The Winter Hill Gang: A Few Hoodlums With A Five Year Life Span (1 of 2)

You heard of the Winter Hill Gang (WHG) I assume. That was the gang James “Whitey” Bulger supposedly headed up. He never did. I do not suppose you can tell me when it started, or where it’s headquarters we’re located; or how long it existed; or who were in it; or whether it was a gang at all.

I suggest the first step in answering these questions is to determine what is meant by the word gang. The federal government has set out its definition of a gang: ” An association of three or more individuals; . . . Whose members collectively identify themselves by adopting a group identity, which they use to create an atmosphere of fear or intimidation, frequently by employing one or more of the following: a common name, slogan, identifying sign, symbol, tattoo or other physical marking, style or color of clothing, hairstyle, hand sign or graffiti; Whose purpose in part is to engage in criminal activity and which uses violence or intimidation to further its criminal objectives.” It excludes “drug trafficking organizations, . . . traditional organized crime groups, such as La Cosa Nostra, . . .” 

The states have a different definition: “criminal street gang’ means any ongoing organization, association or group of three or more persons, whether formal or informal, having as one of its primary activities the commission of one or more of the criminal acts […], having a common name or common identifying sign or symbol, and whose members individually or collectively engage in or have engaged in a pattern of criminal gang activity.”

The ideas is that it is an association of three or more people gathered together under a common symbol engaged in criminal activity. I suppose if it was two people who associated no one would consider it a gang.

Growing up we talked about gangs. My first encounter with one was shortly after I moved at age 10 to our new home in Savin Hill Dorchester about a mile and a half away from Old Harbor Village in South Boston where I spent my earliest days.

It was in late summer approaching dusk. I was sitting on the stoop of my house when there came what seemed to me hundreds of guys who filled the street from sidewalk to sidewalk from around the corner of Saxon Street onto Belfort Street walking past my house turning right onto Sagamore Street heading toward South Boston.

I was told by one of the boys that they were the Loopers and Trojans which were Savin Hill gangs heading to Southie for a gang fight against the Shamrocks. I never heard what happened. Later on I’d hear stories about other gangs like the Red Raiders from Roxbury who were supposed to be particularly bad. They hung down at the Prairie. In high school there was a gang up at the Eddie Eddie square whose name I now forget who jumped a few of us one night.

I hung around with a large group of kids. We had no name.  In our early teens we came back from a movie called “The Amboy Dukes” seeking to imitate them by getting ourselves switch blade knifes. A year or so later we had a symbol. It was a large diaper pin which was purloined from National Laundry on Dorchester Avenue.  We wore it on a front loop of our dungarees. Supposedly we could hold it in our hand and use it to stab someone which no one ever did. Were we a gang? Probably not under the Fed definition. We weren’t into criminal activity. We hung around, leaned against street poles, played street sports, and engaged in some hijinks that probably could be stretched to be considered criminal .

There were two or three kids among twenty or more of  us who were legitimate criminals stealing cars, breaking into buildings, and the like but they were sole operatives. I assume that did not taint the rest of us even though we were friends. Although I’m sure the Feds could come up with a chart making us all part of their activities.


6 thoughts on “The Winter Hill Gang: A Few Hoodlums With A Five Year Life Span (1 of 2)

  1. Hello Matt, when I played in the Park League as a member of the Jefferson Clubs and then the Chips, we played several games at the Prairie. It was located in the area you have discribed in today’s blog. Their QB was named Harry Festa and he was the best in New England ! He could throw a ball a mile and he was as tough as nails . All those games were usually played on Sundays and would draw sizable crowds ! Our home games were played at Columbia Park, there was a drain , iron cover in the middle of the field. East Boston had the Tornadoes and St Lazarus, Roxbury had the Red Raiders and Jefferson Club, Dorchester had The Lions Club, Brighton had the St Paul Club, South Boston had the Saunders Post , Chippewas, Powers Club, Roxbury had the Panthers, then the NFL started to get popular on Sundays and the league started to dwindle in attendance! The Pats are playing Buffalo tonight and I wish we had Harry Festa of the Roxbury Red Raiders taking our snaps against the Bills! Go Pats! Slainte☘️

    1. JRC:

      That comment brought back a lot of memories. I recall attending games at Columbia Park that you played in. Those were tough games. Funny, my memory of them is there always seemed to be someone carried off the field on a stretcher and sitting on the project side of the stadium we would always give the poor guy a big cheer. I also recall the name Harry Festa – he was some sort of a legend at the time if I knew his name. Another memory I have is this guy who lived on Saxton Street which ran into my street in Savin Hill named Paul Brennan who was a tough as nails and played half back without a helmet. I suppose it probably did not matter in those days because the helmets weren’t the greatest. It is a wonder anyone survived the games and of course it always made me wonder about the iron drain cover in the middle of the field. Great comment. Yes, have to get to tonight’s game but we could use Harry Festa or even Billy O’Shea on the Patriots. Is Harry still around?

  2. Hi Matt and thanks for an interesting article about what makes a gang. I am also looking forward to reading your new book.

    1. In your opinion was the TRC Gang led by Carmello Merlino connected to larger organizations such as the LCN in Boston, because this article seems to suggest that he knew the Salemme brothers, one of the Rossettis and Flemmi?—carmello-merlino.html

    2. What is your understanding of Nicky Giso? As the book Black Mass which has to be taken with a pinch of salt seems to mention that he was an associate of Gennaro Angiulo but he also had meetings with Whitey and Stevie.

    3. Who is Red Assad and how he is connected to the Mafia?

    1. David:

      1. The document you refer to is an FBI document that says he is 78 years old at the time it is posted and he died at age 73. I would not trust it too much especially since the FBI was convinced he was involved in the Gardner Museum heist which to me never made sense. It believed his involvement because some informant gave them that. I do not know of his association with the LCN in Boston other than he might have known some of them. He came across my screen when the drug task force I oversaw wanted to do a wire on his operation on Dorchester Avenue. I declined to do it because the location was difficult and the informant information was too sketchy. He might have known some of the LCN people or Flemmi but as best I knew he was his own small operation.

      2. Giso I know almost nothing about. He had a couple of arrests for minor stuff. He was shown on a chart in 1963 as a member of the LCN in Boston but he kept a low profile. I did not come up in the time period I was examining. I read the portion of Black Mass where he is mentioned. He probably interacted with Whitey and Stevie but not much more than that. Whitey’s relationship with the Mafia was always distant. Gerry Angiulo never trusted him for the simple reason he was Irish – he tolerated him because of Flemmi and the money he brought in.

      3. Richard “Red” Assad is a long time close buddy of Larry Zannino. Back in 1951 he and Zannino went over to hit a guy named James Bratsos and both of them ended up being shot in the leg as he came at them as they fled with a .22 caliber rifle. Over the years he would be arrested in some type of gaming operation when Zannino was arrested. Steve Flemmi said when Zannino was having trouble with a guy it was Red Assad who strangled him. Assad with probably a Lebanese or Syrian background would not have been in the Mafia but he might as well have been because it seems he and Zannino were inseparable.

  3. The Red Raiders had the reputation for being the toughest gang in the city.
    Going to a Y or a settlement house to play a Roxbury team was always met
    with some misgivings which as it turned out never materialized. Just the mention of the
    name today Matt, was enough to bring back those feelings as we took the T to
    Roxbury and hoped to return to East Boston safely.I met some of those opposing
    Roxbury players over the years and they felt the same about going to East Boston.
    Just part of growing up in the City.

    1. Paul:

      The Red Raiders were always on the mind of the Savin Hill folk. It was considered the toughest of gangs which hung out at what was called the Prairie – not sure what or where it was but pictured some type of park in my mind. We once made a trip far off to Brighton to play a baseball game with a team there. We were in the junior league and the team that was there was in the senior league. The game never took place because we ended up in a fight prior to it starting. What was it over? Who knows but as you say it was part of the city life.

      Curious about what the Prarie was and whether my memory was faulty and I imagined it, I Googled it and found and article by Fitzgerald of the Herald back in 2017 who explained talking about a reunion of Roxbury folk: “They remained that gang that could always be found on the Prairie, a hallowed patch of green nestled between Albany, Hampden, Magazine and George streets, a mystic place where games were played and fun was had and lifelong friendships were nurtured.” Then I found this: “Roxbury had a predominantly Italian population, and at the time, street gangs were ways for teens in different neighborhoods to play organized sports. Girolimetti’s dad played baseball in the Roxbury Red Raiders.”

      I also found in an obituary: “While his education was important, John knew how to have some fun, playing football in the Boston Park League for many years. One of his greatest athletic achievements was coaching, as well as playing with, the Roxbury Red Raiders, when they won the 1959 Boston Park League Football Championship.”

      Which brings back memories of Park League Football and the guys who used to play without helmets. I guess you had to be there.

Comments are closed.