The Whitey Bulger Balloon: Has Whitey’s Reputation Been Blown Up Far Beyond Actuality?

Whitey With Weapon

A comment section is good because we all know many minds are better than one. The other day a question came up about the Mafia and Whitey. I responded that Whitey had little to do with the Mafia. The reason was he is Irish. The Mafia in New England had a strong dislike for things Irish, especially if it was South Boston Irish which Whitey represented.

This goes back to the inrush of immigrants into the area. Each ethnic group lived with its own but competed with the other for jobs that required strong backs or hands and little education. In the early part of the 20th Century a couple of gangsters (leaders of the Gustin Gang) from Southie were lured into the North End where they were murdered.  When you only associate with your own kind in a closed society you find others both strange and threatening. The Mafia, being an Italian-only club of murderers, had little to do with most Irish and nothing to do with Whitey.

This went not only to Irish gangsters but to other Irish. I worked in a law firm that had two partners: one Italian and one Irish. On this date a couple of the Mafia bosses entered the office space and then into the Italian partner’s office. Both partners were there. An uncomfortable silence ensued after the Italian partner asked them what they were there for. He asked them again. They indicated with their heads toward the Irish partner. They were not going to talk in front of him.

This is why it’s sort of ironic to suggest that Whitey helped the FBI in its war against the Mafia. Whitey had as much idea of what the Mafia was doing as the Irish law partner. He was made a top echelon informant in the FBI’s war against the LCN (Mafia) which was supposed to mean he had contact with the top level Mafia types and could pass on information to the FBI about what they were doing. The truth is he didn’t have this access. He had no direct knowledge of what the Mafia was doing.

When the FBI placed the electronic bug into 98 Prince Street, the headquarters of the Patriarca family underboss Gerry Angiulo, it had to show Gerry was using that spot to conduct his illegal business. It had information from people who dealt with Angiulo in that spot. One informant was a big bookie who ran Chelsea named Berkowitz. (He was the only top echelon informant of FBI Agent John Morris. Morris took money and gifts from him as well as Whitey. Morris testified against FBI agent John Connolly) The information for the bug was already in place without any help from Whitey. He really had nothing to offer.

The question then arises is why is Whitey a top echelon informant. Who was he supposed to be connected with that gave him that status. The apocryphal story spun by Agent Connolly that he made a deal with Whitey to make him an informant in exchange for him taking down the Mafia makes little sense. Whitey couldn’t help him on that.

I’ve gone through the first few murders Whitey is charged with committing. These murders were all done by Murderman Martorano. He has Whitey lurking somewhere about in a back-up car while he and a guy in the back seat of a car being driven by Jimmy Sims fire machine gun bullets out the car’s windows and manage to murder people other than the targets they are going after. (Apparently the man in the back seat wore a mask since Murderman  identifies him as “a guy from Somerville” as if they picked him up standing on a street corner thumbing a ride.)  These murders were being done as a favor to Gerry Angiulo.

Murderman talks about meeting with Gerry to set them up and get the payment from him for doing them. The meetings are with Murderman, Howie Winter and Gerry. (Murderman’s brother who is a made man in the Mafia is probably there although Murderman doesn’t mention him.  His deal with the feds is he doesn’t have to implicate his brother in anything.)  After each murder these guys meet again with Gerry who gives them further instructions.

The question that came up to me as I was reading this is if Whitey is supposed to be the leader of the Winter Hill gang, where is he?  The obvious answer is nowhere near Gerry Angiulo. Gerry wants to deal with Italians that’s why Murderman is there. Howie Winter for some reason gets a pass and he’s there too. I figure that he is from Somerville and not from the Boston Irish neighborhoods like Southie, Charlestown or Mission Hill so Gerry considers him to be more trustworthy. This turns out to be right because Howie never became a rat like all the others. In his early ‘80s he is still working hard at his profession.

Is it time to reconsider the position of Whitey in the overall scheme of things? Is he really the biggest and meanest bad man to walk the Boston streets or is he just a particularly vicious two-bit hoodlum who at times hung around with the big guys but mainly confined his activities to Southie. Wouldn’t it be something if Whitey isn’t the monster he’s supposed to be, he was set up and used by the Italian gangsters like Murderman. Stevie Flemmi, and Frankie Salemme to take the big hit while they walk free. Can it be we are all being scammed by the gangsters? Just a thought and something for us to consider.


21 thoughts on “The Whitey Bulger Balloon: Has Whitey’s Reputation Been Blown Up Far Beyond Actuality?

  1. I’ve been enjoying this thread without commenting for several months.It raises many interesting questions about the factual basis for much of the Bulger narrative, especially the body count attributed to him. It’s certainly noteworthy that virtually every witness to his most notorious crimes is either dead, or at some point cut his own deal with the government. And Nee, Weeks, and Martorano likely never expected him back in town to contradict them. Perhaps something other than delusion or revisionism is driving Bulger’s reported disgust over what he considers misrepresentations or lies in his colleagues’ books, especially Martorano’s.

    I think it’s entirely possible that Whitey, while a really, really bad guy and the preeminent Southie shakedown artist, was nowhere near the force of nature we’ve been told, didn’t commit all the murders attributed to him, didn’t “make” nearly as much money as we imagine he did during his peak years, and that his rise was 95% attributable to 1)his brother’s political power – and patronage and 2)John Conolly’s protection.

    And I think the picture emerging regarding #2, Connolly, is not that he protected Whitey not because Whitey was a valuable informant againt LCN, but out of loyalty to Bill Bulger. Adding another TE to his careerist fight against LCN was just icing on the cake, and made it more sellable. Basically, Connolly just wrapped Bulger into his existing stable of informants, notably Flemmi. His gratuitous, strictly-for-the-file tag-along to 98 Prince, as described in Cullen/Murphy’s book, seems entirely possible.

    So there is perhaps, too, something to Bulger’s oft-repeated claim that he “got gold and gave the FBI shit in return.” Which raises the question of how big a rat he really was.

    And one wonders, anyway, how basically three guys could shake down all of Boston for so long without someone clipping them. I’m guessing the reputation for violence was far more effective in this regard than actual violence.

    I seem to recall Howie Winter describing him as a “strictly a ham-and-egger” in the ’70s. And Nee certainly takes him down a peg in his book.

    The pictuyr

    1. Roundtop:
      Not that it makes a difference but I think a fair estimate of the people Whitey killed would be less than ten. That’s quite a lot in anyone’s repertoire. Nee, Martorano and Weeks figured Whitey was dead and if not dead he wasn’t coming back so they felt free to spin whatever yarns they wanted. They had done their time so who was ever going to call them to account. Bulger’s big problem is whether their stories are half-truths or outright lies, he’s not in a position to set the record straight, no on will believe his version which will be highly self-serving.
      Whitey was the preeminent Southie shakedown artist that you describe but also as you suggest not this overawing force of nature. I think he made a ton of money with his shake downs and reputation. A lot of people paid to be left alone. I think Billy’s success made Whitey seem bigger than life even though I’m as positive as I can be there was nothing between them other than their relationship. I believe he had Connolly around his thumb.
      Connolly had no reason to be loyal to Billy Bulger. They both were from Southie and they were friendly Connolly like to let everyone know he had a connection with him. He didn’t protect Whitey out of loyalty to Billy. Having Whitey on the books was something he thought enhanced his status in the FBI. He kept Whitey because he needed Flemmi. Cullen/Murphy might think of him as a tag along but without him the FBI may not have had Flemmi.
      I mentioned the other day that an objective review of the evidence supports the idea Whitey was not an informant and that Connolly only had him on the books as one so he could interact with him and Whitey never considered himself as informing.
      I’m not sure what you mean by “three guys shaking down Boston.” You should know by now the whole Whitey thing has been blown out of proportion. Billy Bulger never did anything of a criminal nature and I’ve yet to see the slightest evidence that he did. Winter might have called Whitey that but again that goes to my point that Whitey was puffed up not because of anything he did but because by making Whitey larger than life people could hurt Billy.
      Nee’s got to be taken with a grain of salt. He definitely wrote his book thinking Whitey wasn’t coming back. He tells about making fun of Whitey but then points out it was always behind his back. It seemed no one would tell Whitey face to face what they really thought of him. No doubt he was a tough guy but as far as affecting Boston his effect on it is really unnoticeable.

  2. Keep three facts in mind:
    (1) Heroin addiction has been a problem in South Boston, Savin Hill and throughout the country since the Vietnam War in the 1960s. That’s why NIDA (the National Institute on Drug Abuse) was established in the early 1970s. In the 1960s and early 1970s, narcotic addiction and abuse was rampant in South Boston and Dorchester while Whitey was working as a custodian. Patty is correct in stating that the incidence and prevalence of heroin/oxycontin addiction/abuse and narcotic related overdoses has multiplied since the early 1990s. See DAWN data. If Whitey had spent his entire life as a custodian, narcotics still would have plagued South Boston as they have plagued every other neighborhood in the city and across the country from the 1960s through today. Whitey’s involvement in drugs was marginal and peripheral: he skimmed profits from some cocaine and marijuana dealers.
    (2) In 2002, a federal jury in Boston found that John Connolly was quilty of committing one crime, just one crime, during his 23 years as a law enforcement officer. That crime was giving a case of wine with an envelope in it to Morris from Bulger. (The episode is uncorrobated and is most likely a fabrication by Morris.) He was acquitted of all charges relating to murder. He was acquitted of all other charges relating to bribery. He’s never been convicted of taking a dime. One offense in 23 years as an FBI agent!
    (3) In 2008, Connolly was convicted in Miami of a crime he was acquitted of in Boston. Double jeopardy and statute-of-limitation issues were ignored by the judge and the federal prosecutor Wyshak. What was a federal prosecutor doing trying a case in a state courtroom in Miami?

    1. Bill:
      (1) right – if Whitey was the scourge of the drug trade then once he fled in January 1995 Southie’s drug epidemic would have ended.
      (2) right – all but one of Connolly’s convictions were for acts after he left the FBI – Morris was much worse than Connolly because he was taking money from Berkowitz along with a vacation spot, clothes and other gifts while Berkowitz was destroying Chelsea.
      (3) right – the two sovereign doctrine which allows a case to be tried twice should not have allowed the prosecutor from the original sovereign to again have a chance in the next sovereigh.

  3. I am in the process of reading your book. What is very clear is that many of the Boston FBI Agents have lied to protect their own pensions and did not act for the ‘greater good’. I had expected the ‘bad guys’ to lie. But, it is clear that the ‘good good guys’ lied as well. Does that make them ‘bad guys’ too? And, if so are there any ‘good good guys’ around to help us today?

    Here’s what I do know personally, and have reported to US DOJ: The person who identified himself as John Iuele, in an effort to get into my confidence (he was in the process of making a business loan to me from Drexel Burnam and needed me to front $6000), invited me one day to play tennis with him. When I arrived at the tennis courts another man with with Mr. Iuele. This man was introduced to me a Gus. Neither Mr. Iuele or Gus were very good tennis players.

    At the end of the matches, Gus asked me if I knew who John Iuele was. I said he was the President of Hamilton Funding and had guaranteed to get me a loan. Gus asked if it was personal and I said no – just business. And, then I left. This was in 1989.

    When I recounted this story(cir. late 1990’s), and the rest of my complaint, to the lawyer who brought the case against the US on behalf of Joe Salvati; and, explained that (now) I realized that Mr. Iuele looked like the spitting image of Whitey Bulger, and that his sidekick, Gus, looked like pictures that I have been seeing in the news papers of Francis Salemme, the LNC crime boss. The lawyer asked me some follow up questions. Then I asked the lawyer if he could help me. The lawyer said, no. The case was “too big”.

    1. Jean:
      It sounds like perhaps you were taken advantage of by Whitey, or someone who looked like him, pretending to be John Luele. I would put nothing past Whitey or his partner Steve Flemmie. One thing that intrigued me was you suggesting you played tennis with them. I didn’t know Whitey to have ever played that game, he was not a sports-type person although he liked to work out. But I don’t know that much about him and he could have that interest. If Whitey took your $6000 then it seems that the prosecutors having taken over 800,000 of his money would be in the position to give it back to you. I don’t think you could ever get it from Whitey since he has no assets remaining and there’s a long line of people already trying to sue him.

  4. Well Patty, I thank you for your comments and agree with some but disagree with others. Many of them I just don’t have the knowledge to evaluate one way or the other.

    I disagree with you that it was not possible to have a heroin problem in South Boston until after the introduction of oxycontin as a precursor drug in 1996. If this were so how did all the big cities in the eastern United States have heroin problems in the late sixties through the seventies? In my experience once oxycontin becomes available heroin users move to it rather than vice versa. I was in South Boston daily from 1970 to 1981 and there was both an angel dust and heroin problem at that time. By 1975-76 Whitey was known on the streets as the OC power in South Boston. He did nothing to stop this and instead collected a street tax to let it continue.

    I don’t know what Georgie Hogan has been up to since 1981 but I certainly knew Georgie and his brothers Ronnie and Jerry back then. Georgie was really the only one standing against Bulger who was allowed to go his own way. From his variety store on D Street he controlled all criminal activities in a small surrounding area.

    As an aside, if Pat Nee is running things in South Boston now (per one of your prior posts; I’ve read all of the posts and comments on this blog as well as the book), how are he and Georgie getting along running rival groups? They hated each other back then. I heard both of them say so.

    I don’t know anything about Hogan, Operation Beans, him flipping etc as I was long gone by then. I do know that the motive for the shooting of Ronald Hood (the case linked to) was not a hit for trying to swindle a bookmaker but because Hogan believed Hood was snitching on him. Interesting issue in the opinion re the existence of a letter trying to get Hood in the Witness Protection Program.

    The unsolved murder is that of a witness against Ronnie Hogan. Ronnie knifed a father and son to death in the Lithuanian Club. The witness (I think his name was Shempkis but might be wrong, his brother played with me on the South Boston Chippewas) was being held by MSP in witness protection down the Cape. (Same place they took Hallorhan probably.) However, the victim came back to South Boston to watch the 1976 Olympics with some friends at Kelly’s Cork and Bull down on Dorchester Ave. Georgie was notified and went in with a ski mask, lined everyone up against the wall and then executed him. This is still an open homicide and the Globe covered it extensively.

    I don’t think Connolly is responsible for all law enforcement misconduct. In this case alone there were Boston and MSP officers convicted. There certainly were other FBI agents beyond Connolly and Morris involved who have escaped. I find Connolly a rather sad figure, overmatched by Bulger and not supported by strong supervision. The fact of the matter though is that he has been convicted in two courts of law and cannot escape the label of corrupt law enforcement officer.

    Bulger certainly is not responsible for all organized crime, it was in Boston before he arrived on the scene and is still here 16 years after he fled. But he was a major OC figure in Boston in his day. Others were his equal at least (Howie Winter, Steve Flemmi, LCN) but his relationship with the FBI was the hook for the media to jump on his case and make it what it is today. Back to basics, I don’t think it can be disputed that Bulger had a hand in the murders of Barrett, McIntyre, King, Hallorhan and Donahue, Callahan and Wheeler not to even include Flemmi’s 2 girls. How many murders before he is a bad man?

    Whitey had nothing to do with making South Boston safe. That is a legend he put out there with no basis in fact. He did not stop one gram of drugs from being distributed in South Boston. He did not institute and enforce some sort of mythical “no street crime” edict in South Boston. How safe or dangerous it was or is to live in South Boston has nothing to do with Bulger or any other OC figure. I haven’t been to South Boston since 1981 other than to drive through occasionally. From what I can see gentrification more than anything is what is changing South Boston. Whether for the better or worse is each individual’s call.

  5. Dear JHG,

    You list some good historical facts in your comment. Consciously or not, however, you have been indoctrinated into the fiction that “Bulger is responsible for all organized crime and Connolly is responsible for all law enforcement misconduct, end of story”. It’s very easy to make the mistake you made because the USA sells this fiction so vigorously through their captive b”s in the mainstream media, but the theory’s limitations are becoming obvious here on Matt’s blog. You should read more of the blog posts.

    One of the areas in which you obviate your indoctrination is your declaration that “The heroin scourge that inflicted such deep wounds on South Boston families was aided and abetted by Bulger.” Factually, your declaration is impossible. The heroin scourge that still rages in South Boston got its start from the gateway drug, Oxycontin. Oxycontin wasn’t sold in the US until 1996 when Pharma Penn got regulatory approval. Bulger disappeared in 1994. Again, yours is an easy mistake to make since the media, law enforcement, and even the Southie politicians vigorously sell this rubbish. It works well for each of them for different reasons.

    Since you raised the heroin topic and blame it on Bulger, allow me to introduce you to the real facts. With Bulger gone from South Boston in 1994, another criminal organization filled the vacuum. The Hogan Gang, led by Georgie Hogan had long existed in South Boston by capitalizing on petty crime like football betting cards, etc. They got into selling cocaine via a bunch of small time dealers in the late 1980s and the money was good. In 1990, Georgie got caught on a wiretap during Operation Beans and was facing a cocaine Trafficking charge. Instead of serving his minimum mandatory sentence, he became a federal law enforcement informant and was promptly released to the streets. It’s ironic that Georgie got the informant status because he was also the sole suspect in a still unsolved homicide in South Boston. He shot a guy down in front of a crowd of witnesses following a bar fight. Everyone got amnesia. The homicide actually helped Georgie beat a rap in another case in which he shot a different guy:

    With Bulger gone, it was not long before the Hogan gang started to sell cocaine again, and then Oxycontin. George and his gang have never been known for their intelligence or manners. They have avoided arrest only for two reasons. First, the existence of a separate and distinct, Irish, organized crime group coexisting in South Boston would hurt the USA’s theory of organization in the Bulger case. Second, Hogan is a law enforcement informant.

    Since Oxycontin is essentially heroin in a pill form, it was more socially acceptable in a neighborhood that looked down on junkies. Construction workers, firefighters, even cops would take Oxy’s while out drinking or even while at home on the couch watching football. The drug was quickly addicting and caught on well in a neighborhood where hard drinking was acceptable. Hogan had it coming into South Boston in large quantities from Florida and Mexico to meet the explosive demand. The problems for users arose, however, when there were no Oxy’s available or they didn’t have enough money. The withdrawal from Oxy’s is a terrible form of hell and it became ample motive for guys to grab a $4 bag of heroin to substitute for Oxys. At first, they just sniffed/snorted the heroin “needles are for junkies”. But the leap from snorting to injecting is a small one when you are dope sick and need relief. Through that process, thousands of guys and girls in South Boston became opiate addicts in the late 1990’s and 2000’s. Once addicted and realizing they had ceded control of their lives to the drug and drug dealers, there was a large cluster of suicides in South Boston. Young and old people from good families realized they had become the very junkies they had been warned about. They stole from their families, churches, bingos and friends. In South Boston you could be poor and still proud. Junkies had nothing left to be proud of and nothing to look forward to.

    The politicians periodically hold useless community meetings where they talk tough in front of the invited media and neighbors, but they do nothing of substance. Worse, the politicians and the entire neighborhood knows George Hogan is a main supplier of Oxys. Indeed, at least one of Hogan’s associates has even been convicted for selling heroin in a school zone in South Boston.

    The irony is steep that Hogan, a murderous informant, is being ignored or protected by federal law enforcement as he actually “floods Southie’s streets with drugs.” People have to be almost willfully dumb to blame it on Bulger who hasn’t been there for almost twenty years. Any objective review of the crime statistics (and overdoses and suicides) for South Boston over the past forty years would prove unequivocally that crime in Southie took a sharp upturn after 1994. Worse, the quality of life there plunged as a result of suicides, overdoses, rampant breaking and entering, and two elderly women have been murdered for some junkie to get drug money.

    JHG, it obviously is not in your interest to say so, nor the interest of many others to say it, but Southie was safer and better with Bulger around. If someone wanted to go and get mixed up with organized crime in the neighborhood, good luck to them. In reality, that stuff never impacted the great quality of life enjoyed by the vast majority of us that lived and thrived there.

  6. I would have to disagree with you that Jerry Anguilo was never a made man. He may never have committed a murder but that requirement for membership was/is long gone. After being imprisoned on the Boston RICO case, Jerry was busted from boss back to soldier by the National Commission (which by then was just some or all of the New York families depending upon the time period). If he wasn’t in he couldn’t even be a soldier. It is undisputed that made or not he was at least the LCN defacto underboss in charge of Boston area activities.

    Jerry A. did get to run Boston based upon his kicking upstairs large sums of money to Raymond P. mostly from gambling activities.

    AUSA O’Sullivan did want to bring down LCN. Flemmi might have helped with some intelligence info but Bulger didn’t at least up through the Prince Street bug. The Prince Streeet bug wiped out the Anguilos. After that, as the head of the “Bulger Group”, he could have given Connolly info on LCN.

    RICO was written especially for the war on LCN. I have spoken to the author of the statute, Robert Blakey, several times at length about it. He said he was inspired by the anti-trust laws to turn the focus from the individual criminal to the criminal organization (“the enterprise” in RICO terminology). Passed in the 1970’s, it took years of proselytizing by Blakey to get law enforcement to understand and use it. Massachusetts is one of the few states without its own RICO inspired statute. It also, I believe, lacks the common one party consent taping of conversations with law enforcement’s ok (ie State Police wiring up a CI to go talk to a target w/o any court authorization).

    Steve Flemmi was liked by Patriarca. He was also turned CI by FBI S/A Paul Rico and not John C. When Rico retired Flemmi was given over to Connolly to handle. When Rico retired he became head of security for World Jai Alai based in Miami. This was the company that caused the Wheeler/Callahan murders. Recruiting Whitey was on Connolly. How well that worked out for the government is still to be determined. It didn’t work out very well at all for Connolly.

    While we are talking RICO, I have never seen a RICO case charged in which the first count was not RICO (Racketeering) and the second RICO Conspiracy. Both carry the same 20 year penalty and are treated the same under the federal sentencing guidelines. I assume Bulger’s RICO indictment reads the same. To convict a defendant of RICO conspiracy it is not necessary to prove that the defendant committed any (much less 2) of the underlying charged crimes (“predicate acts” in RICO lingo). The govt need only prove that there was a criminal organization whose members were committing predicate acts and knowing this the defendant joined the conspiracy. RICO conspiracy is virtually undefendable as it requires so little from the defendant to make him a co-conspirator.

    1. JHG:
      Hawaii said Gerry Angiulo was not a made man. I happen to think he was because of his position under Raymond and over Henry and Larry. I assume Gerry committed a few murders, he was mean enough to do it. I’m not sure what the requirement is now or when it ended that murdering someone was not necessary. The Mafia does not keep corporate minutes and different areas have different memberships. Boston only had Italians, Chicago had some Irish guys, New York had some Jews who were all but members. Other areas had Greeks. As you point out the circumstantial evidence makes it clear he was a made man.
      I went to class under Robert Blakey at Cornell. A good man who did much to bring RICO into existence. MA doesn’t need a RICO statute. If it had one it would be abused as the feds are doing as we see in the probation officer case. MA also prohibits one party consent as you noted. I think that’s good because it cuts down on everyone taping each other although there are circumstances during OC investigations when an undercover officer can wear a wire.
      You’re right about the Paul Rico/Flemmi relationship and the circumstances surrounding Connolly.
      Connolly’s case was a RICO which had no conspiracy count. I think Bulger’s case has one but I don’t have that in front of me at the moment. I’ll check it out. Thanks for clarifying the predicate act in the conspiracy situation. Conspiracy charges are brutal especially when it comes to hearsay evidence.

      1. I will of course take your word that Connolly’s was a RICO case without a conspiracy count but it boggles my mind. A substantive RICO count (an enterprise, predicate acts and ongoing course of conduct) per se requires a conspiracy. There are experienced federal prosecutors in Miami who would rather dump the actual RICO count and go with just RICO conspiracy count and the underlying crimes. It makes for a much simpler jury instruction package without giving up much prison time exposure.
        Florida has a RICO statute that mirrors the Feds, Blakey wrote it too. It has been a tremendous boon to state law enforcement and I don’t recall any allegations of prosecutorial abuse of the statute.
        I really think MA is missing the boat by not allowing law enforcement to wire up witnesses and record conversations. I don’t know any more about the recent prosecution of the defense attorney George than I have read in the newspapers. However, it seems to be that the taped conversations between the CI and George were the key to the case. MSP could not have done that case. If the goal is to find out what was really said between two people a tape recording is the best source.

      2. A quick Google check shows the Hartford Courant reporting on 12/23/99 that Connolly had just been indicted on RICO, RICO conspiracy, obstruction of justice (2counts) and conspiracy to obstruct justice charges.

        1. JHG:
          Don’t remember he was convicted on any conspiracy charges. I’ll have to check it out. Thanks

          1. JHG:
            You are right on that:

            Counts 1 & 2-RICO and Conspiracy to Violate RICO, alleging that Connolly had, through a pattern of racketeering activity, participated in the affairs of an association-in-fact enterprise whose members included Bulger, Flemmi, himself, and unidentified others.   The purpose of the enterprise was to protect Bulger, Flemmi, and their associates (including Salemme and members of the Winter Hill Gang) from arrest and prosecution, and to facilitate their criminal activities.   The two counts detail fourteen different “racketeering acts,” including allegations of bribery, extortion, and obstruction of justice.”

            Here why I was confused:

            “In May 2002, the trial against Connolly began on Counts 1, 4, 6, 7, and 9.”

            As you know I don’t profess to know much about federal criminal practice. He wasn’t tried on the conspiracy case. I wonder why. You indicated that it would have been easier to convict him on that. Why would the feds not go with the easier charge.

  7. you do realize that jerry anguilo was never a made man? that jerry anguilo got the chance to run boston by paying raymond patriarca a fee for that chance and boston paid providence 100,000 a month year after year for the boston area and all that it offered. your post omits that jerimiah sullivan wanted more than anything to bring the boston mafia down. john c made a major coup in getting whitey and steve flemi to be top informers. the public may kind of forget that no real progress was made until the 1980s with the full use of rico. raymond patriarca served on the national commision and recieved payments from the skim from las vegas casinos. whitey was helped very much by steve flemmis good working relationship with raymond patriarca. howie winter was the head of winter hill until the 1979 horse racing fix and whitey was always smart enough to try to keep a low profile.

    1. Hawaii:
      One of the problems with saying Gerry Angiulo was not a made man is we really don’t know. There’s no Mafia Register like the Social Register that we can go to in order to resolve this dispute. I tend to think he and his brother’s were because Gerry was in charge of the Boston area and Larry Baione and Henry Tameleo and his brothers who were considered made men were under him. Did he make his bones by killing someone, I can’t say for sure but Gerry had a mean streak to him. It is said they paid Providence 100,000 grand a month to operate, as you noted. You are right that Jeremiah O’Sullivan wanted to destroy the Boston mafia but so did the FBI from Hoover on down.
      Connolly never got Flemmi. Rico got Flemmi and he was handed down to Connolly. Connolly did get Whitey but the more I see of that relationship I’m not sure whether it would not be more accurate to say Whitey got Connolly. Your rightly point to the significance of the RICO.
      Whitey would have gone away with Howie in the 1979 race fixing case. It was not that he kept a low profile it was he had good godfathers. They convinced O’Sullivan to keep Whitey and Stevie out of the indictment. No doubt Raymond Patriarca was well connected and was the boss of Boston and received as significant tribute from Boston.

      1. Patty:
        Nice to hear from you even though you addressed JHG. I agree with you relative to heroin since I always understood Whitey was death on that and did keep it out of Southie. I read the case against Hogan noting it was tried by Tom Mundy before Judge Prince, who was a prince of a guy. Tom would have gone hard on Hogan as we see since Tom did his best for Southie. I’ll let your message to JHG speak for itself. Hope all is well.

  8. Referring only to the specific meeting you just cited, since Howie Winter was present, Whitey was still a relatively minor player in the so called Winter Hill Gang. There was no reason for him to be at the meeting given his status in the hierarchy then in place. Of course, it also raises the question as to why Bulger would have been involved in these murders. He was not very close to Howie Winter. Winter actually didn’t like Whitey. I met Howie a few times and while he was a stone cold gangster he was a personable guy. I met Bulger more than a few times and he was always a very cold person.
    I also don’t think Bulger was close to Martorano yet. Martorano was still in the Howie Winter/Sal Sperlanga circle of crime figures. Winter Hill at that time had a host of other shooters available to do the job (ie Joe MacDonald, Jimmy Kearns …) who were close to Martorano. Why would Winter (as ranking non-Italian he would have picked the hitters) have wanted to reach outside of his hometown team to Bulger? Killing people is a serious business. Picking the hit squad is not done lightly.

    Only once Winter was imprisoned (and Martorano fled Boston)due to the race fixing case did a void in the leadership of the non-Italian OC group open up and Whitey and Flemmi took over. The group’s base of operations moved from Somerville to Boston (Lancaster Street) and then South Boston.

    The race fixing case of course initially was going to take down Bulger and Flemmi too until the FBI interceded with O’Sullivan and got them cut out.

    Why was Bulger considered a TE informant? Good question. Eventually as head of the Irish faction he had direct contact with LCN to coordinate the running of their various turfs, especially the bookmaking in and around Boston. Bulger was not needed for 98 Prince St but LCN didn’t disappear after the Angulios left the stage. You had Junior Patriarca’s reign, then the JR Russo/Vinnie “The Animal” et al’s time and then of course Frank Salemmne’s brief turn at the top. Bulger would have been in contact with all of them to some extent.
    IF Bulger had been legit as a CI I think an argument could be made that he was worth a TE title. (In reality though there is no difference in how the FBI runs a TE vs regular CI. The FBI handler gets more credit in the FBI but nothing special really happens for the CI. In fact, AG Reno’s CI reforms in about 1992 realized this and did away with the TE designation.)
    BUT Bulger was not legit as a CI. I think this will be proven in his upcoming trial if it hasn’t already been to anyone’s satisfaction. He ran Connolly and the FBI and not the other way around.

    So how bad was Whitey Bulger. He was plenty bad. Forget the murders that Martorano is possibly scapegoating him with. There are quite a few murders he was clearly involved in (Bucky Barrett, McIntyre, Hallorhan and his friend…). Also, he did effectively run the criminal world of South Boston for a number of years. He street taxed drugs (both at the street level and at the high quantity level, see Joe Murray’s marijuana warehouse) but a huge drug trade in South Boston thrived under his watch. The heroin scourge that inflicted such deep wounds on South Boston families was aided and abetted by Bulger. This is in addition to his traditional OC activities in bookmaking and extortion (come on down Stippo Rakes).

    And finally, what elevated Bulger above your run of the mill OC/LCN gangster was his success in suborning corruption in Boston, State and federal law enforcement officials. Really this last activity is what the Whitey Bulger case owes it’s notoriety to.

    1. JHG:
      You portray Whitey as a minor player but the media and the gangsters portray him as the leader. I agree with you that his association with Winter Hill was not as close as some would have us believe because he maintained his operations in Southie. He was allegedly at the level of Martorano because they joined Winter Hill at the same time. Jeremiah O’Sullivan would remind us that the Winter Gang and Winter Hill Gang were two different groups. Martorano had it that when he and Whitey joined the Winter Gang (Howie, Sims and McDonald) they became 1/5th partners not as minor players in the Winter Hill Gang. Whether he was a minor or major partner it’s just Angiulo wanted nothing to do with him even though he did arrange for Tameleo to hold the peace conference between the Mullin Gang and the Killeen gangs. I’d like to know more about your meetings with Whitey, you know when and where.
      I agree that Howie had enough killers on his own staff to do the job without involving Whitey. Howie could have been the guy in the back seat with Sims driving. If it were McDonald, Murderman would have named him. I have to differ with you in your suggestion confidential informants and top echelon informants (whatever they are called now) are the same. They are informants for sure but the TE’s seem to be given more leeway than run of the mill guys. I’ve never suggested Whitey was a saint but I tend to believe the gangsters found it profitable to pile murders on him. I have a doubt he was involved in killing McIntyre. McIntyre had nothing on him. McIntyre was killed at the house of Nee’s brother. Nee admits bringing him to the house. Weeks admits tackling him and holding him there. Both admit burying him. Nee had the motive to kill him not Whitey. Barrett we have to rely on Weeks and Flemmi but it’s probable he did that for the money and Halloran he had a good motive to wipe out.
      Drugs have always been a problem in Southie from the time I was a young lawyer. The drug dealers McKenzie and Red Shea say they had to give Whitey a cut of their cocaine and marijuana dealings. I don’t associate Whitey with heroin, in fact, both McKenzie and Shea, or one of them, said he had nothing to do with that.
      I also have no evidence any state law enforcement officials were corrupted by Whitey. The only federal agents were those in the FBI/ Although it is hard to blame Whitey for what they did because approval for Whitey came down from the very top of the FBI.
      I disagree as to its notoriety being the corruption of the FBI. It is more to the idea he is public enemy number one who was aided and abetted by his brother Billy in what Howie Carr and Alan Dershowitz would have us believe corrupted all law enforcement and every state agency which is the media mantra as well as being a notorious murderer.

      1. A few quick points.

        In time Bulger became a major figure. Until Winter went away, in my opinion, while he was a power in South Boston he was second tier in Somerville mainly because Winter did not like him. I think O’Sullivan was splitting hairs trying to differentiate Winter Hill and Winter gangs. Upon the death of Buddy McLean Howie Winter became the head of the Winter Hill gang. Within that gang he was closer to some individuals but I think it was all part of one criminal organization.

        I met Whitey when I was in the company of people he would come over to say hello to and sometimes pass the time with meaningless talk. He didn’t come over to specifically talk to me and he never talked business in front of me. These conversations took place at Triple O’s, Amrheins, Mul’s and a few bars/ restaurants whose names I don’t recall right now.

        The latitude given to a CI by the FBI, in my experience, had little to do with the TE title and much more to do with how productive and important to the FBI the CI was. Yes many producing CI’s were TE but many weren’t. The big deal with the TE title was the prestige it gave to the FBI handler.

        To say that Whitey did not corrupt any state officials is parsing the issue too closely. Yes it was Flemmi that corrupted Schneidermann but Flemmi was Bulger’s partner and he was used to benefit Bulger as well as Flemmi.

        If you leave Boston and travel the country and talk to law enforcement officers,they have all heard of Whitey and the corrupt FBI agents. Not 1 in 20 even knows who his brother was. The focus of the national media coverage of the affair has been overwhelmingly focused on the corrupt FBI angle and not the brother issue.

        1. JHG:
          I agree O’Sullivan splitting hairs. I had never heard of the Winter Group before he said it. He came up with that I think to justify cutting Whitey and Stevie out of the race fixing indictment. Clearly Winter was closer to Sims and McDonald than Martorano Bulger or Flemmi.
          I never met the guy (Whitey) except as a real youngster I knew that there was a Whitey living in Old Harbor Village who had best be avoided. It was interesting to hear you say he was a cold person. I guess he was if he didn’t know you well. I’ll have to check with some people I know who knew him to see what their impression is. That means a trip since they’ve moved out of Southie. One only refers to him as Mr. White and I can’t figure out what that means.
          I forgot about Schneiderhan – you’re right he was part of it. You may be right about the national view of the case. I can’t speak to that. The brother issue might just be the local media’s interest. Thanks for the updates.

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