A Whitey Bulger Quiz: How Well Do You Know Him? The Boston Disease!

 I recall being in Chicago with a classmate, Brian Murphy, who had graduated from law school with me. He had been living there at the time. I was attending a Teamsters’ Convention since my law firm represented a local Teamster Union. Sitting in his house I was talking away saying Boston this and Boston that. I guess he decided I had become too Bostonized  I’d fallen for the old Yankee trap thinking Boston was the hub of the universe.

Brian got out a map. He told me to look at Chicago and then look at all the major cities closer to it than Boston. He talked about all these cities and ended by saying most of the United States doesn’t care about what happens in Boston. That was an awakening for me; too bad others from Boston have never learned it.

O’Neill and Lehr who posit themselves as the experts on James J. “Whitey” Bulger, two men with a barrel full of animosity against his brother Bill, have written about Whitey so to elevate him as a criminal hoping by throwing all the mud they could some of it would stick on Bill. They could only do this by thinking everyone like themselves had the Boston disease which prevents one from knowing much about the rest of the country other than what they may have learned through movies or on television, like Trump.

Here’s what they wrote about him: “in the annals of crime in the United States, Whitey Bulger today stands at the front of the line that includes John Dillinger, Al Capone, Bonnie Parker and Clyde Barrow, and more recently, John Gotti.”

The first thought was did they never heard of Murder, Inc.,  Alvin Karpis. the Barkis brothers, Baby Face Nelson, Pretty Boy Flynn, “Machine Gun” Kelly. I could go on with many others. To justify their heightening of Whitey as a criminal they wrote Whitey: “strangled and shot upwards of two dozens victims.” 

Disregarding Flemmi’s lies, (he told Martorano he “accidentally” strangled his girlfriend then later looking to get a deal from the prosecutor said Whitey did”),  there is no evidence Whitey strangled anyone. There is evidence he may have shot up to five people, no more. What Whitey never did, as far as the public record shows, is murder anyone without help from others.

So here’s the quiz:

Al Capone ran the Chicago “Outfit” a Mafia gang with a lest 50 members; John Gotti ran the Gambino family that was the largest Mafia family in the United States with a like or greater number of members. How many members were there in Whitey’s gang after he took over in 1979 after the boss of Winter Hill Howie Winter went to the can and John Martorano fled? My estimate is three: himself, Weeks and Stevie Flemmi.

Both Gotti and Capone were believed to have infiltrated many legitimate businesses and were said to have judges and politicians on their payrolls. How many legitimate businesses did Whitey take over. I can think of only one, the liquor store in Southie where he hung around. How many judges and politicians were on his payroll, I know of none.

Whitey went to prison after confessing to robbing  three banks. After he associated with Winter Hill in 1972, and after he took over the remnants of that group in 1979, how many banks did he rob? My guess is none. Dillinger is said to have robbed twenty-four banks and four police stations; Bonnie and Clyde robbed a dozen banks but usually small stores and gas stations. The murdered nine police officers and several civilians.

Now on to the final two question: Assuming the Boston disease where everything west of the Connecticut River is a blur and not their vitriol against Bill made the authors put Whitey above real criminals let us focus on Boston:

How would you rank who were the worst criminals in Boston during Whitey’s time?

Here’s my list: Steve Flemmi, John Martorano,  Joseph “the Animal” Barboza,  Vincent “Jimmy the Bear” Flemmi,  Larry Bione, the Angiulo brothers, (under the command of Raymond Patriarca and Henry Tameleo)  Frank Salemme, Joe Russo, Jimmy Martorano, Howie Winter, Joe McDonald, and after them Whitey Bulger. How does he top any of these and except for Patriarca they are Boston guys.  (

Who was the boss between Whitey and Stevie?

I think it was  clearly Stevie. Jimmy “the Sniff” Katz testified the bookies were most frightened by him. He was the one who was connected with the Mafia. He was the one feeding FBI Agent John Connolly the information on the Mafis. He had been protected as an informant for the FBI since the middle of the 1960s.

Only through a desire to “get Bill” Bulger could anyone put Whitey in the hierarchy of criminals. Think of how many have been fooled  – but not all of us.



15 thoughts on “A Whitey Bulger Quiz: How Well Do You Know Him? The Boston Disease!

  1. Matt
    Thanks for the feedback

    In other news El Chapo was found guilty of ALL charges. Took jury 5-6 days to decide his future. I lost a lot of interest because no in depth evaluations of the murders.

    Think El Chapo is headed to SuperMax in Colorado? How bad is SuperMax?

  2. Matt
    Was the fear of Flemmi that he would kill you (I am talking about the bookies). Whereas Bulger hadnt had that fear instilled in the bookies?

    Agree. Steve Flemmi was the REAL DEAL!!!!!!!!

    1. Jerome:

      Flemmi had been killing people in Boston since 1965 when he killed Punchy McLaughlin at the Dedham/West Roxbury bus stop after having two other attempts at him prior to that. Flemmi murdered the two Hughes brothers (along with Sammy Linden) part of the McLaughlin in 1966, he murdered the three Bennet brothers in 1967 and blew up Attorney John Fitzgerald’s car around the same time. He fled Boston and murdered the guy who went with him Paul Poulos. Those are eight murders he would have know to have committed by the word that passes on the street. That was all before Whitey was even on the scene. He looked like he had impunity to murder when the McLaughlin murder case and car bombing cases were dismissed after he came back to Boston after his flight. Were I a bookie I certainly wouldn’t want to give him any backtalk.
      What was known about Whitey. He had no reputation as a murderer.

  3. Matt
    You are on a roll with all these EXCELLENT postings lately regarding organized crime. Suffice to say the lawyers and judges are NOT really interested in justice but status/money/conviction closings etc. Yeah or Nay?

    1. Jerome:

      Judges are going to follow what other judges decide. They have little ability to do an independent investigation. It is not they are not interested in justice it is that they can only put so much time into any case and if another judge decides something and it does not appear go be very egregious they will go along with it. They like to be called judge, they like money as their constant worrying over the next pay raise shows, and they like the comforts of the lifetime job. Most work hard but they can’t get into the nitty gritty of a case like Whitey’s. They know he was a bad guy and will believe what the prosecutors say about him.

  4. Whose accomplishments are more exaggerated, Trump, Liar King; Reagan (Deficit King); or Jimmy Bulger?

    Howie Carr? (Never saw an underdog he could resist kicking). Dershowitz (no trial balls, strictly appellate).

    1. Hutch:

      Dershowitz never tried a felony case to a jury by himself. Always afraid. Hard to know whose are more exaggerated but NC will certainly tell you that Reagan’s are under appreciated. As for Howie, he loves picking on underdogs especially if they are not of the white persuasion.

  5. It should really be called , The legend of Jimmy Bulger! What was true , what was not? One thing no one can deny is that after his release from prison in 1965 to when he was caught in Santa Monica, he never took a pinch. However, the way he went out with his eyes almost ripped out of his head? A long way from family gathered around a hospital bed.

  6. Matt….he corrupted an already corrupt industry…mortgages…the initial indictment shows his act of violence against a broker he intimidated into getting fraudulent loans…a grand way to launder money…the ‘victim’ was helpful to me in those cases. Always figured when I was speaking with him he was wearing a wire.

  7. Whitey had no influence three miles away in East Boston. He had none three miles away in the North End. He had none three miles away in the Combat Zone. This was Mafia territory. He was nowhere to be seen in Brookline five miles away. He was strictly a local hood. What was a greater exaggeration Dukakis’ political skills or Whitey’s power? This was nonsense the local Fake News created. 2. If one wants to read about a real important gangster see Lee Server’s book Handsome Johnny regarding Johnny Roselli. Al Capone’s guy in Hollywood. A very entertaining tail. 3. Trump said the State of the Union is strong. A booming economy and a stronger military, along with more NATO funding would seem to prove his case.

    1. Great Line: ” What was a greater exaggeration Dukakis’ political skills or Whitey’s power? “

  8. Matt,
    Among the purportedly serious accounts of Whitey et al., let’s rank the O’Neil-Lehr report (aka their “book” titled “Black Mass”) dead last, shall we?

    Which books might be ranked near the bottom?

  9. Matt :

    You are obsessed with dead celebrity

    Six feet Deep State

    Responsibility is Dharma

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