Black Mass’s Major Mistakes: – Winter Hill was Threatened by the Mafia

(`) Black MassI pointed out that the authors of Black Mass started with a wrong premise. They did this because they are newspaper writers and are unable to separate the wheat from the chaff. They have no idea what is really going on but make things up to fill their gap in knowledge as they did in their attempt to suggest Whitey was recruited as an informant against the Mafia in 1975.

The suggest that one of the reasons Whitey decided to become one was that FBI agent Connolly “knew Bulger and the Winter Hill gang were facing a two-prong threat from a local Mafia . . . . “ They say there was a dispute over the placing of vending machines; and, a story was going along that Gerry Angiulo local Mafia leader had cooperated with the Boston police to set up “a mob enforcer [who had] veered out of [Angiulo’s] control” by planting guns in his car and having the cops find them and arrest him. The authors say, “no one knew for certain whether Angiulo in fact had the kind of access to manipulate an arrest like that.” They go on to say “Whitey Bulger and Howie Winter’s gang believed it.” You have to wonder how the authors knew what those people believe when they had no contact with them.

Jumping from that, which for all we knew was a story they pulled out of the air, they say: “[Whitey] was clearly concerned about Angiulo setting him up.” Then, as if they had a stenographer hidden in the back seat of the car at the imagined meeting they put Whitey’s words in quotes: “What if three cops stop me at night and say there was a machine gun in my car, . . . Who is the judge gonna believe. Me or the three cops.“

First of all, if they knew Whitey, he would never let himself be set up. He wasn’t worried about that in the least since he took care his car was protected at all times. Ask any of the DEA or Quincy police who tried time and time again to bug it. Next, the authors fail to understand law enforcement. If three Boston police officers grabbed Whitey and said they found a machine gun in his car then there would be nothing the FBI or any other federal agency could do. It would have been sayonara Mr. White. Some things cannot be taken care off and that would have been one of them.

How do I know, think of Mark Rossetti who was also a top echelon informant. His FBI handler said his job was to keep him safe. He did that but when the State Police grabbed him dealing on a wiretap there was nothing he could do to help him. So the whole premise made up by the authors doesn’t hold water except to those who have no idea how things work in law enforcement.

But the scenario of Whitey becoming an informant because of threats from Angiulo runs right up against the actualities of the time. In 1973 and thereafter Angiulo and Winter Hill were working hand-in-hand. John Martorano tells the story. He wrote: “It was the winter of 1973, and [Angiulo] invited his new associates, Howie Winter and Johnny Martorano, to the Dog House. Angiulo got to the point very quickly.” A couple of pages later he tell us about it. He was worried about about Indian Al who was moving in on Angiulo’s territory and had killed one of his bookies. ““He killed my guy,” Angiulo explained to Howie and Johnny.” Martorano continued that after checking it out they went back to Angiulo and agreed to do some hits for him. For a year or so Howie Winter, John Martorano, Whitey and others were doing the bidding of Angiulo in killing off his opposition.

The authors of Black Mass should have known that there was no threat to Whitey or his friends from Winter Hill. They were working together and amicably settling disputes. And, if you want to believe the gangsters from Winter Hill they would suggest that the local Mafia was afraid of them. If you look at it from Winter Hill’s point of view, the Mafia might have had two or three local guys who were capable (able to murder people) while Winter Hill had a stable full of real crazy capable gunmen like Howie Winter, Joe McDonald, Jimmy Sims, John Martorano, Steve Flemmi and Jimmy “Whitey” Bulger along with Frankie Salemme, Jimmy Martorano, Pat Nee, and others who you would really not want to tangle with.

Of course the Mafia could always call upon outside help but it made no sense for them to get in a war since like in the 1960s it would be bloody and most would not survive. It was best they maintain an alliance and work together. Black Mass’s suggestion that a threat from the Mafia existed is nonsense.

18 thoughts on “Black Mass’s Major Mistakes: – Winter Hill was Threatened by the Mafia

    1. Doubting:

      They were. They were also borrowing from the NY Mafia. That is why they killed Castucci. It was not because he was an informer as we have been told by the usuals, it was because he was the guy who would take the money to New York to make the payments. Martorano and Winter came up with a scheme to wipe out that debt. They would give Castucci the money, kill him, and then tell NY Mafia that they gave the money to Castucci and someone must have killed him and proclaim that they had already paid them off.

      1. Matt- That’s right. I also believe that there was a big bookie named Jack Mace connected to the New York crime family that Winter Hill wanted to kill if they needed too. Howie Winter- Joe Mcdonald- Jimmy Sims- John Martorano are guys you probably don’t want to gamble with.

        1. Doubting:

          That’s the big problem with the story told by Martorano and others about the murder of Celucci. It goes like this. Joe McDonald and Jimmy Sims were on the run and we (Whitey, John, and/or Steve, or all of them) got them an apartment through their connection Jack Mace in the Village. Castucci was the informant of FBI Agent Tom Daly who was giving them information on the whereabouts of McDonald/Sims in the New York City area. Connolly somehow got word of that (never any proof he even knew it) and tipped off Winter Hill that Castucci was an informant so they murdered him.

          As I wrote before they murdered him to wipe out a debt to the NY mob. Why would they go to the trouble of telling him they had the money, giving him the money, letting him go down the street to count the money, etc. if they wanted to hit him if he were being an informant? They would have just done it without all the ceremony.

          As far as tipping the FBI off about the apartment, Jack Mace was an FBI informant in NY City. If he arranged to get the apartment there is little doubt the FBI there knew exactly where it was. It may be that Castucci knew also because he was close with Jack Mace; he was feeding Daly information about it but it was never enough to hurt anyone. Daly was giving the information to NY FBI which already had it if it existed.

          An important factor to keep in mind is that Whitey and Stevie had no love for McDonald and Sims. With those two guy on the run they were two less people who were going to be cut into the spoils. They would have been very happy to have them arrested and for Castucci to give them up; Martorano writes that after the Castucci hit Whitey wanted to get hold of McDonald and “Joe Mac refused to meet with them. He always had less use for Whitey and Stevie than anyone else in the gang.”


          1. After simms got out of prison he got married and lived in Mass for a couple of years.
            Why did jimmie disappear?

            1. D:

              I always wondered what happened to him. No one in the Winter Hill gang seemed to care he went missing. He probably knew too much.

  1. I say we all contribute to our own book called “Minimal Outrage” The newest case of this is Rossetti case, dealing Heroin and straight murdering folks 20 yrs deep. It’s all still happening.

    1. Doubting:

      I will write a letter to Lynch and ask him what he found out about Rossetti. I’ll post it here when I do. But yes, the program where the FBI joins with murderers and keeps them safe is still operating today throughout the nation but don’t tell anyone, it is secret.

  2. Matt
    Thank you for the feedback regarding motives for murder and clarifying how unlikely it is that Whitey Bulger murdered some of the people he is accused of murder. You may have already addressed this in previous posts so forgive me for my lack of knowledge BUT why does law enforcement cut “deals” with Flemmi, Weeks, and Martarano simply to get Whitey Bulger indicted and found guilty of charges? I am aware this is Law Enforcement 101 but why does law enforcement care to reduce the sentences of the 3 amigos to convict Whitey Bulger?

    I mean wouldnt Martarano, Weeks, and Flemmi ALL have had longer prison sentences if they didnt cut deals. So those 3 do less time in order to get Whitey Bulger and make sure he does time. Also, could you explain a little more just how law enforcement would have solved some cold cases in relation to Martarano deal. You implied, I believe, that law enforcement was aware that certain individuals were murdered and would eventually have had cases to present to the jury EVEN IF a deal was not made with Martarano.

    John Martarano murdered at least 20 people in his deal confession, no? And all he got was 11 years. Less than 1 year per murder simply to tell the feds what they wanted to hear about Whitey Bulger. Mind you, Whitey Bulger was not found guilty of all 19 murders he was accused of so its safe to say that the jury did not believe some of Martarano’s testimony.

    1. Jerome:

      There was really no need to cut any deals. Why do you think Martorano made a deal? Or Weeks? They were facing charges (prior to the knowledge of any murders) under RICO that could have put them in prison for the rest of their lives. Flemmi also faced the same future. When Flemmi disclosed he was an informant because he was facing charges that could have locked him up for live. So despite what is out there, all those who cooperated saved themselves lots of prison time by telling tales about Whitey Bulger.

      Whitey, too, faced the same RICO charges. That is why he fled. He also knew those charges could have put him away for the rest of his life. No deals had to be made with anyone to put these people in jail since the evidence was already there.

      Whitey was already indicted when the deals were made. The feds were not going to be able to lock Whitey up for a longer period of time because of the deals. Even worse, had Whitey not been captured the feds would have gotten nothing for the deals. Why then did they make them?

      Wyshak and his team were after someone other than Whitey. They were interested in getting Billy Bulger, Whitey’s brother. He was the real target of all this. Nothing else makes sense given that all the deal makers were already under indictment.

      Martorano himself said he was afraid that if he did not tell about his murders then someone else like Flemmi or Winter or others who knew about them might tell about them. He was smart enough to tell about them in exchange for getting a lesser sentence than he already faced and to give protection to his brother and Howie and his girl friend. The deal the government made was horrible as was the deal with Weeks who was allow to protect Pat Nee. Weeks himself said he knew he’d spend the rest of his life in prison if he didn’t make the deal.

      What is really strange is the more murders the people told about and pinned on Whitey even though they were the ones doing them the more they got their sentences reduced.

      There was also another part of this. All the people pushing the case against Whitey (who was willing to plead guilty and spend the rest of his life in prison) loved the publicity. Wyshak has close connections with the authors of Black Mass and others at the Globe. We know the grand jury testimony of Billy Bulger was leaked to the Globe. The publicity was good for the books, etc.

      When Martorano testified against John Connolly in his trial in 2002 the jury disbelieved everything he said. It is unclear how much they believed, if any, in Whitey’s trial. The Martorano deal when considered in the clear light of day is the worst ever made by any prosecutor. Although, if Flemmi is now out on the street in some sort of protection program that will be even worse because he was more evil than all the others packaged together.

      1. Matt
        I agree with everything you stated in this last reply. But what I still do not understand is why the Feds (federal government?) made deals in the first place? As you stated there was enough evidence to convict Flemmi, Martarano, Weeks, and Nee. With that as a given, lest assume there was enough evidence to convict Whitey Bulger too. With that said it makes no sense to me (someone with very little knowledge of law enforcement) why REDUCE all the above mentioned guys testimony “in case” they ever located and got to try Whitey Bulger.

        A big part missing out of all of this is just how much hatred Billy Bulger had towards him by key people in the media and in politics. Are you suggesting that a lot of things surrounding Whitey Bulger were blown out of proportion and magnified in significance simply to tarnish Billy Bulger name and reputation?

        1. Jerome:

          I’ll put it as simply as I can – and you do an excellent job of putting it in perspective – they wanted to get Billy Bulger. Nothing else makes sense. They thought by dealing with these guys they could jam in Connolly and he would give them something on Billy.

          I am suggesting and have in the past that Whitey – who when you look at it is in the lineup of hoodlums in this case a small player when compared to Martorano (who is doing all the murders), Flemmi who has a long history of murders even murdering a friend out in Las Vegas who helped him on his flight and then the two women; Salemme, the head of the New England Mafia, and a known killer – was elevated into the major player which he wasn’t.

          The target was Billy, the media and prosecutor agreed he was bad, Professor Dershowitz had him as the protector of Whitey, Wyshak thought that, but even though their was no evidence of any of that – Billy spent 37 years in the public sector without even getting a speeding ticket – they wanted to destroy him, which they did.

  3. Generally, I’m in agreement with Matt. I don’t see how an Irishman from South Boston would have any significant information about the inner workings of the Mafia. Now, Winter Hill may have carried out contract killings for the Mafia, but I kind of doubt Bulger would want to talk to the FBI about any of the murders he may have had a hand in — Mafia-ordered or not.

    By the way, A.O. Scott, the New York Times’ top film critic, has panned Black Mass the movie. The film’s commercial success will be determined largely by word-of-mouth, but media opinion can have an impact at the box office. Here’s the link to Scott’s review:

    1. Dan:

      Thanks for the information on the review. O.J. Scott hits a home run with the last line of the review which pretty much sums up what I have been trying to say since I became more knowledgeable about these matters. We have the Lehr author of the book Black Mass living in some type of fantasy world when he says Whitey was the “most evil man on the planet” (he also said in the past that when Whitey was in prison and Father Robert Drinan was trying to help him out that Whitey was bringing him in as a member of his gang even though no gang existed at the time) but O.J.Scott rightly says: “It’s possible, though, to think of the shortcomings of “Black Mass” as fitting comeuppance for Mr. Bulger. He may have thought he was a big deal, but in the end all he merits is a minor gangster movie.”

  4. Clarification of “they” and “them”

    And “they” (Gerry and Larry) then knew they could count on Howie, Johnny, Whitey, etc.

    I agree that “they” (G+L and Winter Hill )worked together warily after that (1973), but Whitey could have given “them” (Dennis, John, ((+ Paul)) info on Notarangeli, Milano, Plummer (murders) so “they” (D,J, P) could have had reason to want Whitey on the books as an informant….

    1. Rather:

      Disagree. You are taking what we know now and assuming it was known back then. How would the FBI know that Whitey had any information on the Indian Al gang hits and misses or that they were being done at the behest of Angiulo? If it knew that Howie and John Martorano were doing them why would it need Whitey since it already had the necessary source to tell them that.

      The FBI most likely had no idea what was going on because on the surface these killings did not look related nor were not federal matters. Even if it were investigating them, from an investigative point of view they were not connected to the Mafia – Milano, Plummer, the guy from Southie who was with DiMasi were all done in error – until Martorano tells about them the cops have no idea they are connected to any Italian dispute and he doesn’t do that until the late 1990s. To suggest the FBI had an idea those murders had been done in error as part of the plan to help Angiulo get rid of Indian Al’s gang; and that the FBI figured Whitey could give them information on them, I think is taking it a little too far especially after we know that the FBI seemed at sea after Rico left town in 1970 and Flemmi was not around to give it information.

      The point of the post is that Howie and John M. met with Angiulo which showed Whitey was not in fear of the Mafia setting him up. He was part of the gang that in 1981 Angiulo or Baione said on the FBI intercept that “the Hill is us.”

  5. Matt,
    In a way, your post today conflicts with yesterday’s. You have mentioned before that Whitey would be the last one the FBI would go to looking for info on the Mafia, and again yesterday…”Now anyone with a smidgen of knowledge about the relationship between the Italian Mafia and the Irish, especially the Irish from South Boston, would understand that you don’t go to an Irishman to get information on the Mafia”

    But today you have “for a year or so, Howie Winter, John Martorano, Whitey and others were doing the bidding of Angiulo in killing off his opposition” (1973)

    I would submit that Whitey did have information on the Mafia from that point on. And they then knew they could count on Howie, Johnny, Whitey, etc.
    Hence, after Howie (and Joe, Johnny, Jimmy1, Jimmy2 went on lam) went down, and Bootsie and Benji rose from the ashes to briefly open up on Lancaster St, we see a parade of North Enders leaving their comfort zone and going there in person, even guys as high as Larry Baione and Danny Anguilo.

    I agree that they worked together warily after that, but Whitey could have given them info on Notarangeli, Milano, Plummer so they could have had reason to want Whitey on the books as an informant….

    1. Rather:


      You note that Whitey was not invited to the meetings with Angiulo, only John Martorano and Howie Winter. He could not put his finger on anything that Angiulo said. It is questionable at what level he was in the gang at that point. He had just come over to get protection from them. He had no information to give the FBI other than what he might have picked up from Winter or Martorano – thst would have been little more than anyone in that business could pick up on the street.

      True after Winter went to prison, and after McDonald and Sims fled along with Martorano, the two – Whitey and Benji rose to the top of the mob and located at Lancaster Street. That though was around 1980 which was five years after Whitey had allegedly been brought on as an FBI informant. Keep the dates in mind – in 1975 Whitey had no Mafia connections – by 1980 he might have had some intercourse with Mafia guys at the garage and had he been approached at that time there may have been reason to believe he had information on the Mafia that was useful.

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