How Whitey Bulger’s Lawyer Can Show The People In The U.S. Attorney’s Office in Boston Knew of Whitey’s Depredations

If Winter’s Here
Can Spring Be
Far Behind?

I’ve noted over the past three days that Whitey Bulger’s lawyer J. W. Carney has to convince the Appeals Court that people in the U.S. Attorney’s in Boston at the time Judge Stearns worked there actually knew of Whitey Bulger and his criminal activity.

Jeremiah O’Sullivan, head of the Organized Crime Strike Force, worked there from 1973 to 1989,  Bill Weld was appointed the U.S. Attorney in Boston in 1981 and headed that office until early 1986 when he became be head of the criminal division of the Justice Department in Washington, DC where he stayed until the end of March 1988. Robert Mueller, now director of the FBI, was head of the criminal division in the Boston office from 1982 to 1988; Judge Stearns was there from 1982 to 1990, as head of general crimes and then chief of the criminal division. It seems fair to say that as far as criminal matters were concerned, Mueller and Stearns were Weld’s top assistants.

J.W. Carney has already suggested the obvious that the public would believe that the top guys in the federal criminal prosecutor’s office in Boston from 1981 through 1986 would know something about the top criminals in the Boston area during that time.  He suggests you could almost take judicial notice of this and infers that these prosecutors had to have known of some of Whitey’s actions and have discussed them.  I suggested Carney had to do more than that. He had to show the public is justified in believing these men had specific knowledge of Whitey and his crimes.

I’d suggest Carney show that FBI Agent Morris testified that in 1979 O’Sullivan was told Whitey and Stevie Flemmi were FBI informants and asked not to indict them in a race fixing case. On December 5, 2002, O’Sullivan was asked about this at a congressional hearing. He admitted he was told this by the FBI. Several times he was asked whether back in 1979 he knew they were murderers. He responded yes.

Next I’d show that he filed an affidavit to do an electronic bug on the headquarters of Mafia under boss Gerry Angiulo. Two of the informants in that affidavit were Whitey and Stevie Flemmi.  This operation was carried out from January to May of 1981 just after Bill Weld became U.S. attorney.  During that operation conversations were intercepted showing the Mafia could get Whitey and others to kill people for them.

Weld said: “Jerry and I were very close. . . . And I met frequently with O’Sullivan, every week, as the case against the Angiulos was building.”  The Aguilo case continued for over two years formulating the evidence and presenting it to the grand jury. The Anguilo gang was arrested on September 19, 1983. In the summer of 1985 their trial started.  It lasted through the rest of the year until they were convicted by a jury on February 26,1986.

It’s fair to say Weld was in continuing contact with O’Sullivan during his tenure as Boston’s U.S. attorney. It’s likely the public would believe O’Sullivan briefed him on the evidence especially as it related to the top criminals and that Weld would have told his top staff about it.

The public would also know of Judge Mark Wolf’s 661 page memorandum and order as should the Appeals Court.  On page 200 he states: “By 1984, Bulger and Flemmi were considered by the Boston law enforcement community to be “well known organized crime figures.”  According to Wolf, AUSA Gary Crossen and two DEA agents Al Reilly and Steve Boeri “shared a genuine interest in investigating Flemmi and Bulger” but they feared involving the FBI in their attempt because they believed the targets would be tipped off by the FBI because they were its informants.

Wolf found that at that time it was Weld’s understanding that Whitey had served as a source for the Anguilo wiretap and the FBI was suspected of tipping Whitey off about the state police Lancaster Street investigation.  Wolf noted: “‘Weld knew that his proecutors shared the DEA agents’ deep doubts about working with the FBI in any investigation of . . .[Whitey].”

For the rest of 1984 DEA and AUSA Crossen who was new to the U.S. attorney’s office worked on investigating Whitey. They readied papers to do a wiretap on him and on December 24, 1984, submitted an application for electronic surveillance naming Whitey as their top target. They could not have done this without Weld’s knowledge. Into the spring of 1985 they would continue this operation and resubmit applications to other judges for extensions all of which Weld had to approve.

Judge Wolf shows that there was much discussion and controversy over this because the FBI was opposed to it. At the time Judge Stearns was head of the criminal division. It would seem the public would have every reason to believe if the boss had one of his assistants doing electronic surveillance against Whitey then the head of his criminal division would know this.

O’Sullivan’s knowledge of Whitey, Weld’s knowledge, the targeting of him by Crossen, and the controversies surrounding these matters as set out in Judge Wolf’s findings clearly show that individuals in the Boston U.S. attorney’s office knew Whitey was an informant and was also a top organized crime figure.

There’s even more I’ll mention tomorrow.



  1. dear author, very interesting post . if i were to rate the five men most responsible for whitey bulger not being arrested between 1965 and 2011 i would put jerimiah sullivan at number 1. if i read your post correctly mr. sullivan headed the organized crime task force from 1973 thru 1989 and he was the one who kept whitey and steve out of their horserace fixing arrests back in 1979. john c would be next on my list for his ability to manage the day to day affairs of keeping other investigations of whitey and stevie from coming to a conclusion that resulted in their arrests. number 3 would be former boston mayor kevin white who was mayor of boston from 1968 until 1984. think about that for a minute. as whitey rose to power kevin white had a boston police chief report to him all those many years. did kevin white ever say to a boston chief i want the arrest and incarcaration of whitey bulger to be your number 1 priority? the state police never reported to mass state president billy bulger but the boston police chief does report to the mayor. number 4 would be a person who i do not know the name of . that would be the person who directed dea efforts in massachusetts in the 1980s. getting guys like eddie mac and red shea off the streets of boston in the famed 1990 busts was wonderful. not being able to close the deal on whitey for drug proceeds was unforgivable. number 5 and he could have been any number on this list really is billy bulger. billy bulger failed in 3 significant ways 1st as a catholic , how wonderful to be father to 9 children while your neighborhood in south boston is flooded with drugs as a direct result of whitey bulger and his hunger for money. the 2nd way was as an elected official from south boston the quality of life in billy bulgers district went down as a result of his brothers continued freedom all those many decades. billy bulger put his brother before his district evey step of the way 3rd and last is as an officer of the court. did billy do all he could to uphold the law in his district? never. i thank you once again for this blog and my comments are not meant to provoke. i would be very interested in who you think is most resposible for whitey not EVER being arrested between 1965 and 2011. 46 years ? hard to believe.

    • Norwood Born:
      You seem to have really got something against Billy Bulger. I have to disagree with you relative to him but I recognize we’re all entitled to think what we want since no one really can look into the soul of another person. I like your list of people who you consider responsible for Whitey not being arrested for 46 years so let me give you mine. First, I put the FBI at top. Connolly’s relationship with the Whitey was known to all in the FBI from the top to the bottom, even file clerks knew of it. They probably didn’t get that much from him but he Whitey knew his partner Stevie was giving them good information so he hid behind him. The FBI also did little to look for Whitey after he was indicted which counts for 16 years of the 36. Number two would be John Morris who was supposed to be the supervisor of Connolly but liked the lifestyle Connolly seemed to be living so rather than controlling him he joined in with him. Morris was the case officer on the Angiulo case and to protect Whitey had him put in the application and affidavit as an informant so he could tell him not to get involved with the Mafia at that time. Morris also undermined the Lancaster Street case. Third I’d suggest was Connolly because he was very active in seeking out information as who was doing what and passing it on to Whitey thinking that was part of his job. Fourth I would say the U.S. attorneys office in Boston including the Strike Force. No one seemed to believe that having Whitey as an informant was something that should not be done. Fifth, I would say O’Sullivan because he could have taken them down in the race fixing case or in the evidence gained through the wiretap or in other ways.
      I don’t see Mayor White having anything to do with this. It is a mystery why the Boston police never did anything about Whitey. You may be onto something in that respect but I don’t see White being part of it. Nor do I fault DEA. I worked with those guys and they did a diligent job whenever they had the evidence t go after anyone. They and the Quincy police tried for years to get Whitey. It was difficult for them to accomplish this when they were being undermined by the FBI.
      Back to Billy. Your argument would have some weight if Southie did not have a drug problem before Whitey took over the rackets there or if it didn’t have on for the past 18 years when Whitey was no longer around. Sadly, it is not Whitey that caused the problem but the school drop outs and dismissive attitude of too many about the need for education Billy did a lot of good for the people of Southie but aside from the drugs Southie was adversely impacted by the federal court decision to bus children for the purpose of desegregating the schools and the number of people who were criminals who were also protected federal informants. We disagree on whether Billy should have been assisting the feds in capturing his brother. One thing you don’t want to cede to Billy is his belief that his brother was being railroaded by others who were getting good deals to turn him in.
      You should not worry whether your comments are meant to provoke or not. if you differ in your ideas express them. We can only learn when we ask questions and disagree at times.