Back to the Gangsters: What Secrets Did Whitey Take With Him When He Was Murdered

Yesterday I wrote how Jerome asked me three questions in an email that I told him I would answer on my blog. They were: Does your new Irish Gang War book fill in the gaps and share the “truths” not in the twins oks:

2) Do you think Whitey Bulger took any secrets to the grave regarding his crimes and if so what do you speculate that they are?

3) Is Steve Flemmi somehow the “toughest” gangster of his era given he was never killed and outlasted so many of his peers. From a gangster perspective”

I am not sure what the first question refers to when it states “the twins oks” The book he is referring to is the one that will hopefully be published by Amazon this summer and it is not about the Irish Gang War since that is a fiction. It is about the over 100 gangster murders which occurred mostly in Boston between 1956 and 1976 which takes in the gang war that did occur in the 1960s. It was not an Irish gang war. The gang war that took the most lives was between the Roxbury Italian gang which was comprised of Italians and the McLaughlin gang of Charlestown. Most of the murders during that period were committed by Italians which you would never know from the reporting in the media and the folk who wrote books.

As to the question whether it fills in gaps I suppose that will be up to the reader to determine. It does show how much of what is accepted as true fails that test. The most obvious one that occurs to me at this time is the shooting of Punchy McLaughlin by the two men dressed as rabbis which took a life of its own among the gangsters.

The second question deals with secrets Whitey may have taken with him when he was murdered. On that note there is a documentary coming out on Discovery entitled “My Name Is Bulger” where Catherine Greig who really was the one stand-up person in the whole sordid episode around Whitey and did more time for a nonviolent crime not involving drugs by any person in the United States history without a prior record (Reality Winner is the runner-up) has been interviewed. knows more about Whitey than anyone else. I also may have a cameo appearance in that documentary because the producers did interview me. This question may be best answered by others but I do have my opinion.

Whitey had no secrets he took with him. The idea he had anything to do with or knowledge about the infamous March 18, 1990, Gardner Museum heist is a recent fabrication. I guess his lawyer resurrected that story for some reason but with a 10 million dollar reward for the recovery of those goods if he had information he, or his lawyer, or Catherine, or someone else could make a nice haul. In 1990 Whitey was in his sixties, his FBI protection was going away as Connolly retired, and he had never been involved in doing heists. If he knew something surely Stevie Flemmi or Kevin Woods would have the same information which apparently they don’t or they would have shared it by now.

The authors of books have gone through Whitey’s life with a fine-tooth comb and come up with nothing relating to unknown secrets. His life is simple – ordinary hoodlum up until release from federal prison in mid-sixties, tough guy in Southie until 1972 – over to Winter Hill partnering with Flemmi until 1995 getting tribute from bookies and drug dealers and killing a few guys who were threats to him– on the run until 2011. Maybe I’m wrong but if there are any watch the documentary to see what Catherine Greig has to tell us.

Well, I’m out of space again so I’ll talk about Flemmi tomorrow.




  1. As I heard, Benjamin’s head was removed in order to extract the bullet which had originated with a ‘borrowed’ gun easily traceable.

  2. Matt
    Something doesn’t sit well with me regarding your perspective on Whitey. How is it that Whitey in reality was “small time local hood with a few murders” AND yet be a partner in crime with Steve Flemmi. If Whitey was so insignificant then why didn’t Flemmi just kill him inorder to keep more of the profits?

    We know ( from records and testimony) that Flemmi had no qualms about killing anyone. While I don’t think Whitey was the TOP dog as portrayed by media I don’t think he was just a small time hood.

    That’s why the saga doesn’t add up to me. If Flemmi is already a Top Echelon Informant and works with the Italian Mob and given his resume of killings then wouldn’t Whitey not be even on that level with Flemmi

    I still believe there is something more to this story

  3. The term ” twins oks” was a typo. It is supposed to be TWO BOOKS. The two books being Deadly Alliance and Black Mass. Basically my question is if your new book would add anything new to the Whitey Bulger saga that’s NOT in Deadly Alliance and Black Mass

    On a side note I found Deadly Alliance to be excellent. On the other hand I found Black Mass to be good but a bit long winded

    Thanks for addressing these questions

  4. Matt
    As always you give us your parochial views
    and microcosm view of the Boston FBI Crime

    Whereas I tend towards looking at the Macro view
    of the International FBI Crime Family and it’s role
    in protecting the Deep State.

    I am also interested in moving beyond gotcha journalism
    wanting to create a more use friendly criminal justice
    system that truly protects and serves the community.

    A system that will have standards set and enforced by the
    voters and taxpayers dare I say the primary consumers of
    the criminal justice system.

    The FBI wacked Whitey Bulger to effect Damage Control
    in their long running Boston Soap Opera “As the Mafia Turns”
    or was it “ Days of Our Lives” ?
    Did I mention wacking Whitey in a Federal Prison gave the
    Boston FBI Plausible Denial.

    Of course when Matt tells us it is so we all believe him wink,
    nod know what I mean?

    Angela Clemente says hi to Matt.


    Now sing along with me……

  5. william m. connolly

    That is a fair recapitulation, in a nutshell, from the 1940s, then post wwii, then post Korea, the sixties, seventies, …juvenile to local hoodlum, not a bad guy, just involved in some crime, booking, extorting lower criminals, gambling, peripheral on some drug trafficking, not heroin, then working with the more heinous, Flemmi, . . .remember every Mafia guy was a killer . . .you had to be a killer to be a mafia guy . . .then the FEDs handle Whitey, Flemmi et alia as Top Echelon Informants, sucessefully, JOhn Connolly most responsible for taking down the New England Mafia, according to John’s colleagues, Connolly is retired in 1990, Bulger flees in 1995 when he is driving back from NYC and hears on the radio that Indictments were coming down . .

    Who killed whom> experts in criminal law have better insights , , ,why were guys killed> Usually the gangsters were killing guys they thought might inform on them . . . .local gun shootouts, killings, occurred in every city, in every neighborhood from Boston to NYC to Baltimore to Chicago to Miami to Memphis to Denver to the Wild West, low scale, par for the course in the good old USA

    The MEDIA blew every squall, any ordinary bad day, rainy day into an apocalyptic typhoon, hurricane, earthquake . .Why . .So the MEDIA would sell more books, newspapers, T.V. time rates

    HOw many innocents have been dragged through the mud by the MEDIA and FEDs and ACADEMIA>

    Today, the leftists tell us that systemic racism exists and that whites are devils and whites are, according to Joe Blow Biden, are the greatest threat to democracy . . .just like they said about the South Boston Veterans . . .

  6. Hi Matt and I am looking forward to reading your book in the summer of 2021.

    1. Do you think that it suited Raymond Patriarca, Larry Baione and the Angiulos to have the Mclaughlins fighting with Buddy McLean and his faction?

    2. What is your understanding of the murder of Frank Benjamin?

    3. What do you make of this surveillance photograph of Flemmi meeting Frank Salemme, Frank Jr and Luigi Manocchio?

    • David:

      1. The ware between the McLaughins and the McLeans involved three murders over the space of over four years. Hardly much of a fight. Buddy beat up George McLaughlin in labor day 1961, the McLaughlins had a few sticks of dynamite planted on Buddy’s car (maybe), Buddy killed Bernie McLaughlin (10/31/1961), Howie Winter’s car being driven by Alex Rocco’s wife blew up in 1962, Russel Nicholson murdered (5/12/1964) and Buddy McLean (10/31/1965). Seriously, that was it and it is questionable whether Nicholson was killed as par of it. The genius of it and how it benefited Patriarca, Baione, and Angiulo was it allowed them and their allies to murder folk and have the authors and media label the murders as part of the McLean/McLaughlin was. Keep in mind that Somerville and Charlestown are next to each other and the guys in those gangs knew each other and went into each other’s territory of the years even hanging out with each other. A week or maybe more prior to his murder Buddy was in a café in Charlestown when the cops searched him.

      2. Best story on the Frank Benjamin murder which does have some independent evidence to corroborate it is he was out of Walpole State Prison for about two weeks but was addicted to “black beauties.” He went to Wimpy Bennett’s place the Dudley Lounge to get some from his friend Jimmy Flemmi. An argument then fight ensued. He was shot in the hed and decapitated by Jimmy Flemmi, thrown in the trunk of a car where he was discovered.

      3. Billy McDermott of the Brookline police introduced into evidence several photographs which he took of Flemmi and Salemme sitting together in some places in Brookline. Salemme and Flemmi went in to business together after Salemme got out of Walpole – Salemme not being the brightest star in the heavens apparently did not figure out that Flemmi had dimed him out when he was in New York City. AS for being with Manocchio that would be natural since they were both in the New England Mafia family. As for his kid being there, Salemme had his kid as an advisor.