An Overview of Whitey’s Murders: The Last Three Groups (5 of 5)

P1010306As we turn into the 1980s we have two men who are at the top of the Winter Hill Group, James “Whitey” Bulger and Stevie Flemmi. The others in the group who were in a leadership position have been incarcerated, are on the lam, or as in the case of Jimmy Sims not to be heard from again.  The first move that Whitey and Flemmi made was to move their operation from out of Somerville since the guys from that area were no longer players. They moved their operation to Lancaster Street which was in Boston’s North End right around the corner from the old Boston Garden.

There they would set up operations right in the heart of the Mafia’s home base. Observations of them showed that they and the Angiulo Mafia group  were on friendly terms.  It appeared they made weekly payoffs to the Mafia. The Lancaster Street location was where they also received tribute from those who worked under them. They would move from Lancaster Street after they were tipped off that it was being watched by the state police. Whitey having cleared the deck in Southie moved back home into his neighborhood and took his new hard buddy Stevie Flemmi who was a capable replacement of Billy O’Sullivan.

Until Whitey came back in Southie he had left it under the watch of Pat Nee who was his partner in the operations.  It was good timing for Whitey because Pat Nee was not keeping his mind on the family business but was becoming more and more involved with doing all he could to help the Irish Republican Army (IRA) in its fight with the British in Ireland.  Whitey would be able to attend to business while Nee spent his time otherwise.

All of the eight murders in these three groups occurred after Whitey had gone back to South Boston between 1981 and 1985. Two were in 1981, three in 1982, and one in each of the three following years. Whitey would operated out of the Triple O’s on West Broadway next to Broadway MBTA station; he’d move some of his operation over to the South Boston Liquor store at the Old Colony Avenue rotary in 1984.

Whitey at the time of the move is entering his early fifties. He has control of a large criminal gang involved in gambling and its associate crimes such as lending money at high rates of interest and using violence to collect from what are considered “dead beats.” He’s not threatened by anyone and is aware that the feds have just finished a wiretap investigation on the Boston Mafia that will end up putting the Angiulo family group in prison.

He  has been in contact with FBI agents Connolly and Morris for over five years and is fairly confident they are protecting him; Stevie has State Trooper Richard Scneiderhan protecting him on the state side; then there are the local Boston cops who seem to present no  problem but he is wary about the Quincy cops.

It is during this time that he engages in the eight other alleged murders. They are divided into three  groups. The first is the World Jai Alai (WJA) Group where two men were murdered by John Martorano. These murders took place in Oklahoma and Florida. Martorano had been on the lam living in Florida  when John Callahan asked him to murder the owner of WJA Roger Wheeler which Martorano did for fifty grand. Then when he thought the heat was closing in he offed Callahan.

The second group is the Informer Group. These are a group of four men who were murdered to shut them up, or in the case of one, Michael Donahue, who happened to be in the wrong place at the wrong time with the wrong person Brian Halloran. Halloran was trying to get himself out of the jackpot, he was facing first degree murder charges, by putting Whitey into it. Halloran knew he could only get a break if he brought in someone who was higher than him so he picked out Whitey.  The other two, Bucky Barrett in 1983 and John McIntyre in 1984 were killed at the home of Pat Nee’s brother and buried in the basement.

The last group, with the victims being murdered at both ends of this murder period, were Debbie Davis in 1981, and Deborah Hussey in 1985. ThIs is the Ladies Group. The big connection between these murders is Steve Flemmi since both women had been in sexual relationships with him that had ended or were about to end. Flemmi liked to bury women who fell out of favor with him. He’d tell the gullible prosecutors that another made him do it. And you know what? The prosecutor believed him.

Now that I’ve put the murders in the context of time and place I’ll talk in greater detail about them. Unlike the prosecutors I’m not out to get anyone; I’m just trekking toward what I believe is the truth.

29 thoughts on “An Overview of Whitey’s Murders: The Last Three Groups (5 of 5)

  1. Fanciful … non-verifiable … apocryphal …. logical yet … Just a better version of accepted events by a deliberative mind, Connolly’s, than most. A valiant attempt to condense and give an explanatory frame to a Time and to multifarious actors and events, but doomed to explain only as much as it can.

  2. Thank you, Matt, for this series of posts. I’m pleased to read that “Now that I’ve put the murders in the context of time and place I’ll talk in greater detail about them.”

  3. As Stated. Implying/Inferring tricky sides of the same hat … You may infer , as in drawing from what is spoken. or written, certain conclusions , but that does not mean the writer or speaker is … implying … anything. The latter, implying, is a more active agency , so to say.

    That said GOK… as your question is fair I fairly re-state that the Wily Prosecutor from the Norfolk County wolf pack has a better, shrewder, more delightfully plausible version of cited events than most. But he is not introducing or grooving in old fictional elements as that we suspect him bound by ….non-factual … Whitey Mythographies. Now, this closes thusly on that diplomatic note.

  4. Matt
    Thanks for this 5 part series. Look forward to a break down analysis of EACH murder Bulger did do personally or was in someway connected to it (the list of 19 at his trial). I and others anticipate this as it gives a much clearer perspective of what actually did happen during the Bulger era.

    WHEN will you decide whether or not Bulger was an informant. I strongly suggest you watch the WHITEY documentary by Joe Berlinger as you sort through all of this too.

    https://bpl.bibliocommons.com/item/show/4569448075_whitey

    There are 5 copies available at the Central branch currently

    1. Thanks Matt for the continued breakdown. I agree with the Jerome that you should watch the Berlinger documentary. It’s pretty good. Doesn’t come to any definitive conclusions about the informant issue and presents a lot of different angles corresponding to the perspectives of victims, prosecutors, defense attorneys, witnesses, and media. It doesn’t get into the details like you have in these posts, but he’s only got a two-hour documentary to work with. It’s a nice objective look at things. It only lacks the in-depth details necessary to appreciate the different perspectives it presents.

      1. Jon
        I agree with yoru assesment of the WHITEY doc by Berlinger. Whitey Bulger ran his criminal enterprise for so long that it would take a 4-6 hour documentary to tell the whole story in my opinion. The Berlinger doc did not touch upon nor go in depth of some of the other murder victims such as Tommy King, Indian Al, Eddie Connors etc. If someone had the financing and time a great documentary could be made as the Bulger story has different layers and different eras.

      2. Jon:

        I have a sense of the documentary. I’ll watch it but you have to keep in mind the families of the victims are pretty clueless and the lawyers are shilling for thier clients.

  5. Matt- Really great breakdown. Looking forward to more in-depth commentary about each murder. Really great commentators such as Jerome,GOK, JKM etc.. Thanks to all who commented with excellent recommendations and advice much thanks again to all.

    1. Doubting,

      A year or so ago we were supposed to correspond on the doings of Gerry Ouimette and Tim Mello in Fall River. Not sure if you heard, but Ouimette has since passed away.

      1. Jon- Great to hear from you pal. The Frenchman passed i did know of it. Timmy is out of jail he got bumped up on a donor list and actually got a new liver and looks like he is 35 again spotted as recently as 2 months ago. Seems to be back working at his fishery in New Bedford. Matty Guglielmetti is also out and about in the area of Cranston, his brother was killed in a car accident few yrs back also (randomn fact). Matty got pinched for his last crime protecting 60 kilos of cocaine through a concrete mix union of sorts, but did his time and seems to be staying safe. That is about all i got on my end of the Jon, Great to hear from you!

  6. Matt
    I dont understand how you are still inconclusive on whether or not Whitey Bulger was an informant. You have read so much and researched so much on the matter I would think you would have made a decision one way or another at this point. I wouldnt say you contradict yourself but you have stated that Bulger was able to avoid investigations and able to run his criminal “empire” for at least 15-20 years BECAUSE he supplied information to the Feds. You have no hesitation stating that Flemmi was an informant yet still hesitant to call Bulger an informant.

    HOW else could Bulger have been treated with kids gloves by law enforcement and never been indicted until 94 or 95 UNLESS he was an informant.

    Another thing that has bothered me is how would Bulger know that Halloran was “ratting on him” regarding the Wheeler murder UNLESS someone in the FBI TOLD Bulger? Either Connolly or Morris told Bulger what Halloran was saying and to me that makes them partly responsible for the murder of Halloran. Halloran was co-operating with the FBI right? Therefore ONLY the FBI could have given Bulger that information.

    1. Jerome:

      I thought I had explained this before. I am inconclusive because the definition of what is an informant is vague. There is no doubt Whitey provided information to Connolly. I have mentioned how he complained about my office and Connolly put that into the FBI file that listed Whitey as an informant. Does that make him an informant if all he does is provide Connolly with his complaints and does not provide him with actionable information about other people?

      There was no doubt Bulger was protected by the FBI from 1975 to 1991; I have explained how any inquiry about him made on the CJIS machine controlled by the FBI and used by all of the nation’s law enforcement would be directed to his handler. It was the policy of the FBI to advise the handlers of informants if they came across information about his informant. As long as the FBI file existed Whitey would be protected; even when it did no exist the FBI would keep the agent who handled him informed about news about him. Maybe if I explain it this way you’ll understand. If an FBI agent opened a file on me listing me as an informant which I did not know about that would not make me an informant. I would then be protected by the FBI SOP in dealing with informants even though I never gave any information.

      Steve Flemmi testified that he was an informant. Whitey averred the opposite. That is how I can put them in different categories.

      I have friends who were close to Halloran. Some were in a club with him earlier in the day of his murder. They tell me that everyone knew he was an informant. Connolly did not have to tell Whitey. Weeks, Whitey’s girlfriend, and others say part of their abilty to operated was to know what was going on out in the street. Halloran had been indicted for first degree murder; he had done prior time. The wise guys know that a person in that type of situation is normally held without bail. Halloran was free on $50,000 bail. Callahan knew he was an informant because he started to avoid him. Halloran would disappear out of town and then come back in. They all knew he wasn’t around his usual hangouts. FBI agent Montanari said that Halloran had told his lawyer that he was an informant; who else did he tell? It just was not something that would be secret among the wise guys. That’s how they survive.

      But that’s not to say Connolly did not give them that information also. It was his job to protect his informants and telling them that a guy was giving information against them certainly was part of the protection. That is why the Top Echelon Program is so evil.

      1. Matt
        You state that Bulger did give Connolly information. You bring up a great point. How do we know WHAT Bulger provided to Connolly. Lets say for arguments sake that Bulger did not provide any useful information to Connolly and/or Morris. If we go by that assumption then the TEI file on Bulger is ALL bogus, no? If Whitey Bulger provided one piece of information on another gangster or criminal then that would make him an informant.

        My question is WHY would there be a TEI file on Bulger then? Why would Connolly and Morris make up a TEI file on Bulger UNLESS they were “crooked” cops and Bulger was paying them for information? Who else would know that Bulger was an informant (if he was officially one)? Jeremiah O Sullivan.

        Given that Whitey Bulger MADE UP A PREPOSTEROUS story that he agreed to protect O’Sullivan from being murdered in return for getting information I am led to believe that Bulger WAS an informant. For me, Whitey Bulger got ALL the benefits and perks of being a TEI so I am concluding he was an informant. Why else would O Sullivan leave him and Flemmi off the race-fixing indictment?

        Of course we will never know what Bulger told Connolly and/or Morris. ALL 3 of them have been caught telling lies, no?

  7. Matt
    You are missing my point about Halloran. Lets say you are right and all these gangsters who have street smarts were well aware that Halloran was an informant. BUT MY POINT is how the heck did Whitey Bulger KNOW what Halloran was saying. You said that Bulger and Flemmi had nothing to do with Wheeler being murdered and that Bulger and Flemmi did not at first give the hit to Halloran. That was a tale Martorano made up to sweeten his deal.

    Bulger , not having ANYTHING to do with Halloran regarding Wheeler would NOT know what Halloran was saying UNLESS someone in the FBI TOLD Bulger Halloran was implicating him. That brings up right back to either Connolly or Morris telling Bulger that Halloran was ratting on him. Why else would Bulger go and shoot Halloran in public?

    I think you may be a little too cautious as to believing that Conolly and/or Morris DID NOT feed a lot of potentially dangerous information to Bulger.

  8. Hi Matt and wouldn’t the Mafia have a motive to kill Halloran so that he could not testify against a Mafia soldier about a murder in Chinatown?

    Did the Blackfriars massacre have anything to do with Bulger or Flemmi?

  9. Jerome:
    Whitey didn’t need any information from the FBI to target Halloran. Much of the criminal element in Boston was gunning for Halloran for a variety of reasons. The Mafia specifically wanted him dead so he couldn’t dime the guys he was with when he committed the murder in Chinatown.
    It was not just the Mafia that wanted to kill Halloran. Halloran’s mistaken dying declaration that Jimmy Flynn shot him was not confusion due to the shooters’ disguises. Halloran assumed it was Flynn shooting because Flynn had recently taken a shot at Halloran and missed. (Or maybe it was the presence of Pat Nee again that led Halloran to the wrong dying assumption.)
    Everybody else who did any crimes with Halloran also wanted him dead. In light of the Barboza fiasco, a flipper like Halloran could even croak innocent guys. (It was clear to criminals at that time that some prosecutors don’t care about the accuracy of their purchased testimony.)
    Anyway, it is very narrow to assume Bulger killed Halloran because of what Bulger was told by the FBI, if anything. Widespread motive to kill Halloran existed in the absence the FBI. In addition, John Connolly was on sabbatical from the FBI at this time while he attended graduate school. That leaves Morriss and O’Sullivan.

    Since Halloran was pinched on a murder rap, it’s likely he needed to give prosecutors something very valuable to save his own skin. He needed to help the law in either another murder case or give up a bigger fish, like Jackie Salemme or Whitey Bulger. The point is that Halloran had a very powerful incentive to drop Bulger’s name into the Wheeler hit, whether or not Bulger had any involvement.
    Halloran may have been the first to throw Whitey into the Wheeler hit, but it was an addition that Martorano welcomed.

    1. Patty
      You present a very good insight and perspective. My question still stands though regarding who told Bulger what Halloran was saying about him. Are you suggesting that Bulger didnt need to be told anything by anyone and decided to kill Halloran based on the circumstances? That Bulger, knowing that Halloran had murdered a man in a Chinatown restaraunt, simply “assumed” and “concluded” that Halloran was using his name to set up a deal forhimself?

      1. I think Halloran was just a friggin mess at the time. He was coked up and drunk so often. Halloran may have had 5-6 people who wanted him dead anyway, I feel he was just such a mess that it was only a matter of time before he was to be killed bar hopping or caught in a compromising situation. I feel really for Donahue who had to give him a ride home and caught the wrath and hate for Halloran in a barrage of gunfire. I also wonder if they really gave Halloran that 20-25G?

  10. Jerome,

    Correct. It was widely known that Halloran was cooperating to get out of a murder charge. Whitey knew he had exposure to Halloran. Nee knew he had exposure to him. The Salemmes/Mafia knew they had exposure to him. Jimmy Flynn obviously had exposure to him. The Charlestown crew had exposure to him.
    Halloran was virtually radioactive. He could do harm to a wide range of people as indiscriminately as radiation could. The specifics of what Halloran could give law enforcement, such as the Wheeler hit, weren’t a prime motive for his demise. In fact, I don’t believe Whitey had anything to do with the Wheeler hit.
    Doubting Thomas is also correct. Brian was addled by cocaine and booze. Overall, the Halloran family was then, and remains today, very highly regarded by all who know them. Unfortunately, Brian went off the tracks.
    That is one of the reasons I doubt Whitey actually asked Halloran to go to Oklahoma to kill Wheeler. Whitey had no tolerance for drinks like Halloran. He didn’t trust them and he believed they were weak and unreliable. The other reasons I don’t think Whitey had anything to do with Wheeler were stated best by Weeks, ‘Jimmy said he’d never have gone along with the Wheeler hit because “the guy is legitimate and he’s a zillionaire. We’d have problems forever.” The Wheeler hit was also waay out of Whitey’s comfort zone. “The purpose of committing a crime is to get away with it.”
    The Wheeler hit was reckless and foolhardy. It was more consistent with the sloppy, partiers in the gang, Martorano, Callahan, MacDonald, Nee, Flynn, Halloran. These guys were the “donworryboutit” cokeheads and drunks.
    As the gang’s armorer, Nee provided the guns for the Wheeler hit. Nee was sloppy at that job too and the gun exploded in Martorano’s hand when he shot Wheeler. When Nee was shooting Halloran and Donahue, he claimed his machine gun jammed. Later when he got caught robbing a bank in Abbington, his machine gun “allegedly” was missing the firing pin, so Nee got a second break from the Feds for being a convicted felon in possession of a machine gun while committing a life felony(first was Valhalla). Maybe Nee has the luck of the Irish? But I digressed.
    The point is that the Wheeler hit looks a lot more like the work of a sloppy bunch of drunks than a Whitey production.
    The partier faction of the gang first tried to take out Halloran when he went mad dog. Nee and Jimmy Flynn made a move on Halloran, but they missed him. Since Halloran saw Nee and Flynn try to hit him, that gave Whitey one more reason to step in and wipe Halloran out. Halloran could dime Nee and Flynn for the botched hit.
    P

    1. Brandon:

      Agree that one of those you mentioned was not done by Whitey, but not as to the others although the evidence of his involvement does come from a suspect source.

      1. Those suspect sources you mention, are protecting the real man responsible. Those suspect sources are protecting him by putting dirt on Jim.

        1. Brandon:

          I will be writing soon about the McIntyre murder which identifies another as his probable murderer. He (or they) is someone we have already heard from. Do you suggest that there is another actor involved that we have not heard about?

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