Black Mass comes the definitive biography of Whitey Bulger, the most brutal and sadistic crime boss since Al Capone.
 
Drawing on a trove of sealed files and previously classified material, Whitey digs deep into the mind of James J. “Whitey” Bulger, the crime boss and killer who brought the FBI to its knees. He is an American original --a psychopath who fostered a following with a frightening mix of terror, deadly intimidation and the deft touch of a politician who often helped a family in need meet their monthly rent. But the history shows that despite the early false myths portraying him as a Robin Hood figure, Whitey was a supreme narcissist, and everything--every interaction with family and his politician brother Bill Bulger, with underworld cohorts, with law enforcement, with his South Boston neighbors, and with his victims--was always about him. In an Irish-American neighborhood where loyalty has always been rule one, the Bulger brand was loyalty to oneself.
                
Whitey deconstructs Bulger's insatiable hunger for power and control. Building on their years of reporting and uncovering new Bulger family records, letters and prison files, Dick Lehr and Gerard O'Neill examine and reveal the factors and forces that created the monster. It's a deeply rendered portrait of evil that spans nearly a century, taking Whitey from the streets of his boyhood Southie in the 1940s to his cell in Alcatraz in the 1950s to his cunning, corrupt pact with the FBI in the 1970s and, finally, to Santa Monica, California where for fifteen years he was hiding in plain sight as one of the FBI's Ten Most Wanted. In a lifetime of crime and murder that ended with his arrest in June 2011, Whitey Bulger became one of the most powerful and deadly crime bosses of the twentieth century. This is his story.

435 pages, Hardcover

First published June 29, 2011

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About the author

Gerard O'Neill

10 books9 followers
Gerard O'Neill was an American journalist, newspaper editor, and writer.

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5 stars
226 (23%)
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412 (42%)
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281 (28%)
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48 (4%)
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Displaying 1 - 30 of 100 reviews
Profile Image for Kelli.
931 reviews444 followers
December 20, 2019
Growing up just south of Boston, I’ve heard stories about Whitey Bulger since I was little. With his capture, trial, incarceration, and murder all occurring within the last eight years, I’d imagine everyone knows who he is now. This is not a book I’d have chosen had it not been recommended to me by my father. The conversations I’ve had with him upon finishing to book have been more interesting to me than the book was. I learned that my dad was stationed at South Boston High School during bussing, which he describes as the worst time of his career. That’s saying a lot considering he went on to become head of homicide.

This book, though a bit bogged down with details at times, was enlightening and also, disturbing, scary, and sad. For me there was a clinical feeling about Whitey’s crimes but I suppose no one can get to his inner most thoughts and decode that which we thankfully do not understand. A monster with charm and swagger and an embarrassingly corrupt FBI make a lethal combination. Not the best holiday reading, but good enough to potentially send me in search of other books about this.
Profile Image for Valerity (Val).
1,107 reviews2,774 followers
September 30, 2015
Informative book on the mob boss Whitey Bulger who was in the news not too long ago, on trial. A vicious killer and controlling boyfriend, he went on the run at one point, dodging the law for many years. Prior to that, he had a relationship with the FBI as an informant that is amazing for its duplicitous nature, and how it kept him safe for a long time while he committed crimes and ran his gang.
Profile Image for Amanda.
25 reviews1 follower
May 5, 2021
This book was very good but if you want more detail on the FBI corruption and Whitey check out Black Mass: Whitey Bulger, the FBI, AND A devils Deal by Dick Lehr. If you are looking to read more about families in Southie and how they were impacted by Whitey read All Souls: A Family Story from Southie by Michael Patrick MacDonald.
Profile Image for NaTaya Hastings .
665 reviews20 followers
February 23, 2020
There just wasn't enough meat in this one to keep me interested. I tried listening on audiobook, and suddenly I'd tune back in and realize I hadn't paid attention to the last 40 minutes. Then I'd back up and try to focus and the same thing kept happening. I finally gave up.
Profile Image for Michael Linton.
331 reviews4 followers
August 12, 2023
This is a book about a guy who was America's most wanted at one point. He was a psychopath who deserved the demise he got. It's a fascinating disturbing story.
Profile Image for Kris.
256 reviews5 followers
October 6, 2015
I bought this book before I knew of its predecessor “Black Mass” written by the same authors and now a motion picture. For some reason I have picked up quite a few books on the New England mob this year. In this book, I feel like I have finally been able to see the Bulger story in its entirety and to better understand how the FBI utterly failed in its role as shepherd for its CI program.

The book outlines the Bulger family history from their initial immigration from Ireland to Newfoundland, Canada and then on to Boston Massachusetts. Like many poor neighborhoods, the bonds between family groups of any single ethnicity can be very tight as people rely on one another to make ends meet.

The Bulger clan is tight and although they all took different roads in life – from State Senator to America’s Most Wanted Man, they all continued to support one another. Whitey spent the majority of his life incarcerated up until John Connelly, his former neighbor became his FBI handler. He did time at Walpole in Boston as well as Alcatraz. Whitey did not waste his time while incarcerated. He was a voracious reader and highly intelligent. A lot of planning went into everything he did and he had a lot of time to examine past errors.

There were so many conflicts of interest in this relationship it’s a wonder that it lasted as long as it did. Connelly was younger than Whitey and looked up to him. He felt indebted to Whitey due to a childhood bullying incident where Whitey had run interference for Connelly.

In addition, once the graft train had pulled out of the station with Connelly firmly aboard and Whitey giving generously, there was no stopping it. In fact, Whitey had such a handle on this that when Connelly started lavishly spending by purchasing a luxury boat which was obviously way outside of his FBI pay check, that Whitey made him return the boat.

In exchange, Connelly provided Whitey with tip offs on everything: when indictments might be handed down, criminal investigations into Whitey as well as his associates, information on opposing gangs and what they were up to in terms of territory and operations. In addition to Connelly, Bulger had state police, local Boston PD and politicians and other city, county and state officials in pocket.
As for Whitey’s 13 years on the run as the second most wanted fugitive, moving up to number one after the death of Osama Bin Laden, I was curious as to how he was able to hide so successfully. The answer in short – easily. Despite the FBI’s press releases that they were all over it or nearly had him, they were not even really looking for the first 12 years.

They had at most one or two agents on the case at any one time. They had hundreds of tips coming in – many very viable that with manpower would have resulted in easy captures. The truth was they decided to focus on Europe and they never wavered from that idea. The truth was, Whitey moved around for about 3 years, had an extensive array of false i.d.’s and then settled with his girlfriend in California.

In the end, the capture was easy. But not due to the FBI. A tipster had to call the FBI three times to finally get someone to take her seriously. His neighbors liked him but were able to make it easy for the FBI to take him down peacefully. He was also a man in his 70’s and from the reading of the book, was starting to get worn down by life on the run.

Whitey Bulger was a bad dude but the FBI look like a bunch of incorrigibly corrupt Keystone Cops. It doesn’t give me any peace to think that this agency is in charge of tracking down the bad guys.
For those without a lot of information about Whitey Bulger and a knowledge base that covers the bare bones of the case, this is a good book, knowledgeably written that provides many details that help explain the heinous nature of Bulger’s criminal enterprises and then the reason he was able to evade capture for so long.

I haven’t seen the movie but I suggest the book first which might help put some of the movie into perspective. Boston, the Irish mafia, a worldwide chase….what’s not to like? And it’s all true.
Profile Image for Wayne Fitzpatrick.
44 reviews2 followers
January 5, 2014
The third book in the trilogy of Whiter Bulger books by Dick Lehr and Gerard O'Neil(the other two books are "Black Mass" and "The Underboss"), "Whitey" is a comprehensive, all encompassing look at the life of Whitey Bulger.

Lehr and O'Neil do a yeoman's work of tracing Whitey's life first as a young, disaffected child to a intimidating, controlling crime boss. Lehr and O'Neil include testimony and interviews from all of the key players in the crime world that Whitey traversed. They also illustrate how the tables could turn quickly and how loyalty and trust were just words in their lives of those in the underworld as well as with those sworn to protect us from them.

The authors painstakingly show how the FBI would often give special consideration to their informants even if it meant endangering suspects or even innocent civilians. In many instances it was unsettling to know these are the people sworn to protect the public.

The most interesting section of the book was the descriptions of the lengths Whitey and his girlfriends had to take to evade the law for so long and the close brushes with the law they experienced. At any moment their fabricated identities could be shattered. Yet, he always seemed to either talk his way out of things or flee just in time before the law caught up to him. Until the end that is.

At times, it could get a little slow and dry. The authors went into great length to give details that were not relevant or pertinent to the story. For instance, they describe the trim of the apartment complex Whitey and his girlfriend were hiding out.

many books have been written about Whitey and his cohorts. This book is easily one of the best.
27 reviews
February 24, 2013
Was looking fwd to this for a while, was very good. To me, problem was that their last book on subject (Black Mass) was just so pefect that all of the best stuff about Whitey was already told.
It does tell everything that happened since WB disapeared and answers a lot of questions that have been brought up in the slew of books written on subject.
Profile Image for Christopher Borden.
15 reviews
March 5, 2013
Not as good as Black Mass by same authors, lots of rehashing old points, would have been better as a multi-part series in a magazine or newspaper.
Profile Image for Joanne.
829 reviews49 followers
May 31, 2014
A horrifying account of greed, evil, and a complete disregard for the law. There was stuff about Whitey too.
1 review
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October 12, 2016
I believe I have made a pretty large dent in this book and still I am not entertained. The slow pace of the biography makes it boring and hard to follow. Had to cut this book short.
1,579 reviews7 followers
February 22, 2018
For awhile I tho't it was much too detailed, but I found so much of it interesting, beyond the piece-of-dirt Whitey, and his enabling, politically-powerful brother, Billy.

Also much about how the US prison system works --or doesn't. Some sections difficult to hear, but I think we owe it to the victims, some innocent, to get thru it.

It seems as if, from his childhood on, Whitey was given every opportunity to turn his life around, but when it seemed as if he was, it was superior acting. Except for his years in fed prison, he was able to escape from being caught over and over.

Much of it was due to Southie Boston's Irish clannish acceptance of any behavior, but later, his brother Billy was able to influence higher-ups or initiate legislation to protect him.

I kept waiting for Billy to be indicted before or after Whitey was caught, but thanks to US's 5th amendment, he's doing well and when this was written, was still collecting $200K pension. Unbelievable!

It also more than confirmed what I already knew about dirty, self-serving FBI agents, at least in PA in the mid to late 1980s, but I hadn't realized how wide-spread and long-term the FBI's criminal activity was -- terrible when they're supposed to protect people, but did/do just the opposite. I feel sorry for honest agents as the FBI's reputation has become so besmirched.

This summary of Billy's "fate" is from the UK's Mail in Sept 2005:

"William 'Billy' Bulger, 81, lives in brother's South Boston stomping ground
Mr Bulger lives discreetly with his wife of 55 years and is close to his nine children - but still keeps in touch with mobster brother Whitey
He became a politician but career ended in disgrace when he took Fifth Amendment over knowing about his brother's crimes
Fought to keep his $200,000-a-year pension despite refusing to testify
Three of Bulger's victims, including blonde sex-crime victim Deborah Hussey were buried in basement in neighboring house
Whitey enforcer claims he was in Billy's house '100 times' - but politician said he hadn't even heard his brother's gang's names"

Read more: http://www.dailymail.co.uk/news/artic...
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6 reviews
April 10, 2025
I listened to the audiobook. This is a good book that is informative and well researched. The story is mostly linear, although it occasionally will jump way into the future to finish up a thread and then jump back in time again. It can feel a little unorganized at times. The writers go overboard with their primary sources describing every single piece of paperwork they have. This is especially bad when they're describing his early life in prison. The authors didn't need to go that far into detail. I'm also not sure if some of the evidence holds face value to say some of the things they argued. This book just is too long. I'm pretty sure Whitey took the editor out back and shot him so he couldn't finish the book.

The idea they're getting into the head of Whitey Bulger is kind of a gimmick. The authors say he's an angry, business minded, psychopath with family issues, but I don't know if you really get the deep level of psychoanalysis they start off looking for. They also didn't need to go into detail about what a psychopath was to prove their point. It's pretty well known what a psychopath is, and that just made for one more tangent. The book could be better organized, but it is pretty well documented which is nice, and it definitely goes into detail on his life. It should really just be shorter.

I also felt like the book glossed over the racism of Whitey and the area. The authors should have paid more attention to that and called it out. Was Bill Bulger still praising their fight against segregation in the 2010s? I'm honestly not sure since they barely talked about it. All this moralizing about the FBI and Whiteys actions, they could have had some with the racism as well.
Profile Image for Diane.
395 reviews
October 9, 2019
I learned a lot of history about my adopted state and area, none of it nice. I kept thinking about all the chances Whitey got, and how others weren't given those opportunities, or those chances. Others didn't have family and politicians looking out for them, making deals, putting pressure on the system. I thought of all the disenfranchised and felt sad, and also annoyed at the unfairness of it all, the injustice of the justice system. I was most disgusted by the corrupt FBI and its continual denial and ineffectiveness, the lack of humanity. That the penal system used prisoners - and students - for experiments is not new information but it nonetheless makes me ill to think about. It is a warning to those who come after - these things have happened. These things do happen. Except for vigilance and vigilance and more vigilance, they will happen again and again and again.

I also felt that the author had a number of pages he needed to complete: this led to many repetitions. Perhaps they thought that they were saying the same thing in a different way or giving it a different weight, but it was it was it was just annoying as the previous repetition would also be annoying to anyone who can read.

There was also a flare for the 1950's TV show by Jack Webb, Dragnet with Harry Morgan. It gets rather heavy handed.
266 reviews
September 11, 2022
I’d never heard of Whitey Bulger, but I had heard the phrase “Where’s Whitey?” in passing before and it’s nice to have the background knowledge of what that phrase means. I know people say that history in schools is lacking (and it is) and I’m not saying we have to dive into mob bosses and crime history too deep but man, it woulda been nice to know of one of the most embarrassing histories for the FBI. I know the FBI and the CIA and the government overall has some dark history but Whitey’s may be one of the worst (tied is the LSD history). Whitey killed 19 people, 11 of which was when he was an FBI informant so the FBI knew about them and even warned Whitey about people snitching on him. It took 16 years for the FBI to truly find Whitey and Carol and that was only after they allowed the US Marshall’s to step in - but not lead the investigation. I find whenever I learn something knew, coincidentally something pops up about it. When I was reading this book, I learned that after Whitey was released from his solitary prison sentence into the crowds with other inmates, he lasted 6 minutes before someone killed him. Overall, it was a dark and fascinating read about a true sociopath and the inner workings of his mind and life.
This entire review has been hidden because of spoilers.
Profile Image for Amy.
746 reviews14 followers
September 27, 2021
Wow did this book end abruptly!
I was expecting it to cover the trial and subsequent death but it slammed to an end not long after his capture - it felt like the author was rushing to capitalize on the sensation of Whitey finally being captured.

Not sure how he got all the detail about life on the lam - unless Whitey told more/gave more interviews than I'm aware of (I'm a child of 1980s-90s Boston suburbs - we all heard about Whitey growing up). I suppose a lot of the detail came from the apartment they lived in - once he was caught the drapes on the windows and hidden nooks would be revealed....

This book solidified in my mind that Billy was TOTALLY complicit in the escape and life on the lam. I'm amazed that nothing could be pinned on him... well done Bulger brothers.

Decent read, maybe not the best for someone not already familiar with Whitey Bulger.
Profile Image for Judy.
143 reviews18 followers
August 21, 2021
There are some really good reviews about this book. Some mention the Black Mass: An Unholy Alliance between the FBI and the Irish Mob. The book is written by the same authors as Whitey. That is another book I will put on my list to listen (to). What struck me about this story is the time frame in which Whitey was doing his evil deeds. I know the mob exists, however, I think of the 20s-50s being the mob era. When Whitey was rising to power I was married and raising my son. That struck me as bizarre. I think talking with Kelli who grew up in South Boston would be interesting.
When Whitey was finally captured, the authors stated something to the effect that Whitey was captured because of his girlfriend and her cat.
Profile Image for Jackie.
744 reviews16 followers
September 18, 2022
Interesting, just way too long/detailed in the wrong places. There are some really great insights in parts of this, but it felt somewhat meandering at times trying to fit everything in.

Great perspective and details on the FBI, growing up in Southie, time in prison and experiments with LSD, burying bodies, his psychopathic actions, and time on the lam. I feel like the part that was glossed over was his rise to power and daily operations as a crime boss. Some bank robberies, and then the informant angle covers a lot of it, but there was limited information on the continued revenue, besides some mention of drugs here and there.

Definitely get the perspective that he was a terrible, racist, murderer, and psychopath, but also a bit of a genius manipulator.
Profile Image for Steph.
374 reviews8 followers
October 26, 2020
Summer 2011, when Whitey Bulger was finally caught and arrested, I was working as a lifeguard before by Junior year at OU. I don’t remember hearing about this at all.

The book goes through Whitey Bulger’s life. He started at a very early age getting into trouble. He was arrested for bank robbery, and while in prison he participated in an LSD program. He was transferred to Alcatraz, and then back out. If I remember correctly, he had one of the shortest stints in Alcatraz compared to other inmates.

Once out, he moves on to murder, being a big time mob boss, and an FBI informer.

109 reviews2 followers
March 31, 2018
A biography of the Irish gangster_mafia boss Whitey Bulger who was at one stage the second most wanted man in the world by the FBI and moved to the no. 1 spot after Osama Ben Laden was killed.
He was able to escape most punishment in his 30 Yr crime spree and 12 odd yrs on the run because he controlled the corrupt parts of the police force and FBI with bribes. They turned a “blind eye” to his crimes and gave him a licence to kill.
Profile Image for Seashelly.
234 reviews9 followers
June 9, 2019
2.5 !

There's not much I want to say, honestly. I appreciate the authors' attempts to fill in history when discussing about how certain events came to be. And it was entertaining! But beyond that, it has too many skipped over details for me to actually care.

Yes, I recognise this is a biography and not a history book, I'd still appreciate less focus on a man losing his shit when one good thing leaves him when he has about 50 other ones.
Profile Image for Aaron Battey.
92 reviews3 followers
July 14, 2021
Very good book. I learned a lot about the mob in general. I had no idea who Whitey Bulger was before reading this. Who knew he was America's #1 Most Wanted after the capture of Osama Bin Laden. Many people knew, but I didn't, and this book gives a good explanation of what made him just that. It was very interesting to learn of the corrupt partnership that Whitey had with the FBI and specifically Agent John Connelly. Interesting book if you are looking for a historical biography.
Profile Image for Gregg.
629 reviews9 followers
November 4, 2018
This book provides a detailed summary of everything Whitey did. This gets both a hometown and timeliness bump (Whitey was killed when I was in the middle of this book). The successful manhunt epilogue also finishes strong.
This entire review has been hidden because of spoilers.
Profile Image for Amy Rohn.
98 reviews
December 27, 2020
I read half of the book and couldn’t really get into it. So I tried it on audiobooks, and would listen to it for about 45 mins and realized I wasn’t paying attention. It was just background noise. I never did finish it.
Profile Image for Simeon.
240 reviews1 follower
May 3, 2018
A/UN Pretty interesting story when they has access to facts - lots of peripheral filler and use of the term "likely" ended before results of final conviction trial
Profile Image for Kevin Koppelmann.
642 reviews1 follower
January 10, 2019
Great book about the notorious gangster and his corrupt family. I never realized his brother was such a powerful congressman. Possibly the more corrupt Bulger of the two.
38 reviews
June 13, 2019
A fun book about a gorey topic
This entire review has been hidden because of spoilers.
Profile Image for Rachel.
605 reviews
September 8, 2019
Parts were fascinating and parts droned on. All in all it was good and I learned about a guy I didn't previously know much about.
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