Billy Bulger Thrust Into A Talk On Whitey

Billy BulgerLast Wednesday down the Cape I spoke to a group at a library on the subject of Whitey Bulger. My talk lasted about 2 hours including the time for questioning. It went well, I was told. No one left before it ended and the questions were challenging and interesting. I used power point for the first time and that helped me to stay on topic and to maintain the interest of those who came out. I wished I had had it when I was teaching search and seizure to the cops.

I had hardly begun speaking when one of the person’s raised his hand and asked what about his brother? I knew he wasn’t asking about Jackie; but I was surprised the subject came up at all, nevermind being the first question asked. It showed how closely Whitey Billy is linked with Whitey in the minds of some. I suppose I should have expected this.

From what I read about the pitch made by Brian Kelly last Wednesday for what the prosecution believed the appropriate sentence for Whitey he was supposed to have suggested to Judge Denise Casper that Whitey was responsible for Billy losing his job. Now that’s one for the ages. It wasn’t Whitey, it was the people who kept insisting there was a connection between Whitey and Billy, and one of those people was the person addressing the court.

I wondered if Kelly forgot that he pulled out of his hat the totally irrelevant question he asked one witness inquiring whether or not Billy Bulger attended the retirement party of convicted FBI Agent John Connolly. Or did Kelly forget it was his co-counsel Fred Wyshak who commented when asked what made Connolly go wrong that: “he got too close to the Bulgers and South Boston.” 

The Globe reporters, Howie Carr, Alan Dershowitz, the prosecutors, our Cowardly Congress, a guy planning ahead to run for president, cops including FBI agents who wrote books, and who knows who else have all connected Billy with Whitey suggesting there was some sinister connection. Of course no one did a better job than the FBI which some day I’ll tell you about; it gave me one of my early sad insights into that Bureau.

All these have done a very good job of this as you can tell by my being asked right off the bat about Billy. Speaking of bats, I suppose the question could be a fast ball or a soft ball depending on one’s knowledge. Fortunately, I had the experience that no one else has had when it comes to Billy so it was easy to answer.

All these people who manufactured scary scenarios of Billy in his powerful position as president of the state senate protecting Whitey which had an effect of causing state, city and local law enforcement agencies to back off in their investigations of Whitey knew nothing of what was being done. None of them worked in this area.

I did. From the late 1970s to the time Whitey fled, I was involved in investigating organized crime in the Boston area. I did more organized crime wiretaps than all the other prosecutors in the state combined. I worked with state cops, DEA agents, skilled city and local detectives. These wiretaps produced thousands upon thousands of intercepted conversations among people in Whitey’s and other organizations.

I’m sure most if not all of these investigating officers knew that Whitey Bulger was a gangster. I certainly knew. Yet during all this time and all these investigations not once did anyone suggest that perhaps we lay off Whitey because Billy might be upset. Not once did the name of Billy Bulger come up in any way in connection with Whitey.

I was able to tell the questioner this. I was able to speak from my own experience. I was able to say that any connection between Billy and Whitey other than as brothers was a recent contrivance done by willful people for reasons of financial gain, revenge, or just out of pure ignorance.

I told the questioner of the statement made by the family of the young man who killed the TSA worker recently in Los Angeles. They said:

“Paul is our son and brother. We will continue to love him and care for him. We will support him through the difficult times ahead.“ 

I suggested Billy only did in connection with Whitey nothing more than any brother would do.

I didn’t get into it since Billy was beyond the scope of my talk, but there was one agency that did connect Billy with Whitey. It was the FBI. It justified its use of Whitey as an informant because of Billy’s position. It never suggested a wrongful connection between them it just used Billy to push back against those wanting it to sever the relationship with Whitey. Of course all of that was done in the usual FBI manner, behind Billy’s back.

That’s why this saga is not over as Carmen Ortiz suggested. There’s a lot to be done to expose the wrongs done to other people. There’s a lot to be done to hold accountable those who wrongfully took advantage of the existence of Whitey and the feigned connection to Billy to benefit themselves.

18 thoughts on “Billy Bulger Thrust Into A Talk On Whitey

  1. Matt, Jay et al.,

    Thank you for this exchange.
    I’m just getting to reading it.
    It’s terrific.

    As I’ve looked at the hearing a number of times, here’s my impression:
    It felt like the Massachusetts guys promised to ask “tough” questions in exchange for any oversight of the FBI at all.
    Billy answered the questions, contributed to our understanding of what happened with Whitey, and made it through the witch hunt.

    Massachusetts comes out looking bad, Boston especially, and the Republican saviors bully their way around the city. Mitt saved the Olympics and Boston.


  2. Often the most powerful realities are powerful because of their simplicity. So many people are so jealous of Bill Bulger because they know that they can never be what he is, to wit, a bona fide Mensch. Look it up in the dictionary and you’ll see Bill Bulger’s picture.

    1. Hopalong:

      Billy’s problems is he didn’t tolerate fools and he had the courage to stand up against them. Since the fools controlled much of the media, he became a natural target.


    Please note that there are in fact SIX questions which I have posed, as the number “5” was twice listed. Thank you again, Matt. Your insight and experience is one of a kind, and I hope you are able to shed some light on William Delahunt’s knowledge at that time, when he was District Attorney, to understand what his own motives, incentives, and overall mindset may have been when pressing these questions forth to William Bulger at the June 19, 2003 Committee hearing.

    If Delahunt knew some of the issues raised were untrue all along (especially when William Bulger offered an affidavit by Harold Brown himself — while Delahunt still insists some nefarious relation to O’Sullivan when he said it was “not a close call”), then why would he raise them? That speaks for itself, even without your six cents…

    1. Jay:

      As for Delahunt asking Billy Bulger the questions that he did, my best guess is that what he knew of the matter he had picked up from reading the newspapers or possibly he had been contacted by Gerry O’Neill of the Globe with whom he hd a friendly relationship. I don’t know whether that contact took place but I sense in the questions something that could suggest it.

      Keep in mind, Delahunt would not know much what I wrote about since he was not down in the trenches with the detectives doing the investigations every day nor would he be listening to the wiretaps or preparing the affidavits. I would brief him on the investigations in a general manner as I was required to do under the law and keep him posted as to their progress.

      Also remember, that I started this blog saying Black Mass and some other books were good reads; it was only late as I got more and more into these matters that I began to understand the animus behind those books.

  4. Dear Matt,

    I have five questions regarding your recollection of events in the Office of the District Attorney of Norfolk County, while you served as Assistant District Attorney. As a preliminary matter, I note that William Delahunt served as District Attorney between 1975 and 1996. That’s 21 years — a long stretch of time. You have stated in the past that you worked under Delahunt during his time there — as you say, “From the late 1970s until the time Whitey fled [in December 1994].” It would appear that during this entire time, William Delahunt was Norfolk County District Attorney. Bearing that in mind, I hope you may offer some insight to the extent that you are permitted to discuss office activities, or at least offer your opinion.

    I also realize that the following line of inquiry may evoke some conflict of interest, because Delahunt is your former boss, although he aggressively suggested that William Bulger somehow had a cozy relationship with the FBI when he served as U.S. Representative as a guest of the House Committee on Government Reform. Delahunt was visiting in his capacity as a member of the House Judiciary Committee, which has oversight over U.S. Attorneys, the FBI, and U.S. Marshalls, inter alia.

    Here are my questions:

    1) Did your office ever have enough evidence to issue a state level in your district indictment against James Bulger, based on these surveillance activities? If not, why not?

    2) Did District Attorney Delahunt know about the content of these surveillance activities?

    3) Was a grand jury ever convened at the state level in your district, because of information gleaned from these surveillance activities relating specifically to James Bulger? If not, why not?

    4) Did your surveillance ever reveal any evidence of criminal activity perpetrated by James Bulger?

    5) Based on your surveillance of James Bulger, was there ever any evidence that he was serving as an informant for any of your office’s law enforcement partners, including the FBI?

    5) Would Delahunt, as your supervisor, have been as aware of what you openly declare here — that there were never any instructions to “back off” in your investigatory activities?

    If he was aware of the same facts you declare here, then William Delahunt’s Committee testimony below is of even greater interest.

    To illustrate, during the June 19, 2003 House Committee on Government Reform hearings, William Delahunt relentlessly asked William Bulger questions about 75 State Street and John Connolly using his association with William to his advantage. He also loftily praised Agent Morris for telling the Boston Globe that James Bulger was an informant, saying he was responsible for subsequent reform measures.

    Relevant testimony is pasted below, for those who are interested. Rather than a random listing, this is actual testimony dialog, categorized by topic. For the full hearing, see the link below.



    Mr. Delahunt. Others have indicated that on multiple
    occasions John Connolly would introduce you, either at your
    office or elsewhere, to members of the FBI?
    Mr. Bulger. At his house?
    Mr. Delahunt. Not at his house, no. I’m sorry, either at
    your office.
    Mr. Bulger. That is how I remember him coming through;
    someone new was in town and would you like to say hello, and I
    saw them. But that is very common, lots of people did it; the
    place was open for traffic all of the time.
    Mr. Delahunt. I understand. But, you know, others have
    asked the frequency. I am not asking you.
    Mr. Bulger. It wasn’t very frequent. I am sure there were a
    couple times a year. That would be the way I would think of it.
    Mr. Delahunt. But one inference could be drawn that Mr.
    Connolly enhanced his own status by bringing FBI officials in
    to meet the president of the Massachusetts Senate. That is an
    inference that could be drawn. Would you agree?
    Mr. Bulger. Sure. We assume that anyone who comes through
    is doing it either for a social purpose or a self-promotion
    purpose. But I think it happens to all of us in public office.


    Representative Delahunt also pressed the issue of 75 State Street despite the multiple investigations which had taken place and the affidavit from Harold Brown himself offered by William Bulger:

    Mr. Delahunt. Did he ever raise with you an issue regarding
    a request or a suggestion by the Federal Government that would
    entail that investigation being conducted by another U.S.
    Attorney’s Office or by a different office of the FBI?
    Mr. Bulger. I never heard of that. By the way, it had been
    already investigated.
    Mr. Delahunt. I understand that.
    Mr. Bulger. And then it went to a grand jury and they said
    Mr. Delahunt. I understand that all.
    Mr. Bulger. And you know there are no accusers.
    Mr. Delahunt. Well, let me explain the reason, again, why I
    am posing these questions, is that your brother was an
    informant for the FBI.
    Mr. Bulger. Right.
    Mr. Delahunt. The individuals that were either involved in
    the investigation of 75 State Street, or even were in the
    periphery, were fully aware of your brother’s status as an
    I was doing some reading last night, and in a story that
    was dated December 9, 1988, it appeared in the Globe,
    indicating that the FBI had called off an investigation of some
    2\1/2\ years into the matter involving 75 State Street. And I
    am quoting now: “FBI Agent John Clorrity yesterday confirmed
    that there was a formal investigation, started in March 1986.
    This investigation failed to develop any evidence of a
    violation within the jurisdiction of the FBI.” In December
    1988, as you have indicated, the investigation was closed.
    Let me just interpose a question here. At that point in
    time, it has been reported that you had never been interviewed
    by the FBI. Do you have a memory of being interviewed by the
    FBI as it related to 75 State Street?
    Mr. Bulger. No, of course not.
    Mr. Delahunt. Thank you. But they did go ahead and made an
    announcement closing the investigation.
    Mr. Bulger. I think that is exactly the same time as the
    grand jury spoke. I think it is the same time.
    Mr. Delahunt. Now, let me try to refresh your memory. The
    grand jury was subsequent to the announcement by the FBI, and
    obviously it was John Clorrity who made that particular
    Mr. Bulger. I never knew there was any kind of an
    investigation going on. I didn’t.


    Delahunt also somehow saw something nefarious in how Jeremiah O’Sullivan used the phrasing that his investigation of 75 State Street “was not a close call.” That, as well as Delahunt’s concerns about John Connolly advising William Bulger to consent to be interviewed during 75 State Street, are relayed here:

    Mr. Delahunt. I am not in any way suggesting that you did.
    What I am saying, Mr. Bulger, is that the Federal Bureau of
    Investigation in Boston made an announcement that they were
    closing an investigation of some 2\1/2\ years that you were
    unaware of, and then made that announcement. That doesn’t
    happen very often with the FBI. In fact, back in December I
    asked a question of the head of the Organized Crimes Strike
    Force and the U.S. Attorney, Mr. O’Sullivan, regarding his
    statement after the grand jury concluded its work, and he made
    the announcement that it was not even a close call. And I posed
    the question to Mr. O’Sullivan, in your 16 years as a Federal
    prosecutor, when did you ever make an announcement that it was
    not a close call or that someone was vindicated.
    Now, I am not suggesting that is a policy that should be
    rejected out of hand, but what I am saying, it is very
    exceptional policy. And his response to me was that it was very
    rare, and he could only think of, his words were, maybe one
    other time. And I requested that he, as he left, to go reflect
    and submit to the committee a letter outlining that other time,
    and I don’t think we have ever received that.
    Have we, Mr. Chairman?
    Mr. Tierney. Not that I know of.
    Mr. Delahunt. No.
    Mr. Burton. Is the gentleman about to conclude his
    questions? Do you have more questions, sir?
    Mr. Delahunt. I do.
    Mr. Burton. No, go ahead. If there is continuity of
    questions we want to make sure we get completed. Go ahead.
    Mr. Delahunt. I will do whatever the Chair recommends.
    And, again, it was Mr. O’Sullivan that reopened that case,
    supervised that investigation, and presented evidence to the
    grand jury which, in a public statement, he exonerated you. And
    I think his words were no close call.
    But what I find interesting here is we have Morris, John
    Morris, whom you have made a serious allegation about here
    today, who is in charge of that investigation; Mr. Ahearn, who
    was the special agent in charge of the Boston office, who
    clearly was not only aware of the informant status of your
    brother, but would sign off on any statement that was made in
    the name of the FBI, and also would have supervised Mr. Morris;
    we have Mr. Clorrity, who was the former partner of John
    Connolly; and, in addition to that, we have Mr. O’Sullivan, who
    exonerated you. And then we have testimony from Morris that he
    was approached by Connolly, and Connolly sought his advice as
    to whether you should testify in front of the grand jury.
    Mr. Bulger. It was a meeting.
    Mr. Delahunt. There was a meeting.
    Mr. Bulger. That is what it was. It was my own request. I
    asked Popeo is there some way I could talk to these people. So
    it was not the grand jury, Congressman, it was a meeting with
    the prosecutors.
    Mr. Delahunt. No, this is prior to that, Mr. Bulger. There
    was an approach made by John Connolly to John Morris, and this
    has been testimony, you know, in the Federal court.
    Mr. Bulger. I wasn’t aware of that, then.
    Mr. Delahunt. And what I am trying to do is clarify the
    record, because one could draw an inference that you requested
    John Connolly to make the approach to Morris.
    Mr. Bulger. Be absolutely certain. I never made such a
    request. Never.
    Mr. Delahunt. But what I am trying to relate to you is the
    testimony of John Morris that was never refuted by Mr.
    Connolly. Now, many things are said in all of our names that we
    are unaware of.
    Mr. Bulger. That is true.
    Mr. Delahunt. But again, I guess the bottom line for me is
    that the Federal authorities, having knowledge that your
    brother was an informant, and that you were either the subject
    of a target of an investigation, concluded that it was fine for
    those that I mentioned to proceed with the investigation into
    75 State Street, as opposed to referring the matter, like
    occurs frequently, to either another FBI office or to another
    U.S. Attorney’s Office. What I am suggesting is that I have
    reservations as to whether that is a very good practice,
    particularly when, several months after you are cleared, that
    these same FBI officials invite you to be a master of
    ceremonies for a departing member of the FBI. And, again, I am
    not leveling criticism at you, Mr. Bulger. What I am suggesting
    is that in terms of appearances and the confidence of people in
    our justice system, that just doesn’t, as the former Governor
    Weld I think once said, that doesn’t pass the smell test.
    Mr. Bulger. May I just say a couple of things? First of
    all, as to the publicity, it was a Boston Globe, I would call
    it a concoction, and it ran from that time, about December 8,
    1988, and it ran right to March 31. I remember it well because
    it was a daily, daily drumbeat upon me. And ultimately Bob
    Popeo asked the people who were conducting this thing, please,
    there has never been so much publicity, if one were to go back
    and look at the publicity during that period, and he,
    therefore, asked if you would please just make a public
    announcement so that my own opportunity to be made whole would
    Another thing about being a master of ceremonies, I have to
    tell you I bet I was a master of ceremonies for more State
    police than I have been for any FBI. I just did it all the
    time. It seemed to go OK. I am just telling you it was a
    constant problem for me because people would so frequently ask
    me to do it, and it becomes difficult not to do so. Elliott
    Richardson, would you please, he said, do it, and I did it with
    Art Buchwald, and we retired his debt, and he was ever
    grateful. But Elliott Richardson. I mean, it was everyone, and
    I didn’t know how to turn it off, and I did it all of the time.
    It is one of the things in my opening statement I don’t
    mention, but the fact is these offices, they keep you very,
    very busy. So there is nothing sinister about my having agreed
    to be.

    Delahunt further praised Agent Morris for leaking to the Boston Globe that James Bulger was an informant and believed that it was responsible for Connolly’s indictment and subsequent reform measures:

    Mr. Delahunt. Mr. Bulger, let me be really clear. I am not
    even suggesting sinister. What I am suggesting is
    responsibility of the office.
    Mr. Bulger. My office.
    Mr. Delahunt. No, not your office. The office of the FBI.
    Mr. Bulger. Oh, OK.
    Mr. Delahunt. Because they were aware of the informant
    status of your brother.
    Mr. Bulger. Right.
    Mr. Delahunt. They knew that your brother was an informant
    for the Federal Bureau of Investigation, and they proceeded to
    conduct an investigation into the matter involving 75 State
    Street. And I just say the appropriate action by the Government
    should have been to refer that matter to another U.S.
    Attorney’s Office, to another office of the FBI.
    And far be it from me, Mr. Bulger, to defend the Globe, but
    they were correct in the information they provided relative to
    the status of your brother as an informant. My understanding is
    it was Mr. Morris that was the source of that particular
    information. But that information did lead to, I dare say, the
    Wolfe hearings, the hearing of this particular committee that
    have really given us some insights into what was occurring with
    the Department of Justice, not just in Boston, but, by
    implication, elsewhere.
    Mr. Bulger. No, I appreciate that, Congressman. I can’t
    even be in disagreement with you on it, not at all.

    1. Jay:

      I see you have read the Congressional hearings where Delahunt asked Bulger the questions you listed. I hope I can clarify things for you. Keep in mind that the Attorney General for Massachusetts, Scott Harshbarger, who was supported by the Boston Globe ran against James Shannon the incumbent attorney general, both Democrats, and Harshbarger’s push was based on Shannon not conducting a thorough enough probe of Billy Bulger. He conducted his own probe after he was elected and came up with nothing. As for their being something sinister about O’Sullivan’s involvement, he had delegated the investigation of Bulger to two of his assistants who were beyond reproach (one is now a MA Supreme Court Justice) – it was they and not O’Sullivan who concluded nothing was wrong with what Billy did.

      Also, the US Attorney before O’Sullivan became acting U.S. Attorney also found noting wrong. Morris testified that they had investigated the matter for 2 1/2 years and found nothing. Don’t forget Morris did not like Billy Bulger. Morris also testified that Gerry O’Neill of the Globe (author of two anti-Billy books) called him and urged him not to close out the investigation and got angry at him for doing this. Morris would be O’Neill’s informant that Whitey was an informant.

      Now on to your questions:

      1. Whitey operated mostly in Boston. Norfolk County was south and west of Boston and we had no juridiction there. We only intercepted Whitey once in a wiretap and that was when he had a conversation with Stevie Flemmi when we were doing a wiretap on the home of one of the person’s who ended up being murdered by Whitey and Stevie. The extent of the conversation was Whitey saying to Stevie something to the effect “I’m back.” The reasons we didn’t have enough evidence was as I said most of the stuff he did was outside our jurisdiction, Whitey never discussed his business over the phone or in private areas. Whitey was rarely in Norfolk County doing his criminal business even though he lived in Quincy which was in Norfolk County. FBI agent Connolly filed several reports indicating that Whitey was complaining about us harrassing him. That was becasue we were taking down a lot of his bookies; it was also because the Quincy police with whom I worked off and one were very active in going after him and he attributed their aggressiveness to our office.

      2. Delahunt had to approve all the wiretaps. I would verbally brief him on what we were doing.

      3. No grand jury was convened for reasons stated in #1. If you read the Naimovich series of posts you’ll see that we did use the grand jury to bring in a lot of the bookies who refused to answer taking the fifth in October of 1987 – those bookies were part of the Whitey operation. We had been at the level just under Whitey and Stevie when the top investigator on those wiretaps and who was working the grand jury with me was indicted by the federals in an attempt to protect Stevie and Whitey.

      4. None of my surveillance was directed at Bulger directly because he didn’t operate in my county. Keep in mind, Bulger was known as a racket guy and a South Boston hoodlum – he was not the big man that the media has made him – much that has come out now was not known by us back then. You will note that all his drug business was in South Boston and not in Norfolk County. Detective Lt. McDermott of Brookline which was in Norfolk County surveilled Stevie and Frankie Salemme meeting in Brookline with some other hoods. Had McDermott found anything that they were doing of a criminal nature he would have come to me which he didn’t.

      5. One of the Globe writers Kevin Cullen called me in 1988 and asked me if I thought Whitey was an FBI informant. I laughed at him. I said absolutely not. Things like that don’t happen. I was as surprised as everyone else when Flemmi came out in ’97 or ’98 and disclosed he and Whitey were informants.

      6. You ask would Delahunt have been aware there were never any instructions to back off. The question is sort of surprising since no one could tell me (by the way I was the Deputy District Attorney the one in charge under Delahunt) to back off? Perhaps Delahunt could since he was the boss but he never would even think of doing it nor did he. Outside of him there is no one who could tell me to back off. As I mentioned, in ’87 I was close to the very top when my investigation was undermined.

      I hope I answered your questions, if not, ask for clarifications.

  5. Great post, this blog clarified this relationship that had become cloudy of the years with all the not so clever inferences in the media. During the reign of Whitey, I found that his brother being a powerful politician to be amusing, along the lines of him winning the lottery. Nothing necessarily incriminating, just an amusing twist in the story. The storytellers with their agenda stop just short of having Billy hovering over a grave.

    In fact, I would say that throughout this whole ordeal, I respect Billy’s loyalty to family. I can not honestly say that I could stand by my sibling if they cause me such humiliation.

  6. Matt- People need to try and convince themselves that William Bulger was/is corrupt, they themselves refuse to grasp the level of dignity and decency the man conducted himself with. Challenge the man on his politics or his ideology, if you disagree, Yes he was a clever, even ruthless political leader. He was NOT a gangster or responsible for what his older brother chose to do with his life. The man was a politician, But like we all know, that field of work can be just as filthy as the crime in the streets.

  7. Matt, thanks for all the great articles and posts. They are better than any book ever to come out on these subjects except

    Don’t embarrass the family!, TODAY’S ARTICLE IS GREAT, Lets hear some more on that line. THANKS AGAIN

      1. Agreed. Another excellent article. I am looking forward to your book in the near future Matt which will put this whole sad and dark saga in Boston crime in its COMPLETE PICTURE. On a side note, any theories as to why Whitey had over 30 weapons in his apartment? To shoot it out with cops if they got to him while in the apartment? I mean 30 weapons is a little over the top, no? A man only has 2 hands.

        The other thing is, is it possible Whitey committed any criminal acts while on the run besides being on the lam? If not he just went cold turkey on the adrenaline rush associated with committing crimes and making fast money?

        1. Jerome- That is a great question about the end of his actual violent crimes. I know whitey is a gun nut and I believe he would of shot it out if he had the advanced notice. I also believe he was egotistical enough to have that many guns just so when he gets caught his legend supersizes.

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