An Overview of Whitey’s Murders: The Roxbury Gang. (1 of 5 )

For months Jerome has been asking me to talk about each of the 19 murders that are attributed James “Whitey” Bulger. In his latest comment he asked in addition to that whether he had murdered other people than those he was alleged to have done in the indictment naming 19 people.

To answer Jerome’s question I have to go back to the time Whitey was in prison to set the stage for the discussion.

I will first set them out by setting out the background of the murders and putting them into six groups in the first five parts of the series. I will then consider them individually as part of a follow-up series.

Starting with Jerome’s last question. Was Whitey involved in other murders? Outside of Louis Litif for which he was not indicted and Donald McGonagle which some have pinned on him, I have not heard of any others.

One thing to keep in mind is that during the so-called Boston Irish Gang wars of the early 1960s when upwards of 80 hoodlums were murdered (a war that got its name because it allegedly began because of a feud between two Irish gangs, one in Somerville under the leadership of Buddy McLean and the other in Charlestown under the McLaughlin brothers) Whitey Bulger was sitting in federal prison for robbery.

Whitey was not known to have murdered anyone before he went to prison or during the time he was in prison. That would bring him up to his mid-thirties. It is rarely a time for people to start murdering people.

For a reason that is difficult to understand, in the tales of the Irish Gang War and the later tales involving the Winter Hill Gang there is little mention of the gang that was right in the middle of it. It was the Roxbury Gang consisting mostly of Italians who were working  in cooperation with the Boston Mafia. That is the gang that had the men who were doing murders in their early twenties, a time when most gangsters who get involve in murders usually begin. Many of them do not survive to their mid-thirties but this inner group from Roxbury were very close and did not turn on each other as other sociopaths are likely to do. It is because they were restrained by long-term relationships. They were more professional “hitmen” than street type killers.

The Roxbury group consisted of Frank Salemme, eventually the head of the New England Mafia, John “Murderman” Martorano of 20 murder fame who called himself the hitman, his brother Jimmy Matrorano a reputed Mafia member, Joe “The Animal” Barboza the famous FBI cooperating witness in the Deegan case; Steven “Benji Ditchman” Flemmi the long time FBI  protected murderer of women and others; and his brother Vincent “Jimmy” “the Bear” Flemmi, also proposed for membership in the FBI informant club club even though it knew he said he wanted to become the most capable hitman in New England.

Those and some others such as George Kaufman were the members of the Roxbury gang who did not go down by gunfire during the Boston Irish Gang war. Others, mainly Irish guys who were their former partners, were eliminated.

When the Boston Massacre of gangsters ended the Somerville gang’s leadership passed on to Howie Winter. Buddy McLean had been gunned down by one of the McLaughlins. The McLaughlins had been eliminated and their gang went out of business permanently. The McLaughlins lost because the Roxbury gang swung its allegiance from them to Somerville.

Howie Winter led what was called “the Winter gang” consisting of Jimmy Sims, and Joe McDonald as other major members. They were known to be capable of murdering people. They were loosely joined by John Martorano, Jimmy Martorano, Frankie Salemme and Steve Flemmi. Joe Barboza had become a cooperating witness for the FBI; Jimmy Flemmi died in prison. They operated out a garage called Marshall Motors that was located in the Winter Hill section of Somerville.

They would eventually be called the Winter Hill Gang but that was later when Stevie Flemmi and Whitey Bulger joined it. Steve Flemmi and Frankie Salemme were indicted for blowing up Boston attorney John Fitzgerald’s car so they were not around during the years 1969 to 1974. Whitey would go over to Winter Hill sometime in 1972.

63 thoughts on “An Overview of Whitey’s Murders: The Roxbury Gang. (1 of 5 )

  1. Rather ,

    Like Chinese Gordon, We Always practiced a muscular Christianity, and Soldier on . That Office was appreciated Brother .

  2. What about the bad BPD detective. Got kicked off the job.Bill Steward. Part of the Bennitt bros demise & beheading. Worked for Stevie for years as head of security for booze dist.

    1. It’s Bill “Stewart” and yes, this guy was a straight-out gangster with a badge.

    2. Lewis:

      Billy Stewart had a real bad reputation. Was clearly involved with some of those guys especially Billy Kelly who is now on death row in Florida. He’s gone now so much of what he did has gone with him.

  3. RN ,

    Welcome back .
    … to Double Secret Probation.
    Look around.We are ALL IN .

    1. JKM,
      I come and go, as always, at my leisure.
      In for a penny (actually my two cents),…and in for a pound.
      : )

  4. He is pivotal . All of these events whirl and gyre in the heavy weather he always carried and hugged into. This SEVEN DEGREES OF WHITEY BULGER exercise in fraternal bonds as it were between … murders, murderers, murder groups and grouped murderers on the OC Chart is taking on a frenzied fantasy football feel to it.

    In my Telecom engineering lifetime we had an expression … ” Trash in Trash out ” that underscored the danger of working out of … corrupt databases. All of this ” Deal ” is filed under the rubric of CORRUPT DATABASE. The fact sets are tawdry facsimiles of truth.

    1. John:

      That is what we really have to keep in mind and it is that the database is totally corrupt. Good point.

  5. Thanks for answering my questions earlier and what can you tell me about the Bennett brothers’s connections to the Roxbury Group? As I heard that Wimpy bennett was a mentor to the Flemmi brothers and Frank Salemme?

    Was Jimmy the Bear flemmi the craziest in the group?

    1. Mr. Fishwick,
      Do a little research on Walter’s (Wimpy’s) Lounge and the Uphams Corner/Dudley area. Benji had a R.E. office and across the street there was a furniture store that strangely never sold any furniture.

    2. Mr. Fishwick,

      Barboza and the Bear……..hands down, the two craziest, ruthless, loose-cannon gangsters in the history of the Commonwealth, in my opinion.

  6. Jerome,
    Thank you for your persistence in influencing Matt to bring this series to fruition.

    Thanks for doing it.

    “The McLaughlins lost because the Roxbury gang swung its allegiance from them to Somerville.”
    …..I think the wiping out of the Bennett brothers by Benji and Cadillac Frank paved the way for the switch of allegiance. From then on it was Roxbury/Winter Hill/Rico/Condon/Connolly vs. the Mafia by whatever means necessary, which gave us the myth of whitey bulger.

    1. Rather Not
      Thanks. There are so many loose ends and open ended questions its all hard for me to tell when (if ever) I will be satisfied that I understand what REALLY happened. Because it involves criminals, and they lie so much its hard to sort all of this out at times. Your contributions are appreciated and needed as well.

      1. Jerome:

        Remember I’m only trekking toward the truth – I may be wrong on some stuff – much we may never know because of the corrupt people justifying their actions and a prosecutor bent on getting people rather than seeking the truth. I’m not sure the people involved know the true story by now but we can look and compare things and find out what seems closer to the truth which is much better than taking the word of people whose lives depend on lies.

    2. Rather Not
      What books have you read on all of this? Have you seen the Joel Berlinger documentary WHITEY?

      1. Jerome,
        I have read nearly every single book written on this subject.

        I was at the premier of the Berlinger documentary in Cambridge two years ago with Berlinger, Jay Carney, the Donahues, Steve Davis, David Boeri, Brian Kelly…..the Q+A was interesting and Jay Carney almost sideswiped me in his huge BMW sedan pulling out of the parking lot.

        And I finally broke down and saw Black Mass two nights ago. Blatant fiction. Semi-entertaining.
        I almost jumped out of my seat and had a heart attack when my old apartment (First house on the left, Silver St ) was in the movie. Johnny Depp and whoever played Benji (horrible, horrible acting) walked out the front door of my old apartment, crossed Silver and jumped into a car in the exact spot that I used to park my old 94 Town Car right against the brick wall. That was cool. Rumor was when I lived there that Whitey owned the building through Kevin O’Neill, but I never saw either one of them near the building. Only time you saw O’Neill was down Station News near Broadway. Whitey’s girlfriend Teresa lived on the same street, but I never knew that until years later.

        1. Rather:

          Interesting story about Silver Street. Teresa Stanley did live there and that is where Whitey lived. I also believe my grandparent lived there and I dated a girl from there for a while. If you tripped coming out your door you could probably put your hand out and have the house across the street support you.

          Too bad you missed your 15 minutes of fame when Jay Carney’s car missed you.

          1. Matt
            What are the known addresses of where Whitey Bulger ACTUALLY lived? I have seen the “haunty” house where 3 people were murdered supposedly by Bulger

            1. Jerome:

              He lived in Old Harbor Village on O’Callaghan Way (I lived at #18 which was the first the town house) but at the other end from my house in the apartment type houses.

              If you go over the Neponset Bridge into Quincy and bear left going toward Wollaston Bech you will see a group of town house condominiums off to your left, he lived in there. He did not live at the death house, Pat Nee’s brother owned it.

        2. Rather Not
          It sounds like no one saw or even knew about Whitey Bulger (even in Southie) UNTIL the Globe did a 4 part series on his relationship with the FBI, no? Criminals knew him and dealt with him and law enforcement but not everyday people? Where did Whitey and Theresa Stanly live on Silver Street?

          Have you read PADDY WHACKED by TJ English?

          1. Jerome:

            Whitey was known in South Boston but not really outside of there. I knew him as a leading gangster but had no idea he was involved in murdering people. Others in law enforcement would have known about him. In 1988 when the Globe did its series it suggested Whitey was connected to the FBI but even there after Whitey was out of the business of murdering people did it suggest he was a murderer. Even after the 1988 article few paid attention to him. It was only after Flemmi testified he was an informant that he began to achieve some type of notoriety but that was after he had fled town in 1994/95. As far as “terrorizing” the area as Ortiz and others would have it that was all made up.

            I did read that book by English.

      2. Jerome,
        here’s two books NOT on the subject of Whitey
        1. The Purple Shamrock-you will appreciate the the dry Irish wit woven into the fictional story of Frank Skeffington (based on Hon. JMC)
        2. While The Music Lasts- Billy Bulger’s charming self-effacing auto-bio

        Both good, entertaining reads.

        1. Jerome,
          Almost forgot….if you read #1 and #2 above, you must read…

          3. James Michael Curley-A Short Biography with Personal Reminiscences by William M. Bulger

          Billy’s biography of Curley.
          I have not read it yet, but I plan to.

          1. Jerome,
            Here’s more….(I love Curley)

            Superbly written article about Curley’s public fight against the “Goo-Goo’s” in the 1914 run for mayor of Boston by Michael C. Connolly (tip of the hat), who I do not know if he is a relation of Matt. If he is, ….excellent job, thank you. The good writing gene obviously is possessed the entire Connolly clan.

            The First Hurrah- by Michael Connolly Westfield State

            and another book…
            The Last Hurrah-by Thomas O’Connor…fictional bio of Curley as Frank Skeffington (I was mistakenly referring to this book above, I got mixed up. I read both Purple Shamrock and The Last Hurrah years and years ago)

        2. Rather:

          I’d think Billy may have regretted writing that book when he was at the top. The music, like that of the band on the Titanic, ended much too soon and much before the final dance.

      1. Dave,
        Matt talked about that a few weeks ago.
        Howie and Murderman were contracted by Gerry to go after Notarangeli and his brother because they whacked one of his bookies. Whitey was mingling around Marshall St. then, post-Chandler St sit-down, war with Mullens is over….or is it? (McGonagle, King, Leonard, etc.) and we (Matt and I) were debating whether Whitey was “in” yet with the Hill, and was privy to what Howie and Murderman were doing (or even involved) and therefore was a suitable subject for Condon to take an unsuccessful second run at recruiting as an informant.

      2. Dave:

        1973 to 1974 Howie Winter and John Martorano were paid by Angiulo to chase away the Notarangelli group – they even got one of them in Florida. You are right.

  7. This is a real treat. The commentators are just as informed. I enjoy all your information and comments. This is by far the most highly knowledgable group of individuals commenting on Massachusetts/Rhode Island underworld .

  8. Matt,

    Glad to see you revisiting the complexities of underworld activities in the Boston area. Am I right that what you’re calling the Roxbury gang was not an organized syndicate like the Italian mafia or Buddy McLean’s Somerville gang or even the McLaughin gang but a collection of like-minded wiseguy killers who happened to all be from Roxbury? A small point perhaps, but might help explain why media types have not identified the gang as a significant faction in the underworld milieu.

    Also, I recall Vinny Teresa (always to taken with a grain of salt of course, but at the same time one who is worth reading since he had major skin in the game and gives you a real flavor of that life) saying in his book that the Irish gang wars escalated after a failed peacemaking attempt by Raymond, whereby Tameleo called a meeting between Somerville and the McLaughlins and ordered both sides to come unarmed. But when one of the McLaughlin brothers showed up with a gun, Tameleo was infuriated, the meeting broke up, and Raymond decided to give up and let them kill each other.

    Probably a bad idea to lend a lot of credence to Fat Vinny, but then again the whole Irish gang war erupted when George McLaughlin insulted Alex Petricone’s (of the McLaughlin gang; did I spell his name right?) girlfriend in a bar.


    P.S. Fun fact: Alex Petricone supposedly ended up moving the Hollywood, changing his name to Alex Rocco, and played Mo Greene in the Godfather.

    1. Jon:

      I’d say the Roxbury gang was like both Buddy McLean’s and the McLaughlin gang. None of them was organized like the Mafia. It was a group as you described of like-minded wiseguy killers as where the other two groups. It was more closely allied with the Mafia than the others since some of the guys who hung around with it were Mafia guys; it also had guys from the other groups like Somerville and Charlestown hanging around with them. If I had to figure out why they were overlooked I’d suggest that back then all the gangs were overlooked to an extent since few seemed interested in all the murders. An attitude expressed by one cop was as long as they are killing each other who cares.

      It was the authors and media who made the gangs into more than they were. When Gerry O’Sullivan was first asked about the Winter Hill gang he answered “Do you mean the Winters gang.” My point in mentioning the Roxbury group is that its members were more vicious than any other group but we hear little about it because it doesn’t play into the Whitey story where he is elevated to be the most vicious when in truth he was less than those others.

      I represented Vinny Teresa for a day or two. Went to a hospital in Worcester to tell him the judge had just defaulted him and ordered him held on bail. He was on a gurney covered in a white sheet and he was so fat that he bulged up a good four feet. The Tameleo story could be right. The Mafia did not like the war because it put it under the spotlight although it did take advantage of it to take down some people it did not like.
      The story of how the war started at Hampton Beach or is it Salisbury Beach an old one. Who knows if it is true but it matters little since it had only a small bearing on Whitey’s case.

      1. Thanks Matt. It is quite interesting how the way things are on the streets gets filtered through the lens of media stories and legal cases and suddenly we have this quasi-distorted perception of factions facing off with each other like Somerville and Charlestown and Roxbury when the situation is much more fluid and osmotic on the streets even if there is at least some kind of gang leadership within geographic domains.

        But the Italian mafia was of course the exception in being exceptionally well-organized and powerful. That often seems to be forgotten in all the sensation around the Whitey saga.

        And to think, the Whitey saga really has its origin in a simple meeting between weepy John Morris and the Globe reporters where John was hoping to get Whitey killed in order to save his own skin. I’d say John succeeded beyond all expectation in creating a media sensation, though he utterly failed in his immediate objectives. Did I get most of that right?

        1. Jon:

          I think you nailed the point of this matter. The Whitey saga began with John Morris and the Globe; the former was out to have Whitey murdered to cover up his corruption, the latter were out to take revenge on Billy Bulger and the way to get him was through Whitey. If that is kept in mind much can be understood.

          John succeeded in getting his pension and taking a walk on his corruption; he did this with the help of his friends at the Globe who convinced Wyshak that Whitey was this monster and that he was in league with his brother Billy. Wyshak commenced to give away the house to get the brothers – along with the help of the media – and they fell far short with Billy because there was nothing there. No gangster knew of any connection except a John Martorano concocted tale of Whitey telling him Billy asked Connolly to take care of his which is ludicrous since Whitey would never have mentioned Billy to anyone.

          You are right about the looseness of the whole deal – it was mainly a bunch of gangsters doing their own things without any semblance of any control by one. Winter Hill was composed of loose gangsters and was not a structured hierarchy which Connolly’s counsel pointed out at his trial. The three Winters guys, Howie, McDonal and Sims dealt mostly in stolen goods; Whitey had his shakedowns; Martorano had his Roxbury businesses to attend to mainly running gaming an loan sharking, etc. What they did on their own they kept. There was sharing of the tribute paid by bookies but the idea they shared in everything and there was a leader was never the case. The McLauglins were guys from Charlestown, Dorchester and other places that hung around. They also did their own things.

          You are on the right track. Keep trekking.

      2. Flemmi, Martoranos Bros. and Salemme had a hand in killing the “leaders” the Bennett brothers, Wimpy, and I forget the others’s name, correct?

        1. Edward, William, and Walter Bennett – Edward called Wimpy which was a name common to a lot of guys from the Irish neighborhoods. They ran the rackets in Roxbury until they were taken down by the guys you mentioned as a favor for Angiulo from Boston who convinced his fellow Italians to his dirty work.

          1. why did Jerry want the bennett brothers killed? and if Bulger killed them-why arent they getting any of the money?

            1. Barb:

              Bulger was in prison when the Bennet brothers were killed. The family of the Bennets should be entitled to the money since the Bennets were murdered by Stevie Flemmi who was Whitey’s partner and was an FBI informant at the time of their murder. Gerry had no interest in the Bennets. It was Larry Baione who wanted to take over the rackets in Roxbury and the South End. Of course, Gerry would have gotten a cut out of it.

  9. Connors the top gangster in Savin Hill brought Roxbury gang associates Kelley, Red Conlin and Steve the Greek into that part of Dorchester. The Roxbury killers weren’t limited to the top guys you mentioned. Connors ran the rackets in Savin Hill until his death in 1975. Then the Frenchman took over.

    1. NC:

      I did not intend to suggest the Roxbury guys were limited to the ones I mentioned. They had a big crew and you mentioned some of the others. I do suggest that was the gang that did the most murders yet it is hardly mentioned by the media or the book writers about Whitey because it would put Whitey into proper light as just another one of those heartless killers.

  10. I am a first time blogger but I have read some of your articles before. So what brought the Roxbury Group together?

    What is your understanding of Nick Femia as I heard that he was an associate of Bulger, Barboza and Flemmi?

    1. David:

      Welcome aboard. Back in the time when these guy were young Roxbury was a an area in Boston that was probably more ethnically mixed than any other. There were lots of pockets of Italians, Irish, Germans, Jews, blacks, Lebanese and East Europeans. It and the South End were more ethnically mixed than any other area. The Flemmis grew up with a future Mafia enforcer Larry Zannino in the Orchard Park area that was heavily Italian. The Martoranos were from Milton but their Mafia connected father owned a bar in Roxbury so when they got into their twenties they started hanging out there. Barboza, being Portuguese, felt more at home in the gangster bars there than other neighborhoods. It was known for its after hours clubs and they attracted the gangsters who operated by night and slept by day so it became a magnet for a lot of the criminal types. They got to know each other; some even worked during the day in Roxbury at auto repair shops where they chopped up and put together cars. They were brought together with a commonality of interests.
      Femia was supposed to be a buddy of Barboza and he hung around with Whitey when they were operating out of Lancaster Street. He was killed I believe i a 1983 holdup.

  11. Matt
    Is there a book or government document or article that breaks down the Irish Gang War that cost 80 men their lives? That names the 80 men and possible motive for each killing?

    1. Jerome:

      No book sets them all out. An article in Look magazine had the photograpsh of a few dozen. Martorano’s book hitman tells about some of them.

      1. I wouldnt bother reading the TJ English book. Nothing really new if one has read your blog, teh book BLACK MASS, and a few of Howie Carr books (inaccuracies and all).

        I do recommend the WHITEY documentary by Joel Berlinger. I thought that was good upon my second viewing but far too short. There is really an excellent documentary that could be made about the Irish Gang Wars, the Kileens and Mullens rivalry, the Winter Hill gang and then the Steve Flemmi and Bulger reign of “terror”.

        Was there ANY TESTIMONY during the trail in which you learned some new things? If so, whose testimony stood out the most to you?

        1. Jerome:

          English has a certain way of writing and early on he bought into the Black Mass fiction. I’ll have to take a look at the Joel Berlinger documentary. I’d have to review the testimony to answer the question but I’d say nothing from the gangsters (other than that Martorano told the prosecutors Flemmi told Martorano that he accidentally strangle Debbie Davis which would foreclose any discussion of how she died) did a lot from some other witnesses as to the extent of Whitey’s control of the bookies who I was doing wiretaps on.

  12. Oh yeah, Carney also claims that Whitey Bulger has some explosive information as to WHY he (Whitey) was “allowed” to run his criminal empire unscathed and unbothered for 25 years and THAT explosive information would finally be revealed during Whitey testimony. Only Whitey never testifies.

    Whitey Bulger also says that there were other corrupt FBI officials besides Connolly BUT he refuses to name names. Why is he comfortable naming Connolly but not the other FBI officials? All part of his manipulations and stories, no?

    1. Jerome:

      Whitey ran his gang along with Flemmi from 1980 to 1995. That is 15 years. Whitey was an informant f rom 1975 to 1990 which is 15 yeas. He was allowed to run his operation for 15 years because he was an FBI top echelon informant and protected. Carney is being Carney making a lot out of a little.

      Whitey said he could have six FBI men go to war with Uzi machine guns for him. Flemmi said he knew that four out of five FBI agents were going to murder George McLaughlin because he called J. Edgar Hoover a homosexual. You have to take much of what is said with a grain of salt.

      1. Matt
        In other words Whitey Bulger is “claiming” he has all this explosive information when in fact he really doesnt. Most (if not ALL) of this story and saga has been told and written about? There is really no new information involved in this drama.

        Do you really believe Steve Flemmi is out of prison and living in the Witness Protection Program?

        1. Jerome:

          We know he is not in the custody of the Bureau of Prisons. Unless he is in some secret CIA dark prison, he has to be back on the street. Wyshak at the trial became a little too sneaky when the issue of Flemmi getting out of prison came up. Remember Wyshak and Flemmi laughing together in the Miami trial when talking about the Halloran murder. I’d suggest Flemmi has conned Wyshak into letting him out.

          1. Matt
            Is footage of the John Connolly trial in Miami available to the public? I saw some footage in the Whitey documetary.

            How could Flemmi con Whyshak into letting him out? Why free Flemmi and then go after Robert Fitzpatrick and Catherine Greig? The last 2 chapters of TJ English book WHERE THE BODIES WERE BURIED should be read by you. I am sure the book is at your local library.

            1. Jerome:

              I have looked for it an have a hard time finding it. There is a segment of Wyshak being interviewed after the trial where he said Connolly went wrong by getting involved with the Bulgers and South Boston that I heard; there was on line at one point a video of the sentencing hearing.
              Flemmi and Wyshak became buddies; they were on the same team like Morris and Wyshak. Whyshak has to keep him happy hoping he won’t recant any of his testimony. Fitzpatrick and Greig were not part of the team. Like with the Top Echelon Program where the FBI and gangsters get into the same boat; the prosecutor dealing with scum witnesses gets into the same boat with them and has to keep them under control and happy after that.
              I’ll look at his book when it becomes available at my library. I just requested it.

  13. Matt
    THANKS. I am looking forward to reading your 5 part analysis. For me, it would tie some loose ends up and start to bring some order to the chaos of this whole mess among Whitey, Flemmi, and the FBI.

    I just watched the Joel Berlinger “documentary” for a second time. I am not sure you have watched it. It is called WHITEY. Upon the second viewing I kept in mind some of the valid points you have made in this blog. In the documentary one still doesnt know if Whitey Bulger was or was not an informant. Each side presents their case regarding the issue. One point that came up was that Whitey Bulger claims that in RETURN for protecting Jeremiah O’Sullivan LIFE (from retaliation by the Anguilos?) he was granted immunity from being prosecuted for his crimes. This convenient “deal” allows Whitey to say he wasnt an informant yet still got protection by the FBI/DOJ.

    But this deal with Jeremiah O’Sullivan sounds VERY similar to teh extortion tactic Whitey used on legit people. He would tell them he was hired to kill them BUT if they gave him X amount of money then he wouldnt kill them.

    Another interesting thing in the WHITEY documentary that I missed was Whitey denying he killed the 2 Debbies AND his explanation that he had nothing to do with the Wheeler and Callahan murders. His recorded conversations with Carney were all self-serving.

    I am still perplexed as to what Connolly was guilty of in doing his job using Whitey as a TEI. I am also perplexed as to what else could be revealed by Whitey Bulger if he were to tell the truth.

    Finally , an analysis of each of the 19 murders Whitey Bulger is accused of does help to make sense of WHY each murder was done and by whom. I cant THANK YOU enough for finally going over each murder to seperate teh facts from lies/embellishment.

    1. Jerome:

      I’ll put the series out over the next couple of week but it will be interrupted as I go along with some other things so be patient.

      Whether Whitey was an informant depends upon the definition of the word “informant.” The opening of an FBI informant file does not mean that he was one. We saw back in 1971 Dennis Condon opened a file listing him as one but Condon had to close the file within a couple of months when FBI headquarters put the heat on him to find out more information. So we know the FBI sets up phony informant files.

      In defining informant you have to decide whether a person has to give a specific type of information or any general information to be deemed on. It is clear Whitey was giving Connolly information – he complained about my office chasing after him which was true. Does that make him one? Or does he have to give information that results in arrests or starts investigations? Is someone who tell an agent generally what is happening in a group an informant?

      Whitey isn’t claiming O’Sullivan made a deal with him because he wanted to protect himself from Whitey, Whitey is saying he wanted protection from the Mafia. That’s the big story but it makes little sense; If O’Sullivan was worried about the Mafia he wouldn’t have gone to Whitey.
      As for Whitey killing the two Debbies, before you believe he did you have to come up with a motive why he would do it. Can you? With respect to Wheeler and Callahan, how do you put Whitey into that?

      You ask if Whitey could reveal more stuff, probably but why would you ever believe anything he had to say and how would you be able to ever decide if his version was the truth anymore you can believe what the other other criminals are saying about their roles.

      As for Connolly they say he took a lot of dough from Whitey so that would make him corrupt in one sense if he did; as for his protecting Whitey and Stevie that is what he was supposed to do. It was when the news media made such a big ado about it that the FBI was successfully able to hide its Top Echelon program and say Connolly was a rogue agent. Connolly was never convicted of taking money. If he didd’t take any, then what he did he was supposed to do. However, the way it was presented in Florida it was as if he had no right to tell Whitey that Cllahan was being investigated by the FBI. If his job was to protect Whitey he was supposed to tell him to stay away from Callahan.

      1. Matt
        I and MANY others are looking forward to your break down of each murder Whitey Bulger was accused of during the trial. I can only speak for myself put your efforts in explaining to the best of anyones ability (outside of the main players) what ACTUALLY most likely occured is highly appreciated. I originally took every sentence in the book BLACK MASS as fact and now I see there are many errors.

        I understood that Whitey claimed he was going to protect O’Sullivan from being murdered by others in exchange for information but I knew that was ludicrous. Because Whitey makes that claim I believe he was in fact an informant but in his mind he didnt see it that way. He sees himself as “playing” and “using” the FBI for his gains.

        I conclude there is no motivation to kill the 2 Debbies but seeing that he had no problem killing anyone for money or to avoid being ratted on it wouldnt surprise me if he helped Steve Flemmi murder these 2 women. We also dont know if Whitey himself had some sort of intimate relationship with these 2 women too. I dont put it past Whitey Bulger doing much of anything. Heck maybe Steve Flemmi wanted the 2 Debbies dead and couldnt bring himself to do it and asked or paid Bulger to do it. Given that these 2 men are sociopaths ANY SCENARIO is possible, no?

        The Wheeler and Callahan murders are also speculation. Whitey Bulger may or may not have known of the plan to murder Wheeler. He may have had nothing to do with it or he may have sat down, discussed it, and decided he wanted the profits from the skims, no? Same with Callahan. No one really knows who plotted to kill these 2 men. We do know Martarano killed them based on his own admission. Then again, isnt it possible McDonald or Sims helped to murder these 2 men also?

        I was asking WHAT MORE DAMAGING information could Whitey Bulger reveal? John Connolly is in jail, Morris looked like a manipulative weasel, O”Sullivan reputation was tarnished, and Schneiderhan (sp?) was implicated also.

        1. Jerome:

          The reason the O’Sullivan deal came up is because the Court of Appeals said the real deal (which was between the FBI and the criminals) was not enforceable since it had to be made by the prosecutors. So Whitey just invented the O’Sullivan story. He couldn’t say he was an informant for O’Sullivan because prosecutors don’t deal with informants; and he did not want to be an informant; so he came up with the scam of protecting O’Sullivan from some sinister groups. Unfortunately even the time lines don’t work for Whitey.

          You are ahead of me on the Debbie so wait and see what I figure. Whitey had nothing to do with those women. As far as suggesting Flemmi could not bring himself to murder someone that borders on being a joke when you think of all the people he did murder, even his friend who went west with him to California and then Las Vegas. Murder to Flemmi meant nothing. As for sociopaths, they do have some lines over which they will not cross but you bring up good points.
          I’ll also discuss Wheeter – remember where the information is coming from – ask yourself (your read Hitman) if Martorano ever needed to clear any murders with anyone. McDonald did help in both the Wheeler and Callahan hit, he was with Martorano. Sims I think had gone to meet his maker by that time.
          Whitey has no damaging information. Even if he did, who is going to believe him. Morris believed Whitey had made tape recordings of their conversations – that is the one thing that could still be out there if he did and found a way to protect them.

          1. Matt
            I may be jumping ahead of the blog but you have helped me to develop a critical eye. For example,the version of Halloran being killed in DEADLY ALLIANCE has some differences with Weeks version. In DA Ranalli says there was 3 men in the hit car. Weeks says there were 2 men. In DA a witness says a man in his 40s was sitting in the watch car with binoculars. This was in 1982. How could that have been Weeks? Weeks was NOT in his 40s in 1982.

            Also, WHY would Whitey Bulger kill Halloran IF he had nothing to do with Wheeler being murdered? Why would Whitey fear Halloran talking to the Feds when he was already an informant?

            1. Jerome:

              Eye witnesses are usually unreliable so pointing to one and suggesting that must contradict someone else does not necessarily mean it is so. I would not discount there being three men in the car; Weeks, Nee and Whitey. Weeks has always separated himself from the killings and making himself look like a passive bystander but in other situations not involving murders where the statute of limitations has run he is very much an active participant in pushing people around. he’s also give two different accounts of the car he was in when he went to Halloran’s murder.

              Put yourself in Whitey’s position, you are a gangster and have a guy telling the FBI that he has evidence you were involved in killing Bill Door. Even if you didn’t have anything to do with it do you feel comfortable that he might go before a grand jury and put your name out there and you might be indicted? I think you can see that even if you were not involved you wouldn’t be too happy having someone put you into the murder.

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