Re-Examining Whitey Bulger: The Thirty Years, 1965 to 1995, Separated Into Segments: Part Four

I’m reviewing Whitey’s life to determine if his reputation as the most evil of criminals is justified rather than being erroneously posited to us by people who need us to accept it as true. I’ve run through his time up to getting released from prison in 1965 and suggested the next 30 years are the times within which he has made his reputation.  Prior to 1965 the worst that could be said of him was he robbed a handful of banks, was caught, and did nine years, some of it hard time, before he got out in ‘65.

As of January 1995 Whitey was a man on the lam for 16 years unconnected with the Boston scene. He traveled over parts of the U.S. finally settling in Santa Monica, California.  He lived in a multi-apartment building with his female friend, Catherine Greig, in a third floor walk up with the covered windows that blocked prying eyes from looking in and the inhabitants from seeing out. They lived with little contact with others in a hermit-like existence, hardly one step up from being confined in a cell with conjugal visits.

He was imprisoned by the money hidden in the walls ever fearful of its loss to criminals like himself limiting his ability to make forays from his hole-up. The pillow he put his head on never gave a decent night’s sleep. He depended on an arsenal of guns including military-type weapons that he would never use to maintain what he thought was his freedom.  Now he probably sleeps better at night in the Plymouth County jail than he did in Santa Monica where he allegedly stayed up at night peeking out the window at threatening spectres.

I divided these years from 1965 to 1995 into four segments because certain factors exist that make them somewhat easy to segregate out although there may be a small amount of overlapping.  The four periods are in sum: The Early Years, 1965 to 1972, 8 years; The Learning Years, 1973 to 1977, 5 years; The Boss Years, 1978 to 1988, 11 years; and The Gathering Years, 1989 to 1994, 6 years.  All the murders charged in the indictment occurred in the learning years 11 murders, and the boss years, 8 murders.

The Early Years period is the time he got out of jail up until the time he became involved with the Winter Hill gang. These seem to be years of figuring out what he will eventually do with his life.  He’s on parole so he has to watch his step. He’s out of prison at age 36 and has yet to have murdered anyone unlike Martorano, Flemmi, Salemme, Nee, and some of the Mafia people who were veteran murderers by his age. Whitey may have begun his first murders around the time he turned 40 in 1969 when he became involved in the Southie Killeen/Mullen gang wars.

The Learning Years from the time White joined Winter Hill in 1972 up through 1977, a period of about four to five years when he’s an understudy. During this period it was clear that there was one boss of Winter Hill and that was Howie Winter. Howie who took over from Buddy McClean had two close associates, Joe McDonald and Jimmy Simms. Next to associate with them were the Martorano brothers, Murderman John and Jimmy. Whitey was somewhat down the line.

Eleven of the murders alleged in the indictment against Whitey occurred during this time of the learning years when Whitey was somewhat down the command level of the group.  Howie, who was in charge, and who was in 2012 charged with extortion has never been charged with any of these murders. The first, Michael Milano, occurred in 1973  and the last Richard Castucci happened in 1976.

According to Pat Nee, Howie had not even heard of Whitey in 1972 when outside interests were trying to establish a Southie gang war truce. Whitey didn’t walk into that group of murderers with much status despite what we are told now.  It was probably not until 1974 when Stevie Flemmi returned from his years on the run and Whitey teamed up with him that he slowly accrued power.

Howie ran the operation through 1977. Howie was indicted for extortion by prosecutors in the Middlesex DA’s office under the oversight of our new Secretary of State, John Kerry. He and Sal Sperlinga went to trial for trying to force pin ball machines, of all things, into some bar rooms through threats and intimidation. Howie was convicted and got 18-20 years in prison. That left room at the top.

Although Whitey was not in line for the big job of boss, the race fixing case in 1979 would cause Joe McDonald, Jimmy Sims, and John Murderman Martorano to flee town. Jimmy Martorano who was also indicted in that case was already in prison for extortion.

The whole Winter Hill Gang could have been put out of existence had both Whitey Bulger and Stevie Flemmi been indicted in the race fixing case. Whitey with his record would have been convicted and gone back to prison for what I have called his boss years. However that was not to be.

FBI Supervisor Agent John Morris and FBI Agent John Connolly went to AUSA Jeremiah O’Sullivan and asked him to keep them out of the indictment. They told him these vicious gang leaders were FBI informants. O’Sullivan would later say he didn’t keep them out because they asked but the facts seem irrefutable that he did accommodate Morris and Connolly.

Whitey and Stevie Flemmi’s ascension to the leadership of the Winter Hill Gang can be directly attributed to the FBI and US Attorneys office.


4 thoughts on “Re-Examining Whitey Bulger: The Thirty Years, 1965 to 1995, Separated Into Segments: Part Four

  1. Matt, happy New Year. Keep up the good work. This blog is great; lots of good insights from different viewpoints. Now here’s a long post with a different viewpoint:
    As you have indicated elsewhere, O’Sullivan may have decided not to prosecute Bulger and Flemmi for many different reasons that had nothing to do with their informant status. It seems reasonable, however, that the FBI would ask that these informants be kept on the streets. Bulger and Flemmi were a lot more valuable to law enforcement on the streets. In retrospect, if they had been imprisoned, the New England Mafia would not have been taken down in the 1980s. In retrospect, O’Sullivan’s decision was a good one. Now, you could counter and say that if Bulger and Flemmi were in prison, they could not have committed murders in the 1980s, but then again how many more murders would the Mafia have committed, how many more Mafia-related drug deaths would have occurred? We just don’t know. We are in that Monday morning quarterbacking role. Even the use of the term “vicious” to describe Bulger and Flemmi in the late 1970s has a bit of a historical revisionistic taint to it. Surely, they were known to be gangsters, but much of their “viciousness” was not revealed until the late 1990s. There were lots of “tough” men, tough gangsters in our neighborhoods; there were lots of gunmen, drug dealers, hijackers, bookies; but in the 1970s who in the newspapers or law enforcement had described them as “vicious” or as “vicious killers” or even as “killers”? The point is we have to be careful in looking back forty years and pretending everyone knew then what we now know. If you could put yourself back in the 1970s and had this choice to make, which would you choose? 1. The New England Mafia taken down, the top bosses and 20 gunmen in prison; or 2. two local gunmen in South Boston taken down? I think the numbers nationwide were 650 Mafia imprisoned and 150 on the East Coast imprisoned. So, I’d estimate that along with the top bosses about 20 gunmen were put away in New England alone. Even if the deal in 1978 was to let these two local hoodlums remain free on the chance to take down a few top Mafia men, then that may have looked like a wise choice and a good deal in the 1970s.
    I don’t credit any statements of O’Sullivan in the late 1990s that he “knew” in the 1970s that Bulger and Flemmi were “murderers”. Where did he write that down in the 1970s? What document did he produce that said Bulger murdered so and so in the 1970s? The best they had in the 1980s was uncorroborated hearsay evidence from unreliable sources, such as the Halloran and Murray stories. So, in conclusion, I’d say that looking back forty years and nailing down what anyone knew about these criminals is fraught with uncertainty. We should keep an open mind. We should give people the benefit of the doubt. We shouldn’t throw stones. And we should distinguish rumor, innuendo and what’s said on the streets from actual facts. No doubt, Bulger and Flemmi by the 1980s were suspected killers, just as the Martorano brothers were allegedly murderers, just as every made man in the Mafia was and is a suspected murderer. But no one in law enforcement had the probable cause to arrest any of those aforementioned four for murders in the 1980s and no one in the press had linked them to specific murders in the 1980s as far as I know.
    Happy, peaceful New Year to one and all!

    1. Bill:
      Happy New Year’s to you. Some I agree with but others not so much. I don’t think O’Sullivan needed Whitey or Stevie to take down the North Ends. Everyone agrees FBI Agent Quinn had already written the affidavit for 98 Prince Street and Baione’s hangout with their input. I suggest you give Whitey and Stevie too much credit in the war against the Mafia. In fact, until the Ferrarra incidents in the mid-80s, Whitey and Flemmi were giving the FBI no real good information against the Mafia. As I see it we could have had both the Angiulos and the Winter Hill gang wiped out rather than just choosing one. I go with the bird in the hand theory. O’Sullivan had a chance to wipe out Winter Hill and he fumbled the ball.
      I think it is appropriate to describe Bulger and Flemmi as vicious, especially Flemmi, because there was good information on him that he blew up Fitzgerald’s car and had murdered the Bennetts. Whitey was under the radar at that time. Your description of Bulger and Flemmi as two local gunmen in South Boston does not seem to fit their role as members of Winter Hill which was running the rackets in all Eastern Massachusetts.
      I don’t know what O’Sullivan knew in the late ’70s or early ’80s. He said he knew of several people who were informants and was privy to a lot more information, much of which may have been scuttlebutt, than most people. There’s no doubt Bulger and Flemmi had reputations as vicious hoodlums. Harrington told Green who was threatened by them in 1976 or 1977 that Whitey would cut out his tongue, cut off his ears, and stuff them down his throat. I’d say there were a lot more sources than just Halloran and Murray who were feeding the FBI and others information on Whitey. Just look at the surveillance photos of Whitey meeting with Nick Angiulo, Larry Baione, and other Mafia guys at Lancanster Street and you have a pretty good idea what he was about.
      Even Connolly said the idea behind the Top Echelon Informant program was to team the FBi agents up with murderers.
      By 1980 Flemmi was arrested and indicted for murder and blowing up a car, JImmy Martorano was arrested and incarcerated for extortion, race fixing and gun possession; Johnny Martorano jailed for being a bookie kingpin and then indicted for race fixing, Howie Winter was incarcerated for extortion, Joe McDonald and Jimmy Sims were charged with murders and other offenses. These men were all known to be part of Winter Hill as was Whitey.
      These are facts that were known back then. Most offenses did not relate to murder. The purpose of my going back is to see what was known and when it was known. Hope your New Year is fine and your buddy John Connolly finally gets some good legal represntation.

  2. as always an interesting post. you are correct in stating that not being included in the racefixing case in 1979 by jerimiah sullivan was key for whitey and stevie to continue living free. i would also add that the lottery ticket win in 1991 did not cast massachusetts in a favorable light.whitey on the cover of usa today in 1991 and living free another 3 years made massachusetts look like bumblers. from joe murray to the south boston liqor mart takover whitey seemed to lead a charmed life. regards

    1. Norwood Born:
      It’s interesting to go back through the history over again and see how big that decision by O’Sullivan was to making Whitey into a somebody. The lottery ticket is a strange story that I’ll talk about some day. The US Attorney alleged one thing and took the winnings away from Whitey. Then when Weeks turned state’s evidence it had to change course and make a different allegation to let Weeks keep his winnings. It seems the facts change with the direction of the wind. Whitey’s charmed life was due to the FBI deal, as shown by O’Sullivan’s actions.

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