Whitey : – A Quick Overview of His Life To 1995

Whitey Bulger lived with his family on LoganWay in the Old Harbor Village, South Boston (Southie).  (Logan connected with O’Callaghan Way.)  This was one of the first housing projects in America.  He had a reputation as a bully.  Brother Billy wrote that while a kid Whitey  became “known to the police.”   It wasn’t for his participation in the Police Athletic League since he eschewed sports other than batting around much younger kids.

At 19 he went off to the Air Force.  When he came home he took to robbing banks.  His brother Billy said Whitey was a leader, that being “the only role he would tolerate.”  Except perhaps in some things.  Billy writes, Whitey “fell in with some much older men” and he “accompanied” them on robberies.   I can imagine  the conversation:

Older man:  “Hey kid, now that you’re out of the Air Force would you like to hang around with us older men?”

Whitey:  “Gee, whiz!  Can I?”

 Older man:  “Sure  kid.  Come on take a ride.  We’re a little bit lonely and need some company.”

Whitey:   “Wow, this is great.  Hey, you mind if I ask where we’re going?”

Older man:  “To Indiana to rob a bank.”

Whitey:  “Oh, OK.  How should I dress?”

Unfortunately Billy’s tale is a little off the mark.  Whitey returned from the Air Force four years later as wild and bold as when he joined. Whitey led several robberies with younger and older men.  In one he walked into the bank carrying a revolver in each hand.  With the loot he’d take some young blond and go off to a warm clime on a spree.

At age 26 he was arrested by the FBI in a Revere gin mill.  One of the agents in the arrest was Paul Rico.  Whitey ended up doing around ten years in Atlanta, Alcatraz, Leavenworth and Lewisburg.

He came back to Boston in 1965 just about the time the gang war between Winter Hill of Somerville and the McLaughlins of Charlestown was winding down because few targets were left.  The war was over an alleged insult to a young moll.  Whitey got himself involved in a Southie gang war between the Mullens and the Killeens, always ready to switch sides as the power switched, always taking good care of Whitey.

In 1972 he joined Winter Hill which had emerged victorious over the mostly deceased McLaughlins.  He was introduced to its leader, Howie Winter, by Johnny Martorano who also joined at the same time.

In 1972 Stevie Flemmi was on the lam and hiding out in Montreal.  He had wired an attorney’s car with a bomb that blew off the lawyer’s leg.  He had been an informant for Agent Rico since 1965 so he stayed in touch with him.  He came back to Boston in 1974 after Agent Rico managed to get his case dismissed.   Stevie became partners with the others in Winter Hill.

The first record of Whitey being a snitch for the FBI is dated May 13, 1971 when he was opened by FBI Agent Dennis Condon, Rico’s partner.

The FBI records showed Condon closed out Whitey after about four months.   Its records also show Flemmi was closed out in 1967.   The official records on Whitey is he was closed in September 1971, reopened in September 1975, and finally closed on December 3, 1990.  The records on Flemmi show he was closed in December, 1967, reopened in September, 1980, closed in 1982, reopened in 1986 and finally closed on December 3, 1990.  The reason both were closed in December 1990 was Connolly’s retirement.

Flemmi testified he never knew he was ever closed.  The opening and closing of informants in the FBI had really two components: what the records said; and what actually happened.

Kevin Weeks in his book, Brutal, said John Connolly told him after he retired he still met with Whitey exchanging information he received from his friends in the FBI.  Whitey always appreciative would give him a cash “thank you” card.

Tom Foley in his book, Most Wanted, complained that even after Connolly retired the FBI still undermined his investigations of Whitey.  The protection seemed to never end.

I’d suggest it’s fair to say Flemmi was an informant from 1965 up until 1994.  Whitey ratted people out from 1971 up through 1994.  In 1995 things turned sour.

3 thoughts on “Whitey : – A Quick Overview of His Life To 1995

  1. Dear Mr. Connolly, I have been following your blog for a few months now and I must say that you are doing a great job and your information and insights are highly informative. Nowhere else is this story being followed and analyzed like it is here. Although born, raised , and bred on these same streets, but not involved personally, I have been an armchair follower of the entire saga for years and have several connections to people, places,and things within the sphere of “Jimmy and Stevie’s” world. Maybe you could give me some further insight at a later time. My specific question is….. is there any indication anywhere that Jimmy and Stevie knew eachother prior to 1974 ( Stevie’s return from Montreal )…., and if not, what do you think precipitated the partnership that they formed, and why? I am of the same opinion as you regarding Flemmi, and I’ve come to see Whitey in a slightly different light than I had before following this site. Not to diminish his culpability. Also, do you think he actually trusted and liked Flemmi, or was it strictly a businesss arrangement? Thank you.

    1. Name Withheld:
      Thanks for the complement and for following the blog. I’ve censored your name at your request. You ask a good question that I have been thinking about since I’ve finished up with the pre-Flemmi years and reached the point where Flemmi comes back to Massachusetts to join the gang. In late 1972 Martorano said he had never heard of Whitey and Martorano was part of the Roxbury group as was Flemmi. So I think it is unlikely that they knew each other before Stevie came back.
      Salemme was Flemmi’s good friend but he was in prison because Flemmi set him up to be arrested. In May 1974 Whitey was still feeling his way into Winter Hill. I don’t see that he was particularly close to Howie, McDonald or Sims, who were long time friends. He’d be wary of Murderman Martorano and his brother Jimmy. When Flemmi comes back, he’s really only got one close connection to the group and that would be Martorano. I’m not sure how close he was to Martorano. Martoranos said Flemmi had been informing on him for years even trying to set him up in a murder plot so Flemmi although he knows Martorano probably doesn’t like him that much. That would leave Flemmi as somewhat of an outsider and seeing that Whitey was in the same category, they might have come together because it would be natural for outsiders to come together. I’m sure that had a lot to do with it. Weeks tells us that in the summer of 1974 he was a bouncer at Flix’s at the Somerset Hotel om Boston. The bar had been closed and Whitey and Stevie walked in together after hours. This would be within a couple of months of Flemmi coming back to Boston and they’re hanging around together. Another thing that drew them together would be their love. Salemme said only two things mattered in Flemmi’s life, women and money, and not necessarily in that order. The same seemed to apply to Whitey. Another attraction would be Whitey’s love to talk about military matters (which Pat Nee mentioned) and Flemmi having seen a lot of combat would have attracted Whitey to him. Nee said that “One day it just seemed to happen – Stevie became attached to Whitey’s hip” I think each man saw something of himself in the other man and that produced a bond between them.
      Flemmi was described as being more quiet than Whitey so he was probably also a good listener to Whitey’s stories. Pat Nee said from 1974 to 1995 he had no more than a dozen conversations with Flemmi and could never warm up to him. Usually a talker and a listener bind.
      Then again, Flemmi is working for the FBI at the time – he was in the process of being transferred from Rico/Condon to Connolly. It seems clear Flemmi was with the FBI before Whitey. Within a year of his return, Whitey has become an FBI informant. I’ve got to think more about how that would have come about.
      To sum up they probably got together because they were both outsiders, both tough guys and had the same goals. I’d say that it was more than a business arrangement. They had their disagreement with Flemmi complaining Whitey kept him out of the lottery winnings and Whitey complained Flemmi was hanging around too much with Salemme after he got out of jail but they remained close for many years and were together a lot of the time. I have to do more reading and thinking on this before I say much more. Thanks for writing.

    2. Name Withheld:
      If you write again please remind me to edit out your name and address. I already forget your name so I’ll have to be reminded not to publish it.

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