General Thoughts on Whitey Bulger — The Road Less Traveled

Last week on Catch All Saturday I wrote about Billy Bulger.   I said it is my intent to examine each allegation against him that suggests he is corrupt.  This is a process that will take some time.  I am working on it. I’ll set them out as a group and then discuss each one individually.  The big one that we all know is his involvement in the 75 State Street Affair.

Billy being a public figure has no forum in which to defend himself  — as you know the burden in a courtroom for such a person is extremely high as is the cost of going to court.  The likelihood of success is remote.

I’m also curious to show how the idea that Billy was somehow involved with Whitey gained currency.  An offshoot is that it somehow adversely affected what was done by people working in law enforcement against Whitey.  My research so far shows that it may not have come from the media but rather from a surprising source.  I’ll keep you posted.

When I attended FBI Agent John Conolly’s trial I had a sense that the government was after Billy Bulger.  I expressed that to Connolly.  I spell out the reason in my upcoming book “Don’t Embarrass The Family.”  A person who wrote a comment to this blog said Freddie Wyshak the AUSA (federal prosecutor) behind the unraveling of Whitey’s empire when asked where Connolly went wrong replied, “He got too close to the Bulgers.”  I tried but cannot verify that.

It is interesting to juxtapose what Billy in his book While the Music Lasts said about government prosecutors and the reality of his situation.  That will be the subject of a future post.  Full disclosure prompts me to say I have high regard for what Freddie Wyshak and his team accomplished in breaking up and disclosing the FBI and Whitey love fest.  Do I know for a fact that Wyshak believes Billy Bulger is corrupt or somehow assisted Whitey?  The answer is no.  I’ve mentioned before about my relationship with Billy Bulger.  I like the guy.  We are not close.  I haven’t spoken with him in over 20 years.  I hope I can let the chips fall where they may.  I’ll set out what I find, my interpretations and let you decide.  I know for sure they’ll be disagreement.

I’m off to a side subject.  Howard Carr is very much involved in the Bulger matters.   Some may recall his puerile behavior when he sat behind Billy at the Congressional hearing.  I’ve pondered over his labeling of people with cruel nick names.  I’m tempted to call him Coward Carr or Cowie.  There are some stories of him running and hiding in situations when he should have stayed.  However I’m uncomfortable putting labels on people.  We’re all so complex that what one sees in a person or group of persons another may see the opposite. We saw what the labeling of the Japanese did to American Japanese in WWII.  So despite the temptation, I’ll avoid it.

Carr’s use of vituperative terminology against a person for characteristics over which the person has no control is out of line.  I’m referencing his use of “Corrupt Midget” when he refers to Billy Bulger.  Carr’s friend, Alan Dershowitz who endorsed Carr’s book on the flap, is certainly no taller than Billy.  He would not take kindly to have midget added to any description of him.

Carr’s playing of Mexican music while reading of the names of Latino people who may have gotten into trouble is disdainful.  It appeals to the xenophobes and nativists who have an askew idea of what America is about.   Carr’s message engenders hate — he sends an opposite message than that guy who told us to judge people not by the color or their skin but by the content of their character.  The denigrating of the Latinos who are newly arrived and Catholic is reminiscent of the great US hate party — the Know Nothing which had an anti-Catholics and anti-immigrants ticket.

Hate sells, it seems to rear its ugly head every so often in America as it did just before the Civil War with the Know Nothings who came very close to electing a president.  Ironically, that’s what makes America great — our Constitution protects our hate speech as well as other forms.  It doesn’t protect you from the consequences for speaking freely — in Carr’s case it puts money in his pocket but in others it gives them a pocketful of regret, but it gives all of us the chance to be heard for better or worse.

I mention this because I suggest it will play into my analysis of Billy Bulger.  One of the big knocks on him is that somehow he did not speak out against his brother Whitey or work with law enforcement to apprehend him.  It is said that because Billy had a position of high trust in the government he should have put his loyalty to his job in front of his loyalty to his family.  I’ll examine that.  But I would note that the criminal law recognizes the special relationship between siblings to the extent that it allows one to be an accessory after the fact to a sibling’s crime without suffering consequences.

I’ll also want to talk about a common phenomena within families which is they do not see a family member in the same way as that person is perceived by outsiders.   In a case in Norfolk Superior Court not too many years ago a Wellesley doctor was accused of murdering his wife.  The case was fairly solid and he was convicted.  Their three children, all doctors, stood by their father throughout the trial believing despite the evidence he did not kill their mother.  Then we have the Amy Bishop case which you are familiar with which is another example of this.

There’s also the observation made by W. Somerset Maugham that there are contradictory aspects within each person noting “I have known crooks who were capable of self-sacrifice, sneak thieves who were sweet-natured, and harlots for whom it was a point of honor to give good value for money.”

Billy is reported to have once said, “have you ever tried to tell your older brother to do something?”  Whitey’s life showed that from a young age he did what he wanted to do.  We don’t know whether Billy talked to him about his life style or whether he found it so painful to accept his brother was a villain that he shut his eyes to it.  We do know Billy has been excoriated for standing by Whitey.  He lost his position as president of the University of Massachusetts.  The investigation of him by the Congressional Committee is also part and parcel of the whole picture relating to Whitey, especially the part of the FBI’s relationship with Congress and the failure of Congress to require our law enforcement officers adhere to higher standards.

In his autobiography Billy dismissed much of the talk against Whitey as something manufactured by others to hurt him.  Is it farfetched to assert that Billy is incapable of believing his brother would murder people like the Wellesley doctor’s children believed in his innocence?

Who was it who was going to approach Billy and tell him of his brother’s evil life?

Remember, much of what we are learning about Whitey’s murders has only come to light since his flight in 1995 and the deals given to his fellow felons.  How was Billy to know when most in law enforcement whose job it is to know these things were unaware of them?

There’s much to explore and learn about in considering the events surrounding Whitey.  The more we do the more I will be accomplishing the purpose for which I am writing the blog.   I hope you follow along with me.


2 thoughts on “General Thoughts on Whitey Bulger — The Road Less Traveled

  1. As I remember it, the term “corrupt midget” used to describe Billy Bulger was first uttered by Johnny Powers, after what Billy did to him in revenge, and partly about Whitey. Didn’t Billy destroy Powers’ garden atop the Courthouse?

    1. Billy Bulger did have a run in with Johnny Powers. Powers and Billy were Southie rivals . Powers was not as tall as Billy so there was no way he’d have hung the term “midget” on Billy. Powers took Whitey off the payroll of Suffolk County even though Whitey was not receiving any compensation. It was s gratuitous move. Billy correctly considered it a slap at him. He then tied up the budget of Powers’s Office of the Clerk for Suffolk Country Supreme Court for years.

      There’s no question Billy played hardball politics. If you hit out at him you had to expect to be hit back.

      E. George Daher who was the chief judge of the Housing Court in Boston. Daher became a judge in 1974. He graduated from Suffolk Law School in 1961. He set up a firm with a guy named Clancy, if my memory serves me right. He was one of those typical light weight ambulance chaser lawyers doing small time criminal and civil work. I’d see him hanging around the corridors of the Dorchester Court house trying to pick up business. He somehow managed to get appointed to the housing court judgeship. I guess he was a Republican because he was made a judge by Governor Sargent near the end of his term. Here he is a couple of years ago endorsing Bill Keating for Congress. ( The reason he endorsed Keating, which he does not reveal, is that Keating was a former senator who led a failed revolt in the Senate against Billy Bulger.

      What happened was that Billy gave a pledge to Sonny McDonough (someone I never liked) on his death bed that he’d get Sonny’s son a job in Daher’s court. Daher wanted someone else. To get that person, Daher promised Billy he’d appoint Sonny’s kid when the next opening occurred. (Daher, said he never promised him but would take him into consideration. Knowing the little I do about Billy, he would not have let the first guy get appointed without an iron clad promise so I go with Billy on that.) Daher reneged on his promise and Billy tied up his budget and caused Daher’s pay to be reduced.

      This article from the Globe Spotlight team covers it. (

      Daher in desperation lashed out at Dukakis who was then running for president saying: “How can he stand up to the Russians if he can’t stand up to a corrupt midget?” He was called on the carpet by the SJC and he immediately apologized but the name stuck and Carr has used it since to the delight of the begrudgers.

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