Tuesday, April 9, 2024

A Look Back At The Infamous Boston Criminal Whitey Bulger: My Crime Beat Column On 'Whitey: The Life Of America's Most Notorious Mob Boss'

Back in 2013 I reviewed a good book on the notorious Boston criminal Whitey Bulger for the Washington Times, and I later interviewed one of the authors in my Crime Beat column. 

You can read the Crime Beat column and link to the Washington Times review below:

As I wrote in my Washington Times review of Whitey: The Life of America's Most Notorious Mob Boss (Crown), there have been many books written about James “Whitey’ Bulger, the Boston Irish mob boss currently on trial in Boston for 19 murders and other crimes, and up to now Black Mass by Dick Lehr and Gerard O’Neill was the best of the bunch.

But with Whitey, Lehr and O’Neill have surpassed themselves.

Dick Lehr (seen in the below photo) is a professor of journalism at Boston University and a former Boston Globe reporter. He is the co-author of Black Mass and The Underboss, along with Gerald O’Neill.

I contacted Dick Lehr and my interview with him is below: 

DAVIS:  I worked for a Defense Department command in Philadelphia and for a time Boston was our regional headquarters. During those years I was a frequent visitor to Boston and I grew fond of the city.           

LEHR:  There is a small-big city feel, or a big-small city feel. 

DAVIS:  I liked the bars as well. 

LEHR: Then we have something else in common.

DAVIS:  I enjoyed your previous books, such as Black Mass and I enjoyed Whitey. Whitey Bulger is an interesting guy, although he is a God-awful criminal. I’ve covered organized crime for a good number of years now and I most recently interviewed Philip Leonetti, the former underboss of the Philadelphia Cosa Nostra organized crime family in Philadelphia and South Jersey. He said that he killed “bad guys.” They were trying to kill him, so he killed them. He said he never killed innocent people. Whitey Bulger, on the other hand, not only killed rival criminals, he reportedly strangled and murdered two innocent women. 

LEHR: His first known murder was a mistake. He intended to kill a competing gang member but he ended up killing the guy’s brother. He just shrugged it off.  

DAVIS: That’s a bad start. So it seems Bulger is in a class by himself, would you agree? 

LEHR: Yes, I think it shows the extreme depravity and viciousness that you referred to when you said he was God-awful. In the last month or so, through his attorney, he is putting out a new line - it sounds like Leonetti – that the people he killed deserved to be killed and he never killed those girls. It’s just Whitey being Whitey.        

DAVIS:  That’s been a mob thing for years, saying we only kill each other.       

LEHR: Whitey is trying to take back those murders, saying that I didn’t kill those girls. I wouldn’t do that. He is trying to get himself back to being what is more gangster-respectable. His problem is that the evidence seems overwhelming against him in connection to those two murders and already federal court judges have ruled that he killed them.      

DAVIS:  His partner-in-crime, Steven “the Riflemam” Flemmi, testified that Bulger killed the girls, right?

LEHR:  Yes, and Kevin Weeks. 

DAVIS:  Philip Leonetti recently wrote a piece in the Huffington Post. He wrote that when he was the Philadelphia underboss and Nicodemo Scarfo, his uncle and the Philadelphia boss, was in prison, he met with the New England Cosa Nostra guys and they were complaining about Bulger. Leonetti said they were described him disdainfully as a drug dealer and not a mob guy or true gangster. Do you think that is an accurate view of him by the Boston mob? 

LEHR: I think that is a true view of how someone in their shoes would look at someone like Whitey Bulger. He was a drug dealer in the 80’s and he made a ton of money off of cocaine. I think they underestimated him if they considered him just a nasty little drug dealer. They are underestimating or under-evaluating his position and his standing in the underworld. He was “it” in the 1980’s. So whether you are from New England or Leonetti from Philadelphia, that is a snapshot that does not capture the scope of this man’s power at the time, partly rooted from the power of the FBI watching his back. 

DAVIS: Bulger is unique in the annuals of crime in that sense as well.

LEHR: Totally, totally.

DAVIS:  Being an informant to gain police protection is not uncommon in crime and organized crime, but in that Bulger was able to manipulate the FBI agents and have them protect him so well over the years is unique, I think, in crime history. 

LEHR: I think so. We say in the book that is why history will view him as one of the more significant crime figures in America. You can’t mention him without saying in the same breath, corrupt FBI. 

DAVIS: How big was his crime empire? In terms of dollars and business, was he a rival and competitor to Cosa Nostra?     

LEHR: Well, certainly in the Boston branch, which reported to Providence, yes, I think so. This was unique too, in the sense that it was a cult of personality – Whitey’s. We describe it in the book as a closely-held corporation, where he surrounded himself with an immediate circle of unbelievably ruthless killers - Martorano, Weeks, and Flemmi – who were loyal and trusting. Just like his own physique, he kept it lean. He didn’t bother with some kind of extended organization. 

DAVIS: Yes, it was small in numbers compared to other organized crime outfits. 

LEHR:  Yes, and yet he controlled plenty because he was feared and powerful and vicious. There were all these sort of affiliates. All of these drug dealers in “Southie” were under his thumb. He had a drug operation, but they rarely saw him. There was all this insulation in between. So he ran an organization and then beyond the organization he accomplished and had the knack to intimidate major New England drug traffickers. They paid him a tax in order for them to do business. There are estimates of $10 million to $50 million, but who knows? 

DAVIS:  And where is that money today?

LEHR: Exactly. That is the big final question. But he would get a half of million dollar cut out of some major pot load moving through Boston heading up New England. So that speaks to his presence in a big way, even though he had no extensive organization and no lines of succession like the mafia. It was a cult of personality.      

DAVIS: All based on his reputation that he can and will kill you, and kill you viciously. Those stories of him torturing people before he killed them.     

LEHR: Yeah, and this all reinforced the myth of Whitey being the ultimate “stand-up guy,” which was his reputation.  

DAVIS: The Robin Hood of Boston.

LEHR: He despised and hated informers. Psychologically, he was projecting. He was known for that viciousness and torturing. When he was killing an informant, a rat, he brought a special viciousness to bear. That helped feed the notion that Whitey absolutely can’t stand a rat. It was such an anathema to him, such a horror – in part because he hates himself.      

DAVIS: Where did the phrase “Whitey is a good bad guy” come from? 

LEHR: The first time I heard that was from the mouth of FBI agent John Connelly back in 80’s. Isn’t that funny?  We heard that before we knew what we know today. Connelly was simply an FBI agent who was describing this kind of Robin Hood mythic Whitey Bulger crime boss.  

DAVIS:  Connelly was saying this to reporters like you? 

LEHR: Yes. Looking back in hindsight, John Connelly was one of Whitey’s best marketers and PR agents. He was spinning the myth of Robin Hood. Sure he’s a bad guy, but he’s does nice things for people. And we show in the biography, it is an extension of what Whitey has always tried to project all of his life. When he went away to prison he was trying to say I don’t belong here. It jumps off the page, some of these assessments from Alcatraz. How Whitey was complaining about the vulgarity of his cell mates. Give me a break!      

DAVIS: I read Black Mass when it came out years ago and I thought it was outstanding. It was a comprehensive look at Whitey Bulger’s criminal career and his FBI connection. So why did you and your co-author decide to write a biography of Whitey Bulger? And how does the biography differ from Black Mass?

LEHR: That’s a good question. And the answer is the bulk and the focus of Black Mass is the Whitey Bulger/FBI years, basically two decades from 1975 to 1995. It has been called the “Unholy Alliance,” and the “the Devil’s Deal.” So when Whitey was captured, we realized that this guy actually now warrants a biography. Part of it was realizing that in 1975 when he cut his deal with the Boston FBI, he was already 48. He lived half a life that we barely scratched in Black Mass and no one else has. There was this whole life that had not been explored and the sense that we talked about – he’s unique now. He has a place as a significant crime figure in American history. We wanted to put the Black Mass years in a larger context of his life story, of a biography, in which we try to not just tell this dramatic and horrific story, but get more into the why and how in the making of this monster. I think the challenge of any biographer, regarding any subject, is to go behind the “he did this and he did that” and try to reveal some insight and meaning.              

DAVIS: I thought Whitey was outstanding. The prison years and the LSD tests were particularly interesting. How were you able to get Bulger’s prison records?   

LEHR: That was a huge breakthrough. In the original outline, we had one chapter for his nine years in prison. Two months later we got hold of his prison file because it has become a public record and one chapter became four, four and a half. It is fascinating.   

DAVIS: I knew he was connected to his Boston politician brother, but from your book I learned that the U.S. Speaker of the House was writing letters for Bulger as well.    

LEHR: Around here we knew that the family had a connection to House Speaker John McCormack, but that’s all we knew. But from the prison file, and also the McCormack papers at Boston University where I teach, we suddenly have all this meat and muscle to put on that skeletal fact. Whitey had a benefit in prison that no other inmate did, which is access to power like that.     

DAVIS: You’ve been covering Whitey Bulger since you were a Boston Globe reporter. How long has it been? 

LEHR: Go back to the late 80’s, that’s when we started and broke the story about some kind of special thing going on between Whitey and John Connelly and the Boston FBI. 

DAVIS: That was your first story? 

LEHR: That was it. It was historic in the sense that it was the beginning of the end. It is another reminder how journalism can play a role in history.  

DAVIS: Have you met Whitey Bulger?

LEHR: No. I was in court when he came back to Boston and I’ve written him at least five times since he’s been back about the biography. Boy, did I want a meeting for the biography but he refused. He wants everything on his terms. He writes letters to a friend of his, a guy we mention in the book named Richard Sunday and then Sunday gives the letters to the Globe. It’s news in the sense that it is Whitey’s letters, but it is the world according to Whitey. It’s like he has open mike time. It’s not a question of anyone challenging him in any way. That’s where he puts out things like I don’t kill girls and things like that.            

DAVIS: Do you think he is going to write a book or have someone ghost a book for him?

LEHR: He was writing one while he was in Santa Monica, which I think he had stopped. I hope that it gets released because it will be fascinating to read, although not so much for its truth. I think he got almost a hundred pages out, but the government has it. He needs to find someone who will close their eyes and hold their nose.          

DAVIS: And cash the check. Are you covering the trial? 

LEHR: I’ll be there and we’ll probably write a new chapter about the trial for the paperback.  

DAVIS: Do you plan on writing another Bulger book? 

LEHR: I don’t think so. But I think one can get a book out of a trial that goes three months.  

DAVIS: The trial is already making headlines. 

LEHR: Oh, sure. It is a big story. I’ll be there and maybe do some commentary and maybe some op-ed stuff. I’ve already written one op-ed piece.    

DAVIS: I read that director Barry Levinson is going to film Black Mass. Are you involved in the film production?     

LEHR: Yes, in a consulting way. We have heard quite regularly from Barry and his people. They finished the script and they are polishing it now. They are asking all kinds of interesting questions.

DAVIS: I heard there is also another Whitey Bulger film in the works with Ben Affleck and Matt Damon.  

LEHR: We hear that it is a back burner project now.   

DAVIS: You write in Whitey that Bulger is an avid reader. Do you think he read Black Mass and Whitey?   

LEHR: We’ve been told that he had just about all of the books written about him when they raided his apartment they discovered nearly all of the books written about him in his library.

DAVIS: That's not real smart. I guess he figured that no one would raid his apartment. I read somewhere that you consider Whitey to be the third part of a trilogy with Black Mass and The Underboss, your book on the Boston Cosa Nostra. I read The Underboss a couple of weeks ago and I was curious to find that John Connelly was featured in the book in a much better light than he was in Black Mass and Whitey. Did you meet him when you were researching The Underboss?

LEHR: Yes, that was when we met all of these guys. We wrote the FBI's bugging operation of the Boston mob underboss in a series in the Globe and then expanded it into the first book. That was a "high five" moment for the FBI. The framework of The Underboss is a dramatic reconstruction of the bugging operation.  

DAVIS: At that time you had no idea that the Boston FBI was shielding Bulger.

LEHR: No. The Boston FBI cooperated for that project so they would look good. Journalistically, we interviewed the entire organized crime squad extensively, taping interviews in order to get all the details to do the drama. So we met all of these guys and fast forward a year and a half and we are going down the Whitey/FBI road. We knew all of these players and it’s no secret now, one in particular, became our source. The history-making stuff might not have happened had we not done that first story. There were unforeseen collateral benefits.  

DAVIS: Was Connelly a source?            

LEHR: He was a source for a lot of reporters for what was going on in law enforcement and the Boston underworld. In Black Mass we identify the two FBI sources that confirmed our story so we could publish that special relationship fact. One was John Morris and one was a retired supervisor named Robert Patrick, who also has a book out. We could not have written that breakthrough story in 1988 without confirmation inside the FBI. Our editors wouldn’t have let us. 

DAVIS: What do you think of John Connelly? 

LEHR: He still has quite a following of “free John Connelly” type of supporters. These are people who have their head in the sand. They are in denial. In my view, he desires to be in prison. He is just corrupt as they come. 

DAVIS: Well, it is not just a case of taking money, he was also convicted of setting up murders, am I right? 

LEHR: Yes. He’s taken money and he’s got blood on his hands. That’s what the Miami jury verdict was all about. He was, as the government proved in that Miami case, a member of the Bulger gang. But that said, it is doing an injustice to Connelly and to the story to say only Connelly and John Morris were the problem. We’re talking about a lawlessness that permeated at least the Boston office of the FBI for years. Too many other agents and supervisors, maybe all the way to Washington, have skated on this scandal. 

DAVIS: I know a good number of detectives and federal agents and all of them have informants and all them protect their informants as best as they can. Most criminals become informant to receive that protection, I’ve been told. What was different with Connelly and Bulger?

LEHR: I think that the detectives and agents you know would look at this relationship and they would see that the power dynamic was all off. They would never let their informants call the shots. At that is what’s become clear in the history of the Connelly/Whitey thing – Whitey was in charge. 

DAVIS: I also enjoyed reading about the history of Boston you included in Whitey. It was interesting how you included the Bulger family within that history. 

LEHR: The idea was to give the readers some context.

DAVIS: Was Whitey Bulger a unique Boston story? Do you think he could have achieved the same success in Philadelphia or New York?

LEHR: I don’t know. There was, to use a cliché, a perfect storm of events in Boston in the mid-70’s. You may have had in New York or Chicago a crime boss who has an agent from the neighborhood. I think it is possible. But it did require an unusual and unique set of factors that blended together. 

DAVIS: New York had the Westies. I can picture Bulger as a member of the Westies.

LEHR: New York is big and has five mafia crime families. There is something focused about Boston, where you have one mafia family and one unique and powerful Irish crime guy. 

DAVIS: How do you think the Bulger trial will end?

LEHR: I don’t think he’ll ever see the light of day. He’s stuck behind bars for however much time he has remaining. I can’t imagine a jury, despite the best and very creative efforts of a very able defense attorney, coming up with any other verdict other than guilty. 

DAVIS: Thank you for talking to us and good luck with Whitey and the upcoming film. 

Note: Bulger was murdered in prison in 2018.

You can read my Washington Times review of Whitey (Crown) via the below link:


And you can read my interview with Philip Leonetti via the below link:


The above photos were provided by Dick Lehr and Crown Publishing.


  1. Paul, I enjoyed reading your post. Excellent as usual. I hope you are in good health. Richard

  2. Richard, Thanks. I'm in good health, how are you?